Compounds having activity as inhibitors of cytochrome P450RAI
AssigneeAllergan Sales, Inc.
InventorsJayasree Vasudevan, Alan T. Johnson, Liming Wang, Dehua Huang, Roshantha A. Chandraratna
Life of this patent
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Abstract
Compounds having Formulas 5 and 6 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.
Claims11
A compound of the formula
- wherein
- A is phenyl or naphthyl said groups being optionally substituted with one or two R2 groups;
- X is O;
- Y is 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—;
- 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 3;
- R7 is alkyl of 1 to 6 carbons, cycloalkyl of 3 to 6 carbons or lower alkyl substituted cycloalkyl of 1 to 6 carbons;
- n is an integer having the values of 1 to 4, and
- R8 is H, alkyl of 1 to 6 carbons, —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base.
A compound of the formula
- wherein
- Y is branched-chain alkyl of 3 to 6 carbons;
- R2 is H or F;
- R3 is branched-chain alkyl of 3 to 6 carbons;
- R7 is lower alkyl of 1 to 6 carbons, and
- R8 is H, alkyl of 1 to 6 carbons, —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base.
A pharmaceutical composition containing an effective amount of a compound for inhibiting the enzyme cytochrome P450RAI in a mammal where such inhibition results in a therapeutic benefit, and a pharmaceutically acceptable excipient, said compound having the formula
- wherein
- A is phenyl or naphthyl, said groups being optionally substituted with one or two R2 groups;
- X is O;
- 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—;
- 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 3;
- R7 is H, alkyl of 1 to 6 carbons, cycloalkyl of 3 to 6 carbons or lower alkyl substituted cycloalkyl of 1 to 6 carbons;
- n is an integer having the values of 1 to 4, and
- R8 is H, alkyl of 1 to 6 carbons, —CH2O(C1-6-alkyl), or a cation of a pharmaceutically acceptable base.
Dependencies are inferred from the claim text.