Patent ID: 6222048
Filing Date: 2001-04-24
Classification: C07D

Abstract:
A compound of formula I ##STR98##or a pharmaceutically acceptable salt thereof wherein:Y is oxygen,R.sup.1 is selected from the group consisting of(a) S(O).sub.2 CH.sub.3,(b) S(O).sub.2 NH.sub.2,(c) S(O).sub.2 NHC(O)CF.sub.3,(d) S(O)(NH)NH.sub.2,(e) S(O)(NH)NHC(O)CF.sub.3,(f) P(O)(CH.sub.3)NH.sub.2,(g) P(O)(CH.sub.3).sub.2,R.sup.2 is selected from the group consisting of(a) C.sub.1-6 alkyl,(b) C.sub.3-7 cycloalkyl,(c) mono-, di- or tri-substituted phenyl or naphthyl wherein the substituent is selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkoxy,(4) C.sub.1-6 alkylthio,(5) CN,(6) CF.sub.3,(7) C.sub.1-6 alkyl,(8) N.sub.3,(9) --CO.sub.2 H,(10) --CO.sub.2 --C.sub.1-4 alkyl,(11) --C(R.sup.5)(R.sup.6)--OH,(12) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl, and(13) --C.sub.1-6 alkyl--CO.sub.2 --R.sup.5 ;(14) benzyloxy,(15) --O--(C.sub.1-6 alkyl)--CO.sub.2 R.sup.5,(16) --O--(C.sub.1-6 alkyl)--NR.sup.5 R.sup.6 ;(d) 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 0-3 additional N atoms; orthe heteroaryl is a monocyclic ring of 6 atoms, said ring having one hetero atom which is N, and 0-4 additional N atoms, said substituents are selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.5)(R.sup.6)--OH, and(10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl;(e) a mono- or di-substituted benzoheterocycle in which the heterocycle is a 5, 6, or 7-membered ring which contains 0-2 heteroatoms chosen independently from O, S, or N and which contains or does not contain a carbonyl group or a sulfonyl group; the said substituents are selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.5)(R.sup.6)--OH, and(10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl;(f) a heterocycloalkyl group of 5-7 members which contains 1 or 2 heteroatoms chosen from O, S, or N and contains or does not contain a carbonyl group or a sulfonyl group;(g) a mono- or di-substituted benzocarbocycle in which the carbocycle is a 5, 6, or 7-membered ring which contains or does not contain a carbonyl group, the said substituents are selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.5)(R.sup.6)--OH, and(10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl;R.sup.3 is a mono- or di-substituted phenyl, a mono- or di-substituted benzyl, a mono- or di-substituted heteroaryl, a mono- or di-substituted heteroarylmethyl wherein the substituents are selected from(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.5)(R.sup.6)--OH, and(10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl;CH.sub.2 OR.sup.7, CN, CH.sub.2 CN, C.sub.1-6 fluoroalkyl, F or CONR.sup.7.sub.2 ;R.sup.4 is(a) a mono- or di-substituted phenyl, a mono- or di-substituted benzyl, a mono- or di-substituted heteroaryl or a mono- or di-substituted heteroarylmethyl as defined above, said substituents are selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.5)(R.sup.6)--OH, and(10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl, or(b) C.sub.1-7 alkyl, CH.sub.2 OR.sup.7, CN, CH.sub.2 CN, C.sub.1-6 fluoroalkyl, F or CONR.sup.7.sub.2 or R.sup.3 and R.sup.4 together with the carbon to which they are attached form a saturated monocyclic ring of 3, 4, 5, 6 or 7 atoms, containing 0-2 heteroatoms chosen independently from O, S and N, and hexa-substituted by R.sup.12 and containing or not containing a carbonyl or sulfonyl group;each R.sup.12 is independently selected from the group consisting of(a) hydrogen,(b) C.sub.1-6 alkyl,(c) phenyl or monosubstituted phenyl wherein the substituent is selected from the group consisting of: halo, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, CN, and CF.sub.3,(d) benzyl or monosubstituted benzyl wherein the substituent is selected from the group consisting of: halo, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, CN, and CF.sub.3,(e) --CO.sub.2 -alkyl,(f) halo,R.sup.5, R.sup.6 and R.sup.7 are each independently selected from the group consisting of(a) hydrogen, and(b) C.sub.1-6 alkyl,or R.sup.5 and R.sup.6 together with the carbon to which they are attached form a saturated monocyclic carbon ring of 3, 4, 5, 6 or 7 atoms;R.sup.8 and R.sup.9 are independently selected from the group consisting of:(a) hydrogen,(b) C.sub.1-7 alkyl, orR.sup.8 and R.sup.9 together form a double bonded O or S;R.sup.10 and R.sup.11 are independently(a) hydrogen,(b) a mono- or di-substituted phenyl, a mono- or di-substituted benzyl, a mono- or di-substituted heteroaryl, or a mono- or di-substituted heteroarylmethyl, said substituents are selected from the group consisting of(1) hydrogen,(2) halo,(3) C.sub.1-6 alkyl,(4) C.sub.1-6 alkoxy,(5) C.sub.1-6 alkylthio,(6) CN,(7) CF.sub.3,(8) N.sub.3,(9) --C(R.sup.13)(R.sup.14)--OH, and(10) --C(R.sup.13)(R.sup.14)--O--C.sub.1-4 alkyl, or(c) C.sub.1-7 alkyl, CH.sub.2 OR.sup.7, CN, CH.sub.2 CN, C.sub.1-6 fluoroalkyl, F or CONR.sup.7.sub.2, or(d) R.sup.10 and R.sup.11 together form a double bonded O; orR.sup.10 and R.sup.11 together with the carbon to which they are attached form a saturated monocyclic carbon ring of 3, 4, 5, 6 or 7 atoms;R.sup.13 and R.sup.14 are independently selected from the group consisting of:(a) hydrogen,(b) C.sub.1-7 alkyl, orR.sup.13 and R.sup.14 together form a double bonded O or S.