Back to results
US 6,713,647 B2Granted
Compounds having activity as inhibitors of cytochrome P450RAI
AssigneeAllergan, Inc.
InventorsJayasree Vasudevan, Alan T. Johnson, Liming Wang, Roshantha A. Chandraratna
Life of this patent
Estimating the term…
Abstract
Compounds having Formula 4 wherein the symbols have the meaning defined in the specification are inhibitors of the cytochrome P450RAI (retinoic acid inducible) enzyme, and are used for treating diseases responsive to treatment by retinoids.
Claims20
A compound of the formula
- wherein A is a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted with one or two R2 groups;
- X1 is OR or SR where R is H, alkyl of 1 to 6 carbons or benzyl;
- Y is H, alkyl of 1 to 10 carbons, benzyl, lower alkyl or halogen substituted benzyl, fluoro-substituted alkyl of 1 to 10 carbons, cycloalkyl of 3 to 6 carbons, lower alkyl substituted cycloalkyl of 3 to 6 carbons, Cl, Br, or I;
- Z is —C≡C—,
- —(CR1═CR1)n′ where n′ is an integer having the value 1-5,
- —CO—NR1—,
- NR1—CO—,
- —CO—O—,
- —O—CO—,
- —CS—NR1—,
- NR1—CS—,
- —CO—S—,
- —S—CO— or
- —N═N—;
- R1 is independently H or alkyl of 1 to 6 carbons;
- R2 is independently H, alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R3 is independently alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, alkylthio of 1 to 6 carbons or benzyl;
- m is an integer having the values 0 to 2;
- R4 is independently H, alkyl of 1 to 6 carbons, or F;
- fluorosubstituted alkyl of 1 to 6 carbons, or halogen;
- o is an integer having the values of 0 to 4;
- n is an integer having the values of 0 to 4, and
- R8 is H, alkyl of 1 to 6 carbons, or —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base, with the proviso that when Y is H, A is phenyl and X1 is OH then n is 1 to 4.
20 more elements
A compound of the formula
- wherein A is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrazolyl, said heteroaryl groups being optionally substituted with one or two R2 groups;
- X1 is NRR6 where R is H, alkyl of 1 to 6 carbons or benzyl;
- Y is H, alkyl of 1 to 10 carbons, benzyl, lower alkyl or halogen substituted benzyl, fluoro-substituted alkyl of 1 to 10 carbons, cycloalkyl of 3 to 6 carbons, or lower alkyl substituted cycloalkyl of 3 to 6 carbons, Cl, Br, or I;
- Z is —C≡C—,
- —(CR1═CR1)n′ where n′ is an integer having the value 1-5,
- —CO—NR1—,
- NR1—CO—,
- —CO—O—,
- —O—CO—,
- —CS—NR1—,
- NR1—CS—,
- —CO—S—,
- —S—CO— or
- —N═N—;
- R1 is independently H or alkyl of 1 to 6 carbons;
- R2 is independently H, alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R3 is independently alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, alkylthio of 1 to 6 carbons or benzyl;
- m is an integer having the values 0 to 2;
- R4 is independently H, alkyl of 1 to 6 carbons, or F;
- fluorosubstituted alkyl of 1 to 6 carbons, or halogen;
- o is an integer having the values of 0 to 4;
- R6 is H, lower alkyl, cycloalkyl of 3 to 6 carbons, lower alkyl substituted cycloalkyl of 3 to 6 carbons;
- n is an integer having the values of 0 to 4, and
- R8 is H, alkyl of 1 to 6 carbons, or —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base.
21 more elements
A compound of the formula
- wherein A is phenyl or naphthyl, said phenyl or naphthyl groups being optionally substituted with one or two R2 groups;
- X1 is NRR6 where R is H, alkyl of 1 to 6 carbons or benzyl;
- Y is H, alkyl of 1 to 10 carbons, benzyl, lower alkyl or halogen substituted benzyl, fluoro-substituted alkyl of 1 to 10 carbons, cycloalkyl of 3 to 6 carbons, lower alkyl substituted cycloalkyl of 3 to 6 carbons, CI, Br, or I;
- Z is —(CR1═CR1)n′ where n′ is an integer having the value 1-5,
- —CO—NR1—,
- NR1—CO—,
- —CO—O—,
- —O—CO—,
- —CS—NR1—,
- NR1—CS—,
- —CO—S—,
- —S—CO— or
- —N═N—;
- R1 is independently H or alkyl of 1 to 6 carbons;
- R2 is independently H, alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R3 is independently alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, alkylthio of 1 to 6 carbons or benzyl;
- m is an integer having the values 0 to 2;
- R4 is independently H, alkyl of 1 to 6 carbons, or F;
- fluorosubstituted alkyl of 1 to 6 carbons, or halogen;
- o is an integer having the values of 0 to 4;
- R6 is H, lower alkyl, cycloalkyl of 3 to 6 carbons or lower alkyl substituted cycloalkyl of 3 to 6 carbons;
- n is an integer having the values of 0 to 4, and
- R8 is H, alkyl of 1 to 6 carbons, or —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base.
20 more elements
Dependencies are inferred from the claim text.