Phenyl heterocycles as COX-2 inhibitors

Claim 1

A compound of formula I ##STR219## or a pharmaceutically acceptable salt thereof wherein: X--Y--Z-- is selected from the group consisting of: (a) --CH 2 CH 2 CH 2 --, (b) --C(O)CH 2 CH 2 --, and (c) --CH 2 CH 2 C(O)--, wherein side b is a double bond, and sides a an c are single bonds; R 1 is selected from the group consisting of (a) S(O) 2 CH 3 , (b) S(O) 2 NH 2 , (c) S(O) 2 NHC(O)CF 3 , (d) S(O)(NH)CH 3 , (e) S(O)(NH)NH 2 , (f) S(O)(NH)NHC(O)CF 3 , (g) P(O)(CH 3 )OH, and (h) P(O)(CH 3 )NH 2 , R 2 is selected from the group consisting of (a) C 3 , C 4 , C 5 , C 6 , and C 7 , cycloalkyl, (b) mono-, di- or tri-substituted phenyl wherein the substituent is selected from the group consisting of (1) hydrogen, (2) halo, (3) C 1-6 alkoxy, (4) C 1-6 alkylthio, (5) CN, (6) CF 3 , (7) C 1-6 alkyl, (8) N 3 , (9) --CO 2 H, (10) --CO 2 --C 1-4 alkyl, (11) --C(R 5 )(R 6 )--OH, (12) --C(R 5 )(R 6 )--O--C 1-4 alkyl, and (13) --C 1-6 alkyl-CO 2 --R 5 ; (c) mono-, di- or tri-substituted heteroaryl wherein the heteroaryl is a monocyclic aromatic ring of 5 atoms, said ring having one hetero atom which is S, O, or N, and optionally 1, 2, or 3 additional N atoms; or the heteroaryl is a monocyclic ring of 6 atoms, said ring having one hetero atom which is N, and optionally 1, 2 or 3 additional N atoms; said substituents are selected from the group consisting of (1) hydrogen, (2) halo, including fluoro, chloro, bromo and iodo, (3) C 1-6 alkyl, (4) C 1-6 alkoxy, (5) C 1-6 alkylthio, (6) CN, (7) CF 3 , (8) N 3 , (9) --C(R 5 )(R 6 )--OH, and (10) --C(R 5 )(R 6 )--O--C 1-4 alkyl; R 5 and R 6 are each independently selected from the group consisting of (a) hydrogen, and (b) C 1-6 alkyl, or R 5 and R 6 or R 7 and R 8 together with the carbon to which they are attached form a monocyclic saturated carbon ring of 3, 4, 5, 6 or 7 atoms.