Antiviral prodrugs of tenofovir
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Abstract
Compounds of Formula I: and pharmaceutically acceptable salts and co-crystals thereof are useful for the inhibition of HIV reverse transcriptase. The compounds may also be useful for the prophylaxis or treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antiviral agents, immunomodulators, antibiotics or vaccines.
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Citations
18 Claims
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1. A compound of structural Formula I:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
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2. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein one of R1 is —
- H or —
C1-4alkyl, and R2 is —
H, —
C1-4alkyl or —
CH2-phenyl.
- H or —
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3. The compound of claim 2 or a pharmaceutically acceptable salt thereof wherein R5 and R6 are independently selected from —
- C1-4alkyl, or R5 and R6 are joined together with the carbon to which they are both attached to form —
C3-6cycloalkyl.
- C1-4alkyl, or R5 and R6 are joined together with the carbon to which they are both attached to form —
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4. The compound of claim 3 or a pharmaceutically acceptable salt thereof wherein R3 is:
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(a) —
C1-8alkyl, —
CH2CH2OH, —
CH2CH2CH2OH, —
CH2CH2SH, —
CH2CH2CH2SH, —
CH2CH2NH2, —
CH2CH2CH2NH2,(b) —
CH2-phenyl, unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8a, —
SH, —
NR9aR10a or —
C1-3alkyl,(c) —
C3-6cycloalkyl, unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8a, —
SH, —
NR9aR10a or —
C1-3alkyl,(d) phenyl or naphthyl, each unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8a, —
SH, —
NR9aR10a or —
C1-3alkyl,(e) —
CH2CH2OCH3, —
CH2CH2CH2OCH3, —
CH2CH2SCH3, —
CH2CH2CH2SCH3, —
CH2CH2NHCH3, —
CH2CH2CH2NHCH3,(f) pyridyl, unsubstituted or substituted with one to three substituents independently selected from fluoro chloro, bromo, —
OR8a, —
SH, —
NR9aR10a or —
C1-3alkyl, or(g) piperidinyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8a, —
SH, —
NR9aR10a or —
C1-3alkyl.
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5. The compound of claim 4 or a pharmaceutically acceptable salt thereof wherein R4 is:
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(a) —
C1-8alkyl, —
CH2CH2OH, —
CH2CH2CH2OH, —
CH2CH2SH, —
CH2CH2CH2SH, —
CH2CH2NH2, —
CH2CH2CH2NH2,(b) —
CH2-phenyl, unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8b, —
SH, —
NR9bR10b or —
C1-3alkyl,(c) —
C3-6cycloalkyl, unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8b, —
SH, —
NR9bR10b or —
C1-3alkyl,(d) phenyl or naphthyl, each unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8b, —
SH, —
NR9bR10b or —
C1-3alkyl,(e) —
CH2CH2OCH3, —
CH2CH2CH2OCH3, —
CH2CH2SCH3, —
CH2CH2CH2SCH3, —
CH2CH2NHCH3, —
CH2CH2CH2NHCH3,(f) pyridyl, unsubstituted or substituted with one to three substituents independently selected from fluoro chloro, bromo, —
OR8b, —
SH, —
NR9bR10b or —
C1-3alkyl, or(g) piperidinyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each unsubstituted or substituted with one to three substituents independently selected from fluoro, chloro, bromo, —
OR8b, —
SH, —
NR9bR10b or —
C1-3alkyl.
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6. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each independently unsubstituted or substituted and each is independently selected from —
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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7. The compound of claim 2 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each independently unsubstituted or substituted and each is independently selected from —
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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8. The compound of claim 3 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each independently unsubstituted or substituted and each is independently selected from —
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C1-8alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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9. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each unsubstituted and independently selected from —
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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10. The compound of claim 2 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each unsubstituted and independently selected from —
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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11. The compound of claim 3 or a pharmaceutically acceptable salt thereof wherein R3 and R4 are each unsubstituted and independently selected from —
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
CH2-phenyl.
- C2-6alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or —
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12. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein:
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R1 is —
H or —
CH3;
R2 is —
H, —
CH3 or —
CH2-phenyl;R3 is selected from —
C1-8alkyl, —
C3-6cycloalkyl or —
CH2-phenyl;R4 is selected from —
C1-8alkyl or —
C3-6cycloalkyl; andR5 and R6 are both —
CH3;or R5 and R6 are joined together with the carbon to which they are both attached to form —
C3-6cycloalkyl.
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13. The compound of claim 1 that is:
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Isopropyl 2-4(S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-y0oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-ypoxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-oxo-2-(pentyloxy)ethoxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-oxo-2-(pentyloxy)ethoxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(4R)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((R)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-oxo-1-(pentyloxy)propan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-oxo-1-(pentyloxy)propan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Butyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy) -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Butyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy) -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclohexyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclohexyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclohexyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclohexyl 2-(((R)-((((R)1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclobutyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclobutyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclobutyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclobutyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl) (((R)-1 -is opr op oxy - 1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Propyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Propyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Propyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((R)-1-i sopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Butyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Butyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Butyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((R)-1 -isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Ethyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Ethyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Ethyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((R)-1-i sopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isobutyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-ypoxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Isobutyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxo-3-phenylpropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxo-3-phenylpropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy)-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-(cyclopentyloxy)-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Pentyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-(cyclopentyloxy)-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Isobutyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-(cyclopentyloxy) -1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Propyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-(cyclopentyloxy)-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Cyclopentyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-ethoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Benzyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Benzyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-ethoxy-1-oxopropan -2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Hexyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)((1-isopropoxy-2-methyl-1-oxopropan-2-yl)oxy)phosphoryl)amino)-2-methylpropanoate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)cyclopentane-1-carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)cyclopropane-1-carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)cyclopropane-1 -carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)cyclopentane-1-carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)cyclobutane-1-carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)cyclobutane-l-carboxylate; Isopropyl 1-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(2-isopropoxy-2-oxoethoxy)phosphoryl)amino)cyclohexane-1-carboxylate;
orIsopropyl 1-((((((R) -1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)oxy)phosphoryl)amino)cyclohexane-1-carboxylate; or a pharmaceutically acceptable salt thereof.
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14. A pharmaceutical composition comprising an effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
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15. The pharmaceutical composition of claim 14 further comprising an effective amount of one or more additional HIV antiviral agent selected from HIV protease inhibitors, HIV integrase inhibitors, non-nucleoside HIV reverse transcriptase inhibitors, nucleoside HIV reverse transcriptase inhibitors, HIV fusion inhibitors and HIV entry inhibitors.
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16. A method for the prophylaxis or treatment of infection by HIV or for the prophylaxis, treatment, or delay in the onset of AIDS in a subject in need thereof which comprises administering to the subject an effective amount of the compound of claim 1 or a pharmaceutically acceptable salt thereof.
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17. The method of claim 16 further comprising administering to the subject an effective amount of one or more additional HIV antiviral agent selected from HIV protease inhibitors, HIV integrase inhibitors, non-nucleoside HIV reverse transcriptase inhibitors, nucleoside HIV reverse transcriptase inhibitors, HIV fusion inhibitors and HIV entry inhibitors.
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18. The pharmaceutical composition of claim 14 further comprising an effective amount of one or more additional HIV antiviral agent selected from:
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2. The compound of claim 1 or a pharmaceutically acceptable salt thereof wherein one of R1 is —
Specification
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Current AssigneeMerck Sharp & Dohme LLC (Merck & Co., Inc.)
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Original AssigneeMerck Sharp & Dohme Corporation (Merck & Co., Inc.)
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InventorsDa Costa, Daniel, Dousson, Cyril B., Dukhan, David, Paparin, Jean-Laurent, Rahali, Houcine, Raheem, Izzat
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Primary Examiner(s)Pagano, Alexander R
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Application NumberUS16/327,631Publication NumberTime in Patent Office791 DaysField of SearchNoneUS Class CurrentCPC Class CodesA61K 31/675 having nitrogen as a ring h...A61K 45/05 Immunological preparations ...A61K 45/06 Mixtures of active ingredie...A61P 31/00 Antiinfectives, i.e. antibi...A61P 31/12 AntiviralsC07F 9/65616 containing the ring system ...