×

Sulfonated xanthene derivatives

  • US 6,130,101 A
  • Filed: 09/23/1997
  • Issued: 10/10/2000
  • Est. Priority Date: 09/23/1997
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound having the formula ##STR51## or the formula ##STR52## wherein R2, R3, R4 and R5 are independently H, F, Cl, Br, I, CN;

  • or C1 -C18 alkyl, or C1 -C18 alkoxy, where each alkyl or alkoxy is optionally further substituted by F, Cl, Br, I, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C1 -C6 alcohol;

    or --SO3 X where X is H or a counterionR1 and R6 are H;

    or R1 taken in combination with R2, or R5 taken in combination with R6, or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO3 X;

    A is NR8 R9,R8 and R9 are independently H, C1 -C6 alkyl, C1 -C6 carboxyalkyl, C1 -C6 sulfoalkyl, a salt of C1 -C6 carboxyalkyl, or a salt of C1 -C6 sulfoalkyl, wherein the alkyl portions are optionally substituted by amino, hydroxy, carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C1 -C6 alkyl;

    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, or a carboxylic acid ester of a C1 -C6 alkyl;

    or R8 in combination with R2, or R9 in combination with R3, or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C1 -C6 alkyls or --CH2 SO3 X moieties;

    C is OR17 or NR18 R19 ;

    where R17 is H, or C1 -C18 alkyl;

    where R18 and R19 are independently H, C1 -C6 alkyl, C1 -C6 carboxyalkyl, C1 -C6 sulfoalkyl, a salt of C1 -C6 carboxyalkyl, or a salt of C1 -C6 sulfoalkyl, wherein the alkyl portions are optionally substituted by amino, hydroxy, carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C1 -C6 alkyl;

    or R18 in combination with R19 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, or a carboxylic acid ester of a C1 -C6 alkyl;

    or R18 in combination with R4, or R19 in combination with R5, or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C1 -C6 alkyls or --CH2 SO3 X moieties;

    B is O or N+ R18 R19 ;

    R10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C1 -C6 alcohol;

    or R10 is a saturated or unsaturated C1 -C18 alkyl 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 alcohol, --SO3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons;

    or R10 has the formula ##STR53## where R12, R13, R14, R15 and R16 are independently H, F, Cl, Br, I, --SO3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino;

    or C1 -C18 alkyl, C1 -C18 alkoxy, C1 -C18 alkylthio, C1 -C18 alkanoylamino, C1 -C18 alkylaminocarbonyl, C2 -C36 dialkylaminocarbonyl, C1 -C18 alkyloxycarbonyl, or C6 -C18 arylcarboxamido, 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 alcohol, --SO3 X, 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, or a salt of carboxylic acid; 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 either at least one of R2, R3, R4, and R5 is --SO3 X;

    or R8 in combination with R2, or R9 in combination with R3, or R18 in combination with R4, or R19 in combination with R5, form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH2 SO3 X moiety.

View all claims
  • 3 Assignments
Timeline View
Assignment View
    ×
    ×