9-Acyl-1,2,3,4-tetrahydrocarbazole-3 and 4-carboxylic acids

Claim 2

A compound having the formula ##SPC10## wherein: A. represents 2-thienyl; Q and Q 1 represents substituents selected from lower-alkyl, phenyl-lower-alkyl, lower-alkoxy, phenyl lower-alkoxy, phenoxy, phenyl, di(lower-alkyl)-amino, lower-alkanoylamino, trihalomethyl, trihalomethoxy, halo and hydroxy, where phenyl is unsubstituted or substituted by from one to three of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl and halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkylsulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent integers from 0 to 1 inclusive; R represents hydrogen, lower-alkyl, 4-acetamidophenyl, lower-alkanoyloxymethyl, benzoyloxymethyl or benzoyloxymethyl substituted on phenyl by from one or two of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl, nitro and halo; and R 1 and R 2 each represent hydrogen or methyl, at least one of which is hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 3

A compound having the formula ##SPC11## wherein: A. represents cyclohexyl; Q and Q 1 represent substituents selected from lower-alkyl, phenyl-lower-alkyl, lower-alkoxy, phenyl-lower-alkoxy, phenoxy, phenyl, di(lower-alkyl)-amino, lower-alkanoylamino, trihalomethyl, trihalomethoxy, halo and hydroxy, where phenyl is unsubstituted or substituted by from one to three of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl and halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent integers from 0 to 1 inclusive; R represents hydrogen, lower-alkyl, 4-acetamidophenyl, lower-alkanoyloxymethyl, benzoyloxymethyl or benzoyloxymethyl substituted on phenyl by from one or two of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl, nitro and halo; and R 1 and R 2 each represent hydrogen or methyl, at least one of which is hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 4

A compound having the formula ##SPC11## wherein: A. represents cyclohexyl; Q and Q 1 represent substituents selected from lower-alkyl, phenyl-lower-alkyl, lower-alkoxy, phenyl-lower-alkoxy, phenoxy, phenyl, di(lower-alkyl)-amino, lower-alkanoylamino, trihalomethyl, trihalomethoxy, halo and hydroxy, where phenyl is unsubstituted or substituted by from one to three of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl and halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent integers from 0 to 1 inclusive; R represents hydrogen, lower-alkyl, 4-acetamidophenyl, lower-alkanoyloxymethyl, benzoyloxymethyl or benzoyloxymethyl substituted on phenyl by from one or two of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl, nitro and halo; and R 1 and R 2 each represent hydrogen or methyl, at least one of which is hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 5

9-(2-Thenoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 1.

Claim 6

9-Cyclohexanecarbonyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 2.

Claim 7

4-Acetamidophenyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate.

Claim 8

4-Acetamidophenyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate.

Claim 9

A compound having the formula ##SPC12## wherein: A. represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl, lower-alkoxy, benzyloxy, phenyl, trihalomethyl and hydroxy; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkylsulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent the integer 0; and R, R 1 and R 2 each represent hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 10

A compound having the formula ##SPC12## wherein: A. represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl, lower-alkoxy, benzyloxy, phenyl, trihalomethyl and hydroxy; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkylsulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent the integer 0; and R, R 1 and R 2 each represent hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 11

A compound according to claim 6 wherein (A) represents phenyl.

Claim 12

A compound according to claim 7 wherein m and p represent integers from 0 to 1 inclusive.

Claim 13

A compound according to claim 8 wherein Q and Q 1 represent substituents selected from lower-alkyl and lower-alkoxy.

Claim 14

A compound according to claim 9 wherein a substituent represented by Q occurs at the 6-position of the tetrahydrocarbazole ring; and a substituent represented by Q 1 occurs at the 4-position of phenyl.

Claim 15

9-Benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 16

9-(4-Toluoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 17

9-(4-Anisoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 18

9-(4-Anisoyl)-6-methyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 19

9-Benzoyl-6-methoxy-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 20

9-Benzoyl-6-methyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 10.

Claim 21

A compound having the formula ##SPC13## wherein: A. represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl and halo, at least one of which is halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m and p represent integers from 0 to 1 inclusive; n and g represent the integer 0; and R, r 1 and R 2 each represent hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 22

A compound having the formula ##SPC13## wherein: A. represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl and halo, at least one of which is halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m and p represent integers from 0 to 1 inclusive; n and g represent the integer 0; and R, r 1 and R 2 each represent hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 23

A compound according to claim 17 wherein (A) represents phenyl.

Claim 24

9-(4-Fluorobenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 18.

Claim 25

9-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 18.

Claim 26

9-Benzoyl-6-fluoro-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 18.

Claim 27

9-(3-Chlorobenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 18.

Claim 28

9-(3-Fluorobenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 18.

Claim 29

A compound having the formula ##SPC14## wherein (A) represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl, phenyl-lower-alkyl, lower-alkoxy, phenyl-lower-alkoxy, phenoxy, phenyl, di(lower-alkyl)-amino, lower-alkanoylamino, trihalomethyl, trihalomethoxy, halo and hydroxy, where phenyl is unsubstituted or substituted by from one to three of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl and halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent integers from 0 to 1 inclusive; R represents lower-alkanoyloxymethyl, benzoyloxymethyl or benzoyloxymethyl substituted on phenyl by from one or two of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl, nitro and halo; and R 1 and R 2 each represent hydrogen or methyl, at least one of which is hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 30

A compound having the formula ##SPC14## wherein (A) represents phenyl or naphthyl; Q and Q 1 represent substituents selected from lower-alkyl, phenyl-lower-alkyl, lower-alkoxy, phenyl-lower-alkoxy, phenoxy, phenyl, di(lower-alkyl)-amino, lower-alkanoylamino, trihalomethyl, trihalomethoxy, halo and hydroxy, where phenyl is unsubstituted or substituted by from one to three of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl and halo; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent integers from 0 to 1 inclusive; R represents lower-alkanoyloxymethyl, benzoyloxymethyl or benzoyloxymethyl substituted on phenyl by from one or two of the same or different substituents selected from lower-alkyl, lower-alkoxy, trihalomethyl, nitro and halo; and R 1 and R 2 each represent hydrogen or methyl, at least one of which is hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 31

Pivaloyloxymethyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate according to claim 24.

Claim 32

Benzoyloxymethyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate according to claim 24.

Claim 33

A compound having the formula ##SPC15## wherein: (A) represents phenyl or naphthyl; Q and Q 1 represent lower-alkyl; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; g, m, n, and p represent integers from 0 to 1 inclusive; R represents hydrogen or lower-alkyl; R 1 represents hydrogen or methyl; and R 2 represents hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 34

A compound having the formula ##SPC15## wherein: (A) represents phenyl or naphthyl; Q and Q 1 represent lower-alkyl; Z and Z 1 represent substituents selected from lower-alkylthio, lower-alkylsulfinyl, lower-alkyl-sulfonyl, amino and nitro; g, m, n, and p represent integers from 0 to 1 inclusive; R represents hydrogen or lower-alkyl; R 1 represents hydrogen or methyl; and R 2 represents hydrogen; or (Q) m taken together with (Z) n , or (Q 1 ) p taken together with (Z 1 ) g represents methylenedioxy attached to adjacent carbon atoms.

Claim 35

Ethyl 9-(4-toluoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylate according to claim 27.

Claim 36

Ethyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate according to claim 27.

Claim 37

9-(3,4-Methylenedioxybenzoyl)-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid according to claim 27.

Claim 38

A compound having the formula ##SPC16## wherein: (Ar) represents phenyl or naphthyl; Q 2 and Q 3 represent substituents selected from lower-alkyl and lower-alkoxy; Z 2 and Z 3 represent lower-alkylthio; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent the integer 0; and R 3 and R 4 represent hydrogen; or (Q 2 ) m taken together with (Z 2 ) n , or (Q 3 ) p taken together with (Z 3 ) g represent methylenedioxy attached to adjacent carbon atoms.

Claim 39

A compound having the formula ##SPC16## wherein: (Ar) represents phenyl or naphthyl; Q 2 and Q 3 represent substituents selected from lower-alkyl and lower-alkoxy; Z 2 and Z 3 represent lower-alkylthio; m represents an integer from 0 to (3-n) inclusive; p represents an integer from 0 to (3-g) inclusive; n and g represent the integer 0; and R 3 and R 4 represent hydrogen; or (Q 2 ) m taken together with (Z 2 ) n , or (Q 3 ) p taken together with (Z 3 ) g represent methylenedioxy attached to adjacent carbon atoms.

Claim 40

A compound according to claim 31 wherein (Ar) represents phenyl.

Claim 41

A compound according to claim 32 wherein m and p represent an integer from 0 to 1 inclusive.

Claim 42

A compound according to claim 33 wherein a substituent represented by Q 2 occurs at the 6-position of the tetrahydrocarbazole ring; and a substituent represented by Q 3 occurs at the 4-position of phenyl.

Claim 43

9-Benzoyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid according to claim 34.

Claim 44

9-(4-Toluoyl)-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid according to claim 34.

Claim 45

9-Benzoyl-6-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid according to claim 34.

Claim 46

9-Benzoyl-6-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid according to claim 34.

Claim 47

A compound having the formula ##SPC17## wherein: (Ar) represents phenyl or naphthyl; Q 2 and Q 3 represent halo; Z 2 and Z 3 represent lower-alkylthio; m and p represent an integer from 0 to 1 inclusive; n and g represent the integer 0; and R 3 and R 4 represent hydrogen; or (Q 2 ) m taken together with (Z 2 ) n , or (Q 3 ) p taken together with (Z 3 ) g represent methylenedioxy attached to adjacent carbon atoms.

Claim 48

A compound having the formula ##SPC17## wherein: (Ar) represents phenyl or naphthyl; Q 2 and Q 3 represent halo; Z 2 and Z 3 represent lower-alkylthio; m and p represent an integer from 0 to 1 inclusive; n and g represent the integer 0; and R 3 and R 4 represent hydrogen; or (Q 2 ) m taken together with (Z 2 ) n , or (Q 3 ) p taken together with (Z 3 ) g represent methylenedioxy attached to adjacent carbon atoms.

Claim 49

A compound according to claim 39 wherein (Ar) is phenyl.

Claim 50

9-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid according to claim 40.