e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

… and potent gastrokinetic agents. 2. Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl] methyl] benzamide …

…, T Morie, T Kon, N Yoshida, T Karasawa…

Index: Kato; Morie; Kon; Yoshida; Karasawa; Matsumoto Journal of Medicinal Chemistry, 1991 , vol. 34, # 2 p. 616 - 624

Full Text: HTML

Citation Number: 45

Abstract

The title compounds (19-55) with a 4-substituted 2-(aminomethy1) morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds la and lb enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2- ...

N-[(4-benzylmorpholin-2-yl)methyl]acetamide Structure

N-[(4-benzylmor...

~%

c-[4-(3,4-dichloro-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(3,4-dichl...

(2-(acetylamino)methyl)morpholine acetyl salt Structure

(2-(acetylamino...

~%

c-[4-(3,4-dichloro-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(3,4-dichl...

N-((4-(3,4-dichlorobenzyl)morpholin-2-yl)methyl)acetamide Structure

N-((4-(3,4-dich...

~%

c-[4-(3,4-dichloro-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(3,4-dichl...

N-[(4-benzylmorpholin-2-yl)methyl]acetamide Structure

N-[(4-benzylmor...

~%

c-[4-(4-methoxy-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(4-methoxy...

(2-(acetylamino)methyl)morpholine acetyl salt Structure

(2-(acetylamino...

~%

c-[4-(4-methoxy-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(4-methoxy...

2-Acetylaminomethyl-4-(p-methoxybenzyl)morpholine Structure

2-Acetylaminome...

~%

c-[4-(4-methoxy-benzyl)-morpholin-2-yl]-methylamine dihydrochloride Structure

c-[4-(4-methoxy...

N-[(4-benzylmorpholin-2-yl)methyl]acetamide Structure

N-[(4-benzylmor...

~%

[4-[(3-fluorophenyl)methyl]morpholin-2-yl]methanamine,dihydrochloride Structure

[4-[(3-fluoroph...

(2-(acetylamino)methyl)morpholine acetyl salt Structure

(2-(acetylamino...

~%

[4-[(3-fluorophenyl)methyl]morpholin-2-yl]methanamine,dihydrochloride Structure

[4-[(3-fluoroph...

N-((4-(3-fluorobenzyl)morpholin-2-yl)methyl)acetamide Structure

N-((4-(3-fluoro...

~%

[4-[(3-fluorophenyl)methyl]morpholin-2-yl]methanamine,dihydrochloride Structure

[4-[(3-fluoroph...

Methyl 4-acetamido-5-chloro-2-ethoxybenzoate Structure

Methyl 4-acetam...

~97%

4-Amino-5-chloro-2-ethoxybenzoic acid Structure

4-Amino-5-chlor...

N-[(4-benzylmorpholin-2-yl)methyl]acetamide Structure

N-[(4-benzylmor...

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

Methyl 4-acetamido-5-chloro-2-ethoxybenzoate Structure

Methyl 4-acetam...

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

Ethopabate Structure

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

2-[(acetylamino)methyl]-4-[3-(trifluoromethyl)benzyl]morpholine Structure

2-[(acetylamino...

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

(2-(acetylamino)methyl)morpholine acetyl salt Structure

(2-(acetylamino...

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

4-Amino-5-chloro-2-ethoxybenzoic acid Structure

4-Amino-5-chlor...

N/A Structure

~%

4-amino-5-chloro-2-ethoxy-N-[[4-[[3-(trifluoromethyl)phenyl]methyl]morpholin-2-yl]methyl]benzamide Structure

4-amino-5-chlor...

N-[(4-benzylmorpholin-2-yl)methyl]acetamide Structure

N-[(4-benzylmor...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

Methyl 4-acetamido-5-chloro-2-ethoxybenzoate Structure

Methyl 4-acetam...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

Ethopabate Structure

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

N-((4-(4-chlorobenzyl)morpholin-2-yl)methyl)acetamide Structure

N-((4-(4-chloro...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

(2-(acetylamino)methyl)morpholine acetyl salt Structure

(2-(acetylamino...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...

4-Amino-5-chloro-2-ethoxybenzoic acid Structure

4-Amino-5-chlor...

C-[4-(4-CHLORO-BENZYL)-MORPHOLIN-2-YL]-METHYLAMINE DIHYDROCHLORIDE Structure

C-[4-(4-CHLORO-...

~%

4-amino-5-chloro-N-[[4-[(4-chlorophenyl)methyl]morpholin-2-yl]methyl]-2-ethoxybenzamide Structure

4-amino-5-chlor...