Pharmaceutically active phenylcarboxylic acid derivatives

Claim 2

A compound of the following formula (I); (II) or (III): ##STR7## wherein R 1 is hydrogen or iodine; R 2 is hydrogen, lower alkyl, phenyl or phenyl substituted with one to three halogen, alkyl or alkoxy groups; X is independently halogen, nitro, hydroxy, lower alkyl or lower alkoxy; Alk 1 is methylene; Alk 2 is alkenyl of 2 or 3 carbon atoms; m is 1; n is 0 or 1; and p is 0, 1 or 2 or a pharmaceutically acceptable base-addition salt thereof.

Claim 3

A compound of claim 1, said compound being of the formula (I) wherein R 1 is hydrogen; R 2 is hydrogen; p is 0; and the --OCH 2 COOH group is meta or para.

Claim 4

A compound of claim 1, said compound being of the formula (II) wherein R 1 is hydrogen; R 2 is hydrogen; n is 0; and the --COOH group is para to the --CHR 2 -- group; R 1 is hydrogen; R 2 is methyl or phenyl; p is 0; n is 0; and the --COOH group is para to the --CHR 2 -- group;

Claim 5

R 1 is hydrogen; R 2 is hydrogen; p is 0; n is 1; and the --CH 2 COOH group is meta or para to the --CHR 2 -- group; R 1 is hydrogen; R 2 is hydrogen; n is 0; p is 1; X is lower alkoxy and is ortho to the --CHR 2 -- group; and the --COOH group is para to the --CHR 2 -- group; or R 1 is hydrogen; R 2 is hydrogen; n is 0; p is 1; X is halogen and is meta to the --CHR 2 -- group; and the --COOH group is para to the --CHR 2 -- group.

Claim 6

R 1 is hydrogen; R 2 is hydrogen; p is 0; n is 1; and the --CH 2 COOH group is meta or para to the --CHR 2 -- group; R 1 is hydrogen; R 2 is hydrogen; n is 0; p is 1; X is lower alkoxy and is ortho to the --CHR 2 -- group; and the --COOH group is para to the --CHR 2 -- group; or R 1 is hydrogen; R 2 is hydrogen; n is 0; p is 1; X is halogen and is meta to the --CHR 2 -- group; and the --COOH group is para to the --CHR 2 -- group.

Claim 7

A compound of claim 1, said compound being of the formula (III) wherein R 1 is hydrogen; Alk 1 is methylene; p is 0; Alk 2 is trans ethenyl and is meta or para to Alk 1 ; or R 1 is hydrogen; Alk 1 is methylene; p is 1; X is lower alkoxy and is ortho to Alk 1 ; Alk 2 is trans ethenyl and is meta or para to Alk 1 .

Claim 8

A compound of claim 1, wherein R 1 is hydrogen; R 2 is hydrogen, lower alkyl or phenyl; X is fluoro, chloro, bromo, iodo, methyl, ethyl, propyl, butyl, methoxy, propoxy or butoxy; Alk 1 is methylene; Alk 2 is alkenyl of 2 or 3 carbon atoms; m is 1; n is 0 or 1; and p is 0 or 1.

Claim 9

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier or diluent.

Claim 10

A method of antagonizing the slow reacting substance of anaphylaxis or components thereof in a warm blooded animal comprising administering to the animal the pharmaceutical composition of claim 6.

Claim 11

A method of preparing a compound of claim 1 comprising saponifying a corresponding ester.

Claim 12

A compound of claim 1, which is 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenoxyacetic acid; 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; or 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid, or a pharmaceutically-acceptable base-addition salt thereof.

Claim 13

A compound of the following formula (VI) or (VIII): ##STR8## wherein R 1 is hydrogen or iodine; R 2 is hydrogen, lower alkyl, phenyl or phenyl substituted with one to three halogen, alkyl or alkoxy groups; X is independently halogen, nitro, hydroxy, lower alkyl or lower alkoxy; Alk 1 is methylene; Alk 2 is alkenyl of 2 or 3 carbon atoms; R 3 is --O--CH 2 -- or --(CH 2 ) n --; m is 1; n is 0 or 1; p is 0, 1 or 2; and R 4 is an organic moiety which is replaceable by hydrogen.

Claim 14

A compound of the following formula (VI) or (VIII): ##STR8## wherein R 1 is hydrogen or iodine; R 2 is hydrogen, lower alkyl, phenyl or phenyl substituted with one to three halogen, alkyl or alkoxy groups; X is independently halogen, nitro, hydroxy, lower alkyl or lower alkoxy; Alk 1 is methylene; Alk 2 is alkenyl of 2 or 3 carbon atoms; R 3 is --O--CH 2 -- or --(CH 2 ) n --; m is 1; n is 0 or 1; p is 0, 1 or 2; and R 4 is an organic moiety which is replaceable by hydrogen.

Claim 15

A compound of claim 10, wherein said compound is of the formula (VI).

Claim 16

A compound of claim 10, wherein said compound is of the formula (VIII).

Claim 17

A compound of claim 10 in which R 4 is lower alkyl.

Claim 18

A compound selected from the group consisting of: 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-nitro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-fluoro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenoxyacetic acid; 4-(4-acetyl-3-hydroxy-6-iodo-2-propylphenoxy)methylbenzoic acid; 3-[1-(4-acetyl-3-hydroxy-2-propylphenoxy)ethyl]benzoic acid; 3-ethoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-bromo-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-[1-(4-acetyl-3-hydroxy-2-propylphenoxy)benzyl]benzoic acid; 2-bromo-5-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenylacetic acid; 2-methoxy-5-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 2-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 4-methoxy-3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; and 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; and the pharmaceutically-acceptable base-addition salts thereof.

Claim 19

A compound selected from the group consisting of: 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-nitro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 3-fluoro-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenoxyacetic acid; 4-(4-acetyl-3-hydroxy-6-iodo-2-propylphenoxy)methylbenzoic acid; 3-[1-(4-acetyl-3-hydroxy-2-propylphenoxy)ethyl]benzoic acid; 3-ethoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-bromo-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 2-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-[1-(4-acetyl-3-hydroxy-2-propylphenoxy)benzyl]benzoic acid; 2-bromo-5-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylbenzoic acid; 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenylacetic acid; 2-methoxy-5-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 2-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; 4-methoxy-3-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; and 3-methoxy-4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylcinnamic acid; and the pharmaceutically-acceptable base-addition salts thereof.