Quinoline derivatives, their use in the treatment of hypersensitive ailments and a pharmaceutical composition containing the same

Claim 2

A compound of the formula where: A is O or S; B is O, S, SO, S02 NR 1 , D is O, S, NR, or a chemical bond; E is a chemical bond or a is 0-2; b is 0-1; c is 0-4; d is 0-5; e is 0-4; f is 0-5; n is 0-2; R is independently hydrogen, alkyl, hydroxy, alkoxy, carboxy, carbalkoxy, halo, nitro, haloalkyl, cyano or acyl; R is independently hydrogen, alkyl, hydroxy, alkoxy, halo or haloalkyl; R 1 is independently hydrogen, alkyl or aralkyl; R 2 is -(CH2) x - X, where x is 0-3; X is hydrogen, alkyl, alkenyl, cycloalkyl, aryl aralkyl, hydroxy, alkoxy, aralkoxy, amino, mono-and dialkylamino, aralkylamino, acylamino, carbamyl, carboxy, carbalkoxy, tetrazolyl, or acylsulfonamido; vicinal R 2 groups together may be (CH 2 )y - where y is 1-4, thus forming a 3-6 membered ring; geminal R 1 and R 2 groups may together form a spiro substituent, -(CH 2 ) 2 -, where z is 2 to 5; geminal R 1 or R 1 and R 2 groups may together form an alkylidenyl substituent, =CHR 1 ; Z is -COOR 1 . CN. - -OR, tetrazolyl or substituted tetrazolyl where the substituent may be alkyl, carboxyalkyl or carbalkoxyalkyl; and R 3 is hydrogen, alkyl, haloalkyl, phenyl or benzyl; or a pharmaceutically acceptable salt thereof.

Claim 3

A compound according to claim 1 where: A is 0 or S; B is 0 or S; n is 0-1; - a + b is 1; c + d is 1-2; e + f is 0-5; R and R are hydrogen, alkyl or alkoxy; R 1 is hydrogen or alkyl; R 2 is - (CH 2 ) x - X where x is 0-3 and X is hydrogen or alkyl; and Z is-COOR 1 , -CN, or tetrazolyl.

Claim 4

A compound according to claim 2 where: A and B are O; n is 0; c + d is 1; and Z is -COOR1, -CN or tetrazolyl.

Claim 5

A compound according to claim 3 where: a is 1; b is 0; c is 1; and d is 0.

Claim 6

A compound according to claim 4 where: D is 0; and E is a chemical bond.

Claim 7

A compound according to claim 4 where: D is S; and E is a chemical bond.

Claim 8

A compound according to claim 4 where: e + f is 0; D is a chemical bond; and E is a chemical bond.

Claim 9

A compound according to claim 4 where: e + f is 1-5; D is a chemical bond; and E is a chemical bond.

Claim 10

A compound according to claim 4 where: D is 0; and E is

Claim 11

A compound according to claim 4 where: D is a chemical bond or and E is

Claim 12

A compound according to claim 3 where: a is 1: b is 0; c is 0; and d is 1.

Claim 13

A compound according to claim 2 where: a is 1; b is 0: c is 0; and d is 2.

Claim 14

A compound according to claim 11 where: D is 0; and E is a chemical bond.

Claim 15

A compound according to claim 11 where: c + f is 0; D is a chemical bond; and E is a chemical bond.

Claim 16

A compound according to claim 13 where e + f is 1-5.

Claim 17

A compound according to claim 1 which is 5-(3-(3-(2-quinolinylmethyloxy)benzyloxy)phenyl)-tetrazole; 5-[4-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenyl]tetrazole; 5-[3-methoxy-4-(3-(2-quinolinyl- methyloxy)benzyloxy)phenyl]tetrazole; 5-[4-methoxy-3-(3-(2-quinolinylmethyloxy)benzyloxy)-phenyl]-tetrazole; 5-[4-(4-(2-quinolinylmethyloxy)benzyloxy)phenyl]tetrazole; 5-[4-(4-(2-quinolinylmethyloxy)-benzyloxy)benzyl]tetrazole; 5-(4-(3-(4-(2-quinolinylmethyloxy)benzyloxy)phenyl)-3-methylbutyl]tetrazole; 5-[3-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenyl]-tetrazole; 5-[2-(3-(2-quinolinylmethyloxy)-phenoxymethyl)phenyl]-tetrazole; 5-[4-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenyl]-tetrazole; 4-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzonitrile; 4-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoic acid; 3-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoic acid; a-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)-phenoxy) acetonitrile; 5-[3-(4-(2-quinolinylmethyloxy)phenoxymethyl)-phenoxymethyl]tetrazole; 5-[4-(3-(2-quinolinylmethyloxy)phenoxymethyl)-phenoxymethyl]tetrazole; 5-[3-(3-(2-quinolinylmethyloxy)-phenoxymethyl)-phenoxymethyl]tetrazole;5-carboxy-2-(3-(2-quinolinylmethyloxy) phenoxymethyl)-phenoxyacetic acid; 5-[2-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenoxymethyl]tetrazole: 5-[2-(3-(2-quinolinylmethyloxy)phenoxymethyl)-5-carbomethoxyphenoxymethyl]tetrazole; 3-methoxy-4-(3-(2-quinolinyl- methyloxy)benzyloxy)benzoic acid; methyl 3-methoxy-4-(3-(2-quinolinylmethyloxy)-benzyloxy)benzoate: 5-[3-methoxy-4-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenyl]tetrazole; N-(3-methoxy-4-(3-(2-quinolinyl- methyloxy)benzyloxy)-benzoyl]benzenesulfonamide; 3-methoxy-4-(3-(2-quinolinylmethyloxy)-phenoxymethyl)-benzoic acid; or a pharmaceutically acceptable salt thereof.

Claim 18

A compound according to claim 1 which is 5-[2-(4-(2-quinolinylmethyloxy)phenoxymethyl)benzyl]-tetrazole or a pharmaceutically acceptable salt thereof.

Claim 19

A compound according to any one of the preceding claims for use in the treatment of hypersensitive ailments or disorders in humans and mammals.

Claim 20

A pharmaceutical composition, which composition comprises a compound according to any one of claims 1 to 17 together with a pharmaceutical carrier.