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US 6,306,892 B1Granted
Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use
AssigneesAgouron Pharmaceuticals, Inc., Syntex Corporation
InventorsSteven L. Bender, Arlindo L. Castelhano, Wesley K. M. Chong, Melwyn A. Abreo, Roland J. Billedeau, Jian Jeffrey Chen, Judith G. Deal
Life of this patent
Estimating the term…
Abstract
The present invention is directed to compound of the formula I: wherein R1, R2, R3, R4, R 5, X, Y, and are as defined herein. These compounds are useful for inhibiting the activity of a metalloproteinase by contacting the metalloproteinase with an effective amount of the inventive compounds.
Claims20
A compound of the formula I:
- wherein
- X is a single bond or a straight or branched, saturated or unsaturated chain containing 1 to 6 carbon atoms, wherein one or more of the carbon atoms are optionally independently replaced with O or S, and wherein one or more of the hydrogen atoms are optionally replaced with F;
- Y is a single bond, —CH(OH)—, or —C(O)—;
- R1 is an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group;
- R2 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, or C(O)R10,
- wherein R10 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, an O-aryl group, an O-alkyl group, or NR11R12;
- wherein R11 is H, an alkyl group, an O-alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, and
- wherein R12 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group,
- or wherein R11 and R12 form, together with the nitrogen to which they are attached, a heteroaryl group or a heterocycloalkyl group, and
- R3 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, NR11R12, or OR11 wherein R11 and R12 are as defined above,
- or R2 and R3, together with the atom(s) to which they are attached, form a cycloalkyl group or a heterocycloalkyl group;
- R4 is H or any suitable organic moiety;
- R5 is C(O)NHOH, C(O)OR13, SH, N(OH)CHO, SC(O)R14, P(O)(OH)R15 or P(O)(OH)OR13,
- R13 is H, an alkyl group, or an aryl group,
- R14 is an alkyl group or an aryl group, and
- R15 is an alkyl group;
- and
- is a heteroaryl group having five ring atoms, including 1, 2 or 3 S heteroatoms;
- or a pharmaceutically acceptable salt or solvate thereof, or a pharmaceutically acceptable prodrug thereof, said prodrug being different from a compound of the formula (I).
16 more elements
A compound of the formula 1:
- wherein
- X is a single bond;
- Y is a single bond, —CH(OH)— or —C(O)—;
- R1 is an aryl group or a heteroaryl group;
- R2 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, or C(O)R10,
- wherein R10 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, an O-aryl group, an O-alkyl group, or NR11 R12;
- wherein R11 is H, an alkyl group, an O-alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group, and wherein R12 is H, an alkyl group, an aryl group, a heteroaryl group, a cycloalkyl group, or a heterocycloalkyl group,
- or wherein R11 and R12 form, together with the nitrogen to which they are attached, a heteroaryl group or a heterocycloalkyl group, and
- R3 is H, an alkyl group, a heteroaryl group, NR11R12, or OR11
- wherein R11 and R12 are as defined above,
- or R2 and R3, together with the atoms to which they are attached, form a cycloalkyl group or heterocycloalkyl group;
- R4 is H, an alkyl group, or OH;
- R5 is C(O)NHOH, C(O)OR13, SH, or SC(O)R14,
- wherein R13 is H, an alkyl group, or an aryl group, and R14 s an alkyl group or an aryl group;
- and
- is thienyl;
- or a pharmaceutically acceptable salt or solvate thereof, or a pharmaceutically acceptable prodrug thereof, said prodrug being different from a compound of the formula (I).
14 more elements
Dependencies are inferred from the claim text.