Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds for treating hepatitis virus infections
First Claim
1. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an anti-hepatitis virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
1 Assignment
0 Petitions
Accused Products
Abstract
Provided are methods and compositions for treating hepatitis virus infections in mammals, especially humans. The methods comprise (1) administering N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds alone or in combination with nucleoside antiviral agents, nucleotide antiviral agents, mixtures thereof, or immunomodulating/immunostimulating agents, or (2) administering N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds alone or in combination with nucleoside antiviral agents, nucleotide antiviral agents, or mixtures thereof, and immunomodulating/immuno-stimulating agents.
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Citations
180 Claims
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1. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an anti-hepatitis virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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2. The method of claim 1, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
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3. The method of claim 2, wherein R is nonyl.
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4. The method of claim 1, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
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5. The method of claim 4, wherein R is nonyl.
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6. The method of claim 5, wherein said alkanoyl is butanoyl.
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7. The method of claim 1, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
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N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
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8. The method of claim 1, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
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9. A method as set forth in claim 1 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
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10. A method as set forth in claim 1 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
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2. The method of claim 1, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
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11. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an antiviral composition comprising an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (12, 13, 14, 15, 16, 17, 18, 19, 20)
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12. The method of claim 11, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
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13. The method of claim 12, wherein R is nonyl.
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14. The method of claim 11, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
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15. The method of claim 14, wherein R is nonyl.
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16. The method of claim 15, wherein said alkanoyl is butanoyl.
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17. The method of claim 11, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
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N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
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18. The method of claim 11, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
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19. A method as set forth in claim 11 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
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20. A method as set forth in claim 11 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
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12. The method of claim 11, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
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21. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an antiviral composition consisting essentially of an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (22, 23, 24, 25, 26, 27, 28, 29, 30)
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22. The method of claim 21, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
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23. The method of claim 22, wherein R is nonyl.
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24. The method of claim 21, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
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25. The method of claim 24, wherein R is nonyl.
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26. The method of claim 25, wherein said alkanoyl is butanoyl.
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27. The method of claim 21, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
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N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
28. The method of claim 21, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsul fate, ethanesulfonate, glucoheptano ate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
29. A method as set forth in claim 21 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
30. A method as set forth in claim 21 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
-
22. The method of claim 21, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
31. A method for treating a hepatitis virus infection in a mammal, consisting essentially of administering to said mammal an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (32, 33, 34, 35, 36, 37, 38, 39, 40)
-
32. The method of claim 31, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
33. The method of claim 32, wherein R is nonyl.
-
34. The method of claim 31, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
35. The method of claim 34, wherein R is nonyl.
-
36. The method of claim 35, wherein said alkanoyl is butanoyl.
-
37. The method of claim 31, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
38. The method of claim 31, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
39. A method as set forth in claim 31 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
40. A method as set forth in claim 31 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
32. The method of claim 31, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
41. A method for treating a hepatitis virus infection in a mammal, consisting essentially of administering to said mammal an antiviral effective amount of an antiviral compound consisting essentially of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (42, 43, 44, 45, 46, 47, 48, 49, 50)
-
42. The method of claim 41, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
43. The method of claim 42, wherein R is nonyl.
-
44. The method of claim 41, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
45. The method of claim 44, wherein R is nonyl.
-
46. The method of claim 45, wherein said alkanoyl is butanoyl.
-
47. The method of claim 41, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
48. The method of claim 41, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsul fate, ethanesulfonate, glucoheptano ate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
49. A method as set forth in claim 41 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
50. A method as set forth in claim 41 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
-
42. The method of claim 41, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
51. A method for treating a hepatitis virus infection in a mammal, consisting essentially of administering to said mammal a first amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63)
-
52. The method of claim 51, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
53. The method of claim 52, wherein RA is nonyl.
-
54. The method of claim 51, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
55. The method of claim 54, wherein RA is nonyl.
-
56. The method of claim 55, wherein said alkanoyl is butanoyl.
-
57. The method of claim 51, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
58. The method of claim 51, wherein said nucleoside or nucleotide antiviral compound is selected from the group consisting of:
-
(+)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine;
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
(−
)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine (FTC);
(−
)2′
,3′
, dideoxy-3′
-thiacytidine [(−
)-SddC];
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine (FIAC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU);
1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide;
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-dexocytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-cytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-cytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-cytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluorothymidine (FddThd);
2′
,3′
-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC);
2′
,3′
-dideoxy-beta-L-5-thiacytidine;
2′
,3′
-dideoxy-beta-L-5-cytidine (beta-L-ddC);
9-(1,3-dihydroxy-2-propoxymethyl)guanine;
2′
-deoxy-3′
-thia-5-florocytosine;
3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2-amino-1,9-[(2-hydroxymethyl-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one (gancyclovir);
2-[2-(2-amino-9H-purin-9y)ethyl]-1,3-propandil diacetate (famciclovir);
2-amino-1,9-dihydro-9-[(2-hydroxy-ethoxy)methyl]6H-purin-6-one (acyclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (penciclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)-6-deoxy-guanine, diacetate (famciclovir);
3′
-azido-3′
-deoxythymidine (AZT);
3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
9-(2-phosphonyl-methoxyethyl)-2′
,6′
-diaminopurine-2′
,3′
-dideoxyriboside;
9-(2-phosphonylmethoxyethyl)adenine (PMEA);
acyclovir triphosphate (ACVTP);
D-carbocyclic-2′
-deoxyguanosine (CdG);
dideoxy-cytidine;
dideoxy-cytosine (ddC);
dideoxy-guanine (ddG);
dideoxy-inosine (ddI);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate;
fluoro-arabinofuranosyl-iodouracil;
1-(2′
-deoxy-2′
-fluoro-1-beta-D-arabinofuranosyl)-5-iodo-uracil (FIAU);
stavudine;
9-beta-D-arabinofuranosyl-9H-purine-6-amine monohydrate (Ara-A);
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP);
2-deoxy-3′
-thia-5-fluorocytidine;
2′
,3′
-dideoxy-guanine; and
2′
,3′
-dideoxy-guanosine.
-
-
59. A method as set forth in claim 51 wherein RA is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
60. A method as set forth in claim 51 wherein RA is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
61. The method of claim 59, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
- and
wherein said nucleoside or nucleotide antiviral compound is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC).
- and
-
62. A method as set forth in claim 51 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof.
-
63. A method as set forth in claim 51 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof
-
52. The method of claim 51, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
64. A method for treating a hepatitis B virus infection in a mammal, comprising administering to said mammal from about 0.1 mg/kg/day to about 100 mg/kg/day of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76)
-
65. The method of claim 64, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
66. The method of claim 65, wherein RA is nonyl.
-
67. The method of claim 64, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
68. The method of claim 67, wherein RA is nonyl.
-
69. The method of claim 68, wherein said alkanoyl is butanoyl.
-
70. A method as set forth in claim 64 wherein RA is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
71. A method as set forth in claim 64 wherein RA is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
72. The method of claim 64, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
73. The method of claim 64, wherein said nucleoside or nucleotide antiviral compound is selected from the group consisting of:
-
(+)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine;
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
(−
)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine (FTC);
(−
)2′
,3′
, dideoxy-3′
-thiacytidine [(−
)-SddC];
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine (FIAC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU);
1-beta-D-ribo furanosyl-1,2,4-triazole-3-carboxamide;
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-dexocytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-cytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-cytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-cytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluorothymidine (FddThd);
2′
,3′
-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC);
2′
,3′
-dideoxy-beta-L-5-thiacytidine;
2′
,3′
-dideoxy-beta-L-5-cytidine (beta-L-ddC);
9-(1,3-dihydroxy-2-propoxymethyl)guanine;
2′
-deoxy-3′
-thia-5-fluorocytosine;
3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2-amino-1,9-[(2-hydroxymethyl-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one (gancyclovir);
2-[2-(2-amino-9H-purin-9y)ethyl]-1,3-propandil diacetate (famciclovir);
2-amino-1,9-dihydro-9-[(2-hydroxy-ethoxy)methyl]6H-purin-6-one (acyclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (penciclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)-6-deoxy-guanine, diacetate (famciclovir);
3′
-azido-3′
-deoxythymidine (AZT);
3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
9-(2-phosphonyl-methoxyethyl)-2′
,6′
-diaminopurine-2′
,3′
-dideoxyriboside;
9-(2-phosphonylmethoxyethyl)adenine (PMEA);
acyclovir triphosphate (ACVTP);
D-carbocyclic-2′
-deoxyguanosine (CdG);
dideoxy-cytidine;
dideoxy-cytosine (ddC);
dideoxy-guanine (ddG);
dideoxy-inosine (ddI);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate;
fluoro-arabinofuranosyl-iodouracil;
1-(2′
-deoxy-2′
-fluoro-1-beta-D-arabinofuranosyl)-5-iodo-uracil (FIAU);
stavudine;
9-beta-D-arabinofuranosyl-9H-purine-6-amine monohydrate (Ara-A);
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP);
2-deoxy-3′
-thia-5-fluorocytidine;
2′
,3′
-dideoxy-guanine; and
2′
,3′
-dideoxy-guanosine.
-
-
74. The method of claim 64, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
- and
wherein said nucleoside or nucleotide antiviral compound is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC).
- and
-
75. A method as set forth in claim 64 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
76. A method as set forth in claim 64 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
-
65. The method of claim 64, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
77. A method for treating a hepatitis B virus infection in a human patient, comprising administering to said human patient from about 0.1 mg/kg/day to about 100 mg/kg/day of an N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound selected from the group consisting N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof, and from about 0.1 mg/person/day to about 500 mg/person/day of (−
- )-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate. - View Dependent Claims (78, 79)
-
78. A method as set forth in claim 77 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
79. A method as set forth in claim 77 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
-
78. A method as set forth in claim 77 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
- )-2′
-
80. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (81, 82, 83, 84, 85, 86, 87, 88, 89, 90)
-
81. The method of claim 80, further comprising administering said at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier, excipient, or diluent.
-
82. The method of claim 80, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
83. The method of claim 82, wherein R is nonyl.
-
84. The method of claim 80, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
85. The method of claim 84, wherein R is nonyl.
-
86. The method of claim 85, wherein said alkanoyl is butanoyl.
-
87. The method of claim 80, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
88. The method of claim 80, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
89. A method as set forth in claim 80 comprising treating a hepatitis B virus infection comprising administering to said mammal an anti-hepatitis B virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof.
-
90. A method as set forth in claim 80 comprising treating a hepatitis C virus infection comprising administering to said mammal an anti-hepatitis C virus effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof
-
81. The method of claim 80, further comprising administering said at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier, excipient, or diluent.
-
91. A method for treating a hepatitis virus infection in a mammal, comprising administering to said mammal an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (92, 93, 94, 95, 96, 97, 98, 99)
-
92. The method of claim 91, further comprising administering said at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier, excipient, or diluent.
-
93. The method of claim 91, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
94. The method of claim 93, wherein R is nonyl.
-
95. The method of claim 91, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
96. The method of claim 95, wherein R is nonyl.
-
97. The method of claim 96, wherein said alkanoyl is butanoyl.
-
98. The method of claim 91, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
99. The method of claim 91, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
92. The method of claim 91, further comprising administering said at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier, excipient, or diluent.
-
100. A pharmaceutical composition, comprising an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (101, 102, 103, 104, 105, 106, 107)
-
101. The pharmaceutical composition of claim 100, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
102. The pharmaceutical composition of claim 101, wherein R is nonyl.
-
103. The pharmaceutical composition of claim 100, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
104. The pharmaceutical composition of claim 103, wherein R is nonyl.
-
105. The pharmaceutical composition of claim 104, wherein said alkanoyl is butanoyl.
-
106. The pharmaceutical composition of claim 100, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
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107. The pharmaceutical composition of claim 100, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
101. The pharmaceutical composition of claim 100, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
108. A pharmaceutical composition, consisting essentially of an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (109, 110, 111, 112, 113, 114, 115)
-
109. The pharmaceutical composition of claim 108, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
110. The pharmaceutical composition of claim 109, wherein R is nonyl.
-
111. The pharmaceutical composition of claim 108, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
112. The pharmaceutical composition of claim 111, wherein R is nonyl.
-
113. The pharmaceutical composition of claim 112, wherein said alkanoyl is butanoyl.
-
114. The pharmaceutical composition of claim 108, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
115. The method of claim 108, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
109. The pharmaceutical composition of claim 108, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
116. A pharmaceutical composition, comprising an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (117, 118, 119, 120, 121, 122, 123)
-
117. The pharmaceutical composition of claim 116, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
118. The pharmaceutical composition of claim 117, wherein R is nonyl.
-
119. The pharmaceutical composition of claim 116, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
120. The pharmaceutical composition of claim 119, wherein R is nonyl.
-
121. The pharmaceutical composition of claim 120, wherein said alkanoyl is butanoyl.
-
122. The pharmaceutical composition of claim 116, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
123. The pharmaceutical composition of claim 116, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
117. The pharmaceutical composition of claim 116, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
124. A pharmaceutical composition, comprising an antiviral effective amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula I or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (125, 126, 127, 128, 129, 130, 131)
-
125. The pharmaceutical composition of claim 124, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
126. The pharmaceutical composition of claim 125, wherein R is nonyl.
-
127. The pharmaceutical composition of claim 124, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
128. The pharmaceutical composition of claim 127, wherein R is nonyl.
-
129. The pharmaceutical composition of claim 128, wherein said alkanoyl is butanoyl.
-
130. The pharmaceutical composition of claim 124, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
131. The pharmaceutical composition of claim 124, wherein said pharmaceutically acceptable salt is selected from the group consisting of acetate, adipate, alginate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, cyclopentanepropionate, dodecylsulfate, ethanesulfonate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, fumarate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxy-ethanesulfonate, lactate, maleate, methanesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, palmoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, succinate, tartrate, thiocyanate, tosylate, mesylate, and undecanoate.
-
125. The pharmaceutical composition of claim 124, wherein R is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
132. A composition, comprising at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (133, 134, 135, 136, 137, 138, 139, 140, 141, 142)
-
133. The composition of claim 132, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
134. The composition of claim 133, wherein RA is nonyl.
-
135. The composition of claim 132, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
136. The composition of claim 135, wherein RA is nonyl.
-
137. The composition of claim 136, wherein said alkanoyl is butanoyl.
-
138. A method as set forth in claim 132 wherein RA is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
139. A method as set forth in claim 132 wherein RA is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
140. The composition of claim 132, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
141. The composition of claim 132, wherein said nucleoside or nucleotide antiviral compound is selected from the group consisting of:
-
(+)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine;
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
(−
)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine (FTC);
(−
)2′
,3′
, dideoxy-3′
-thiacytidine [(−
)-SddC];
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine (FIAC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU);
1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide;
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-dexocytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-cytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-cytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-cytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluorothymidine (FddThd);
2′
,3′
-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC);
2′
,3′
-dideoxy-beta-L-5-thiacytidine;
2′
,3′
-dideoxy-beta-L-5-cytidine (beta-L-ddC);
9-(1,3-dihydroxy-2-propoxymethyl)guanine;
2′
-deoxy-3′
-thia-5-fluorocytosine;
3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2-amino-1,9-[(2-hydroxymethyl-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one (gancyclovir);
2-[2-(2-amino-9H-purin-9y)ethyl]-1,3-propandil diacetate (famciclovir);
2-amino-1,9-dihydro-9-[(2-hydroxy-ethoxy)methyl]6H-purin-6-one (acyclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (penciclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)-6-deoxy-guanine, diacetate (famciclovir);
3′
-azido-3′
-deoxythymidine (AZT);
3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
9-(2-phosphonyl-methoxyethyl)-2′
,6′
-diaminopurine-2′
,3′
-dideoxyriboside;
9-(2-phosphonylmethoxyethyl)adenine (PMEA);
acyclovir triphosphate (ACVTP);
D-carbocyclic-2′
-deoxyguanosine (CdG);
dideoxy-cytidine;
dideoxy-cytosine (ddC);
dideoxy-guanine (ddG);
dideoxy-inosine (ddI);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate;
fluoro-arabinofuranosyl-iodouracil;
1-(2′
-deoxy-2′
-fluoro-1-beta-D-arabinofuranosyl)-5-iodo-uracil (FIAU);
stavudine;
9-beta-D-arabinofuranosyl-9H-purine-6-amine monohydrate (Ara-A);
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP);
2-deoxy-3′
-thia-5-fluorocytidine;
2′
,3′
-dideoxy-guanine; and
2′
,3′
-dideoxy-guanosine.
-
-
142. The composition of claim 132, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
- and
wherein said nucleoside or nucleotide antiviral compound is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC).
- and
-
133. The composition of claim 132, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
143. A pharmaceutical composition, comprising:
-
a first amount of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof;
wherein RA is selected from the group consisting of branched or straight chain alkyl having a chain length of C, to C20 in the main chain, alkoxyalkyl, arylalkyl, and cycloalkylalkyl, and wherein W, X, Y and Z are each independently selected from the group consisting of hydrogen, alkanoyl, aroyl, and trifluoroalkanoyl;
a second amount of an antiviral compound selected from the group consisting of a nucleoside antiviral compound, a nucleotide antiviral compound, an immunomodulator, and immunostimulant, and mixtures thereof; and
a pharmaceutically acceptable carrier, diluent, or excipient, wherein said first and second amounts of said compounds together comprise an antiviral effective amount of said compounds. - View Dependent Claims (144, 145, 146, 147, 148, 149, 150, 151, 152, 153)
-
144. The pharmaceutical composition of claim 143, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
145. The pharmaceutical composition of claim 144, wherein RA is nonyl.
-
146. The pharmaceutical composition of claim 143, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
147. The pharmaceutical composition of claim 146, wherein RA is nonyl.
-
148. The pharmaceutical composition of claim 147, wherein said alkanoyl is butanoyl.
-
149. A method as set forth in claim 143 wherein RA is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
150. A method as set forth in claim 143 wherein RA is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
151. The pharmaceutical composition of claim 143, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
152. The pharmaceutical composition of claim 143, wherein said nucleoside or nucleotide antiviral compound is selected from the group consisting of:
-
(+)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine;
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
(−
)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine (FTC);
(−
)2′
,3′
, dideoxy-3′
-thiacytidine [(−
)-SddC];
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine (FIAC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU);
1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide;
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-dexocytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-cytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-cytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-cytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluorothymidine (FddThd);
2′
,3′
-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC);
2′
,3′
-dideoxy-beta-L-5-thiacytidine;
2′
,3′
-dideoxy-beta-L-5-cytidine (beta-L-ddC);
9-(1,3-dihydroxy-2-propoxymethyl)guanine;
2′
-deoxy-3′
-thia-5-fluorocytosine;
3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2-amino-1,9-[(2-hydroxymethyl-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one (gancyclovir);
2-[2-(2-amino-9H-purin-9y)ethyl]-1,3-propandil diacetate (famciclovir);
2-amino-1,9-dihydro-9-[(2-hydroxy-ethoxy)methyl]6H-purin-6-one (acyclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (penciclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)-6-deoxy-guanine, diacetate (famciclovir);
3′
-azido-3′
-deoxythymidine (AZT);
3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
9-(2-phosphonyl-methoxyethyl)-2′
,6′
-diaminopurine-2′
,3′
-dideoxyriboside;
9-(2-phosphonylmethoxyethyl)adenine (PMEA);
acyclovir triphosphate (ACVTP);
D-carbocyclic-2′
-deoxyguanosine (CdG);
dideoxy-cytidine;
dideoxy-cytosine (ddC);
dideoxy-guanine (ddG);
dideoxy-inosine (ddI);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate;
fluoro-arabinofuranosyl-iodouracil;
1-(2′
-deoxy-2′
-fluoro-1-beta-D-arabinofuranosyl)-5-iodo-uracil (FIAU);
stavudine;
9-beta-D-arabinofuranosyl-9H-purine-6-amine monohydrate (Ara-A);
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP);
2-deoxy-3′
-thia-5-fluorocytidine;
2′
,3′
-dideoxy-guanine; and
2′
,3′
-dideoxy-guanosine.
-
-
153. The pharmaceutical composition of claim 143, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
- and
wherein said nucleoside or nucleotide antiviral compound is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC).
- and
-
144. The pharmaceutical composition of claim 143, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
-
154. A pharmaceutical composition for treating a hepatitis virus infection in a mammal, comprising:
-
from about 0.1 mg to about 100 mg of at least one N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA or a pharmaceutically acceptable salt thereof;
wherein RA is selected from the group consisting of branched or straight chain alkyl having a chain length of C, to C20, alkoxyalkyl, arylalkyl, and cycloalkylalkyl, and wherein W, X, Y and Z are each independently selected from the group consisting of hydrogen, alkanoyl, aroyl, and trifluoroalkanoyl;
from about 0.1 mg to about 500 mg of a compound selected from the group consisting of a nucleoside antiviral compound, a nucleotide antiviral, and mixtures thereof; and
a pharmaceutically acceptable carrier, diluent, or excipient. - View Dependent Claims (155, 156, 157, 158, 159, 160, 161, 162, 163, 164)
-
155. The pharmaceutical composition of claim 154, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
156. The pharmaceutical composition of claim 155, wherein RA is nonyl.
-
157. The pharmaceutical composition of claim 154, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
158. The pharmaceutical composition of claim 157, wherein RA is nonyl.
-
159. The pharmaceutical composition of claim 158, wherein said alkanoyl is butanoyl.
-
160. A method as set forth in claim 154 wherein RA is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
161. A method as set forth in claim 154 wherein RA is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
162. The pharmaceutical composition of claim 154, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
163. The pharmaceutical composition of claim 154, wherein said nucleoside or nucleotide antiviral compound is selected from the group consisting of:
-
(+)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine;
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
(−
)-cis-5-fluoro-1-[2-(hydroxy-methyl)-[1,3-oxathiolan-5-yl]cytosine (FTC);
(−
)2′
,3′
, dideoxy-3′
-thiacytidine [(−
)-SddC];
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine (FIAC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-methyluracil (FMAU);
1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide;
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-dexocytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluoro-5-methyl-cytidine (FddMeCyt);
2′
,3′
-dideoxy-3′
-chloro-5-methyl-cytidine (ClddMeCyt);
2′
,3′
-dideoxy-3′
-amino-5-methyl-cytidine (AddMeCyt);
2′
,3′
-dideoxy-3′
-fluorothymidine (FddThd);
2′
,3′
-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC);
2′
,3′
-dideoxy-beta-L-5-thiacytidine;
2′
,3′
-dideoxy-beta-L-5-cytidine (beta-L-ddC);
9-(1,3-dihydroxy-2-propoxymethyl)guanine;
2′
-deoxy-3′
-thia-5-fluorocytosine;
3′
-amino-5-methyl-dexocytidine (AddMeCyt);
2-amino-1,9-[(2-hydroxymethyl-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one (gancyclovir);
2-[2-(2-amino-9H-purin-9y)ethyl]-1,3-propandil diacetate (famciclovir);
2-amino-1,9-dihydro-9-[(2-hydroxy-ethoxy)methyl]6H-purin-6-one (acyclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (penciclovir);
9-(4-hydroxy-3-hydroxymethyl-but-1-yl)-6-deoxy-guanine, diacetate (famciclovir);
3′
-azido-3′
-deoxythymidine (AZT);
3′
-chloro-5-methyl-dexocytidine (ClddMeCyt);
9-(2-phosphonyl-methoxyethyl)-2′
,6′
-diaminopurine-2′
,3′
-dideoxyriboside;
9-(2-phosphonylmethoxyethyl)adenine (PMEA);
acyclovir triphosphate (ACVTP);
D-carbocyclic-2′
-deoxyguanosine (CdG);
dideoxy-cytidine;
dideoxy-cytosine (ddC);
dideoxy-guanine (ddG);
dideoxy-inosine (ddI);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate;
fluoro-arabinofuranosyl-iodouracil;
1-(2′
-deoxy-2′
-fluoro-1-beta-D-arabinofuranosyl)-5-iodo-uracil (FIAU);
stavudine;
9-beta-D-arabinofuranosyl-9H-purine-6-amine monohydrate (Ara-A);
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP);
2-deoxy-3′
-thia-5-fluorocytidine;
2′
,3′
-dideoxy-guanine; and
2′
,3′
-dideoxy-guanosine.
-
-
164. The pharmaceutical composition of claim 154, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof, N-(n-nonyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
- and
wherein said nucleoside or nucleotide antiviral compound is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC).
- and
-
155. The pharmaceutical composition of claim 154, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
-
165. A pharmaceutical composition for treating a hepatitis virus infection in a human patient, comprising:
-
from about 0.1 mg to about 100 mg of an N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound selected from the group consisting of N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol or a pharmaceutically acceptable salt thereof N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate or a pharmaceutically acceptable salt thereof, and mixtures thereof;
from about 0.1 mg to about 500 mg of (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate; and
a pharmaceutically acceptable carrier, diluent, or excipient.
-
-
166. A salt of an N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound of Formula IA:
- View Dependent Claims (167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178)
-
167. The salt of claim 166, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
168. The salt of claim 167, wherein RA is nonyl.
-
169. The salt of claim 166, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each alkanoyl.
-
170. The salt of claim 169, wherein RA is nonyl.
-
171. The salt of claim 170, wherein said alkanoyl is butanoyl.
-
172. A method as set forth in claim 166 wherein R is selected from the group consisting of straight chain alkyl having a chain length of C7 to C20 and branched chain alkyl having a chain length of C3 to C20 in the main chain.
-
173. A method as set forth in claim 166 wherein R is selected from the group consisting of alkoxyalkyl, arylalkyl, and cycloalkylalkyl.
-
174. The salt of claim 166, wherein said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of:
-
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(n-heptyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate N-(n-octyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-undecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-dodecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tridecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-pentadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-hexadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-heptadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-octadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-nonadecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(n-eicosyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-methyloctyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(2-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-ethylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(5-methylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-propylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-pentylpentylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-butylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-methyloctyl-)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(8-methylnonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(9-methyldecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(10-methylundecyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-cyclohexylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(4-cyclohexylbutyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(2-cyclohexylethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-cyclohexylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(3-(4-methyl)-phenylpropyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(6-phenylhexyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate;
N-(7-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(9-oxa-n-decyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(7-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetraacetate;
N-(3-oxa-n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol; and
N-(7,10,13-trioxa-n-tetradecyl)-1,5-dideoxy-1,5-imino-D-glucitol.
-
-
175. The salt of claim 166, wherein said nucleoside having an acidic moiety is selected from the group consisting of compounds of Formula II, III, IV, V, and VI.
-
176. The salt of claim 166, wherein said nucleotide is selected from the group consisting of compounds of Formula II, III, IV, V, and VI.
-
177. The salt of claim 176, wherein said nucleotide is selected from the group consisting of:
-
(−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate (3TC);
1-(2′
-deoxy-2′
-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine triphosphate (FIACTP);
acyclovir triphosphate (ACVTP);
E-5-(2-bromovinyl)-2′
-deoxyuridine triphosphate; and
9-beta-D-arabinofuranosyl-9H-purine-6-amine-5′
-monophosphate monohydrate (Ara-AMP).
-
-
178. The salt of claim 166, wherein:
-
said N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compound is selected from the group consisting of N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol and N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol, tetrabutyrate; and
said nucleotide is (−
)-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate.
-
-
167. The salt of claim 166, wherein RA is straight chain alkyl having a chain length of C7 to C20, and W, X, Y, and Z are each hydrogen.
-
179. A method, comprising reacting N-(n-nonyl)-1,5-dideoxy-1,5-imino-D-glucitol and (−
- )-2′
-deoxy-3′
-thiocytidine-5′
-triphosphate under salt-forming conditions. - View Dependent Claims (180)
-
180. A salt formed by the method of claim 179.
-
180. A salt formed by the method of claim 179.
- )-2′
Specification
- Resources
-
Current AssigneePharmacia Corporation (Pfizer Inc.)
-
Original AssigneePharmacia Corporation (Pfizer Inc.)
-
InventorsBryant, Kimberly, Mueller, Richard A., Bryant, Martin L.
-
Application NumberUS10/203,769Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/328CPC Class CodesA61K 2300/00 Mixtures or combinations of...A61K 31/445 Non condensed piperidines, ...A61K 45/06 Mixtures of active ingredie...A61P 1/16 for liver or gallbladder di...A61P 31/14 for RNA virusesA61P 31/20 for DNA viruses