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US 5,847,153 AGranted
.beta.-sulfonyl hydroxamic acids
AssigneePharmacia & Upjohn Company
InventorsMartha A. Warpehoski, Donald E. Harper
Life of this patent
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Abstract
The present invention provides a compound of formula I ##STR1## or pharmaceutical acceptable salts thereof wherein R.sub.1 is C.sub.4-12 alkyl, C.sub.4-12 alkenyl, C.sub.4-12 alkynyl, --(CH.sub.2).sub.h -C.sub.3-8 cycloalkyl, --(CH.sub.2).sub.h -aryl, or --(CH.sub.2).sub.h -het; R.sub.2 is C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl, --(CH.sub.2).sub.h -C.sub.3-8 cycloalkyl, --(CH.sub.2).sub.h -C.sub.3-8 cycloalkenyl, --(CH.sub.2).sub.h -aryl, --(CH.sub.2).sub.h -het, --(CH.sub.2).sub.h -Q, --(CH.sub.2).sub.i -X-R.sub.4, or --(CH.sub.2).sub.i CHR.sub.5 R.sub.6. The compounds are inhibitors of matrix metalloproteinases involved in tissue degradation.
Claims18
A compound of formula I
- or pharmaceutical acceptable salts thereof wherein:
- R.sub.1 is
- a) C.sub.4-12 alkyl,
- b) C.sub.4-12 alkenyl,
- c) C.sub.4-12 alkynyl,
- d) --(CH.sub.2).sub.h -C.sub.3-8 cycloalkyl,
- e) --(CH.sub.2).sub.h -aryl,
- f) --(CH.sub.2).sub.h -aryl substituted with C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, --NO.sub.2, --CF.sub.3, --CN, or --N(C.sub.1-4 alkyl).sub.2,
- g) --(CH.sub.2).sub.h -het, or
- h) --(CH.sub.2).sub.h -het substituted with C.sub.1-4 alkyl, or halo;
- R.sub.2 is
- a) C.sub.1-12 alkyl,
- b) C.sub.1-12 alkyl substituted with one to three halo, --CN, --NO.sub.2, --CF.sub.3, --N(R.sub.3).sub.2, --SR.sub.3, or OH,
- c) C.sub.2-12 alkenyl,
- d) C.sub.2-12 alkenyl substituted with one to three halo, --CN, --NO.sub.2, or --CF.sub.3,
- e) C.sub.2-12 alkynyl,
- f) C.sub.2-12 alkynyl substituted with one to three halo, --CN, --NO.sub.2, or --CF.sub.3,
- g) --(CH.sub.2).sub.h -C.sub.3-8 cycloalkyl,
- h) --(CH.sub.2).sub.h -C.sub.3-8 cycloalkyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or halo,
- i) --(CH.sub.2).sub.h -C.sub.3-8 cycloalkenyl,
- j) --(CH.sub.2).sub.h -C.sub.3-8 cycloalkenyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or halo,
- k) --(CH.sub.2).sub.h -aryl,
- l) --(CH.sub.2).sub.h -aryl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --CF.sub.3 --OH, --NO.sub.2, --CN, --N(R.sub.3).sub.2, --SR.sub.3, --SO.sub.2 (C.sub.1-4 alkoxy), --C(.dbd.O)R.sub.3, or --NC(.dbd.O)R.sub.3,
- m) --(CH.sub.2).sub.h -aryl substituted with one to five halo,
- n) --(CH.sub.2).sub.h -het,
- o) --(CH.sub.2).sub.h -het substituted with one to two C.sub.1-4 alkyl, or halo,
- p) --(CH.sub.2).sub.h -Q,
- q) --(CH.sub.2).sub.h -Q substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, or phenyl,
- r) --(CH.sub.2).sub.i -X-R.sub.4, optionally the --(CH.sub.2).sub.i - chain can be substituted with C.sub.1-4 alkyl or phenyl, which in turn can be substituted with one to three halo or C.sub.1-4 alkyl, or
- s) --(CH.sub.2).sub.i CHR.sub.5 R.sub.6 ;
- R.sub.3 is
- a) H,
- b) C.sub.1-4 alkyl,
- c) --(CH.sub.2).sub.h -phenyl, or
- d) --(CH.sub.2).sub.h -phenyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or halo;
- X is
- a) --O--,
- b) --S(.dbd.O).sub.j -,
- c) --NR.sub.7 -,
- d) --S(.dbd.O).sub.2 NR.sub.8 -, or
- e) --C(.dbd.O)--;
- R.sub.4 is
- a) H,
- b) C.sub.1-4 alkyl,
- c) --(CH.sub.2).sub.h -phenyl,
- d) --(CH.sub.2).sub.h -phenyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, --NO.sub.2, or --CN, or
- e) --(CH.sub.2).sub.h -het;
- R.sub.5 is
- a) C.sub.1-4 alkyl, or
- b) --C(.dbd.O)R.sub.3 ;
- R.sub.6 is
- a) --C(.dbd.O)R.sub.3, or
- b) --(CH.sub.2).sub.h C(.dbd.O)R.sub.3 ;
- R.sub.7 is
- a) H,
- b) C.sub.1-4 alkyl,
- c) --(CH.sub.2).sub.h -phenyl,
- d) --(CH.sub.2).sub.h -phenyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or halo,
- e) --C(.dbd.O)--R.sub.3,
- f) --S(.dbd.O).sub.2 R.sub.3, or
- g) --C(.dbd.O)OR.sub.3 ;
- R.sub.8 is
- a) C.sub.1-4 alkyl,
- b) --(CH.sub.2).sub.h -phenyl, or
- c) --(CH.sub.2).sub.h -phenyl substituted with one to three C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or halo;
- aryl is monocarbocyclic, or bicarbocyclic aromatic moiety;
- het is 5- to 10-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur;
- Q is 5- to 10-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur;
- h is 0, 1, 2, 3, 4, 5, or 6;
- i is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
- and
- j is 0, 1, or 2.
69 more elements
Dependencies are inferred from the claim text.