Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase
AssigneeMerck Frosst Canada, Inc.
InventorsW. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
Life of this patent
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Abstract
Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries. ##STR1##
Claims18
A compound of formula I ##STR12## or a pharmaceutically acceptable salt thereof wherein:
- R.sup.1 is selected from the group consisting of
- (a) C.sub.1-7 alkyl, and
- (b) mono-, di-, tri-, tetra- and per-substituted C.sub.1-7 alkyl, wherein the substitutent is fluoro;
- X is O, S, or --CH.sub.2 --;
- Ar is a mono or disubstituted aromatic ring, said ring selected from
- (a) a ring of 5 atoms containing one O, S or N atom and optionally, 1, 2 or 3 additional N atoms;
- and
- (b) a ring of 6 atoms containing 3 or 4 nitrogen atoms;
- wherein the substituents are independently selected from
- (a) hydrogen,
- (b) C.sub.1-7 alkyl,
- (c) F, Cl, Br, and I,
- (d) OCH.sub.3,
- (e) SCH.sub.3,
- (f) CF.sub.3,
- (g) COCH.sub.3 and
- (h) S(O).sub.2 CH.sub.3.
A compound of formula I ##STR13## or a pharmaceutically acceptable salt thereof wherein:
- R.sup.1 is selected from the group consisting of
- (a) C.sub.1-7 alkyl, and
- (b) mono-, di-, tri-, tetra- and per-substituted C.sub.1-7 alkyl, wherein the substitutent is fluoro;
- X is O, S, or --CH.sub.2 --;
- wherein:
- Ar is a mono or di-substituted aromatic group wherein the aromatic group is selected from the group consisting of
- (1) furanyl,
- (2) triazinyl and tetrazinyl,
- (3) imidazolyl,
- (4) isooxazolyl,
- (5) isothiazolyl,
- (6) oxadiazolyl,
- (7) oxazolyl,
- (8) pyrazolyl,
- (9) pyrrolyl,
- (10) thiadiazolyl,
- (11) thiazolyl,
- (12) thienyl,
- (13) triazolyl, and
- (14) tetrazolyl,
- wherein the substituents are independently selected from
- (a) hydrogen,
- (b) C.sub.1-7 alkyl,
- (c) F, Cl, Br, and I,
- (d) OCH.sub.3,
- (e) SCH.sub.3,
- (f) CF.sub.3,
- (g) COCH.sub.3, and
- (h) S(O).sub.2 CH.sub.3.
A compound of formula ##STR14## Z is pharmaceutically acceptable monovalent counterion, Ar is a mono or di substituted aromatic group wherein the aromatic group is selected from the group consisting of
- (1) 3-isothiazolyl,
- (2) 4-isothiazolyl,
- (3) 5-isothiazolyl,
- (4) 2-oxazolyl,
- (5) 4-oxazolyl,
- (6) 5-oxazolyl,
- (7) 2-thiazolyl,
- (8) 4-thiazolyl, and
- (9) 5-thiazolyl,
- wherein the substituents are independently selected from
- (a) hydrogen,
- (b) methyl or ethyl,
- (c) F or Cl, and
- (d) OCH.sub.3.
Dependencies are inferred from the claim text.