Tri- or tetrasubstituted diphenylphthalides

Claim 2

3-(2-X-4-X-Phenyl)-3-(2-Y 2 -4-Y 4 -phenyl)-4-Z 4 -5-Z 5 -6-Z 6 -7-Z 7 -phthalide of the formula ##STR35## wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y 4 is the same as Y 2 when Y 2 is dialkylamino; or dialkylamino, pyrrolidino, piperidino, alkylbenzylamino, alkyl(4-alkoxyphenyl)amino or alkyl(Q-(CH 2 ) n -amino, wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkoxy is non-tertiary alkoxy of one to four carbon atoms, Q is hydroxy or chloro and n is two to four when Y 2 is other than dialkylamino; Z 4 is hydrogen or halo; Z 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 6 and Z 7 are each hydrogen; Z 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 3

A compound according to claim 1 wherein Z 4 , Z 5 , Z 6 , and Z 7 are each hydrogen.

Claim 4

A compound according to claim 2 wherein Y 2 is hydrogen.

Claim 5

A compound according to claim 3 wherein Y 4 is dialkylamino.

Claim 6

A compound according to claim 4 wherein Y 4 is dimethylamino.

Claim 7

A compound according to claim 5 wherein X is dimethylamino.

Claim 8

A compound according to claim 4 wherein Y 4 is diethylamino.

Claim 9

A compound according to claim 7 wherein X is dimethylamino.

Claim 10

A compound according to claim 3 wherein Y 4 is alkylbenzylamino.

Claim 11

A compound according to claim 9 wherein Y 4 is ethylbenzylamino.

Claim 12

A compound according to claim 10 wherein X is dimethylamino.

Claim 13

A compound according to claim 2 wherein Y 2 is alkyl.

Claim 14

A compound according to claim 12 wherein Y 2 is methyl.

Claim 15

A compound according to claim 13 wherein Y 4 is dialkylamino.

Claim 16

A compound according to claim 14 wherein Y 4 is dimethylamino.

Claim 17

A compound according to claim 15 wherein X is dimethylamino.

Claim 18

A compound according to claim 14 wherein Y 4 is diethylamino.

Claim 19

A compound according to claim 17 wherein X is dimethylamino.

Claim 20

A compound according to claim 1 wherein Z 4 , Z 5 , Z 6 and Z 7 are each halo.

Claim 21

A compound according to claim 19 wherein Z 4 , Z 5 , Z 6 and Z 7 are each chloro.

Claim 22

A compound according to claim 20 wherein Y 2 is hydrogen.

Claim 23

A compound according to claim 21 wherein Y 4 is dialkylamino.

Claim 24

A compound according to claim 22 wherein Y 4 is dimethylamino.

Claim 25

A compound according to claim 23 wherein X is dimethylamino.

Claim 26

A compound according to claim 24 wherein Y 4 is diethylamino.

Claim 27

A compound according to claim 25 wherein X is dimethylamino.

Claim 28

A compound according to claim 25 wherein X is diethylamino.

Claim 29

A compound according to claim 20 wherein Y 2 is alkyl.

Claim 30

A compound according to claim 28 wherein Y 2 is methyl.

Claim 31

A compound according to claim 29 wherein Y 4 is dialkylamino.

Claim 32

A compound according to claim 30 wherein Y 4 is diethylamino.

Claim 33

A compound according to claim 31 wherein X is dimethylamino.

Claim 34

A compound according to claim 31 wherein X is diethylamino.

Claim 35

A compound according to claim 20 wherein Y 2 is dialkylamino.

Claim 36

A compound according to claim 34 wherein Y 2 is dimethylamino.

Claim 37

A compound according to claim 35 wherein X is dimethylamino.

Claim 38

A compound according to claim 1 wherein Z 6 is dialkylamino.

Claim 39

A compound according to claim 37 wherein Z 6 is dimethylamino.

Claim 40

A compound according to claim 38 wherein Y 2 is hydrogen.

Claim 41

A compound according to claim 39 wherein Y 4 is dialkylamino.

Claim 42

A compound according to claim 40 wherein Y 4 is dimethylamino.

Claim 43

A compound according to claim 41 wherein X is dimethylamino.

Claim 44

The process for preparing 3-(2-X-4-X-phenyl)-3-(2-Y 2 -4-Y' 4 -phenyl)-4-Z 4 -5-Z" 5 -6-Z" 6 -7-Z 7 -phthalide which comprises condensing 2-(2-Y 2 -4-Y' 4 -benzoyl)-3-Z 4 -4-Z" 5 -5-Z" 6 -6-Z 7 -benzoic acid with 1-X-3-X-benzene in contact with the anhydride of an alkanoic acid of two to five carbon atoms, phosphorus oxychloride or thionyl chloride, wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y' 4 is the same as Y 2 when Y 2 is dialkylamino; or dialkylamino, pyrrolidino, piperidino, alkylbenzylamino, alkyl(4-alkoxyphenyl)amino or alkyl(Q'-(CH 2 ) n )amino, wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkoxy is non-tertiary alkoxy of one to four carbon atoms, Q' is chloro and n is two to four when Y 2 is other than dialkylamino; Z 4 is hydrogen or halo; Z" 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 6 and Z 7 are each hydrogen; Z" 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 45

The process for preparing 3-(2-X-4-X-phenyl)-3-(2-Y 2 -4-Y' 4 -phenyl)-4-Z 4 -5-Z" 5 -6-Z" 6 -7-Z 7 -phthalide which comprises condensing 2-(2-Y 2 -4-Y' 4 -benzoyl)-3-Z 4 -4-Z" 5 -5-Z" 6 -6-Z 7 -benzoic acid with 1-X-3-X-benzene in contact with the anhydride of an alkanoic acid of two to five carbon atoms, phosphorus oxychloride or thionyl chloride, wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y' 4 is the same as Y 2 when Y 2 is dialkylamino; or dialkylamino, pyrrolidino, piperidino, alkylbenzylamino, alkyl(4-alkoxyphenyl)amino or alkyl(Q'-(CH 2 ) n )amino, wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkoxy is non-tertiary alkoxy of one to four carbon atoms, Q' is chloro and n is two to four when Y 2 is other than dialkylamino; Z 4 is hydrogen or halo; Z" 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 6 and Z 7 are each hydrogen; Z" 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 46

The process for preparing 3-(2-X-4-X-phenyl)-3-(2-Y 2 -4-Y' 4 -phenyl)-4-Z 4 -5-Z" 5 -6-Z" 6 -7-Z 7 -phthalide which comprises condensing 2-(2-X-4-X-benzoyl)-3-Z 4 -Z" 5 -5-Z" 6 -6-Z 7 -benzoic acid with 1-Y 2 -3-Y' 4 -benzene in contact with the anhydride of an alkanoic acid of two to five carbon atoms, phosphorus oxychloride or thionyl chloride, wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y' 4 is the same as Y 2 when Y 2 is dialkylamino; or dialkylamino, pyrrolidino, piperidino, alkylbenzylamino, alkyl(4-alkoxyphenyl)amino or alkyl(Q'-(CH 2 ) n )amino, wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkoxy is non-tertiary alkoxy of one to four carbon atoms, Q' is chloro and n is two to four when Y 2 is other than dialkylamino; Z 4 is hydrogen or halo; Z" 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 6 and Z 7 are each hydrogen; Z" 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 47

The process for preparing 3-(2-X-4-X-phenyl)-3-(2-Y 2 -4-Y' 4 -phenyl)-4-Z 4 -5-Z" 5 -6-Z" 6 -7-Z 7 -phthalide which comprises condensing 2-(2-X-4-X-benzoyl)-3-Z 4 -Z" 5 -5-Z" 6 -6-Z 7 -benzoic acid with 1-Y 2 -3-Y' 4 -benzene in contact with the anhydride of an alkanoic acid of two to five carbon atoms, phosphorus oxychloride or thionyl chloride, wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y' 4 is the same as Y 2 when Y 2 is dialkylamino; or dialkylamino, pyrrolidino, piperidino, alkylbenzylamino, alkyl(4-alkoxyphenyl)amino or alkyl(Q'-(CH 2 ) n )amino, wherein alkyl is non-tertiary alkyl of one to four carbon atoms, alkoxy is non-tertiary alkoxy of one to four carbon atoms, Q' is chloro and n is two to four when Y 2 is other than dialkylamino; Z 4 is hydrogen or halo; Z" 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 6 and Z 7 are each hydrogen; Z" 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z" 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 48

3-(2-X-4-X-Phenyl)-3-(2Y 2 -4-Y 4 -phenyl)-4-Z 4 -5-Z 5 -6-Z 6 -7-Z 7 -phthalide according to claim 1 wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y 4 is pyrrolidino; Z 4 is hydrogen or halo; Z 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 6 and Z 7 are each hydrogen; Z 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 49

A compound according to claim 45 wherein Z 4 , Z 5 , Z 6 and Z 7 are each hydrogen.

Claim 50

A compound according to claim 46 wherein Y 2 is hydrogen.

Claim 51

A compound according to claim 47 wherein X is dimethylamino.

Claim 52

3-(2-X-4-X-Phenyl)-3-(2-Y 2 -4-Y 4 -phenyl)-4-Z 4 -5-Z 5 -6-Z 6 -7-Z 7 -phthalide according to claim 1 wherein: X is dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms; Y 2 is hydrogen, non-tertiary alkyl of one to four carbon atoms, alkanoylamino of two to five carbon atoms, non-tertiary alkoxy of one to four carbon atoms or halo; Y 4 is piperidino; Z 4 is hydrogen or halo; Z 5 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 6 and Z 7 are each hydrogen; Z 6 is hydrogen or halo; or non-tertiary alkyl of one to four carbon atoms, nitro, amino or dialkylamino wherein alkyl is non-tertiary alkyl of one to four carbon atoms when Z 4 , Z 5 and Z 7 are each hydrogen; and Z 7 is hydrogen or halo.

Claim 53

A compound according to claim 49 wherein Z 4 , Z 5 , Z 6 and Z 7 are each hydrogen.

Claim 54

A compound according to claim 50 wherein Y 2 is hydrogen.

Claim 55

A compound according to claim 51 wherein X is dimethylamino.