Biologically reversible phosphate and phosphonate protective gruops
First Claim
Patent Images
1. Compounds having the formula ##STR16## where R1 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and amines having the formula NR4 R5, where R4 and R5 are independently selected from the group consisting of H and alkyl hydrocarbons having 1-10 carbons;
- R3 is selected from the group consisting of H and alkyl hydrocarbons having 1-3 carbons;
X1 is selected from the group consisting of H andX2 is selected from the group consisting of R2 and OR2 ; and
R2 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and nucleosides.
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Abstract
Protective groups are provided which are suitable for masking phosphates and phosphonates. The protected compositions can be introduced in a biological system and then demasked under certain biological conditions. This method permits phosphates and phosphonates which would themselves degrade in the biological system and therefore be ineffective to be introduced in a protected form and late released under the proper conditions.
164 Citations
20 Claims
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1. Compounds having the formula ##STR16## where R1 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and amines having the formula NR4 R5, where R4 and R5 are independently selected from the group consisting of H and alkyl hydrocarbons having 1-10 carbons;
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R3 is selected from the group consisting of H and alkyl hydrocarbons having 1-3 carbons; X1 is selected from the group consisting of H and X2 is selected from the group consisting of R2 and OR2 ; and R2 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and nucleosides. - View Dependent Claims (2, 3, 4, 5, 6)
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6. The compounds of claim 1, where R2 is selected from the, group consisting of
2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-ethyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5'"'"'-propyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxyctidin-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyadenosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyguanosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyxanthosin-5'"'"'-yl --CH2 CH2 OCH2 --Guanine --CH2 CH2 OCH2 --Adenine --CH2 CH2 OCH2 --Thymine --CH2 CH2 OCH2 --Uracil --CH2 CH2 OCH2 --Cytosine --CH2 CH2 OCH2 --Xanthine.
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7. Compounds having the formula ##STR17## where R1 is selected from the group consisting of CH3,CH2 CH3, CH(CH3)2, and C(CH3)3 ;
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X1 selected from the group consisting of H and R1 COOCH2 ; and R2 is selected from the group consisting of
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- 8. '"'"' . 3'"'"'-dideoxyuridin-5'"'"'-yl groups
2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl groups 2'"'"',3'"'"'-dideoxyguanosin-5'"'"'-yl groups, and groups having the formula - space="preserve" listing-type="equation">CH.sub.2 CH.sub.2 OCH.sub.2 B
where B is a base selected from the group consisting of thymine, uracil, cytosine, guanine, adenine, and xanthine.
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9. Compounds having the formula ##STR18## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
R2 is selected from the group consisting of
- and
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10. '"'"' . 3'"'"'-dideoxyuridine-5'"'"'-yl
2'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-diideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-ethyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-propyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyadenosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyguanosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyxanthosin-5'"'"'-yl --CH2 CH2 OCH2 --Guanine --CH2 CH2 OCH2 --Adenine --CH2 CH2 OCH2 --Thymine --CH2 CH2 OCH2 --Uracil --CH2 CH2 OCH2 --Cytosine --CH2 CH2 OCH2 --Xanthine
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11. Compounds having the formula ##STR19## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
R2 is selected from the group consisting of
- and
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12. '"'"' . 3'"'"'-dideoxyuridine-5'"'"'-yl
2'"'"'fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl; -
'"'"' -fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-ethyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-propyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-diedoxycytidin-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methy-3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyadenosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyguanosin-5'"'"'-yl 2'"'"',3'"'"'-dideoxyxanthosin-5'"'"'-yl --CH2 CH2 OCH2 ---Guanine --CH2 CH2 OCH2 --Adenine --CH2 CH2 OCH2 --Thymine --CH2 CH2 OCH2 --Uracil --CH2 CH2 OCH2 --Cytosine --CH2 CH2 OCH2 --Xanthine.
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13. Compounds having the formula ##STR20## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3;
- and
R2 is selected from the group consisting of
- and
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14. '"'"' . 3'"'"'-dideoxyuridine-5'"'"'-yl
2'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'amino-2'"'"',3'"'"'-didoxyuridine-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-bromo-2,3'"'"'-dideoxyuridine-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-ethyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-propyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin- 5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl.
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15. Compounds having the formula ##STR21## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
R2 is selected from the group consisting of
- and
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16. '"'"' . 3'"'"'-dideoxyuridine-5'"'"'-yl
2'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-bromo-2,3'"'"'-dideoxyuridine-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-methyl-3'"'"'-amino-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-ethyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 5-propyl-2'"'"',3'"'"'-dideoxyuridine-5'"'"'-yl 2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 2'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-chloro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-bromo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-iodo-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-fluoro-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl 5-methyl-3'"'"'-azido-2'"'"',3'"'"'-dideoxycytidin-5'"'"'-yl.
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17. Compounds having the formula ##STR22## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
R2 is selected from the group consisting of
- and
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18. '"'"' . 3'"'"'-dideoxyadensosin-5'"'"'-yl, and
2'"'"',3'"'"'-dideoxyxanthosin-5'"'"'-yl. 2'"'"',3'"'"'-dideoxyxanthosin-5'"'"'-yl.
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19. Compounds having the formula ##STR23## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
B is a base selected from the group consisting of guanine, adenine, thymine, uracil, cytosine, and xanthine.
- and
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20. Compounds having the formula ##STR24## where R1 is selected from the group consisting of H, CH3, CH2 CH3, CH(CH3)2, and C(CH3)3 ;
- and
B is a base selected from the group consisting of guanine, adenine, thymine, uracil, cytosine, and xanthine.
- and
Specification
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Current AssigneeBoard of Regents of the University of Texas System (University of Texas System)
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Original AssigneeBoard of Regents of the University of Texas System (University of Texas System)
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InventorsFarquhar, David
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Primary Examiner(s)Rollins, John W.
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Assistant Examiner(s)Wilson, James O.
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Application NumberUS07/300,264Time in Patent Office652 DaysField of Search536/23, 536/27, 536/28, 536/29US Class Current536/25.31CPC Class CodesC07F 9/091 with hydroxyalkyl compounds...C07F 9/12 with hydroxyaryl compoundsC07F 9/6512 having the nitrogen atoms i...C07H 19/10 with the saccharide radical...C07H 19/20 with the saccharide radical...Y02P 20/55 Design of synthesis routes,...
