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US 6,555,535 B2Granted
Tricyclic biphenyl sulfonamide matrix metalloproteinase inhibitors
AssigneeWarner-Lambert Company
InventorsPatrick Michael O'Brien, Drago Robert Sliskovic
Life of this patent
Estimating the term…
Abstract
Matrix metalloproteinase inhibitors are tricyclic sulfonamides of the Formula I or a pharmaceutically acceptable salt thereof, wherein R1 and R2 include hydrogen, alkyl, and substituted alkyl; R3 is OH or NHOH; X is O or S(O)n; n is 0, 1, or 2; p is 0, 1, 2, or 3; — is absent or a bond; and the sulfur atom bearing (O)q is bonded to the benzo ring at position a or position b.
Claims13
A compound of Formula I
- or a pharmaceutically acceptable salt thereof,
- wherein:
- the sulfur atom bearing (O)q is bonded to the benzo ring at position a or position b;
- R1 and R2 independently are hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, or (CH2)t aryl;
- R3 is NHOH or OR4;
- R4 is H, C1-C6 alkyl, or (CH2)t aryl;
- X is O or S(O)n;
- each n and q independently are 0, 1, or 2;
- m is 0, 1,or 2;
- p is 0,1,2, or 3;
- each t is an integer from 0 to 6;
- and
- — is absent or is a bond.
10 more elements
A compound of Formula II
- or a pharmaceutically acceptable salt thereof,
- wherein R1 and R2 independently are H or C1-C6 alkyl;
- R3 is NHOH or OH;
- the sulfonyl diradical is bonded to the benzo ring at position a or position b;
- n is 0,1, or 2;
- p is 1 or 2;and
- — is absent or is a bond.
4 more elements
A compound of Formula III
- or a pharmaceutically acceptable salt thereof,
- wherein R1 and R2 independently are H or C1-C6 alkyl;
- R3 is NHOH or OH;
- the sulfonyl diradical is bonded to the benzo ring at position b;
- n is 0, 1, or 2;
- p is 1 or 2;
- and
- — is absent or is a bond.
5 more elements
A compound selected from:
- (S)-2,2-Dimethyl-4-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonyl)-thiomorpholine-3-carboxylic acid 1,1-dimethyl ester;
- (S)-2,2-Dimethyl-4-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonyl)-thiomorpholine-3-carboxylic acid;
- (S)-2,2-Dimethyl-4-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonyl)-thiomorpholine-3-carboxylic hydroxamide;
- 4-(2,3-Dihydro-1H-8-oxa-cyclopenta[a]indene-6-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxyamide;
- 2,2-Dimethyl-4-(6,7,8,9-tetrahydro-5H-10-oxa-benzo[a]azulene-2-sulfonyl)thiomorpholine-3-carboxylic acid hydroxyamide;
- 4-(5,6,7,8,9,10-Hexahydro-11-oxa-cycloocta[a]indene-2-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxyamide;
- (S)-2,2-Dimethyl-1,1-dioxo-4-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonyl)-1l6-thiomorpholine-3-carboxylic acid hydroxyamide;
- 4-(2,3-Dihydro-1H-8-oxa-cyclopenta[a]indene-6-sulfonyl)-2,2-dimethyl-1,1-dioxo-1l6-thiomorpholine-3-carboxylic acid hydroxyamide;
- 2,2-Dimethyl-1,1-dioxo-4-(6,7,8,9-tetrahydro-5H-10-oxa-benzo[a]azulene-2-sulfonyl)-1l6-thiomorpholine-3-carboxylic acid hydroxyamide;
- and
- 4-(5,6,7,8,9,10-Hexahydro-11-oxa-cycloocta[a]indene-2-sulfonyl)-2,2-dimethyl-1,1-dioxo-116-thiomorpholine-3-carboxylic acid hydroxyamide.
8 more elements
Dependencies are inferred from the claim text.