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Fluorinated xanthene derivatives

DC
  • US 6,162,931 A
  • Filed: 04/12/1996
  • Issued: 12/19/2000
  • Est. Priority Date: 04/12/1996
  • Status: Expired due to Term
2
Associated Cases
3
Associated Defendants
8
Product Citations
0
Petitions
212
Forward Citations
3
Assignments
First Claim
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1. A compound having the formula ##STR10## or the formula ##STR11## wherein R1 and R6 are independently H, F, Cl, Br, I, C1 -C18 alkyl or C1 -C18 alkoxy;

  • R2, R3, R4 and R5 are independently H, F, Cl, Br, I, CN;

    or C1 -C18 alkyl, C1 -C18 alkoxy or C1 -C18 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 where R18 is a C1 -C4 alkyl;

    or amino, alkylamino, dialkylamino, or alkoxy, the alkyl portions of which independently have 1-6 carbons;

    or one or both of R3 and R4 are --CH2 N(CH2 COOR17)2, where R17 is H, a biologically compatible counterion, a linear or branched alkyl having 1-6 carbons, or --CH2 --O--(C═

    O)--R18 ;

    A is OR7 or NR8 R9,where each R7 is independently H, C1 -C18 alkyl, a C1 -C18 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 ;

    or a trialkylsilyl wherein each alkyl group independently has 1-6 carbons;

    R8 and R9 are independently H, C1 -C6 alkyl, C1 -C6 carboxyalkyl, C1 -C6 sulfoalkyl, a salt of C1 -C6 carboxyalkyl, a salt of C1 -C6 sulfoalkyl, or C1 -C18 acyl wherein the alkyl portions are optionally substituted by amino, hydroxy, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 ;

    or R8 in combination with R2, or R9 in combination with R3, or both, form a saturated 5- or 6-membered ring that is optionally substituted by one or more methyls;

    or R8 in combination with R9 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 C1 -C6 alkyl, or a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 ;

    R10 is F, carboxylic acid, a salt of carboxylic acid, a carboxylic acid ester of a C1 -C6 alkyl, or a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 ;

    or R10 is C1 -C18 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18, sulfonic acid, salt of sulfonic acid, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons;

    or R10 has the formula ##STR12## where R12, R13, R14, R15 and R16 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18, CN, nitro, hydroxy, azido, amino, hydrazino;

    or C1 -C18 alkyl, C1 -C18 alkoxy, C1 -C18 alkylthio, C1 -C18 alkylamino, C1 -C18 alkylester, C1 -C18 alkylamido or C1 -C18 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18, 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 R13 and R14, R14 and R15 or R15 and R16, 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 C1 -C6 alkyl, a carboxylic acid ester of --CH2 --O--(C═

    O)--R18 ; and

    R11 is H, hydroxy, CN or a C1 -C6 alkoxy;

    or R10 in combination with R11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring;

    or R11 in combination with R12 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 CH3 ;

    or R10 when taken in combination with R11 is a carbonyl oxygen;

    provided that at least one of R1, R2, R3, R4, R5, R6, and R10 is F, or at least three of R12, R13, R14, R15 and R16 are F.

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