Patent ID: 6162931
Filing Date: 2000-12-19
Classification: C07C,C07D,C09B,G01N,Y10S

Abstract:
A compound having the formula ##STR10## or the formula ##STR11## wherein R.sup.1 and R.sup.6 are independently H, F, Cl, Br, I, C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.18 alkoxy;R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently H, F, Cl, Br, I, CN; or C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or C.sub.1 -C.sub.18 alkylthio, where each alkyl, alkoxy or alkylthio is optionally further substituted by F, Cl, Br, I, sulfonic acid, salt of sulfonic acid, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 where R.sup.18 is a C.sub.1 -C.sub.4 alkyl; or amino, alkylamino, dialkylamino, or alkoxy, the alkyl portions of which independently have 1-6 carbons; or one or both of R.sup.3 and R.sup.4 are --CH.sub.2 N(CH.sub.2 COOR.sup.17).sub.2, where R.sup.17 is H, a biologically compatible counterion, a linear or branched alkyl having 1-6 carbons, or --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ;A is OR.sup.7 or NR.sup.8 R.sup.9,where each R.sup.7 is independently H, C.sub.1 -C.sub.18 alkyl, a C.sub.1 -C.sub.18 acyl wherein each alkyl group independently has 1-6 carbons and is optionally substituted by amino, hydroxy, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ; or a trialkylsilyl wherein each alkyl group independently has 1-6 carbons;R.sup.8 and R.sup.9 are independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 carboxyalkyl, C.sub.1 -C.sub.6 sulfoalkyl, a salt of C.sub.1 -C.sub.6 carboxyalkyl, a salt of C.sub.1 -C.sub.6 sulfoalkyl, or C.sub.1 -C.sub.18 acyl wherein the alkyl portions are optionally substituted by amino, hydroxy, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ; or R.sup.8 in combination with R.sup.2, or R.sup.9 in combination with R.sup.3, or both, form a saturated 5- or 6-membered ring that is optionally substituted by one or more methyls; or R.sup.8 in combination with R.sup.9 forms a saturated 5- or 6-membered heterocycle that is a piperidine, a morpholine, a pyrrolidine or a piperazine, each of which is optionally substituted by methyl, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, or a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ;R.sup.10 is F, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, or a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ; or R.sup.10 is C.sub.1 -C.sub.18 alkyl, alkenyl or alkynyl that is optionally substituted one or more times by F, Cl, Br, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18, sulfonic acid, salt of sulfonic acid, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or R.sup.10 has the formula ##STR12## where R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 are independently H, F, Cl, Br, I; or sulfonic acid, salt of sulfonic acid, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18, CN, nitro, hydroxy, azido, amino, hydrazino; or C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 alkylamino, C.sub.1 -C.sub.18 alkylester, C.sub.1 -C.sub.18 alkylamido or C.sub.1 -C.sub.18 arylamido, the alkyl or aryl portions of which are optionally substituted one or more times by F, Cl, Br, I, hydroxy, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18, sulfonic acid, salt of sulfonic acid, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R.sup.13 and R.sup.14, R.sup.14 and R.sup.15 or R.sup.15 and R.sup.16, when taken in combination, form a fused 6-membered aromatic ring that is optionally further substituted by carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C.sub.1 -C.sub.6 alkyl, a carboxylic acid ester of --CH.sub.2 --O--(C.dbd.O)--R.sup.18 ; andR.sup.11 is H, hydroxy, CN or a C.sub.1 -C.sub.6 alkoxy; or R.sup.10 in combination with R.sup.11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R.sup.11 in combination with R.sup.12 forms a 5- or 6-membered spirolactone ring or a 5- or 6-membered spirosultone ring that is optionally and independently substituted by H, F or CH.sub.3 ; or R.sup.10 when taken in combination with R.sup.11 is a carbonyl oxygen;provided that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.10 is F, or at least three of R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 are F.