US6130101A — Sulfonated xanthene derivatives

Claim 1

Independent Claim 963 words

A compound having the formula ##STR51## or the formula ##STR52## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is NR 8 R 9 , R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or R 10 has the formula ##STR53## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety.

Claim 2

Dependent Claim 963 words

A compound having the formula ##STR51## or the formula ##STR52## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is NR 8 R 9 , R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or R 10 has the formula ##STR53## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety.

Claim 3

Dependent Claim 18 words

A compound, as claimed in claim 1, wherein R 3 and R 4 are each --SO 3 X.

Claim 4

Dependent Claim 36 words

A compound, as claimed in claim 1, wherein R 10 has the formula ##STR54## wherein R 12 is a carboxylic acid, a salt of carboxylic acid, or --SO 3 X; and R 11 is not present.

Claim 5

Dependent Claim 28 words

A compound, as claimed in claim 3, wherein at least three of R 13 , R 14 , R 15 , and R 16 are F or Cl.

Claim 6

Dependent Claim 51 words

A compound, as claimed in claim 3, wherein one of R 14 and R 15 is a carboxylic acid or salt of a carboxylic acid or is --S-(CH 2 ) n COOH, wherein n is 1-15, and wherein the other of R 14 or R 15 is H, F or Cl.

Claim 7

Dependent Claim 24 words

A compound, as claimed in claim 1, wherein A is NR 8 R 9 , B is O and C is OR 17 .

Claim 8

Dependent Claim 32 words

A compound, as claimed in claim 1, wherein A is NR 8 R 9 , B is N + R 18 R 19 , and C is NR 18 R 19 .

Claim 9

Dependent Claim 18 words

A compound, as claimed in claim 7, wherein R 3 and R 4 are each --SO 3 X.

Claim 10

Dependent Claim 85 words

A compound, as claimed in claim 7, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties.

Claim 11

Dependent Claim 43 words

A compound, as claimed in claim 9, wherein R 9 and R 18 are independently H, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 12

Dependent Claim 46 words

A compound, as claimed in claim 9, wherein R 8 in combination with R 2 , and R 19 in combination with R 5 , each form a 5- or 6-membered ring that is saturated; and R 3 and R 4 are each --SO 3 X.

Claim 13

Dependent Claim 67 words

A compound, as claimed in claim 9, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted by --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by --CH 2 SO 3 X.

Claim 14

Dependent Claim 68 words

A compound, as claimed in claim 8, wherein R 1 , R 2 , R 5 , and R 6 are H; R 8 , R 9 , R 18 , and R 19 are H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 15

Dependent Claim 315 words

A compound, as claimed in claim 1, having the formula ##STR55## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or --SO 3 X; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 12 , R 13 , R 14 , R 15 and R 16 are independently H, Cl, F, amino, nitro, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, or --S-(CH 2 ) n COOH where n=1-15; provided that R 3 and R 4 are each --SO 3 X; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by --CH 2 SO 3 X.

Claim 16

Dependent Claim 1060 words

A compound having the formula ##STR56## or the formula ##STR57## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is NR 8 R 9 , R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-R x ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-R x ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-R x ; or R 10 has the formula ##STR58## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-R x , each L is a covalent linkage; and R x is a reactive group; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; and that at least one of R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 is --L-R x .

Claim 17

Dependent Claim 1060 words

A compound having the formula ##STR56## or the formula ##STR57## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is NR 8 R 9 , R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-R x ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-R x ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-R x ; or R 10 has the formula ##STR58## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-R x , each L is a covalent linkage; and R x is a reactive group; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; and that at least one of R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 is --L-R x .

Claim 18

Dependent Claim 65 words

A compound, as claimed in claim 15, wherein each L is independently a single covalent bond, or L is a covalent linkage having 1-24 nonhydrogen atoms selected from the group consisting of C, N, O, P, and S and is composed of any combination of single, double, triple or aromatic carbon-carbon bonds, carbon-nitrogen bonds, nitrogen-nitrogen bonds, carbon-oxygen bonds, carbon-sulfur bonds, phosphorus-oxygen bonds, and phosphorus-nitrogen bonds.

Claim 19

Dependent Claim 82 words

A compound, as claimed in claim 15, wherein R x is an acrylamide, an activated ester of a carboxylic acid, hydroxy, an aldehyde, an alkyl halide, a sulfonate, an amine, an anhydride, an aniline, an aryl halide, an azide, an aziridine, a boronate, a carboxylic acid, a carbodiimide, a diazoalkane, an epoxide, a glycol, a haloacetamide, a halotriazine, a hydrazine, a hydroxylamine, an imido ester, an isocyanate, an isothiocyanate, a ketone, a maleimide, a phosphoramidite, a sulfonyl halide, or a thiol group.

Claim 20

Dependent Claim 45 words

A compound, as claimed in claim 15, wherein L is a single covalent bond and R x is a carboxylic acid, an activated ester of a carboxylic acid, an amine, an azide, a hydrazine, a haloacetamide, an alkyl halide, an isothiocyanate, or a maleimide group.

Claim 21

Dependent Claim 17 words

A compound, as claimed in claim 15, wherein R 2 and R 5 are F or Cl.

Claim 22

Dependent Claim 26 words

A compound, as claimed in claim 15, wherein one of R 13 , R 14 , R 15 , and R 16 is --L-R x .

Claim 23

Dependent Claim 29 words

A compound, as claimed in claim 15, wherein one of R 8 , R 9 , R 17 , R 18 , and R 19 is --L-R x .

Claim 24

Dependent Claim 32 words

A compound, as claimed in claim 15, wherein A is NR 8 R 9 , B is N + R 18 R 19 , and C is NR 18 R 19 .

Claim 25

Dependent Claim 36 words

A compound, as claimed in claim 15, wherein R 10 has the formula ##STR59## wherein R 12 is a carboxylic acid, a salt of carboxylic acid, or --SO 3 X; and R 11 is not present.

Claim 26

Dependent Claim 28 words

A compound, as claimed in claim 23, wherein at least three of R 13 , R 14 , R 15 , and R 16 are F or Cl.

Claim 27

Dependent Claim 51 words

A compound, as claimed in claim 23, wherein one of R 14 and R 15 is a carboxylic acid or salt of a carboxylic acid or is --S-(CH 2 ) n COOH, wherein n is 1-15, and wherein the other of R 14 or R 15 is H, F or Cl.

Claim 28

Dependent Claim 18 words

A compound, as claimed in claim 15, wherein R 3 and R 4 are each --SO 3 X.

Claim 29

Dependent Claim 85 words

A compound, as claimed in claim 22, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties.

Claim 30

Dependent Claim 43 words

A compound, as claimed in claim 27, wherein R 9 and R 18 are independently H, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 31

Dependent Claim 46 words

A compound, as claimed in claim 27, wherein R 8 in combination with R 2 , and R 19 in combination with R 5 , each form a 5- or 6-membered ring that is saturated; and R 3 and R 4 are each --SO 3 X.

Claim 32

Dependent Claim 67 words

A compound, as claimed in claim 27, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, that is substituted by --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by --CH 2 SO 3 X.

Claim 33

Dependent Claim 68 words

A compound, as claimed in claim 26, wherein R 1 , R 2 , R 5 , and R 6 are H; R 8 , R 9 , R 18 , and R 19 are H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 34

Dependent Claim 239 words

A compound, as claimed in claim 15, having the formula ##STR60## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I; or C 1 -C 18 alkyl R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 12 , R 13 , R 14 , R 15 and R 16 are independently H, Cl, F, amino, nitro, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, --S-(CH 2 ) n COOH where n=1-15, or --L-R x .

Claim 35

Dependent Claim 1073 words

A compound having the formula ##STR61## or the formula ##STR62## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-S c ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 or NR 8 R 9 , R 7 is H, C 1 -C 18 alkyl; or --L-S c ; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 9 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-S c ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-S c ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-S c ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-S c ; or R 10 has the formula ##STR63## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-S c ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-S c , each L is a covalent linkage; and S c is a conjugated substance; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; and that at least one of R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 18 , and R 19 is --L-S c .

Claim 36

Dependent Claim 1073 words

A compound having the formula ##STR61## or the formula ##STR62## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-S c ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 or NR 8 R 9 , R 7 is H, C 1 -C 18 alkyl; or --L-S c ; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 9 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-S c ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-S c ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-S c ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-S c ; or R 10 has the formula ##STR63## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-S c ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-S c , each L is a covalent linkage; and S c is a conjugated substance; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; and that at least one of R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 18 , and R 19 is --L-S c .

Claim 37

Dependent Claim 65 words

A compound, as claimed in claim 33, wherein each L is independently a single covalent bond, or L is a covalent linkage having 1-24 nonhydrogen atoms selected from the group consisting of C, N, O, P, and S and is composed of any combination of single, double, triple or aromatic carbon-carbon bonds, carbon-nitrogen bonds, nitrogen-nitrogen bonds, carbon-oxygen bonds, carbon-sulfur bonds, phosphorus-oxygen bonds, and phosphorus-nitrogen bonds.

Claim 38

Dependent Claim 42 words

A compound, as claimed in claim 33, wherein S c is an amino acid, peptide, protein, polysaccharide, ion-complexing moiety, nucleotide, nucleic acid polymer, hapten, drug, lipid, lipid assembly, non-biological organic polymer, polymeric microparticle, animal cell, plant cell, bacterium, yeast, virus or protist.

Claim 39

Dependent Claim 22 words

A compound, as claimed in claim 35, wherein S c is further substituted by one or more additional fluorescent or non-fluorescent dyes.

Claim 40

Dependent Claim 20 words

A compound, as claimed in claim 33, wherein S c is a peptide, protein, polysaccharide, nucleotide, or nucleic acid polymer.

Claim 41

Dependent Claim 27 words

A compound, as claimed in claim 33, wherein S c is an antibody, an avidin, a streptavidin, a lectin, a growth factor, an actin, or a toxin.

Claim 42

Dependent Claim 16 words

A compound, as claimed in claim 38, wherein S c is an antibody to a fluorophore.

Claim 43

Dependent Claim 24 words

A compound, as claimed in claim 33, wherein one of R 13 , R 14 , R 15 , and R 16 is --L-Sc.

Claim 44

Dependent Claim 30 words

A compound, as claimed in claim 33, wherein one of R 7 , R 8 , R 9 , R 17 , R 18 , and R 19 is --L-Sc.

Claim 45

Dependent Claim 32 words

A compound, as claimed in claim 33, wherein A is NR 8 R 9 , B is N + R 18 R 19 , and C is NR 18 R 19 .

Claim 46

Dependent Claim 36 words

A compound, as claimed in claim 33, wherein R 10 has the formula ##STR64## wherein R 12 is a carboxylic acid, a salt of carboxylic acid, or --SO 3 X; and R 11 is not present.

Claim 47

Dependent Claim 28 words

A compound, as claimed in claim 43, wherein at least three of R 13 , R 14 , R 15 , and R 16 are F or Cl.

Claim 48

Dependent Claim 51 words

A compound, as claimed in claim 43, wherein one of R 14 and R 15 is a carboxylic acid or salt of a carboxylic acid or is --S-(CH 2 ) n COOH, wherein n is 1-15, and wherein the other of R 14 or R 15 is H, F or Cl.

Claim 49

Dependent Claim 18 words

A compound, as claimed in claim 33, wherein R 3 and R 4 are each --SO 3 X.

Claim 50

Dependent Claim 85 words

A compound, as claimed in claim 42, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties.

Claim 51

Dependent Claim 43 words

A compound, as claimed in claim 47, wherein R 9 and R 18 are independently H, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 52

Dependent Claim 46 words

A compound, as claimed in claim 47, wherein R 8 in combination with R 2 , and R 19 in combination with R 5 , each form a 5- or 6-membered ring that is saturated; and R 3 and R 4 are each --SO 3 X.

Claim 53

Dependent Claim 67 words

A compound, as claimed in claim 47, wherein R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, that is substituted by --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is at a carbon atom substituted by --CH 2 SO 3 X.

Claim 54

Dependent Claim 68 words

A compound, as claimed in claim 46, wherein R 1 , R 2 , R 5 , and R 6 are H; R 8 , R 9 , R 18 , and R 19 are H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 sulfoalkyl.

Claim 55

Dependent Claim 316 words

A compound, as claimed in claim 33, having the formula ##STR65## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, C 1 -C 8 alkyl, C 1 -C 18 alkoxy, or --SO 3 X; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 12 , R 13 , R 14 , R 15 and R 16 are independently H, Cl, F, amino, nitro, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, or --S-(CH 2 ) n COOH where n=1-15; provided that R 3 and R 4 are each --SO 3 X; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted by --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by --CH 2 SO 3 X.

Claim 56

Independent Claim 1081 words

A method of staining a biological sample, comprising: combining a dye solution comprising a compound of the formula ##STR66## or the formula ##STR67## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; --L-S c ; or --SO 3 X where X is H or a counterion; R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 or NR 8 R 9 , R 7 is H, C 1 -C 18 alkyl; or --L-R x ; or --L-S c ; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-R x ; or --L-S c ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; or --L-S c ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-R x ; or --L-S c ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-R x ; or --L-S c ; or R 10 has the formula ##STR68## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or --L-S c ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; each L is a covalent linkage; each R x is a reactive group; and each S c is a conjugated substance; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; with a biological sample in a concentration sufficient to yield a detectable optical response under the desired conditions.

Claim 57

Independent Claim 1081 words

A method of staining a biological sample, comprising: combining a dye solution comprising a compound of the formula ##STR66## or the formula ##STR67## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; --L-S c ; or --SO 3 X where X is H or a counterion; R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 or NR 8 R 9 , R 7 is H, C 1 -C 18 alkyl; or --L-R x ; or --L-S c ; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 8 in combination with R 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, or a carboxylic acid ester of a C 1 -C 6 alkyl; or --L-R x ; or --L-S c ; or R 8 in combination with R 2 , or R 9 in combination with R 3 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; C is OR 17 or NR 18 R 19 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; or --L-S c ; where R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, a salt of C 1 -C 6 carboxyalkyl, or a salt of C 1 -C 6 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 C 1 -C 6 alkyl; or R 18 in combination with R 19 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 C 1 -C 6 alkyl; or --L-R x ; or --L-S c ; or R 18 in combination with R 4 , or R 19 in combination with R 5 , or both, form a 5- or 6-membered ring that is saturated or unsaturated, and is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; B is O or N + R 18 R 19 ; R 10 is H, F, CN, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester of a C 1 -C 6 alcohol; or R 10 is a saturated or unsaturated C 1 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, or dialkylamino, the alkyl groups of which have 1-6 carbons; or --L-R x ; or --L-S c ; or R 10 has the formula ##STR68## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or --L-S c ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 16 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; each L is a covalent linkage; each R x is a reactive group; and each S c is a conjugated substance; provided that either at least one of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; or R 8 in combination with R 2 , R 9 in combination with R 3 , or R 18 in combination with R 4 , or R 19 in combination with R 5 , form a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by at least one --CH 2 SO 3 X moiety; with a biological sample in a concentration sufficient to yield a detectable optical response under the desired conditions.

Claim 58

Dependent Claim 29 words

A method, as claimed in claim 53, further comprising combining the sample with an additional detection reagent that has spectral properties that are detectably different from said optical response.

Claim 59

Dependent Claim 28 words

A method, as claimed in claim 53, further comprising the step of determining a characteristic of the sample by comparing the optical response with a standard response parameter.

Claim 60

Dependent Claim 22 words

A method, as claimed in claim 55, wherein the sample comprises cells, and the characteristic determined is the viability of the cells.

Claim 61

Dependent Claim 33 words

A method, as claimed in claim 53, wherein the sample comprises cells, and the step of combining comprises electroporation, shock treatment, high extracellular ATP, pressure microinjection, scrape loading, patch clamp loading, or phagocytosis.

Claim 62

Dependent Claim 22 words

A method, as claimed in claim 53, further comprising tracing the temporal or spatial location of the optical response within the sample.

Claim 63

Dependent Claim 65 words

A method, as claimed in claim 53, wherein each L is independently a single covalent bond, or L is a covalent linkage having 1-24 nonhydrogen atoms selected from the group consisting of C, N, O, P, and S and is composed of any combination of single, double, triple or aromatic carbon-carbon bonds, carbon-nitrogen bonds, nitrogen-nitrogen bonds, carbon-oxygen bonds, carbon-sulfur bonds, phosphorus-oxygen bonds, and phosphorus-nitrogen bonds.

Claim 64

Dependent Claim 106 words

A method, as claimed in claim 53, wherein for said compound at least one of R 13 , R 14 , R 15 and R 16 is --L-R x or --L-S c ; R x is a carboxylic acid, an activated ester of a carboxylic acid, an amine, an azide, a hydrazine, a haloacetamide, an alkyl halide, an isothiocyanate, or a maleimide group; and S c is a peptide, a protein, a polysaccharide, a nucleic acid polymer, an ion-complexing moiety, a lipid, or a non-biological organic polymer or polymeric microparticle, that is optionally bound to one or more additional fluorophores that are the same or different.

Claim 65

Dependent Claim 40 words

A method, as claimed in claim 53, wherein for said compound at least one of R 13 , R 14 , R 15 , and R 16 is --L-S c ; and S c is an antibody to a fluorophore.

Claim 66

Dependent Claim 35 words

A method, as claimed in claim 53, wherein for said compound A is NR 8 R 9 , B is N + R 18 R 19 , and C is NR 18 R 19 .

Claim 67

Dependent Claim 319 words

A method, as claimed in claim 62, wherein said compound has the formula ##STR69## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or --SO 3 X; R 8 and R 9 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 18 and R 19 are independently H, C 1 -C 6 alkyl, C 1 -C 6 carboxyalkyl, a salt of C 1 -C 6 carboxyalkyl, C 1 -C 6 sulfoalkyl, or a salt of C 1 -C 6 sulfoalkyl; or R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and that is optionally substituted by one or more C 1 -C 6 alkyls or --CH 2 SO 3 X moieties; R 12 , R 13 , R 14 , R 15 and R 16 are independently H, Cl, F, amino, nitro, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, or --S-(CH 2 ) n COOH where n=1-15; provided that R 3 and R 4 are each --SO 3 X; or R 8 in combination with R 2 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted by --CH 2 SO 3 X; and R 19 in combination with R 5 forms a 5- or 6-membered ring that is saturated or unsaturated, and is substituted at a carbon atom by --CH 2 SO 3 X.

Claim 68

Dependent Claim 46 words

A method, as claimed in claim 53, wherein for said compound at least one of R 13 , R 14 , R 15 , and R 16 is --L-S c ; and S c is an antibody to an antibody that is present in said sample.

Claim 69

Dependent Claim 546 words

A compound having the formula ##STR70## or the formula ##STR71## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 , R 7 is H, C 1 -C 18 alkyl; or --L-R x ; C is OR 17 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; B is O; R 10 has the formula ##STR72## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 is alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 6 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-R x , each L is a covalent linkage; and R x is a reactive group; provided that at least two of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; and that at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 is --L-R x .

Claim 70

Dependent Claim 546 words

A compound having the formula ##STR70## or the formula ##STR71## wherein R 2 , R 3 , R 4 and R 5 are independently H, F, Cl, Br, I, CN; or C 1 -C 18 alkyl, or C 1 -C 18 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 C 1 -C 6 alcohol; or --L-R x ; or --SO 3 X where X is H or a counterion R 1 and R 6 are H; or R 1 taken in combination with R 2 , or R 5 taken in combination with R 6 , or both, form a fused aromatic six membered ring that is optionally substituted one or more times by --SO 3 X; A is OR 7 , R 7 is H, C 1 -C 18 alkyl; or --L-R x ; C is OR 17 ; where R 17 is H, or C 1 -C 18 alkyl; or --L-R x ; B is O; R 10 has the formula ##STR72## where R 12 , R 13 , R 14 , R 15 and R 16 are independently H, F, Cl, Br, I, --SO 3 X, a carboxylic acid, a salt of carboxylic acid, CN, nitro, hydroxy, azido, amino, hydrazino; or --L-R x ; or C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 18 alkylthio, C 1 -C 18 is alkanoylamino, C 1 -C 18 alkylaminocarbonyl, C 2 -C 36 dialkylaminocarbonyl, C 1 -C 18 alkyloxycarbonyl, or C 6 -C 18 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 C 1 -C 6 alcohol, --SO 3 X, amino, alkylamino, dialkylamino or alkoxy, the alkyl portions of each having 1-6 carbons; or one pair of adjacent substituents R 13 and R 14 , R 14 and R 15 or R 15 and R 6 , 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 R 11 is H, hydroxy, CN or a C 1 -C 6 alkoxy; or R 10 in combination with R 11 forms a 5-membered spirolactone ring or a 5-membered spirosultone ring; or R 11 in combination with R 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 3 ; or R 10 when taken in combination with R 11 is a carbonyl oxygen; for all --L-R x , each L is a covalent linkage; and R x is a reactive group; provided that at least two of R 2 , R 3 , R 4 , and R 5 is --SO 3 X; and that at least one of R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 is --L-R x .

Claim 71

Dependent Claim 26 words

A compound, as claimed in claim 65, wherein one of R 13 , R 14 , R 15 , and R 16 is --L-R x .

Claim 72

Dependent Claim 18 words

A compound, as claimed in claim 65, wherein R 3 and R 4 are each --SO 3 X.

Claim 73

Dependent Claim 29 words

A compound, as claimed in claim 65, wherein R 12 is a carboxylic acid, a salt of carboxylic acid, or --SO 3 X; and R 11 is not present.

Claim 74

Dependent Claim 65 words

A compound, as claimed in claim 65, wherein each L is independently a single covalent bond, or L is a covalent linkage having 1-24 nonhydrogen atoms selected from the group consisting of C, N, O, P, and S and is composed of any combination of single, double, triple or aromatic carbon-carbon bonds, carbon-nitrogen bonds, nitrogen-nitrogen bonds, carbon-oxygen bonds, carbon-sulfur bonds, phosphorus-oxygen bonds, and phosphorus-nitrogen bonds.

Claim 75

Dependent Claim 82 words

A compound, as claimed in claim 65, wherein R x is an acrylamide, an activated ester of a carboxylic acid, hydroxy, an aldehyde, an alkyl halide, a sulfonate, an amine, an anhydride, an aniline, an aryl halide, an azide, an aziridine, a boronate, a carboxylic acid, a carbodiimide, a diazoalkane, an epoxide, a glycol, a haloacetamide, a halotriazine, a hydrazine, a hydroxylamine, an imido ester, an isocyanate, an isothiocyanate, a ketone, a maleimide, a phosphoramidite, a sulfonyl halide, or a thiol group.

Claim 76

Dependent Claim 45 words

A compound, as claimed in claim 65, wherein L is a single covalent bond and R x is a carboxylic acid, an activated ester of a carboxylic acid, an amine, an azide, a hydrazine, a haloacetamide, an alkyl halide, an isothiocyanate, or a maleimide group.

Claim 77

Dependent Claim 23 words

A compound, as claimed in claim 33, wherein the conjugated substance is a nucleic acid base, nucleoside, nucleotide, or a nucleic acid polymer.

Claim 78

Dependent Claim 22 words

A compound, as claimed in claim 72, wherein the conjugated substance is a nucleoside triphosphate, a deoxynucleoside triphosphate, or a dideoxynucleoside triphosphate.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	2003-10-10	2004-04-10	2004-10-10	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2007-10-10	2008-04-10	2008-10-10	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2011-10-10	2012-04-10	2012-10-10	$7700.00	Window Closed / Lapsed

Sulfonated xanthene derivatives

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