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US 6,274,620 B1Granted
Thiophene integrin inhibitors
AssigneeBioChem Pharma Inc.
InventorsDenis Labrecque, Giorgio Attardo, Monica Bubenik, Laval Chan, Sylvie Charron, Réal Denis, Guy Falardeau, Serge Lamothe, Patrice Préville, Boulos Zacharie
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Abstract
The present invention comprises compounds that are effective inhibitors of integrins, particularly αvβ3 and αvβ5 integrins. Particularly, the compounds are of formula I and pharmaceutically acceptable salts thereof wherein X,Y1 W, R1 to R5, A and B are defined according to the disclosure herein.
Claims38
A compound of formula I:
- and pharmaceutically acceptable salts thereof, wherein:
- X is selected from the group consisting of O and S;
- Y1 is selected from the group consisting of O, S and N;
- W is selected from the group consisting of carbonyl and sulfonyl;
- R1 and R2 are independently selected from the group consisting of H, C5-10aryl, C5-10arylsulfonylamino, C5-10cycloalkylsulfonylamino, C5-10arylamino and C5-10arylC1-6alkyl with the proviso that R1 and R2 are not both H;
- R3 is selected from the group consisting of H, C1-8alkyl, C1-8alkylamino C0-8alkyl, C1-8alkoxy, C1-8alkylepoxy C1-8alkylC1-8alkyl-Y2C(O)Y3—C0-8alkyl, C5-8aryl, C5-8arylC0-8alkyl-Y2C(O)Y3—C0-8alkyl, C5-8aryl, C1-8alkylC5-8aryl, and C5-8arylC1-8alkyl, wherein Y2 and Y3 are independently O or N;
- R4 and R5 are independently selected from the group consisting of H, halogen, C1-6alkyl and C1-6alkoxy;
- A is selected from the group consisting of C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C5-10aryl, C3-10cycloakyl;
- and
- B is selected from the group consisting of amino, C1-6aminoalkyl, C5-10arylamino, guanidino, C1-6guanidinoalkyl, cyclic guanidino, urea, cyclic urea.
7 more elements
The compound of 1, wherein R1 and R2 are represented by the formula N—Y4—R6 wherein
- Y4 is selected from the group consisting of —CO2—, —SO2— and —(CH2)0-2—;
- R6 is selected from the group consisting of:
- wherein R7, R8, R9, R10, R11 are independently selected from the group consisting of H, C1-6alkyl, C1-6alkoxy and halogen.
Dependencies are inferred from the claim text.