Pyridazinone derivatives, their preparation and use

Claim 2

Compounds of formula (I): wherein: R 1 and R 2 are the same or different and each represents a hydrogen atom or a C 1 -C 6 alkyl group; Q represents an oxygen atom or a sulphur atom; A represents a C 1 -C 6 alkylene group; R 3 represents a hydroxy group, a C 1 -C 6 alkox y group, an aryloxy group, an aralkyloxy group in which the alkyl part has from 1 to 6 carbon atoms, a group of formula -(NH) n -NR 6 R 7 , wherein n is 0 or 1; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 10 alkyl group, a substituted C 1 -C 10 alkyl group having at least one substituent selected from: (a) halogen atoms, hydroxy groups, C 1 -C 6 alkoxy groups, aryloxy groups, amino groups, amino groups having one or two C 1 -C 6 alkyl, aryl or heterocyclic substituents, carboxy groups, aliphatic and carbocyclic aromatic acyl groups, substituted C 2 -C 8 aliphatic carboxylic acyl groups having at least one substituent selected from substituents (b) defined hereafter, aliphatic and carbocyclic aromatic carboxylic acylamino groups, C 2 -C 7 alkoxycarbonyl groups, aralkyloxycarbonyl groups where the alkyl part is C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl groups, heterocyclic groups, aryl groups, C 1 -C 6 alkylsulphonyl groups, arylsulphonyl groups, sulphamoyl groups, carbamoyl groups, carbamoyl groups having one or two C 1 -C 6 alkyl substituents, and carbonyl groups having a heterocyclic substituent, C 2 -C 6 alkenyl groups, C 3 -C 7 cycloalkyl groups, aryl groups and heterocyclic groups, or R 6 and R 7 , together with the nitrogen atom to which they are attached, form a heterocyclic group; a group of formula -NH-NH-R 8 , wherein: R 8 represents a C 1 -C 8 aliphatic carboxylic acyl group, a C 2 -C 8 substituted aliphatic carboxylic acyl group having at least one substituent selected from: (b) halogen atoms, C 1 -C 6 alkoxy groups, C 3 -C 7 cycloalkyl groups, aryl groups and heterocyclic groups, a C 2 -C 7 alkoxycarbonyl group, a cinnamoyl group or a carbocyclic aromatic carboxylic acyl group; or a group of formula -NH-N=C H - R 9 , wherein: R 9 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkyl group having at least one halogen substituent or an aryl group; R 4 and R 5 are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkyl group having at least one halogen substituent, a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 7 aliphatic carboxylic acyloxy group, an amino group, a mono- or di-alkylamino group where the or each alkyl group is C 1 -C 6 alkyl, a C 1 -C 7 aliphatic carboxylic acylamino group, a carboxy group, a C 2 -C 7 alkoxycarbonyl group, a carbamoyl group, a carbamoyl group having 1 or 2 C 1 -C 6 alkyl substituents, a ureido group, an alkylureido group wherein the alkyl group is C 1 -C 6 alkyl, a thioureido group, an alkylthioureido group wherein the alkyl group is C 1 -C 6 alkyl, a cyano group or a nitro group; said aryl groups and aryl parts of groups containing an aryl group are C 6 -C 14 carbocyclic aryl groups which are unsubstituted or have at least one substituent selected from substituents (a), C 1 -C 6 alkyl groups and substituted C 1 -C 6 alkyl groups having at least one of substituents (a); said heterocyclic groups contain from 5 to 14 ring atoms, of which from 1 to 5 are nitrogen, oxygen or sulphur hetero-atoms, said heterocyclic groups being unsubstituted or having at least one substituent selected from said substituents (a), oxygen atoms, C 1 -C 6 alkyl groups and substituted C 1 -C 6 alkyl groups having at least one of said substituents (a); and the dotted line indicates a single or double carbon-carbon bond between the carbon atoms at the 4-and 5-positions of the pyridazinone system; and pharmaceutically acceptable acid addition salts thereof.

Claim 3

Compounds as claimed in Claim 1, in which: Q represents an oxygen atom; A represents a C 1 -C 4 alkylene group; R 3 represents a C l -C 4 alkoxy group, a 2,5-dialkylpyrrolyl group in which each alkyl part is C 1 -C 4 alkyl or a group of formula -(NH) n NR 6 R 7 , wherein:. n is 0 or 1: and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 2 -C 8 alkyl group, a C 3 -C 6 alkenyl group, a C 5 or C 6 cycloalkyl group, a phenyl group, a phenyl group having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, a substituted heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a') halogen atoms, hydroxy groups, C 1 -C 4 alkoxy groups, dialkylamino groups wherein each alkyl group is C 1 -C 4 alkyl, C 2 or C 3 alkoxycarbonyl groups, heterocyclic groups having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, substituted heterocyclic groups having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, phenyl groups and phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent; R 4 and R are the same or different and each represents a hydrogen atom, a C -C 4 alkyl group, a halogen atom or a nitro group.

Claim 4

Compounds as claimed in Claim 1, in which: R 1 and R 2 are the same or different and each represents a hydrogen atom or a methyl group; Q represents an oxygen atom; A represents a C 1 -C 4 alkylene group; R represents a group of formula -(NH) n -NR 6 R 7 , wherein: n is 0; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 5 or C 6 cycloalkyl group, a 2,5-dimethylpyrrolyl group, a C 3 or C 4 alkenyl group, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, a substituted heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a'') C 1 -C 4 alkox y groups, C 2 and C 3 alkoxycarbonyl groups, morpholino groups, thiomorpholino groups, piperazinyl groups, homopiperazinyl groups, phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, pyridyl groups and 1-piperazinyl groups having at the 4-position at least one substituent selected from: (c) phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, C 1 -C 4 alkyl groups, substituted C 1 -C 4 alkyl groups having at least one hydroxy substituent, phenyl substituent or phenyl substituent having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, formyl groups, C 2 - C 8 alkanoyl groups, C 2 -C 5 alkoxycarbonyl groups, aralkyloxycarbonyl groups wherein the alkyl part is C 1 -C 4 alkyl and the aryl part is C 6 -C 10 aryl or C 6 -C 10 aryl having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C and C 4 alkenoyl groups, benzoyl groups, benzoyl groups having at least one halogen, sulphamoyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, heterocyclic acyl groups, C 1 -C 4 alkylsulphonyl groups, arylsulphonyl groups wherein the aryl part is C 6 -C 10 aryl or C 6 -C 10 aryl having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, alkylcarbamoyl groups wherein the alkyl part is C 1 -C 4 alkyl and substituted C 2 -C 6 alkanoyl groups having at least one halogen, C 1 -C 4 alkox y, C 3 -C 7 cycloalkyl, phenyl or heterocyclic substituent; R 4 represents a hydrogen atom; and R 5 represents a hydrogen atom or a halogen, nitro or methyl group at the 3- position.

Claim 5

Compounds as claimed in Claim 1, in which: Q represents an oxygen atom; A represents a methylene group; R 1 represents a hydrogen atom; R 2 represents a hydrogen atom or a methyl group; R represents a group of formula - NHR and R represents a C 3 or C 4 alkenyl group, a C 1 -C 6 alkyl group, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen hetero-atoms, said heterocyclic group being unsubstituted or having at least one substituent selected from C 1 -C 4 alkyl groups and phenylalkyl groups wherein the phenyl part is unsubstituted or itself has at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent and wherein the alkyl part is C 1 -C 4 alkyl, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a''') C 1 -C 4 alkox y groups, morpholino groups, thiomorpholino groups, 1-piperazinyl groups, phenyl groups, phenyl groups having at least one halogen, alkyl or alkoxy substituent, pyridyl groups and 1-piperazinyl groups having at the 4-position a substituent selected from: (c') phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C 1 - C 4 alkyl groups, C 1 -C 4 alkyl groups having at least one substituent selected from hydroxy substituents, phenyl substituents and phenyl substituents having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, formyl groups. C 2 -C 5 alkanoyl groups, C 2 -C 5 alkanoyl groups having at least one C 1 -C 4 alkox y, halogen, phenyl, C 3 -C 7 cycloalkyl or heterocyclic substituent, C 2 -C 5 alkoxycarbonyl groups, aralkyloxycarbonyl groups where the alkyl part is C 1 -C 3 alkyl and the aryl part is phenyl or phenyl having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C and C 4 alkenoyl groups, benzoyl groups, benzoyl groups having at least one halogen, sulphamoyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, heterocyclic acyl groups wherein the heterocyclic part has 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, said heterocyclic group being unsubstituted or having at least one halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, C 1 -C 4 alkylsulphonyl groups, C 6 -C 10 carbocyclic arylsulphonyl groups, C 6 -C 10 carbocyclic arylsulphonyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, and alkylcarbamoyl groups where the alkyl part is C 1 -C 4 alkyl; R 4 represents a hydrogen atom; and R 5 represents a halogen atom or a methyl group at the 3-position.

Claim 6

Compounds as claimed in Claim 1, in which: R 1 and R 2 are the same or different and each represents a hydrogen atom or a C 1 -C 6 alkyl group; Q represents an oxygen atom or a sulphur atom; A represents a C 1 -C 6 alkylene group; R represents a hydroxy group, a C 1 -C 6 alkoxy group, an aryloxy group, an aralkyloxy group in which the alkyl part has from 1 to 6 carbon atoms, or a group of formula -(NH) n -NR 6 R 7 , wherein n is 0 or 1; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 10 alkyl group, a substituted C 1 -C 10 alkyl group having one or two substituents selected from: (a) halogen atoms, hydroxy groups, C 1 -C 6 alkoxy groups, aryloxy groups, amino groups, amino groups having one or two C 1 -C 6 alkyl, aryl or heterocyclic substituents, carboxy groups, aliphatic and carbocyclic aromatic carboxylic acylamino groups, C 2 -C 7 alkoxycarbonyl groups, C 3 -C 7 cycloalkyl groups, heterocyclic groups and aryl groups, a C 3 -C 7 cycloalkyl group, an aryl group or a heterocyclic group, or R and R , together with the nitrogen atom to which they are attached, form a heterocyclic group; R 4 and R 5 are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkyl group having at least one halogen substituent, a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 7 aliphatic carboxylic acyloxy group, an amino group, a mono- or di-alkylamino group where the or each alkyl group is C 1 -C 6 alkyl, a C 1 -C 7 aliphatic carboxylic acylamino group, a carboxy group, a C 2 -C 7 alkoxycarbonyl group, a carbamoyl group, a ureido group, an alkylureido group wherein the alkyl group is C 1 -C 6 alkyl, a thioureido group, an alkylthioureido group wherein the alkyl group is C 1 -C 6 alkyl, a cyano group or a nitro group.

Claim 7

5-Methyl-6-[3-chloro-4-(N-propylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 8

5-Methyl-6-[3-chloro-4-(N-propylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 9

5-Methyl-6-[3-chloro-4-(N-butylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 10

5-Methyl-6-[3-chloro-4-(N-butylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 11

5-Methyl-6-[3-chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 12

5-Methyl-6-[3-chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 13

6-[3-Chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 14

6-[3-Chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 15

5-Methyl-6-[3-chloro-4-(N-pentylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 16

5-Methyl-6-[3-chloro-4-(N-pentylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 17

5-Methyl-6-[3-chloro-4-(N-hexylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 18

5-Methyl-6-[3-chloro-4-(N-hexylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 19

6-{3-Chloro-4-[N-(2-ethoxyethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 20

6-{3-Chloro-4-[N-(2-ethoxyethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 21

5-Methyl-6-[3-chloro-4-(N-phenethylcarbamoyl- methoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 22

5-Methyl-6-[3-chloro-4-(N-phenethylcarbamoyl- methoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 23

6-{3-Chloro-4-[N-(p-methoxyphenethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 24

6-{3-Chloro-4-[N-(p-methoxyphenethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 25

5-Methyl-6-{3-chloro-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 26

5-Methyl-6-{3-chloro-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 27

6-(3-Fluoro-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 28

6-(3-Fluoro-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 29

6-{3-Methyl-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 30

6-{3-Methyl-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 31

5-Methyl-6-{3-chloro-4-[N-(p-chlorophenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 32

5-Methyl-6-{3-chloro-4-[N-(p-chlorophenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 33

6-{3-Chloro-4-[N-(2-pyrid-2'-ylethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 34

6-{3-Chloro-4-[N-(2-pyrid-2'-ylethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 35

5-Methyl-6-{3-chloro-4-[N-(2-pyrid-2'-ylethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 36

5-Methyl-6-{3-chloro-4-[N-(2-pyrid-2'-ylethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 37

6-[3-Chloro-4-(N-allylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 38

6-[3-Chloro-4-(N-allylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 39

6-{3-Chloro-4-[N-(1-benzyl-4-piperidyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 40

6-{3-Chloro-4-[N-(1-benzyl-4-piperidyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 41

6-{3-Chloro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 42

6-{3-Chloro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 43

6-{3-Chloro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 44

6-{3-Chloro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 45

5-Methyl-6-{3-chloro-4-[N-(2-morpholinoethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 46

5-Methyl-6-{3-chloro-4-[N-(2-morpholinoethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 47

6-{3-Fluoro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 48

6-{3-Fluoro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 49

6-(3-Methyl-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 50

6-(3-Methyl-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 51

6-{3-Chloro-4-[N-(3-morpholinopropyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 52

6-{3-Chloro-4-[N-(3-morpholinopropyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 53

6-(3-Chloro-4-[N-(2-[4-methyl-l-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 54

6-(3-Chloro-4-[N-(2-[4-methyl-l-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 55

6-{3-Chloro-4-[N-(2-[4-phenyl-1-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 56

6-{3-Chloro-4-[N-(2-[4-phenyl-1-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 57

6-{3-Chloro-4-[N-(2-[4-pyrid-2'-yl-1-piperazinyl]ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 58

6-{3-Chloro-4-[N-(2-[4-pyrid-2'-yl-1-piperazinyl]ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 59

6-{3-Chloro-4-[N-(2-[4-acetyl-1-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 60

6-{3-Chloro-4-[N-(2-[4-acetyl-1-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.

Claim 61

A pharmaceutical composition comprising a compound as claimed in any one of Claims 1 to 32 in admixture with a pharmaceutically acceptable carrier or diluent.

Claim 62

The use of a compound as claimed in any one of Claims 1 to 32 in the manufacture of a medicament for treatment of cardiac disorders and other prophylaxis and therapy.

Claim 63

A process for preparing compounds as claimed in any one of Claims 1 to 32, which process comprises the steps: (A) reacting a compound of formula (IIIa): [wherein: Q is as defined in Claim 1 ; R 4 ' and R 5 ', respectively, are any one of the groups or atoms defined for R 4 and R 5 in which, if necessary, reactive groups are protected; and Z represents either (i) a hydrogen atom or (ii) a group of formula -A-COR 12 in which A is as defined in Claim 1 and R 12 represents any one of the groups represented by R in which, if necessary, reactive groups are protected] under Friedel-Crafts reaction conditions with a compound of formula (VIIa): (wherein R 1 , R 2 and the dotted line are as defined in Claim 1), to give a compound of formula (IVa): (wherein R 1 , R 2 , R 4 ', R 5 ', Q, Z and the dotted line are as defined above); (B) reacting said compound of formula (IVa) with hydrazine, to give a compound of formula (Ic): (wherein R 1 , R 2 , R , R 5 , Q, Z and the dotted line are as defined above); (C) where Z represents (i) a hydrogen atom, at any appropriate time before, during or after either of steps (A) or (B), reacting the compound containing the hydrogen atom represented by Z in the form of its alkali metal salt with a compound of formula (V): (wherein R 12 and A are as defined above and X represents a halogen atom); and (D) optionally, any one or more of the following reactions in any appropriate order: hydrolysis of any ester group; conversion of a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group or an aralkyloxycarbonyl group to an optionally substituted hydrazinocarbonyl or carbamoyl group; conversion of a nitro group into an amino group and optionally conversion of such an amino group into a mono- or di- alkylamino group; elimination of protecting groups on an amino group; conversion of a carboxy group to an alkoxycarbonyl group; conversion of a single bond represented by the dotted line to a double bond; acylation of appropriate heterocycles; salification.

Claim 64

A process as claimed in Claim 35, which comprises the steps: (C') reacting an alkali metal salt of a compound of formula (II):, (wherein R 1 , R 2 , Q and the dotted line are as defined in Claim 1, and R 10 and R 11 represent any of the groups and atoms represented by R 4 and R 5 in which any reactive groups are protected) with said compound of formula (V), to give a compound of formula (Ia): (wherein R 1 , R 2 , Q, A, R 12 and the dotted line are as defined in Claim 1, and R 10 and R 11 are as defined above); and (D) if necessary, any one of more of the reactions defined in step (D) of Claim 35.

Claim 65

A process as claimed in Claim 35, which comprises the steps: (A") reacting a compound of formula (III): (wherein R 4 , R 5 , Q, A and R 12 are as defined in Claim 35) under Friedel-Crafts reaction conditions with a compound of formula (VII): (wherein R 1 , R 2 and the dotted line are as defined in Claim 1) to give a compound of formula (IV): (wherein R 1 , R 2 , R 4 , R 5 , Q, A, R 12 and the dotted line are as defined in Claim 35); (B") reacting said compound of formula (IV) with hydrazine, to give a compound of formula (Ib): (wherein R 1 , R 2 , R 4 , R 5 , Q, A, R 12 and the dotted line are as defined in Claim 35); and (D) optionally any one or more of the reactions defined in step (D) of Claim 35. 1. A process for preparing compounds of formula (I): wherein: R 1 and R 2 are the same or different and each represents a hydrogen atom or a C 1 -C 6 alkyl group; Q represents an oxygen atom or a sulphur atom; A represents a C 1 -C 6 alkylene group; R represents a hydroxy group, a C 1 -C 6 alkoxy group, an aryloxy group, an aralkyloxy group in which the alkyl part has from 1 to 6 carbon atoms, a group of formula -(NH) n -NR 6 R 7 . wherein n is 0 or 1; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 10 alkyl group, a substituted C 1 -C 10 alkyl group having at least one substituent selected from: (a) halogen atoms, hydroxy groups, C 1 -C 6 alkoxy groups, aryloxy groups, amino groups, amino groups having one or two C l -C 6 alkyl, aryl or heterocyclic substituents, carboxy groups, aliphatic and carbocyclic aromatic acyl groups, substituted C 2 -C 8 aliphatic carboxylic acyl groups having at least one substituent selected from substituents (b) defined hereafter, aliphatic and carbocyclic aromatic carboxylic acylamino groups, C 2 -C 7 alkoxycarbonyl groups, aralkyloxycarbonyl groups where the alkyl part is C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl groups, heterocyclic groups, aryl groups, C 1 -C 6 alkylsulphonyl groups, arylsulphonyl groups, sulphamoyl groups, carbamoyl groups, carbamoyl groups having one or two C 1 -C 6 alkyl substituents, and carbonyl groups having a heterocyclic substituent, C 2 -C 6 alkenyl groups, C 3 -C 7 cycloalkyl groups, aryl groups and heterocyclic groups, or R 6 and R 7 , together with the nitrogen atom to which they are attached, form a heterocyclic group; a group of formula -NH-NH-R 8 , wherein: R 8 represents a C 1 -C 8 aliphatic carboxylic acyl group, a C 2 -C 8 substituted aliphatic carboxylic acyl group having at least one substituent selected from: (b) halogen atoms, C 1 -C 6 alkoxy groups, C 3 -C 7 cycloalkyl groups, aryl groups and heterocyclic groups, a C 2 -C 7 alkoxycarbonyl group, a cinnamoyl group or a carbocyclic aromatic carboxylic acyl group; or a group of formula -NH-N=CH-R 9 , wherein: R 9 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkyl group having at least one halogen substituent or an aryl group; R 4 and R 5 are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkyl group having at least one halogen substituent, a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 7 aliphatic carboxylic acyloxy group, an amino group, a mono- or di-alkylamino group where the or each alkyl group is C 1 -C 6 alkyl, a C 1 -C 7 aliphatic carboxylic acylamino group, a carboxy group, a C 2 -C 7 alkoxycarbonyl group, a carbamoyl group, a carbamoyl group having 1 or 2 C 1 -C 6 alkyl substituents, a ureido group, an alkylureido group wherein the alkyl group is C 1 -C 6 alkyl, a thioureido group, an alkylthioureido group wherein the alkyl group is C 1 -C 6 alkyl, a cyano group or a nitro group; said aryl groups and aryl parts of groups containing an aryl group are C 6 -C 14 carbocyclic aryl groups which are unsubstituted or have at least one substituent selected from substituents (a), C 1 -C 6 alkyl groups and substituted C l -C 6 alkyl groups having at least one of substituents (a); said heterocyclic groups contain from 5 to 14 ring atoms, of which from 1 to 5 are nitrogen, oxygen or sulphur hetero-atoms, said heterocyclic groups being unsubstituted or having at least one substituent selected from said substituents (a), oxygen atoms, C 1 -C 6 alkyl groups and substituted C 1 -C 6 alkyl groups having at least one of said substituents (a); and the dotted line indicates a single or double carbon-carbon bond between the carbon atoms at the 4-and 5-positions of the pyridazinone system; and pharmaceutically acceptable acid addition salts thereof, which process comprises the steps: (A) reacting a compound of formula (IIIa): [wherein: Q is as defined above; R 4 ' and R 5 ', respectively, are any one of the groups or atoms defined for R 4 and R 5 in which, if necessary, reactive groups are protected; and Z represents either (i) a hydrogen atom or ( ii ) a group of formula -A-COR 12 in which A is as defined above and R 12 represents any one of the groups represented by R 3 in which, if necessary, reactive groups are protected] under Friedel-Crafts reaction conditions with a compound of formula (VIIa): (wherein R 1 , R and the dotted line are as defined above), to give a compound of formula (IVa): (wherein R 1 , R 2 , R 4 ', R 5 ', Q, Z and the dotted line are as defined above); (B) reacting said compound of formula (IVa) with hydrazine, to give a compound of formula (Ic): (wherein R 1 , R , R , R 5 ', Q, Z and the dotted line are as defined above); (C) where Z represents (i) a hydrogen atom, at any appropriate time before, during or after either of steps (A) or (B), reacting the compound containing the hydrogen atom represented by Z in the form of its alkali metal salt with a compound of formula (V): (wherein R 12 and A are as defined above and X represents a halogen atom); and (D) optionally, any one or more of the following reactions in any appropriate order: hydrolysis of any ester group; conversion of a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group or an aralkyloxycarbonyl group to an optionally substituted hydrazinocarbonyl or carbamoyl group; conversion of a nitro group into an amino group and optionally conversion of such an amino group into a mono- or di- alkylamino group; elimination of protecting groups on an amino group; conversion of a carboxy group to an alkoxycarbonyl group; conversion of a single bond represented by the dotted line to a double bond; acylation of appropriate heterocycles; salification.

Claim 66

A process as claimed in Claim 1. which comprises the steps: (C') reacting an alkali metal salt of a compound of formula (II): (wherein R 1 . R 2 , Q and the dotted line are as defined in Claim 1, and R 10 and R 11 represent any of the groups and atoms represented by R 4 and R 5 in which any reactive groups are protected) with said compound of formula (V), to give a compound of formula (Ia): (wherein R 1 , R 2 , Q, A, R 12 and the dotted line are as defined in Claim 1, and R 10 and R 11 are as defined above); and (D) if necessary, any one of more of the reactions defined in step (D) of Claim 1.

Claim 67

A process as claimed in Claim 1, which comprises the steps: (A") reacting a compound of formula (III): (wherein R 4 , R 5 , Q, A and R 12 are as defined in Claim 1) under Friedel-Crafts reaction conditions with a compound of formula (VII): (wherein R 1 , R and the dotted line are as defined in Claim 1) to give a compound of formula (IV): (wherein R 1 , R 2 , R 4 , R 5 , Q, A, R 12 and the dotted line are as defined in Claim 1); (B") reacting said compound of formula (IV) with hydrazine, to give a compound of formula (Ib): (wherein R 1 , R 2 , R 4 , R 5 , Q. A, R 12 and the dotted line are as defined in Claim 1); and (D) optionally any one or more of the reactions defined in step (D) of Claim 1.

Claim 68

A process as claimed in any one of Claims 1 to 3, in which: Q in said compound of formula (II), (III) or (IIIa) represents an oxygen atom; A in said compound of formula (III), (IIIa) or (V) represents a C 1 -C 4 alkylene group; R or R 12 in said compound of formula (III), (IIIa) or (V) represents a C 1 -C 4 alkoxy group, a 2.5-dialkylpyrrolyl group in which each alkyl part is C 1 -C 4 alkyl or a group of formula -(NH) n NR 6 R 7 , wherein: n is 0 or 1; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 8 alkyl group, a C 3 -C 6 alkenyl group, a C 5 or C 6 cycloalkyl group, a phenyl group, a phenyl group having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, a substituted heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a ' ) halogen atoms, hydroxy groups, C 1 -C 4 alkoxy groups, dialkylamino groups wherein each alkyl group is C 1 -C 4 alkyl, C2 or C 3 alkoxycarbonyl groups, heterocyclic groups having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, substituted heterocyclic groups having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, phenyl groups and phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent; R 4 and R 5 or R 4 ' and R 5 ' or R 10 and R 11 in said compound of formula (II), (III) or (IlIa) are independently selected from the group consisting of hydrogen atoms, C 1 -C 4 alkyl groups, halogen atoms and nitro groups.

Claim 69

A process as claimed in any one of Claims 1 to 3, in which: R 1 and R 2 in said compound of formula (II), (VII) or (VIIa) are independently selected from the group consisting of hydrogen atoms and methyl groups; Q in said compound of formula (II), (III) or (IIIa) represents an oxygen atom; A in said compound of formula (III), (IIIa) or (V) represents a C 1 -C 4 alkylene group; R 3 or R 12 in said compound of formula (III), (IIIa) or (V) represents a group of formula -(NH) n -NR 6 R 7 , wherein: n is 0; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 5 or C6 cycloalkyl group, a 2,5-dimethylpyrrolyl group, a C or C 4 alkenyl group, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, a substituted heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms and having at least one substituent selected from substituents (a) defined in Claim 1, oxygen atoms, C 1 -C 6 alkyl groups and C 1 -C 6 alkyl groups having at least one substituent (a) defined in Claim 1, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a") C 1 -C 4 alkox y groups, C 2 and C 3 alkoxycarbonyl groups, morpholino groups, thiomorpholino groups, piperazinyl groups, homopiperazinyl groups, phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, pyridyl groups and 1-piperazinyl groups having at the 4-position at least one substituent selected from: (c) phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C 1 -C 4 alkyl groups, substituted C 1 -C 4 alkyl groups having at least one hydroxy substituent, phenyl substituent or phenyl substituent having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, formyl groups, C 2 -C 8 alkanoyl groups. C 2 -C 5 alkoxycarbonyl groups, aralkyloxycarbonyl groups wherein the alkyl part is C 1 -C 4 alkyl and the aryl part is C 6 -C 10 aryl or C 6 -C 10 aryl having at least one halogen, C 1 -C 4 alkyl, C l -C 4 alkoxy or trifluoromethyl substituent, C and C 4 alkenoyl groups, benzoyl groups, benzoyl groups having at least one halogen, sulphamoyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, heterocyclic acyl groups, C 1 -C 4 alkylsulphonyl groups, arylsulphonyl groups wherein the aryl part is C 6 -C 10 aryl or C 6 -C 10 aryl having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, alkylcarbamoyl groups wherein the alkyl part is C 1 -C 4 alkyl and substituted C 2 -C 6 alkanoyl groups having at least one halogen, C 1 -C 4 alkoxy, C 3 -C 7 cycloalkyl, phenyl or heterocyclic substituent; R 4 or R 4 ' or R 10 in said compound of formula (II), (III) or (IIIa) represents a hydrogen atom; and R 5 or R 5 ' or R 11 in said compound of formula (II), (III) or (IIIa) represents a hydrogen atom or a halogen, nitro or methyl group at the 3-position.

Claim 70

A process as claimed in any one of Claims 1 to 3, in which: Q in said compound of formula (II), (III) or (IIIa) represents the oxygen atom; A in said compound of formula (III), (IIIa) or (V) represents the methylene group; R 1 in said compound of formula (II), (VII) or (VIIa) represents the hydrogen atom; R in said compound of formula (II), (VII) or (VIIa) represents the hydrogen atom or the methyl group; R or R 12 in said compound of formula (III), (IIIa) or (V) represents a group of formula - NHR 7 and R 7 represents a C 3 or C 4 alkenyl group, a C 1 -C 6 alkyl group, a heterocyclic group having 5 or 6 ring atoms of which 1 or 2 are nitrogen hetero-atoms, said heterocyclic group being unsubstituted or having at least one substituent selected from C 1 -C 4 alkyl groups and phenylalkyl groups wherein the phenyl part is unsubstituted or itself has at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent and wherein the alkyl part is C 1 -C 4 alkyl, or a substituted C 1 -C 4 alkyl group having at least one substituent selected from: (a"') C 1 -C 4 alkoxy groups, morpholino groups, thiomorpholino groups, 1-piperazinyl groups, phenyl groups, phenyl groups having at least one halogen, alkyl or alkoxy substituent, pyridyl groups and 1-piperazinyl groups having at the 4-position a substituent selected from: (c') phenyl groups, phenyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C 1 -C 4 alkyl groups, C 1 -C 4 alkyl groups having at least one substituent selected from hydroxy substituents, phenyl substituents and phenyl substituents having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkox y or trifluoromethyl substituent, formyl groups, C 2 -C 5 alkanoyl groups, C 2 -C 5 alkanoyl groups having at least one C 1 -C 4 alkox y, halogen, phenyl, C 3 -C 7 cycloalkyl or heterocyclic substituent, C 2 - C 5 alkoxycarbonyl groups, aralkyloxycarbonyl groups where the alkyl part is C l -C 3 alkyl and the aryl part is phenyl or phenyl having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, C and C 4 alkenoyl groups, benzoyl groups, benzoyl groups having at least one halogen, sulphamoyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, heterocyclic acyl groups wherein the heterocyclic part has 5 or 6 ring atoms of which 1 or 2 are nitrogen, oxygen or sulphur hetero-atoms, said heterocyclic group being unsubstituted or having at least one halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy substituent, C 1 -C 4 alkylsulphonyl groups, C 6 -C 10 carbocyclic arylsulphonyl groups, C 6 -C 10 carbocyclic arylsulphonyl groups having at least one halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl substituent, and alkylcarbamoyl groups where the alkyl part is C 1 -C 4 alkyl; R 4 or R 4 ' or R 10 in said compound of formula (II), (III) or (IIIa) represents a hydrogen atom; and R or R or R 11 in said compound of formula (II), (III) or (IIIa) represents a halogen atom or a methyl group at the 3-position.

Claim 71

A process as claimed in any one of Claims 1 to 3, in which: R 1 and R 2 in said compound of formula (II), (VII) or (VIla) are independently selected from the group consisting of hydrogen atoms and C 1 -C 6 alkyl groups; Q in said compound of formula (II), (III) or (IIIa) represents an oxygen atom or a sulfur atom; A in said compound of formula (III), (IIIa) or (V) represents a C 1 -C 6 alkylene group; R 3 or R 12 in said compound of formula (III), (IIIa) or (V) represents a hydroxy group, a C 1 -C 6 alkoxy group, an aryloxy group, an aralkyloxy group in which the alkyl part has from 1 to 6 carbon atoms, or a group of formula -(NH) n -NR 6 R 7 , wherein n is 0 or 1; and R 6 and R 7 are the same or different and each represents a hydrogen atom, a C 1 -C 10 alkyl group, a substituted C 1 -C 10 alkyl group having one or two substituents selected from: (a) halogen atoms, hydroxy groups, C 1 -C 6 alkoxy groups, aryloxy groups, amino groups, amino groups having one or two C 1 -C 6 alkyl, aryl or heterocyclic substituents, carboxy groups, aliphatic and carbocyclic aromatic carboxylic acylamino groups, C 2 -C 7 alkoxycarbonyl groups, C 3 -C 7 cycloalkyl groups, heterocyclic groups and aryl groups, a C 3 -C 7 cycloalkyl group, an aryl group or a 6 7 heterocyclic group, or R and R , together with the nitrogen atom to which they are attached, form a heterocyclic group; R 4 and R 5 or R 4 ' and R 5 ' or R 10 and R 11 in said compound of formula (II), (III) or (IIIa) are independently selected from the group consisting of hydrogen atoms, C 1 -C 6 alkyl groups, C 1 -C 6 alkyl groups having at least one halogen substituent, halogen atoms, C 1 -C 6 alkoxy groups, C 1 -C 7 aliphatic carboxylic acyloxy groups, amino groups, mono- and di-alkylamino groups where the or each alkyl group is C l -C 6 alkyl, C 1 -C 7 aliphatic carboxylic acylamino groups, carboxy groups, C 2 -C 7 alkoxycarbonyl groups, carbamoyl groups, ureido groups, alkylureido groups wherein the alkyl group is C l -C 6 alkyl, thioureido groups, alkylthioureido groups wherein the alkyl group is C 1 -C 6 alkyl, cyano groups and nitro groups.

Claim 72

A process as claimed in any one of Claims 1 to 3, wherein the reagents and reaction steps are so selected as to prepare: 5-Methyl-6-[3-chloro-4-(N-propylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-[3 - chloro-4-(N-butylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-[3-chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone 6-[3-Chloro-4-(N-isobutylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-[3-chloro-4-(N-pentylcarbamoylmethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-5-[3-chloro-4-(N-hexylcarbamoylmethoxy)-phenyl]-4.5-dihydro-3(2H)-pyridazinone 6-(3-Chloro-4-[N-(2-ethoxyethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-[3-chloro-4-(N-phenethylcarbamoyl- methoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(p-methoxyphenethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone 5-Methyl-6-{3-chloro-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Fluoro-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Methyl-4-[N-(3,4-dimethoxyphenethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-{3-chloro-4-[N-(p-chlorophenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(2-pyrid-2 1- ylethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 5-Methyl-6-{3-chloro-4-[N-(2-pyrid-2'-ylethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-[3-Chloro-4-(N-allylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(1-benzyl-4-piperidyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4,[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-3(2H)-pyridazinone 5-Methyl-6-{3-chloro-4-[N-(2-morpholinoethyl)-carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Fluoro-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Methyl-4-[N-(2-morpholinoethyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(3-morpholinopropyl)carbamoyl- methoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(2-[4-methyl-1-piperazinyl]-ethyl)carbamoylmethoxy]phenyl)-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(2-[4-phenyl-l-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone 6-{3-Chloro-4-[N-(2-[4-pyrid-2'-yl-1-piperazinyl]ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone or 6-{3-Chloro-4-[N-(2-[4-acetyl-l-piperazinyl]-ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone or a pharmaceutically acceptable salt thereof.

Claim 73

The use of a compound of formula (I) as defined in Claim 1 or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the treatment of cardiac disorders and for other prophylaxis and therapy.

Claim 74

The use as claimed in Claim 9, wherein said compound is as defined in any one of Claims 1 to 7.

Claim 75

The use as claimed in Claim 9, wherein said compound is any one of the compounds listed in Claim 8.