Unsymmetrical fluorescein derivatives

Claim 2

A compound of the formula ##STR6## wherein: one of the γs will be of the formula --(O).sub.ε ρ and the other is δ; wherein ε is 0 or 1 and ρ is an aliphatic group of from about 1 to 12 carbon atoms and 0-1 carboxyl groups; the δ's are the same or different and are hydrogen or halogen of atomic number 17 to 80; L is a bond or divalent organic radical of up to 20 carbon atoms; α may be taken together with Ψ to define an active group capable of forming a stable covalent bond with carbon, nitrogen or oxygen or is an organic compound, and is at other than the ortho position when L is benzene and Ψ and α are taken together to define carboxy; Ψ, when not taken together with α is a linking group to α; v is 1 when Ψ is taken together with α and is otherwise on the average at least 1 and not more than the molecular weight of α divided by 500. with the proviso that when ε is 0, one of the δ's may be an aliphatic group of from about 1 to 12 carbon atoms asymmetrically substituted in relation to ρ.

Claim 3

A compound according to claim 1 conjugated to a support.

Claim 4

A compound of the formula ##STR7## wherein: one of the Gs is of the formula --(O) e R and is otherwise D, where e is 0 or 1 and R is an aliphatic group of from 1 to 6 carbon atoms having from 0 to 1 carboxy groups; Z is carboxy or sulphonoxy; D is hydrogen or halogen of atom number 17 to 80; W is a bond or divalent organic radical having up to 10 carbon atoms; Y may be taken together with A to form an active functionality capable of forming a covalent bond with carbon, nitrogen or oxygen when not taken together with A, Y is a linking functionality; A when not taken together with Y is a ligand or receptor of at least about 125 daltons; X is halo of atomic number 9 to 80; m is 1 to 3;

Claim 5

A compound of the formula ##STR7## wherein: one of the Gs is of the formula --(O) e R and is otherwise D, where e is 0 or 1 and R is an aliphatic group of from 1 to 6 carbon atoms having from 0 to 1 carboxy groups; Z is carboxy or sulphonoxy; D is hydrogen or halogen of atom number 17 to 80; W is a bond or divalent organic radical having up to 10 carbon atoms; Y may be taken together with A to form an active functionality capable of forming a covalent bond with carbon, nitrogen or oxygen when not taken together with A, Y is a linking functionality; A when not taken together with Y is a ligand or receptor of at least about 125 daltons; X is halo of atomic number 9 to 80; m is 1 to 3;

Claim 6

p is 0 to 3, with the sum of m and p being not greater than 4; n will be 1 when Y and A are taken together or otherwise be on the average 1 to the molecular weight of A divided by 500, with the proviso that when W is a bond and Y and A are taken together to define carboxy, Y is at other than the ortho position.

Claim 7

p is 0 to 3, with the sum of m and p being not greater than 4; n will be 1 when Y and A are taken together or otherwise be on the average 1 to the molecular weight of A divided by 500, with the proviso that when W is a bond and Y and A are taken together to define carboxy, Y is at other than the ortho position.

Claim 8

A compound according to claim 3, wherein e is 0.

Claim 9

A compound according to claim 3, wherein e is 1.

Claim 10

A compound of the formula ##STR8## wherein: one of G' or G" is --(O) e' R' and is otherwise D', wherein e' is 0 or 1 and R' is alkyl of from 1 to 3 carbon atoms; D' is hydrogen or halogen of atomic number 17 to 80; Y' may be taken together with A' to define a non-oxo-carbonyl group and is otherwise a non-oxo-carbonyl group forming an amide group with an amino group of A'; A' when not taken together with Y', is a ligand or receptor of at least about 125 daltons; W' is a bond or aliphatic linking group of from 1 to 12 atoms other than hydrogen, which are carbon, nitrogen, oxygen or sulfur, there being from 0 to 8 carbon atoms and 0 to 8 heteroatoms, wherein nitrogen is present as amino or amido; and oxygen and sulfur are present as oxy, oxo or the sulfur analogs thereof; Z' is carboxy; X' is halo of atomic number 9 to 80; n' is 1 when Y' and A' are taken together and is otherwise on the average at least 1 to the molecular weight of A' divided by about 1,000; m' is 0 to 2; p' is 0 to 3, the sum of m' and p' being not greater than 4, with the proviso that, when W' is a bond and Y' and A' are taken together to define carboxy, Y' is at other than the ortho position.

Claim 11

A compound of the formula ##STR8## wherein: one of G' or G" is --(O) e' R' and is otherwise D', wherein e' is 0 or 1 and R' is alkyl of from 1 to 3 carbon atoms; D' is hydrogen or halogen of atomic number 17 to 80; Y' may be taken together with A' to define a non-oxo-carbonyl group and is otherwise a non-oxo-carbonyl group forming an amide group with an amino group of A'; A' when not taken together with Y', is a ligand or receptor of at least about 125 daltons; W' is a bond or aliphatic linking group of from 1 to 12 atoms other than hydrogen, which are carbon, nitrogen, oxygen or sulfur, there being from 0 to 8 carbon atoms and 0 to 8 heteroatoms, wherein nitrogen is present as amino or amido; and oxygen and sulfur are present as oxy, oxo or the sulfur analogs thereof; Z' is carboxy; X' is halo of atomic number 9 to 80; n' is 1 when Y' and A' are taken together and is otherwise on the average at least 1 to the molecular weight of A' divided by about 1,000; m' is 0 to 2; p' is 0 to 3, the sum of m' and p' being not greater than 4, with the proviso that, when W' is a bond and Y' and A' are taken together to define carboxy, Y' is at other than the ortho position.

Claim 12

A compound according to claim 6, wherein A' is taken together with Y'.

Claim 13

A compound according to claims 6 or 7, wherein R' is methyl.

Claim 14

A compound according to claims 6 or 7, wherein at least one of the D's and X's are chloro.

Claim 15

A compound according to claim 6, wherein A' is a ligand.

Claim 16

A compound according to claim 6, wherein A' is a receptor.

Claim 17

A compound of the formula ##STR9## wherein: D' is hydrogen or chloro; e' is 0 or 1; the sum of m' and p' is 0 to 4, wherein m' is 0 to 2; A' is hydroxyl or a ligand or receptor of at least about 125 daltons; and --COA' is at other than the ortho position.

Claim 18

A compound of the formula ##STR9## wherein: D' is hydrogen or chloro; e' is 0 or 1; the sum of m' and p' is 0 to 4, wherein m' is 0 to 2; A' is hydroxyl or a ligand or receptor of at least about 125 daltons; and --COA' is at other than the ortho position.

Claim 19

A compound according to claim 12, wherein e' is 0.

Claim 20

A compound according to claim 12, wherein e' is 1.

Claim 21

A compound according to claims 13 and 14, wherein A' is hydroxyl.

Claim 22

A compound according to claims 13 and 14, wherein A' is a ligand.

Claim 23

A compound of the formula ##STR10## wherein: e' is 0 or 1; m' is 0 to 2; p' is 0 to 3, the sum of m' and p' being not greater than 4; D' is hydrogen or chloro; and A' is hydroxyl or a ligand or receptor of at least about 125 daltons; with the proviso that, when A' is hydroxyl, --COA' is at other than the ortho position.

Claim 24

A compound of the formula ##STR10## wherein: e' is 0 or 1; m' is 0 to 2; p' is 0 to 3, the sum of m' and p' being not greater than 4; D' is hydrogen or chloro; and A' is hydroxyl or a ligand or receptor of at least about 125 daltons; with the proviso that, when A' is hydroxyl, --COA' is at other than the ortho position.

Claim 25

A compound according to claim 17, wherein e' is 0.

Claim 26

A compound according to claim 17, wherein e' is 1.

Claim 27

A compound according to claims 17 and 18, wherein A' is hydroxyl.

Claim 28

A compound according to claims 13 or 17, bound to a support.

Claim 29

A compound according to claims 18 or 19, wherein A' is a ligand.