3-Aminopyridazine derivatives with atypical antidepressant, serotonergic and dopaminergic activities

CG Wermuth, G Schlewer, JJ Bourguignon…

Index: Wermuth; Schlewer; Bourguignon; Maghioros; Bouchet; Moire; Kan; Worms; Biziere Journal of Medicinal Chemistry, 1989 , vol. 32, # 3 p. 528 - 537

Full Text: HTML

Citation Number: 93

Abstract

Minaprine [3-[(~-morpholinoethyl) amino]-4-methyl-6-phenylpyridazine dihydrochloride] is active in most animal models of depression and exhibits in vivo a dual dopaminomimetic and serotoninomimetic activity profile. In an attempt to dissociate these two effects and to ...

 Related Synthetic Route
4-methyl-N-(2-morpholin-4-ylethyl)-6-(4-nitrophenyl)pyridazin-3-amine,dihydrochloride Structure

118269-97-9

4-methyl-N-(2-m...

~59%

6-(4-aminophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine dihydrochloride Structure

118269-96-8

6-(4-aminopheny...

3-chloro-4-methyl-6-(4-nitrophenyl)pyridazine Structure

118270-19-2

3-chloro-4-meth...

~%

6-(4-aminophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine dihydrochloride Structure

118269-96-8

6-(4-aminopheny...

2-hydroxy-2-methyl-4-oxo-4-(o-tolyl)butanoic acid Structure

29242-23-7

2-hydroxy-2-met...

~%

4-methyl-6-(2-methylphenyl)-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-92-4

4-methyl-6-(2-m...

2-Methylacetophenone Structure

577-16-2

2-Methylacetophenone

~%

4-methyl-6-(2-methylphenyl)-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-92-4

4-methyl-6-(2-m...

4-methyl-6-(o-tolyl)pyridazin-3(2H)-one Structure

118270-05-6

4-methyl-6-(o-t...

~%

4-methyl-6-(2-methylphenyl)-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-92-4

4-methyl-6-(2-m...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-methyl-6-(o-tolyl)pyridazine Structure

60855-51-8

3-chloro-4-meth...

~%

4-methyl-6-(2-methylphenyl)-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-92-4

4-methyl-6-(2-m...

Phenylacetone Structure

103-79-7

Phenylacetone

~%

6-benzyl-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118270-00-1

6-benzyl-4-meth...

6-benzyl-4-methylpyridazin-3(2H)-one Structure

118270-13-6

6-benzyl-4-meth...

~%

6-benzyl-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118270-00-1

6-benzyl-4-meth...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

6-benzyl-3-chloro-4-methyl-pyridazine Structure

118270-22-7

6-benzyl-3-chlo...

~%

6-benzyl-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118270-00-1

6-benzyl-4-meth...

(E)-3-(4-chlorobenzylidene)-5-phenylfuran-2(3H)-one Structure

70041-47-3

(E)-3-(4-chloro...

~%

5-[(4-chlorophenyl)methyl]-3-phenyl-1H-pyridazin-6-one Structure

58050-61-6

5-[(4-chlorophe...

4-Chlorobenzaldehyde Structure

104-88-1

4-Chlorobenzaldehyde

~%

5-[(4-chlorophenyl)methyl]-3-phenyl-1H-pyridazin-6-one Structure

58050-61-6

5-[(4-chlorophe...

3-Benzoylpropionic acid Structure

2051-95-8

3-Benzoylpropio...

~%

5-[(4-chlorophenyl)methyl]-3-phenyl-1H-pyridazin-6-one Structure

58050-61-6

5-[(4-chlorophe...

3-chloro-4-methyl-6-phenylpyridazine Structure

28657-39-8

3-chloro-4-meth...

2-(DI-N-PROPYLAMINO)ETHYLAMINE Structure

14165-22-1

2-(DI-N-PROPYLA...

~%

N'-(4-Methyl-6-phenyl-3-pyridazinyl)-N,N-dipropyl-1,2-ethanediami ne ethanedioate (1:2) Structure

118269-77-5

N'-(4-Methyl-6-...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-methyl-6-(p-tolyl)pyridazine Structure

60855-47-2

3-chloro-4-meth...

~%

4-methyl-6-(4-methylphenyl)-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-90-2

4-methyl-6-(4-m...

3-(o-chlorobenzylidene)-5-phenylfuran-2(3H)-one Structure

13294-93-4

3-(o-chlorobenz...

~%

4-[(2-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-83-3

4-[(2-chlorophe...

2-Chlorobenzaldehyde Structure

89-98-5

2-Chlorobenzaldehyde

~%

4-[(2-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-83-3

4-[(2-chlorophe...

3-Benzoylpropionic acid Structure

2051-95-8

3-Benzoylpropio...

~%

4-[(2-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-83-3

4-[(2-chlorophe...

4-(2-Chlorobenzyl)-6-phenyl-3(2H)-pyridazinone Structure

66122-39-2

4-(2-Chlorobenz...

~%

4-[(2-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-83-3

4-[(2-chlorophe...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-(4-chlorobenzyl)-6-phenylpyridazine Structure

118270-15-8

3-chloro-4-(4-c...

~%

4-[(2-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-83-3

4-[(2-chlorophe...

4'-Fluoroacetophenone Structure

403-42-9

4'-Fluoroacetop...

~%

6-(4-fluorophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-88-8

6-(4-fluorophen...

6-(4-fluoro-phenyl)-4-methyl-2H-pyridazin-3-one Structure

68612-32-8

6-(4-fluoro-phe...

~%

6-(4-fluorophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-88-8

6-(4-fluorophen...

1-(2-Methoxyphenyl)ethanone Structure

579-74-8

1-(2-Methoxyphe...

~%

6-(2-methoxyphenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-95-7

6-(2-methoxyphe...

6-PHENYL-3(2H)-PYRIDAZINONE-4-CARBOXYLIC ACID ETHYL ESTER Structure

34753-27-0

6-PHENYL-3(2H)-...

~85%

6-oxo-3-phenyl-1H-pyridazine-5-carboxamide Structure

87769-56-0

6-oxo-3-phenyl-...

ethyl 3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-carboxylate Structure

94011-50-4

ethyl 3-oxo-6-p...

~%

6-oxo-3-phenyl-1H-pyridazine-5-carboxamide Structure

87769-56-0

6-oxo-3-phenyl-...

diethyl 2-phenacylpropanedioate Structure

94011-49-1

diethyl 2-phena...

~%

6-oxo-3-phenyl-1H-pyridazine-5-carboxamide Structure

87769-56-0

6-oxo-3-phenyl-...

diethyl 2-phenacylpropanedioate Structure

94011-49-1

diethyl 2-phena...

~58%

ethyl 3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-carboxylate Structure

94011-50-4

ethyl 3-oxo-6-p...

2-Acetylthiophene Structure

88-15-3

2-Acetylthiophene

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-thiophen-2-ylpyridazin-3-amine,dihydrochloride Structure

94221-54-2

4-methyl-N-(2-m...

2-hydroxy-2-methyl-4-oxo-4-thiophen-2-yl-butyric acid Structure

32176-48-0

2-hydroxy-2-met...

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-thiophen-2-ylpyridazin-3-amine,dihydrochloride Structure

94221-54-2

4-methyl-N-(2-m...

4-methyl-6-(2-thienyl)pyridazin-3-one Structure

28657-57-0

4-methyl-6-(2-t...

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-thiophen-2-ylpyridazin-3-amine,dihydrochloride Structure

94221-54-2

4-methyl-N-(2-m...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-methyl-6-(thien-2-yl)pyridazine Structure

32176-55-9

3-chloro-4-meth...

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-thiophen-2-ylpyridazin-3-amine,dihydrochloride Structure

94221-54-2

4-methyl-N-(2-m...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-methyl-6-(4-nitrophenyl)pyridazine Structure

118270-19-2

3-chloro-4-meth...

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-(4-nitrophenyl)pyridazin-3-amine,dihydrochloride Structure

118269-97-9

4-methyl-N-(2-m...

1-(2-Fluorophenyl)ethanone Structure

445-27-2

1-(2-Fluorophen...

~%

6-(2-fluorophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-89-9

6-(2-fluorophen...

6-(2-fluorophenyl)-4-methylpyridazin-3(2H)-one Structure

118270-03-4

6-(2-fluorophen...

~%

6-(2-fluorophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-89-9

6-(2-fluorophen...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-6-(2-fluorophenyl)-4-methylpyridazine Structure

118270-17-0

3-chloro-6-(2-f...

~%

6-(2-fluorophenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-89-9

6-(2-fluorophen...

2-hydroxy-2-methyllevulinic acid Structure

81416-97-9

2-hydroxy-2-met...

~%

4,6-dimethyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-99-1

4,6-dimethyl-N-...

4,6-dimethyl-2,3-dihydropyridazin-3-one Structure

7007-92-3

4,6-dimethyl-2,...

~%

4,6-dimethyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-99-1

4,6-dimethyl-N-...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4,6-dimethylpyridazine Structure

17258-26-3

3-chloro-4,6-di...

~%

4,6-dimethyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-99-1

4,6-dimethyl-N-...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-ethyl-6-phenylpyridazine Structure

28657-44-5

3-chloro-4-ethy...

~%

4-ethyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

40064-54-8

4-ethyl-N-(2-mo...

1-(2-Aminoethyl)pyrrolidine Structure

7154-73-6

1-(2-Aminoethyl...

3-chloro-4-methyl-6-phenylpyridazine Structure

28657-39-8

3-chloro-4-meth...

~%

4-methyl-6-phenyl-N-(2-pyrrolidin-1-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-78-6

4-methyl-6-phen...

2-(1-Piperidinyl)ethanamine Structure

27578-60-5

2-(1-Piperidiny...

3-chloro-4-methyl-6-phenylpyridazine Structure

28657-39-8

3-chloro-4-meth...

~%

4-methyl-6-phenyl-N-(2-piperidin-1-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-79-7

4-methyl-6-phen...

(E)-3-(4-chlorobenzylidene)-5-phenylfuran-2(3H)-one Structure

70041-47-3

(E)-3-(4-chloro...

~%

4-[(4-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-82-2

4-[(4-chlorophe...

4-Chlorobenzaldehyde Structure

104-88-1

4-Chlorobenzaldehyde

~%

4-[(4-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-82-2

4-[(4-chlorophe...

3-Benzoylpropionic acid Structure

2051-95-8

3-Benzoylpropio...

~%

4-[(4-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-82-2

4-[(4-chlorophe...

5-[(4-chlorophenyl)methyl]-3-phenyl-1H-pyridazin-6-one Structure

58050-61-6

5-[(4-chlorophe...

~%

4-[(4-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-82-2

4-[(4-chlorophe...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-(2-chlorobenzyl)-6-phenylpyridazine Structure

118270-14-7

3-chloro-4-(2-c...

~%

4-[(4-chlorophenyl)methyl]-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine,dihydrochloride Structure

118269-82-2

4-[(4-chlorophe...

3'-Methoxyacetophenone Structure

586-37-8

3'-Methoxyaceto...

~%

6-(3-methoxyphenyl)-4-methyl-N-(2-morpholin-4-ylethyl)pyridazin-3-amine,dihydrochloride Structure

118269-94-6

6-(3-methoxyphe...

2-Morpholinoethanamine Structure

2038-03-1

2-Morpholinoeth...

3-chloro-4-methyl-6-naphthalen-1-yl-pyridazine Structure

28657-42-3

3-chloro-4-meth...

~%

4-methyl-N-(2-morpholin-4-ylethyl)-6-naphthalen-1-ylpyridazin-3-amine,dihydrochloride Structure

118270-01-2

4-methyl-N-(2-m...

ethyl 3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-carboxylate Structure

94011-50-4

ethyl 3-oxo-6-p...

~58%

6-PHENYL-3(2H)-PYRIDAZINONE-4-CARBOXYLIC ACID ETHYL ESTER Structure

34753-27-0

6-PHENYL-3(2H)-...

diethyl 2-phenacylpropanedioate Structure

94011-49-1

diethyl 2-phena...

~%

6-PHENYL-3(2H)-PYRIDAZINONE-4-CARBOXYLIC ACID ETHYL ESTER Structure

34753-27-0

6-PHENYL-3(2H)-...


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