Compounds and compositions are provided for treatment, prevention, or amelioration of a variety of medical disorders associated with viral infections and/or cell proliferation. The compounds provided herein are 5-phosphono-pent-2-en-1-yl nucleosides and esters thereof.
대표청구항▼
1. A compound of Formula IA or IB: or a pharmaceutically acceptable salt thereof,wherein each R is independently hydrogen, a monovalent cation or a lipophilic group and B is a purine or pyrimidine base or an analog thereof, wherein at least one R is a lipophilic group other than methyl or ethyl. 2.
1. A compound of Formula IA or IB: or a pharmaceutically acceptable salt thereof,wherein each R is independently hydrogen, a monovalent cation or a lipophilic group and B is a purine or pyrimidine base or an analog thereof, wherein at least one R is a lipophilic group other than methyl or ethyl. 2. The compound of claim 1, wherein the compound has formula 3. The compound of claim 1, wherein R is hydrogen, a monovalent cation, a substituted or unsubstituted C8-C24 alkyl or substituted or unsubstituted C8-C24 alkenyl having from 1 to 6 double bonds, wherein substituents when present are selected from one or more halogen, alkyl, —OH, —SH, cycloalkyl, or epoxide. 4. The compound of claim 1, wherein R has formula: wherein:R1 and R1a are independently —H, —O(C 1-C24)alkyl, —O(C1-C24)alkenyl, —O(C1-C24)acyl, —S(C1-C24)alkyl, —S(C1-C24)alkenyl, or —S(C1-C24)acyl, wherein at least one of R1 and R1a are not —H, and wherein the alkenyl or acyl moieties optionally have 1 to 6 double bonds,R2 and R2a are independently —H, —O(C1-C7)alkyl, —O(C1-C7)alkenyl, —S(C1-C7)alkyl, —S(C1-C7)alkenyl, —O(C1-C7)acyl, —S(C1-C7)acyl, —N(C1-C7)acyl, —NH(C1-C7)alkyl, —N((C1-C7)alkyl)2, oxo, halogen, —NH2, —OH, or —SH;R6, when present, is: m is an integer from 0 to 6;and wherein R1, R1a, R2, R2a, and R7a are optionally substituted with one to four substituents, each independently selected from alkyl, alkenyl, alkynyl, halo, hydroxyl, pseudohalo, amino, nitro, cycloalkyl, heterocyclyl, aryl and heteroaryl. 5. The compound of claim 1, wherein R has formula: 6. The compound of claim 1, wherein R has formula: 7. The compound of claim 1, wherein R has formula: 8. The compound of claim 1, wherein R is hexadecyloxypropyl, octadecyloxypropyl, or octadecyloxyethyl. 9. The compound of claim 1, wherein R is acetyl, valyl, dipivoxil, bis(pivaloyloxymethyl) or disoproxil. 10. The compound of claim 1, wherein B is wherein R3 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, hydroxy, halo, aryl or heteroaryl;R6 is H or C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl or cycloalkyl;R7 is H, hydroxy, halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl or NR4R5;R8 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl or cycloalkyl; R9 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, halo or NR4R5; andR4 and R5 are each independently H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, or C3-6 cycloalkyl. 11. The compound of claim 1, wherein, B is thymin-1-yl, cytosine-1-yl, uracil-1-yl, adenine-9-yl or guanine-9-yl. 12. The compound of claim 1, wherein B is selected from: 13. The compound of claim 1, wherein the compound is selected from 5-phosphono-pent-2-en- 1-yl adenine, 5-phosphono-pent-2-en-1-yl cytosine, 5-phosphono-pent-2-en-1-yl guanine, 5-phosphono-pent-2-en-1-yl thymine and 5-phosphono-pent-2-en-1-yl uracil. 14. The compound of claim 1, wherein the compound is selected from: 15. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier. 16. A method for treating, a viral infection, wherein the method comprises administering an effective amount of a compound of claim 1. 17. The method of claim 16, wherein the viral infection is a caused by influenza, hepatitis B virus, hepatitis C virus, cytomegalovirus, Varicella zoster virus, Herpes simplex virus types and 2, Epstein-Barr virus, Herpes type 6 and type 8, Varicella zoster virus, Epstein Barr virus infections, retroviral infections, orthopox viruses, vaccinia, ebola virus, adenovirus and papilloma virus. 18. The method of claim 16, wherein the viral infection is drug resistant Hepatitis B.
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