Claims
- 1. A compound of formula (I): ##STR7## R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen atoms and methyl groups;
- Q represents an oxygen atom;
- A represents a C.sub.1 -C.sub.4 alkylene group;
- R.sup.6 and R.sup.7 are independently selected from the group consisting of hydrogen atoms; C.sub.1 -C.sub.6 alkyl groups; C.sub.5 and C.sub.6 cycloalkyl groups; 2,5-dimethylpyrrolyl groups; C.sub.3 and C.sub.4 alkenyl groups; heterocyclic groups selected from the group consisting of:
- tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiofuryl, tetrahydrothiopyranyl, pyrrolidinyl, piperidyl, imidazolidinyl, oxazolidinyl, thiazolidinyl, morpholinyl, thiomorpholinyl and piperazinyl groups;
- said heterocyclic groups having at least one substituent selected from the group consisting of:
- methyl, ethyl, phenyl, methoxycarbonyl, ethoxycarbonyl, benzyl, oxygen, hydroxyethyl, chlorophenyl, methoxyphenyl, trifluoromethylphenyl, pyridyl, benzhydryl, chlorobenzhydryl, difluorobenzhydryl, formyl, acetyl, valeryl, 3-butenoyl, chlorobutyryl, ethoxyacetyl, benzyloxycarbonyl, methanesulfonyl, toluenesulfonyl, benzoyl, chlorobenzoyl, methoxybenzoyl, nicotinoyl, isonicotinoyl, thenoyl, furoyl, methylcarbamoyl, p-chloro-m-sulfamoylbenzoyl, propionyl, isobutyryl, octanoyl, phenylpropionyl, cyclohexylpropionyl, heptanoyl and dimethoxybenzoyl groups;
- and substituted C.sub.1 -C.sub.4 alkyl groups having at least one substituent selected from the group consisting of:
- C.sub.1 -C.sub.4 alkoxy groups, C.sub.2 and C.sub.3 alkoxycarbonyl groups, morpholino groups, thiomorpholino groups, piperazinyl groups, homopiperazinyl groups, phenyl groups, phenyl groups having at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and trifluoromethyl substituents, pyridyl groups and 1-piperazinyl groups having at the 4-position at least one substituent selected from the group consisting of methyl, ethyl, phenyl, methoxycarbonyl, ethoxycarbonyl, benzyl, oxygen, hydroxyethyl, chlorophenyl, methoxyphenyl, trifluoromethylphenyl, pyridyl, benzhydryl, chlorobenzhydryl, difluorobenzhydryl, formyl, acetyl, valeryl, 3-butenoyl, chlorobutyryl, ethoxyacetyl, benzyloxycarbonyl, methanesulfonyl, toluenesulfonyl, benzoyl, chlorobenzoyl, methoxybenzoyl, nicotinoyl, isonicotinoyl, thenoyl, furoyl, methylcarbamoyl, p-chloro-m-sulfamoylbenzoyl, propionyl, isobutyryl, octanoyl, phenylpropionyl, cyclohexylpropionyl, heptanoyl and dimethoxybenzoyl groups;
- R.sup.4 represents a hydrogen atom; and
- R.sup.5 represents a hydrogen atom, halogen atom, nitro group or methyl group at the 3-position;
- 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.
- 2. A compound as claimed in claim 1 in which
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom or methyl group;
- A represents a methylene group;
- R.sup.6 represents a hydrogen atom;
- R.sup.7 represents C.sub.1 -C.sub.6 alkyl groups; C.sub.3 and C.sub.4 alkenyl groups; heterocyclic groups selected from the group consisting of tetrahydrofuryl, tetrahydropyranyl, tetrahydrothiofuryl, tetrahydrothiopyranyl, pyrrolidinyl, piperidyl, imidazolidinyl, oxazolidinyl, thiazolidinyl, morpholinyl, thiomorpholinyl and piperazinyl groups; said heterocyclic groups having at least one substituent selected from the group consisting of methyl, ethyl, benzyl, benzhydryl, chlorobenzhydryl and difluorobenzhydryl; or substituted C.sub.1 -C.sub.4 alkyl groups having at least one substituent selected from the group consisting of C.sub.1 -C.sub.4 alkoxy groups, morpholino groups, thiomorpholino groups, piperazinyl groups, phenyl groups, phenyl groups having at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy substituents, pyridyl groups and 1-piperazinyl groups having at the 4-position at least one substituent selected from the group consisting of methyl, ethyl, phenyl, methoxycarbonyl, ethoxycarbonyl, benzyl, hydroxyethyl, chlorophenyl, methoxyphenyl, trifluoromethylphenyl, pyridyl, benzhydryl, chlorobenzhydryl, difluorobenzhydryl, formyl, acetyl, valeryl, 3-butenoyl, chlorobutyryl, ethoxyacetyl, benzyloxycarbonyl, methanesufonyl, toluenesulfonyl, benzoyl, chlorobenzoyl, methoxybenzoyl, nicotinoyl, isonicotinoyl, thenoyl, furoyl, methylcarbamoyl, p-chloro-m-sulfamoylbenzoyl, propionyl, isobutyryl, phenylpropionyl, cyclohexylpropionyl and dimethoxybenzoyl groups; and
- R.sup.5 represents a halogen atom or methyl group at the 3-position.
- 3. A method of treating cardiac disorders in a mammal comprising administering to said mammal an effective amount of a compound which potentiates myocardial contractivity, and wherein said compound is the compound of claim 1.
- 4. A method of treating cardiac disorders in a mammal comprising administering to said mammal an effective amount of a compound which potentiates myocrdial contractivity, and wherein said compound is the compound of claim 2.
- 5. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-[4-acetyl-1-piperazinyl]ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 6. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-propylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 7. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-butylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 8. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-isobutylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 9. The compound of claim 1 designated 6-[3-(chloro-4-(N-isobutylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 10. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-pentylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 11. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-hexylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 12. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-ethoxyethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 13. The compound of claim 1 designated 5-methyl-6-[3-chloro-4-(N-phenethylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 14. The compound of claim 1 designated 6-{3-chloro-4-[N-(p-methoxyphenethyl)carbamoylmethoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 15. The compound of claim 1 designated 5-methyl-6-{3-chloro-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 16. The compound of claim 1 designated 6-{3-fluoro-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 17. The compound of claim 1 designated 6-{3-methyl-4-[N-(3,4-dimethoxyphenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 18. The compound of claim 1 designated 5-methyl-6-{3-chloro-4-[N-(p-chlorophenethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 19. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-pyrid-2'-ylethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 20. The compound of claim 1 designated 5-methyl-6-{3-chloro-4-[N-(2-pyrid-2'-ylethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 21. The compound of claim 1 designated 6-[3-chloro-4-(N-allylcarbamoylmethoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 22. The compound of claim 1 designated 6-{3-chloro-4-[N-(1-benzyl-4-piperidyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 23. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-morpholinoethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 24. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-morpholinoethyl)carbamoylmethoxy]phenyl}-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 25. The compound of claim 1 designated 5-methyl-6-{3-chloro-4-[N-(2-morpholinoethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 26. The compound of claim 1 designated 6-{3-fluoro-4-[N-(2-morpholinoethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 27. The compound of claim 1 designated 6-{3-methyl-4-[N-(2-morpholinoethyl)carbamoylmethoxy]phenyl}4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 28. The compound of claim 1 designated 6-{3-chloro-4-[N-(3-morpholinopropyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 29. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-[4-methyl-1-piperazinyl]ethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 30. The compound of claim 1 designated 6-{3-chloro-4-[N-(2-[4-phenyl-1-piperazinylethyl)carbamoylmethoxy]phenyl}-4,5-dihydro-3(2H)-pyridazinone and pharmaceutically acceptable salts thereof.
- 31. The compound of claim 1 designated 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.
Priority Claims (1)
Number |
Date |
Country |
Kind |
59-213968 |
Oct 1984 |
JPX |
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Parent Case Info
This application is a continuation of application Ser. No. 102,756, filed Sept. 24, 1987, which is a continuation of Ser. No. 785,452, filed Oct. 8. 1985, both now abandoned.
Foreign Referenced Citations (2)
Number |
Date |
Country |
1383906 |
Feb 1975 |
GBX |
1488330 |
Dec 1977 |
GBX |
Non-Patent Literature Citations (2)
Entry |
Zoller, Chem Abs 102, 220886h (1985). |
Derwent for Japan 8015/83 (1983). |
Continuations (2)
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Number |
Date |
Country |
Parent |
102756 |
Sep 1987 |
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Parent |
785452 |
Oct 1985 |
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