Antiviral macrocycles
AssigneeScynexis, Inc.
InventorsKeqiang Li, Michael Robert PEEL
Life of this patent
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Abstract
Cyclosporin derivatives, methods of manufacturing the cyclosporin derivatives and methods for treating subjects infected with certain viruses, including hepatitis virus or HIV by administering the cyclosporin derivatives are described.
Claims18
A cyclosporine A derivative in which the 3-Sarcosine position is substituted by a group —S—CH2C[CH2(CH2)n]NR2R3, wherein R2 is hydrogen or an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms, the chain is a straight or branched;
- R3 is an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms the chain is a straight or branched;
- and n is 1 or 2.
A compound of formula (I)
- wherein:
- A is (E) —CH═CHCH3 or —CH2CH2CH3;
- B is ethyl, 1-hydroxyethyl, isopropyl or n-propyl;
- n is 1 or 2;
- X is hydroxyl or hydrogen;
- R1 is hydrogen or straight- or branched-chain alkyl containing from one to four carbon atoms optionally substituted by one or more groups R4 which may be the same or different;
- R2 is hydrogen or an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms, the chain is a straight or branched;
- and
- R3 is an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms the chain is a straight or branched;
- R4 is phenyl optionally substituted by from one to five groups which may be the same or different selected from the group consisting of alkyl, haloalkyl, halogen, hydroxyl, alkoxy, amino, N alkylamino, N,N dialkylamino, carboxyl and alkoxycarbonyl;
- or a pharmaceutically acceptable salt thereof.
A composition comprising a cyclosporine A derivative in which the 3 Sarcosine position is substituted by a group SCH2C[CH2(CH2)n]NR2R3, wherein R2 is hydrogen or an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms, the chain is a straight or branched;
- R3 is an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms the chain is a straight or branched;
- and n is 1 or 2;
- and a pharmaceutically acceptable carrier.
A compound of formula (III):
- wherein:
- R2 is hydrogen or an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms, the chain is a straight or branched;
- R3 is an alkyl chain having from one to four carbon atoms and, when the alkyl chain has 3 or 4 carbon atoms the chain is a straight or branched;
- n is one or two;
- and R10 is a leaving group,
- or a salt thereof.
Dependencies are inferred from the claim text.