Patent ID: 6013827
Filing Date: 2000-01-11
Classification: C07C

Abstract:
A compound of Formula I ##STR4## wherein R.sub.1 is OH or an ether or ester thereof,X is YR.sub.2, halogen, nitro, NR.sub.4 R.sub.5 or formyl amine;Y is O or S(O).sub.m, where m is 0, 1 or 2;R.sub.2 is methyl or ethyl, where either methyl or ethyl may be optionally substituted by 1 or more halogens;R.sub.3 is hydrogen, halogen, C.sub.1-4 alkyl, CH.sub.2 NHC(O)C(O)NH.sub.2, halo-substituted C.sub.1-4 alkyl, --CH.dbd.CHR.sub.8' R.sub.8', cyclopropl optionally subsituted by R.sub.8', CN, OR.sub.8, CH.sub.2 OR.sub.8, NR.sub.8 R.sub.10, CH.sub.2 NR.sub.8 R.sub.10, C(Z')H, C(O)OR.sub.8, C(O)NR.sub.8 R.sub.10, or --C.tbd.CR.sub.8' ;R.sub.4 and R.sub.5 are independently hydrogen or C.sub.1-2 alkyl;R.sub.7 is --(CR.sub.4 R.sub.5).sub.q R.sub.12 or C.sub.1-6 alkyl wherein the R.sub.12 or C.sub.1-6 alkyl group is optionally substituted one or more times by C.sub.1-2 alkyl optionally substituted by one to three groups selected from --F, --Br, --Cl, --NO.sub.2, --NR.sub.10 R.sub.11, --C(.dbd.O)R.sub.8, --C(.congruent.O)OR.sub.8, --OR.sub.8, --CN, --C(.dbd.O)NR.sub.10 R.sub.11, --OC(.dbd.O)NR.sub.10 R.sub.11, --OC(.dbd.O)R.sub.8, --NR.sub.10 C(.dbd.O)NR.sub.10 R.sub.11, --NR.sub.10 C(.dbd.O)R.sub.11, --NR.sub.10 C(.dbd.O)OR.sub.9, --NR.sub.10 C(.dbd.O)R.sub.13, --C(.dbd.NR.sub.10)NR.sub.10 R.sub.11, --C(.dbd.N--CN)NR.sub.10 R.sub.11, --C(.dbd.N--CN)SR.sub.9, --NR.sub.10 C(.dbd.N--CN)NR.sub.10 R.sub.11, --NR.sub.10 S(.dbd.O).sub.2 R.sub.9, --S(O).sub.m' R.sub.9, --NR.sub.10 C(.dbd.O)C(.dbd.O)NR.sub.10 R.sub.11, --NR.sub.10 C(.dbd.O)C(.dbd.O)R.sub.10, thiazolyl, imidazolyl, oxazolyl, pyrazolyl, triazolyl or tetrazolyl;R.sub.8 is --H or R.sub.9 ;R.sub.8' is R.sub.8 or fluorine;R.sub.9 is C.sub.1-4 alkyl optionally substituted by one to three --F;R.sub.10 is OR.sub.8, hydrogen, or C.sub.1-4 alkyl optionally substituted by one to three fluorines;R.sub.11 is --H or C.sub.1-4 alkyl optionally substituted by one to three --F; or when R.sub.10 and R.sub.11 are as NR.sub.10 R.sub.11 they may together with the nitrogen form a 5 to 7 membered ring optionally containing at least one additional heteroatom selected from O, N or S;R.sub.12 is C.sub.3-7 cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidyl, pyrazolyl, 1-imidazolyl, 2-imidazolyl, thiazolyl, triazolyl, pyrrolyl, piperazinyl, piperidinyl, morpholinyl, furanyl, 2-thienyl, 3-thienyl, 4-thiazolyl, 5-thiazolyl, quinolinyl, naphthyl or phenyl;R.sub.13 is a heterocyclic ring selected from oxazolidinyl, oxazolyl, thiazolyl, pyrazolyl, triazolyl, tetrazolyl, imidazolyl, imidazolidinyl, thiazolidinyl, isoxazolyl, oxadiazolyl or thiadiazolyl, where R.sub.13 is appended to a compound of Formula (I) through a carbon atom of the heterocyclic ring, and where each heterocyclic ring may be unsubstituted or substituted by one or two C.sub.1-2 alkyl groups;R.sub.14 is H or R.sub.7, or when R.sub.10 and R.sub.14 are as NR.sub.10 R.sub.14, they may together with the nitrogen atom form a 5 to 7 membered ring optionally containing at least one additional heteroatom selected from O, N or S;m' is 0, 1 or 2;q is 0, 1 or 2.Y' is O or S;Z is C(.dbd.Y')R.sub.14, C(.dbd.O)OR.sub.14, C(.dbd.Y')NR.sub.10 R.sub.14, C(.dbd.NR.sub.10)NR.sub.10 R.sub.14, CN, C(.dbd.NOR.sub.8)R.sub.14, C(.dbd.O)NR.sub.8 NR.sub.8 C(.dbd.O)R.sub.8, C(.dbd.O)NR.sub.8 NR.sub.10 R.sub.14, C(.dbd.NOR.sub.14)R.sub.8, C(.dbd.NR.sub.8)NR.sub.10 R.sub.14, C(.dbd.NR.sub.14)NR.sub.8 R.sub.8, C(.dbd.N--CN)NR.sub.10 R.sub.14, C(.dbd.N--CN)SR.sub.9, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 4-triazolyl[1,2,3], 5-triazolyl[1,2,3], 3-triazolyl[1,2,4], 5-triazolyl[1,2,4], 5-tetrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-oxadiazolyl[1,2,4], 5-oxadiazolyl[1,2,4], 2-oxadiazolyl[1,3,4], 2-thiadiazolyl[1,3,4], 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl or 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, or 5-imidazolidinyl; wherein all of the heterocyclic ring systems may be optionally substituted one or more times by R.sub.14 ;Z' is O, NR.sub.9, NOR.sub.8, NCN, C(--CN).sub.2, CR.sub.8 CN, CR.sub.8 NO.sub.2, CR.sub.8 C(O)OR.sub.8, CR.sub.8 C(O)NR.sub.8 R.sub.8, C(--CN)NO.sub.2, C(--CN)C(O)OR.sub.9, or C(--CN)C(O)NR.sub.8 R.sub.8 ; ora pharmaceutically acceptable salt thereof.