3(2H)pyridazinone, and antagonistic agent against SRS-A containing it

Claim 2

A 3(2H)pyridazinone of the formula: ##STR52## wherein R 1 is hydrogen, 2-propenyl or straight chained or branched C 1 -C 4 alkyl; R 2 is hydrogen or C 1 -C 3 alkyl; X is chlorine or bromine; Y is nitro, --NHR 3 wherein R 3 is hydrogen or straight chained or branched C 1 -C 4 alkyl, --AR 4 wherein A is oxygen or sulfur and R 4 is hydrogen, straight chained or branched C 1 -C 6 alkyl, C 3 -C 6 alkenyl having one double bond, C 3 -C 6 alkynyl having one triple bond, phenyl or ##STR53## wherein R 5 is hydrogen or C 1 -C 4 alkyl, or halogen; Z 1 is hydrogen, C 1 -C 4 alkyl, --OR 6 wherein R 6 is hydrogen, straight chained or branched C 1 -C 8 alkyl or ##STR54## wherein n is an interger of from 1 to 4, --N(R 7 ) 2 wherein R 7 is C 1 -C 4 alkyl, or halogen; Z 2 is C 1 -C 4 alkyl, --OR 6 wherein R 6 is as defined above, --N(R 7 ) 2 wherein R 7 is as defined above, or halogen, provided that when R 1 is straight chained or branched C 2 -C 4 alkyl, Y is not hydrogen and when R 1 is hydrogen, methyl or 2-propenyl, Y and R 2 are not simultaneously hydrogen, or a pharmaceutically acceptable salt thereof.

Claim 3

The compound according to claim 1, wherein Z 2 is --OR 6 wherein R 6 is as defined above, --N(R 7 ) 2 wherein R 7 is as defined above, or halogen.

Claim 4

The compound according to claim 2, wherein R 2 is hydrogen.

Claim 5

The compound according to claim 3, wherein R 1 is hydrogen, 2-propenyl, ethyl or isopropyl.

Claim 6

The compound according to claim 4, wherein Y is nitro, amino, --AR 4 wherein A and R 4 are as defined above, or halogen.

Claim 7

The compound according to claim 5, wherein halogen is chlorine.

Claim 8

The compound according to claim 6, wherein Z 1 is hydrogen, C 1 -C 4 alkyl, --OR 6 wherein R 6 is as defined above, --N(CH 3 ) 2 or chlorine, and Z 2 is --OR 6 wherein R 6 is as defined above, --N(CH 3 ) 2 or chlorine.

Claim 9

The compound according to claim 7, wherein R 1 is hydrogen, ethyl or isopropyl.

Claim 10

The compound according to claim 8, wherein Z 1 is hydrogen or --OR 6 wherein R 6 is straight chained C 1 -C 8 alkyl or ##STR55## wherein n is as defined above, and Z 2 is --OR 6 wherein R 6 is straight chained C 1 -C 8 alkyl or ##STR56## wherein n is defined above.

Claim 11

The compound according to claim 9, wherein Y is --OR 4 wherein R 4 is straight chained or branched C 1 --C 6 alkyl, C 3 -C 6 alkenyl having one double bond, C 3 -C 6 alkynyl having one triple bond, phenyl or ##STR57## wherein R 5 is as defined above.

Claim 12

The compound according to claim 10, wherein R 1 is hydrogen.

Claim 13

The compound according to claim 11, wherein each of Z 1 and Z 2 which may be the same or different is --OR 6 wherein R 6 is straight chained C 1 -C 6 alkyl or ##STR58##

Claim 14

The compound according to claim 12, wherein Y is --OR 4 wherein R 4 is straight chained or branched C 1 -C 6 alkyl, --CH 2 C(R 4 ')=C(R 4 ")(R 4 "') wherein each of R 4 ', R 4 " and R 4 "' which may be the same or different is hydrogen or methyl, --CH 2 C.tbd.C--R 4 ' wherein R 4 ' is as defined above, phenyl or ##STR59## wherein R 5 is hydrogen or C 1 -C 4 alkyl.

Claim 15

The compound according to claim 13, wherein Z 1 is 3-OR 6 wherein R 6 is straight chained C 1 -C 6 alkyl or ##STR60## and Z 2 is 4-OCH 3 .

Claim 16

The compound according to claim 14, wherein Y is --OR 4 wherein R 4 is straight chained or branched C 1 -C 6 alkyl, 2-propenyl, propargyl methyl, phenyl or ##STR61## wherein R 5 is hydrogen or methyl.

Claim 17

The compound according to claim 15, wherein X is chlorine.

Claim 18

The compound according to claim 16, wherein Y is --OR 4 wherein R 4 is straight chained or branched C 1 -C 4 alkyl or ##STR62## wherein R 5 is hydrogen or methyl.

Claim 19

An antagonistic agent against SRS-A comprising an effective amount of a 3(2H)pyridazinone of the formula I as defined in claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

Claim 20

A method of reducing the incidence or severity of allergy induced in a subject by SRS-A, which comprises administering to said subject an amount effective to reduce the incidence or severity of the allergy of a 3(2H)pyridazinone as defined in claim 1 or a pharmaceutically acceptable salt thereof.

Claim 21

The compound according to claim 1, which is 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino-6-ethoxy-3(2H)pyridazinone.

Claim 22

The compound according to claim 1, which is 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone.

Claim 23

The compound according to claim 1, which is 4-chloro-5-(3-i-butoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone.

Claim 24

The compound according to claim 1, which is 4-bromo-5-(3-i-butoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone.

Claim 25

The compound according to claim 1, which is 4-chloro-5-(3-i-butoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone

Claim 26

The compound according to claim 1, which is 4-bromo-5-(3-i-butoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone.

Claim 27

The compound according to claim 1, which is 4-chloro-5-(3-i-butoxy-4-methoxybenzylamino)-6-n-propoxy-3(2H)pyridazinone.

Claim 28

The compound according to claim 1, which is 4-chloro-5-(3-i-butoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone.

Claim 29

The compound according to claim 1, which is 4-bromo-5-(3,4-dimethoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone.

Claim 30

The compound according to claim 1, which is 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino)-6-n-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-n-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-i-butoxy-4-methoxybenzylamino)-6-n-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino)-6-benzyloxy-3(2H)pyridazinone, 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-benzyloxy-3(2H)pyridazinone, 4-chloro-5-(3-n-butoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-bromo-5-(3-n-butoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-bromo-5-(3-i-butoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-chloro-5-(3-n-propoxy-4 -methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-propoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-propoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-α-methoxybenzyloxy-3(2H)pyridazinone, 4-bromo-5-(3-n-propoxy-4-methoxybenzylamino)-6-α-methoxybenzyloxy-3(2H)pyridazinone, 4-chloro-5-(3-ethoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-bromo-5-(3-ethoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-chloro-5-(3-ethoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-ethoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-ethoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-bromo-5-(3-ethoxy-4-methoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-chloro-5-(3-ethoxy-4-methoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-bromo-5-(3-ethoxy-4-methoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-chloro-5-(3,4-dimethoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-bromo-5-(3,4-dimethoxybenzylamino)-6-ethoxy-3(2H)pyridazinone, 4-chloro-5-(3,4-dimethoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3,4-dimethoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-bromo-5-(3,4-dimethoxybenzylamino)-6-α-methylbenzyloxy-3(2H)pyridazinone, 4-chloro-5-(3,4-dimethoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-bromo-5-(3,4-dimethoxybenzylamino)-6-sec-butoxy-3(2H)pyridazinone, 4-chloro-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-ethoxy-3(2H)pyridazinone, 4-bromo-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-ethoxy-3(2H)pyridazinone, 4-chloro-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-ethoxy-3(2H)pyridazinone, 4-chloro-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-{3-(2-phenylethoxy)-4-methoxybenzylamino}-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-pentyloxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-bromo-5-(3-n-pentyloxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-n-hexyloxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-i-pentyloxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, 4-chloro-5-(3-sec-butoxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone, or 4-chloro-5-(3-sec-pentyloxy-4-methoxybenzylamino)-6-i-propoxy-3(2H)pyridazinone.