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Results for phenylacetamides translation from French to English

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French

PHENYLACETAMIDES

English

PHENYL ACETAMIDES

Last Update: 2014-11-25
Usage Frequency: 4
Quality:

French

PHENYLACETAMIDES PRESENTANT UNE ACTION ANTAGONISTE DES LEUCOTRIENES

English

PHENYLACETAMIDES HAVING LEUKOTRIENE-ANTAGONISTIC ACTION

Last Update: 2014-11-25
Usage Frequency: 4
Quality:

French

phenylacetamides appropriés en tant qu'inhibiteurs de protéines kinases

English

phenylacetamides suitable as protein kinase inhibitors

Last Update: 2011-07-27
Usage Frequency: 1
Quality:

French

PHENYLACETAMIDES APPROPRIES EN TANT QU'INHIBITEURS DE PROTEINES KINASES

English

PHENYLACETAMIDES SUITABLE AS PROTEIN KINASE INHIBITORS

Last Update: 2014-11-25
Usage Frequency: 3
Quality:

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French

phenylacetamides substitués et leur utilisation en tant qu'activateurs de la glucokinase

English

substituted phenylacetamides and their use as glucokinase activators

Last Update: 2011-07-27
Usage Frequency: 1
Quality:

French

PHENYLACETAMIDES SUBSTITUES ET LEUR UTILISATION EN TANT QU'ACTIVATEURS DE LA GLUCOKINASE

English

SUBSTITUTED PHENYLACETAMIDES AND THEIR USE AS GLUCOKINASE ACTIVATORS

Last Update: 2011-07-27
Usage Frequency: 7
Quality:

French

PHENYLACETAMIDES A SUBSTITUTION AMINOPYRIDINYLE, AMINOGUANIDINYLE ET ALCOXYGUANIDINYLE UTILISES COMME INHIBITEURS DE PROTEASES

English

AMINOPYRIDINYL-, AMINOGUANIDINYL- AND ALKOXYGUANIDINYL- SUBSTITUTED PHENYL ACETAMIDES AS PROTEASE INHIBITORS

Last Update: 2014-11-25
Usage Frequency: 3
Quality:

French

THIENOPYRIDINE-PHENYLACETAMIDES ET LEURS DERIVES UTILES COMME NOUVEAUX AGENTS ANTI-ANGIOGENIQUES

English

THIENOPYRIDINE-PHENYLACET AMIDES AND THEIR DERIVATIVES USEFUL AS NEW ANTI-ANGIOGENIC AGENTS

Last Update: 2014-11-25
Usage Frequency: 4
Quality:

French

Rendement : 92% Point de fusion : 109-110°C Caractéristiques spectrales : Infrarouge : 3240 cm⁻¹ νNH 1640 cm⁻¹ νCO Résonance Magnétique Nucléaire 1H Solvant CDCl₃ : δ : 1,93 ppm, singulet, 3H, COCH₃ δ : 3,96 ppm, singulet, 3H, OCH₃ EXEMPLE 2 : N[2-(7-METHOXY NAPHT-1-YL) ETHYL] PHENYLACETAMIDE Dissoudre 0,01 mole de chlorhydrate de 2-(7-méthoxy napht-1-yl)éthylamine (obtenu par dissolution de la 2-(7-méthoxy napht-1-yl éthylamine dans l'éther et en faisant barboter un courant d'acide chlorhydrique gazeux puis en essorant le précipité formé) dans 60 ml d'un mélange eau-chloroforme.

English

Yield: 92% Melting point: 109 Spectral characteristics: Infrared: 3240 cm.sup.-1 vNH 1640 cm.sup.-1 vCO 1H Nuclear maonetic resonance, solvent CDCl.sub.3 δ: 1.93 ppm, singlet, 3H, COCH.sub.3 δ: 3.96 ppm, singlet, 3H, OCH.sub.3 EXAMPLE 2 N-[2-(7-methoxynaphth-1-yl)ethyl]phenylacetamide 0.01 mol of 2-(7-methoxynaphth-1-yl)ethylamine hydrochloride (obtained by dissolving 2-(7-methoxynaphth-1-yl)ethylamine in ether and bubbling through a current of hydrogen chloride gas, then spinning down the precipitate formed) is dissolved in 60 ml of a water/chloroform mixture.

Last Update: 2014-12-03
Usage Frequency: 1
Quality:

French

En remplaçant dans les exemples précédents la 2-(7-méthoxy napht-1-yl )éthylamine par la 2-(7-méthoxy napht-2-yl)éthylamine, on obtient : N[2-(7-METHOXY NAPHT-2-YL) ETHYL] ACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] PHENYLACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] ISOBUTYRAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] PROPIONAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] PENTANAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] (2-OXO PYRROLIDIN-1-YL)ACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 4-CHLORO BUTYRAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] PYRROLIDIN-2-ONE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-BROMOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-MORPHOLINOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-{4-[2,3,4-TRIMETHOXY PHENYL) METHYL] PIPERAZIN-1-YL}ACETAMIDE, CHLORHYDRATE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] N METHYL ACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] BENZAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] PARATOLUOYLCARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 4-FLUOROBENZAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 3-TRIFLUOROMETHYLBENZAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 3,5-DICHLOROBENZAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] ISONICOTINAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-THIOPHENECARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-QUINOXALINECARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] INDOL-2-YL CARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-BENZYLAMINOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-(N′,N′ DIETHYL) AMINOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-AMINOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-[4-(4-FLUOROPHENYL)PIPERAZIN-1-YL] ACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL]2-[4-(3-TRIFLUOROMETHYLPHENYL)PIPERAZIN-1-YL] ACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] BUTYRAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 4-IMIDAZOLYLACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] 2-IMIDAZOLINONE 4-CARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] CYCLOHEXANE CARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] CYCLOPROPANECARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] IODOACETAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] FORMAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] CYCLOBUTANE CARBOXAMIDE N[2-(7-METHOXY NAPHT-2-YL) ETHYL] CYCLOPENTANE CARBOXAMIDE Si dans ces synthèses on remplace la 2-(7-méthoxy napht-2-yl)éthylamine par la 2-(6-méthoxy napht-2-yl)éthylamine, on obtient les isomères des produits précédents pour lesquels le groupement méthoxy est en position 6.

English

By replacing 2-(7-methoxynaphth-1-yl)ethylamine in the preceding examples by 2-(7-methoxynaphth-2yl)ethylamine, one obtains: N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]ACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]PHENYLACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]ISOBUTYRAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]PROPIONAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]PENTANAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-(2-OXOPYRROLIDIN-1-YL)ACETAMIDE N-[2-(7-METHOXYNAPHTH-2YL)ETHYL]-4-CHLOROBUTYRAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]PYRROLIDIN-2-ONE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-BROMOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-MORPHOLINOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-{4-[(2,3,4-TRIMETHOXY-PHENYL)METHYL]PIPERAZIN-1-YL}ACETAMIDE HYDROCHLORIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-N-METHYLACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]BENZAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]PARATOLUOYLCARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-4-FLUOROBENZAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-3-TRIFLUOROMETHYLBENZAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-3,5-DICHLOROBENZAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]ISONICOTINAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-THIOPHENECARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-QUINOXALINECARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]INDOL-2-YLCARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-BENZYLAMINOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-(N',N'-DIETHYL)AMINOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-AMINOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-[4-(4-FLUOROPHENYL)PIPERAZIN-1-YL]ACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-[4-(3-TRIFLUOROMETHYLPHENYL)PIPERAZIN-1-YL]ACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]BUTYRAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-4-IMIDAZOLYLACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]-2-IMIDAZOLINONE-4-CARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]CYCLOHEXANECARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]CYCLOPROPANECARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]IODOACETAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]FORMAMIDE N-[2-(7-METHOXYNAPHTH-2-YL)ETHYL]CYCLOBUTANECARBOXAMIDE N-[2-(7-METHOXYNAPHTH-2-YL}ETHYL]CYCLOPENTANECARBOXAMIDE If in these syntheses 2-(7-methoxynaphth-2-yl)ethylamine is replaced by 2-(6-methoxynaphth-2-yl)ethylamine, isomers of the preceding products are obtained with the methoxy group at position 6.

Last Update: 2014-12-03
Usage Frequency: 1
Quality:

French

Recristallisation : toluène Point de fusion : 135-136°C En procédant comme dans les exemples 1, 4 à 29, mais en remplaçant la 6-méthoxy benzoxazolinone par la benzoxazolinone elle même, on obtient : N[2-(3-BENZOXAZOLINONYL) ETHYL]ACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]ISOBUTYRAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]PHENYLACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL](2-OXO 1-PYRROLIDINYL)ACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]4-CHLOROBUTYRAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-PYRROLIDINONE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-BROMOACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-MORPHOLINO ACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL] 1-PIPERAZINYL} ACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]N-METHYLACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]BENZAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]PARATOLUOYLCARBOXAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]4-FLUOROBENZAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-[4-(4-FLUOROPHENYL) 1-PIPERAZINYL] ACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL] 3-TRIFLUOROMETHYL BENZAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL] 3,5-DICHLOROBENZAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]ISONICOTINAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL] INDOL-2-YL CARBOXAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL] 2-BENZYLAMINOACETAMIDE N[2-(3-BENZOXAZOLINONYL) ETHYL]2-(N′,N′ DIETHYL)AMINO ACETAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL]2-AMINOACETAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL]2-[4-(3-TRIFLUOROMETHYLPHENYL) PIPERAZIN-1-YL] ACETAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL]CYCLOHEXANE CARBOXAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL] FORMAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL]CYCLOPROPANE CARBOXAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL] VALERAMIDE N[2-(3-BENZOXAZOLINONYL)ETHYL] CYCLOBUTANE CARBOXAMIDE En procédant comme dans les exemples 1, 4 à 29, mais en remplaçant la 6-méthoxy benzoxazolinone par la benzothiazolinone, on obtient : N[2-(3-BENZOTHIAZOLINONYL) ETHYL]ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]ISOBUTYRAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]PHENYLACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL](2-OXO 1-PYRROLIDINYL)ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]4-CHLOROBUTYRAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-PYRROLIDINONE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-BROMOACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-MORPHOLINO ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL] 1-PIPERAZINYL} ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]N-METHYLACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]BENZAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]PARATOLUOYLCARBOXAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]4-FLUOROBENZAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2[4-(4-FLUOROPHENYL) 1-PIPERAZINYL] ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL] 3-TRIFLUOROMETHYL BENZAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL] 3,5-DICHLOROBENZAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]ISONICOTINAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL] INDOL-2-YL CARBOXAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL] 2-BENZYLAMINOACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-(N′,N′ DIETHYL)AMINO ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-AMINOACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-[4-(3-TRIFLUOROMETHYLPHENYL) PIPERAZIN-1-YL] ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL)ETHYL]CYCLOHEXANE CARBOXAMIDE N[2-(3-BENZOTHIAZOLINONYL)ETHYL] FORMAMIDE N[2-(3-BENZOTHIAZOLINONYL)ETHYL]CYCLOPROPANE CARBOXAMIDE N[2-(3-BENZOTHIAZOLINONYL)ETHYL] VALERAMIDE N[2-(3-BENZOTHIAZOLINONYL)ETHYL] CYCLOBUTANE CARBOXAMIDE En procédant comme dans les exemples 61 à 88, mais en remplaçant la 3-méthyl benzoxazolinone par la benzoxazolinone elle même, on obtient : N[2-(6-BENZOXAZOLINONYL) ETHYL]ACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]ISOBUTYRAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]PHENYLACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL](2-OXO 1-PYRROLIDINYL)ACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]4-CHLOROBUTYRAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]2-PYRROLIDINONE N[2-(6-BENZOXAZOLINONYL) ETHYL]2-BROMOACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]2-MORPHOLINO ACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL] 1-PIPERAZINYL} ACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]N-METHYLACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]BENZAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]PARATOLUOYLCARBOXAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]4-FLUOROBENZAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]2[4-(4-FLUOROPHENYL) 1-PIPERAZINYL] ACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL] 3-TRIFLUOROMETHYL BENZAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL] 3,5-DICHLOROBENZAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]ISONICOTINAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL] INDOL-2-YL CARBOXAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL] 2-BENZYLAMINOACETAMIDE N[2-(6-BENZOXAZOLINONYL) ETHYL]2-(N′,N′ DIETHYL)AMINO ACETAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL]2-AMINOACETAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL]2-[4-(3-TRIFLUOROMETHYLPHENYL) PIPERAZIN-1-YL] ACETAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL]CYCLOHEXANE CARBOXAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL] FORMAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL]CYCLOPROPANE CARBOXAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL] VALERAMIDE N[2-(6-BENZOXAZOLINONYL)ETHYL] CYCLOBUTANE CARBOXAMIDE En procédant comme dans les exemples 61 à 88, mais en remplaçant la 3-méthyl benzoxazolinone par la benzothiazolinone elle même, on obtient : N[2-(6-BENZOTHIAZOLINONYL) ETHYL]ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]ISOBUTYRAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]PHENYLACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL](2-OXO 1-PYRROLIDINYL)ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]4-CHLOROBUTYRAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]2-PYRROLIDINONE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]2-BROMOACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]2-MORPHOLINO ACETAMIDE N[2-(3-BENZOTHIAZOLINONYL) ETHYL]2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL] 1-PIPERAZINYL} ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]N-METHYLACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]BENZAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]PARATOLUOYLCARBOXAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]4-FLUOROBENZAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]2[4-(4-FLUOROPHENYL) 1-PIPERAZINYL] ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL] 3-TRIFLUOROMETHYL BENZAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL] 3,5-DICHLOROBENZAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]ISONICOTINAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL] INDOL-2-YL CARBOXAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL] 2-BENZYLAMINOACETAMIDE N[2-(6-BENZOTHIAZOLINONYL) ETHYL]2-(N′,N′ DIETHYL)AMINO ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL]2-AMINOACETAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL]2-[4-(3-TRIFLUOROMETHYLPHENYL) PIPERAZIN-1-YL] ACETAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL]CYCLOHEXANE CARBOXAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL] FORMAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL]CYCLOPROPANE CARBOXAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL] VALERAMIDE N[2-(6-BENZOTHIAZOLINONYL)ETHYL] CYCLOBUTANE CARBOXAMIDE ETUDE PHARMACOLOGIQUE DES DERIVES DE L'INVENTION EXEMPLE A : ETUDE DE LA TOXICITE AIGUE La toxicité aiguë a été appréciée après administration orale à des lots de 8 souris (26 ± 2 grammes).

English

Recrystallization: toluene Melting point: 135 Using the procedure described in Examples 1 and 4 to 29, but replacing 6-methoxybenzoxazolinone by benzoxazolinone itself, the following are obtained: N-[2-(3-BENZOXAZOLINONYL)ETHYL]ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]ISOBUTYRAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]PHENYLACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-(2-OXO-1-PYRROLIDINYL)ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-4-CHLOROBUTYRAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-PYRROLIDINONE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-BROMOACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-MORPHOLINOACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-(4-[(2,3,4-TRIMETHOXYPHENYL)METHYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-N-METHYLACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]BENZAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-PARA-TOLUENECARBOXAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-4-FLUOROBENZAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-[4-(4-FLUOROPHENYL)-1-PIPERAZINYL]ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-3-(TRIFLUOROMETHYL)BENZAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-3,5-DICHLOROBENZAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]ISONICOTINAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-INDOLECARBOXAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-(BENZYLAMINO)-ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-(N',N'-DIETHYLAMINO)ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-AMINOACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-(4-[3-(TRIFLUOROMETHYL)PHENYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]CYCLOHEXANECARBOXAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]FORMAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]CYCLOPROPANECARBOXAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]VALERAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]CYCLOBUTANECARBOXAMIDE Using the procedure described in Examples 1 and to 29, but replacing 6-methoxybenzoxazolinone by benzothiazolinone, the following are obtained: N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]ISOBUTYRAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]PHENYLACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-(2-OXO-1-PYRROLIDINYL)ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-4-CHLOROBUTYRAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-PYRROLIDINONE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-BROMOACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-MORPHOLINOACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-N-METHYLACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]BENZAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-PARA-TOLUENECARBOXAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-4-FLUOROBENZAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-[4-(4-FLUOROPHENYL)-1-PIPERAZINYL]ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-3-(TRIFLUOROMETHYL)BENZAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-3,5-DICHLOROBENZAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]ISONICOTINAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-INDOLECARBOXAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-(BENZYLAMINO)-ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-(N',N'-DIETHYLAMINO)ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-AMINOACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-{4-[3-(TRIFLUOROMETHYL)PHENYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]CYCLOHEXANECARBOXAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]FORMAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]CYCLOPROPANECARBOXAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]VALERAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]CYCLOBUTANECARBOXAMIDE Using the procedure described in Examples 61 to 88, but replacing 3-methylbenzoxazolinone by benzoxazolinone itself, the following are obtained: N-[2-(6-BENZOXAZOLINONYL)ETHYL]ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]ISOBUTYRAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]PHENYLACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-(2-OXO-1-PYRROLIDINYL)ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-4-CHLOROBUTYRAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-PYRROLIDINONE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-BROMOACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-MORPHOLINOACETAMIDE N-[2-(3-BENZOXAZOLINONYL)ETHYL]-2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-N-METHYLACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]BENZAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-PARA-TOLUENECARBOXAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-4-FLUOROBENZAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-[4-(4-FLUOROPHENYL)-1-PIPERAZINYL]ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-3-(TRIFLUOROMETHYL)-BENZAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-3,5-DICHLOROBENZAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]ISONICOTINAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-INDOLECARBOXAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-(BENZYLAMINO)-ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-(N',N'-DIETHYLAMINO)ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-AMINOACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]-2-(4-[3-(TRIFLUOROMETHYL)PHENYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]CYCLOHEXANECARBOXAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]FORMAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]CYCLOPROPANECARBOXAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]VALERAMIDE N-[2-(6-BENZOXAZOLINONYL)ETHYL]CYCLOBUTANECARBOXAMIDE Using the procedure described in Examples 61 to 88, but replacing 3-methylbenzoxazolinone by benzothiazolinone itself, the following are obtained: N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]ISOBUTYRAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]PHENYLACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-(2-OXO-1-PYRROLIDINYL)ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-4-CHLOROBUTYRAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-PYRROLIDINONE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-BROMOACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-MORPHOLINOACETAMIDE N-[2-(3-BENZOTHIAZOLINONYL)ETHYL]-2-{4-[(2,3,4-TRIMETHOXYPHENYL)METHYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-N-METHYLACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]BENZAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-PARA-TOLUENECARBOXAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-4-FLUOROBENZAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-[4-(4-FLUOROPHENYL)-1-PIPERAZINYL]ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-3-(TRIFLUOROMETHYL)BENZAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-3,5-DICHLOROBENZAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]ISONICOTINAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-INDOLECARBOXAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-(BENZYLAMINO)-ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-(N',N'-DIETHYLAMINO)ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-AMINOACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]-2-{4-[3-(TRIFLUOROMETHYL)PHENYL]-1-PIPERAZINYL}ACETAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]CYCLOHEXANECARBOXAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]FORMAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]CYCLOPROPANECARBOXAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]VALERAMIDE N-[2-(6-BENZOTHIAZOLINONYL)ETHYL]CYCLOBUTANECARBOXAMIDE PHARMACOLOGICAL STUDY OF THE COMPOUNDS OF THE INVENTION EXAMPLE A: STUDY OF ACUTE TOXICITY Acute toxicity was assessed after oral administration to batches of 8 mice (26.+-.2 grams).

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French

Spectrométrie dans l'infrarouge : 1760 cm⁻¹, ν CO (OCON) 1640 cm⁻¹, ν CO (amide) EXEMPLE 64 : N[2-(3-METHYL 6-BENZOXAZOLINONYL) ETHYL]PHENYLACETAMIDE En procédant comme dans l'exemple 61, mais en remplaçant le chlorure d'acétyle par le chlorure de phénacétyle, on obtient le produit du titre.

English

Infrared spectrometry: 1760 cm.sup.-1, ν CO (OCON) 1640 cm.sup.-1, ν CO (amide) EXAMPLE 64 N-[2-(3-METHYL-6-BENZOXAZOLINONYL)ETHYL]PHENYLACETAMIDE Using the procedure described in Example 61, but g acetyl chloride by phenacetyl chloride, the product of the title is obtained.

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French

Solvant de recristallisation : Toluène Point de fusion : 161-162°C Rendement : 86% Spectrométrie dans l'infrarouge : 3300 cm⁻¹, ν N-H (3080-2840) cm⁻¹, ν C-H 1760 cm⁻¹, ν CO (O-CO-N) 1640 cm⁻¹, ν CO (amide) 1625 cm⁻¹, ν C=C (aromatique) Spectrométrie de Résonance Magnétique Nucléaire (CDCl 3 ) : 1,10 ppm, (d, 6H), CH( CH 3 ) 2 2,25 ppm, (multiplet, 1H), CH 3,60 ppm, (multiplet, 2H), CH 2 -NH 3,75 ppm, (s, 3H), OCH 3 3,95 ppm, (t, 2H), CH 2 -N= 6,15 ppm, (signal, 1H), NH 6,65 ppm, (massif, 2H), H 5 , H 7 6,95 ppm, (d, 1H), H 4 EXEMPLE 5 : N[2-(6-METHOXY 3-BENZOXAZOLINONYL) ETHYL] PHENYLACETAMIDE En procédant comme dans l'exemple 2, mais en remplaçant le chlorure d'acétyle par le chlorure de phénacétyle, on obtient le produit du titre.

English

Nuclear Magnetic Resonance Spectrometry (CDCl.sub.3): 1.10 ppm, (d, 6H), CH(CH.sub.3).sub.2 ; 2.25 ppm, (multiplet, 1H), CH; 3.60 ppm, (multiplet, 2H), CH.sub.2 --NH; 3.75 ppm, (s, 3H), OCH.sub.3 ; 3.95 ppm, (t, 2H), CH.sub.2 --N═; 6.15 ppm, (signal, 1H), NH; 6.65 ppm, (unresolved peaks, 2H), H.sub.5, H,.sub.7 ; 6.95 ppm, (d, 1H), H.sub.4. EXAMPLE 5 N-[2-(6-METHOXY-3-BENZOXAZOLINONYL)ETHYL]PHENYLACETAMIDE Using the procedure described in Example 2, but replacing acetyl chloride by phenacetyl chloride, the product of the title is obtained. Infrared spectrometry: 3300 cm.sup.-1, ν N--H; 1760 cm.sup.-1, ν CO(O--CO--N).

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French

Point de fusion : 68°C. Caractéristiques spectrales : infrarouge : ν cm⁻¹ : νC = O : 1760, 1735 νO-CH₃ : 2890 νC = C : 1620, 1615, 1610, 1595 STADE B : N-(METHOXY)-N-(CHLORO)PHENYLACETAMIDE Dissoudre 1,65 g (10 mmoles) du N-(méthoxy)-phénylacétamide dans 30 cm³de chloroforme sec. Placer dans un bain de glace et maintenir à une température de 0°C. Verser ensuite progressivement à l'aide d'une ampoule 1,30 g (1,36 cm³, 12 mmoles) d'hypochlorite de tertiobutyle préalablement dissous dans 20 cm³ de chloroforme.

English

Melting point: 68 Spectral characteristics: Infrared: νcm.sup.-1 : νC=O: 1760, 1735 νO--CH.sub.3 : 2890 νC=C: 1620, 1615, 1620, 1595 Step B: N-(methoxy)-N-(chloro)phenylacetamide Dissolve 1.65 g (10 mmol) of N-(methoxy)-phenylacetamide in 30 cm.sup.3 of dry chloroform. Place in an ice-bath and maintain at a temperature of 0 (1.36 cm.sup.3, 12 mmol) of tert-butyl hypochlorite which has previously been dissolved in 20 cm.sup.3 of chloroform.

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French

Les composés des préparations suivantes sont synthésés suivant des procédés connus de l'homme de l'art développés notamment dans Héterocyclic compounds, vol. 3, John Wiley and Sons, Inc, New York pp 129-146, Julian P.L. et al. Préparation 1 : 1-METHOXY-INDOLIN-2-ONE STADE A : N-(METHOXY)-PHENYLACETAMIDE Introduire dans un ballon 6,8 g (50 mmoles) d'acide phénylacétique acide et 4,6 g (55 mmoles) de chlorhydrate de méthoxylamine, 5,55 g (55 mmoles) de triéthylamine et enfin 10,83 g (52,5 mmoles) de N,N-dicyclohexylcarbodimide.

English

The compounds of the following preparations are synthesised in accordance with processes known to the person skilled in the art and detailed especially in Heterocyclic Compounds, vol. 3, John Wiley and Sons, Inc., New York, pp. 129-146, Julian P. L. et al. PREPARATION 1: 1-METHOXYINDOLIN-2-ONE Step A: N-(methoxy)-phenylacetamide Introduce into a round-bottomed flask 6.8 g (50 mmol) of phenylacetic acid and 4.6 g (55 mmol) of methoxylamine hydrochloride, 5.55 g (55 mmol) of triethylamine and finally 10.83 g (52.5 mmol) of N,N-dicyclohexylcarbodiimide.

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French

Parmi les composés de formule (I) ci-dessus rentrant dans le cadre de la présente invention, on peut notamment citer les suivants (seuls ou en mélange) : N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-benzamide 5-{3'-[(Methyl-pyridin-2-yl-amino)-methyl]-biphenyl-4-ylmethyl}-thiazolidine-2,4-dione N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-benzamide 3-{3'-[(Benzoyl-methyl-amino)-methyl]-biphenyl-4-yl}-2-methyl-propionate d'éthyle Acide 2-methyl-3-(3'-{[methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-yl)-propionique N-[4'-(2-Carbamoyl-propyl)-biphenyl-3-ylmethyl]-N-methyl-benzamide N-Methyl-N-[4'-(2-phenylcarbamoyl-propyl)-biphenyl-3-ylmethyl]-benzamide N-[4'-(2-Hydroxycarbamoyl-propyl)-biphenyl-3-ylmethyl]-N-methyl-benzamide 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl)-3-phenyl-urée 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-1-methyl-3-phenyl-urée [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-methyl-carbamate de tert-butyle N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-nonanamide Acide (S)-2-ethoxy-3-(3'-{[methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-yl)-propionique 2-(3'-{[methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-ylmethyl)-malonate de monométhyle 2-(3'-{[Methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-ylmethyl)-malonate de diméthyle 2-(3'-{[Methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-ylmethyl)-malonamate de méthyle N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-ethyl-benzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-pentyl-benzamide [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-ethyl-carbamate de tert-butyle [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-propyl- carbamate de tert-butyle [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-methyl-carbamate de 9H-fluoren-9-ylmethyle N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-2,2,N-trimethyl-propionamide N-octyl-4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-carboxamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-3-phenylpropionamide 2-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-N-phenyl-acetamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-propyl-benzamide [4'-(2,4-dioxo-thiazolidin-5-ylméthyl)-biphenyl-3-yl]-carbamate de tert-butyle N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-3,4-diethoxy-N-methylbenzamide Acide 2-(3'-{[Methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-ylmethyl)-malonamique N-benzyl-N-méthyl-4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-carboxamide N-benzyl-4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-carboxamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-décanamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-2-phenyl-acetamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-octanamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-heptanamide Acide N-Hydroxy-2-(3'-{[methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-ylmethyl)-malonamique N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-methoxy-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-3 -N-dimethyl-benzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-4-propylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4,N-dimethyl-benzamide. N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl- lsoxazole-5-carboxamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-ethoxy-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-fluoro-N-methyl-benzamide 4-Dimethylamino-N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-nicotinamide 3,5-Dichloro-N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-Thiophene-2-carboxamide N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl- Hexanamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-2-methoxy-N-methylbenzamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl- pyridine-2-carboxamide N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl- furan-2-carboxamide 4-Butoxy-N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl- Thiophene-3-carboxamide Acetate de 4-{[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-methylcarbamoyl}-phenyl N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-hydroxy-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-2 N-dimethyl-benzamide 2-Butyl-N- [4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide 4-Acetylamino-N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-carbamate d'hexyle 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-phenyl-uree N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-phenyl-acetamide 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-methyl-3-phenyl-uree 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-heptyl-1-methyl-uree Ester 4-monométhylique de l'acide 2-{3'-[(Heptanoyl-methyl-amino)-methyl]-biphenyl-4-ylmethyl}-succinique Acide 2-{3'-[(Methyl-octanoyl-amino)-methyl]-biphenyl-4-ylmethyl}-succinique N- [4'-(2,5-dioxo-pyrrolidin-3-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-heptanamide. N-Phenyl-carbamate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)]biphenyle N-Heptyl-carbamate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)]biphenyle Phenyl-acetate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)]biphenyle Nonanoate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)]biphenyle N-Heptyl-carbamate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)]biphenyle N-Phenyl-carbamate de 3-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)]biphenyle N-[6-benzyloxy-4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-6-hydroxy-biphenyl-3-ylmethyl]-N-methyloctanamide N-[4-benzyloxy-4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide N-[4"-(2,4-dioxo-thiazolidin-5-ylmethyl)-[1,1';3',1"]terphenyl-5'-ylmethyl]-N-methyloctanamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-2'-methyl-biphenyl-3-ylmethyl]-N-methyloctanamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-3'-methyl-biphenyl-3-ylmethyl]-N-methyloctanamide Acide (S)-2-Ethoxy-3-{3'-[(methyl-octanoyl-amino)-methyl]-biphenyl-4-yl}-propionique 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-ethyl-3-phenyl-urée N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-docanamide N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-nonanamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-(4-butoxy-phenyl)-acetamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-(4-methoxy-phenyl)-acetamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-(4-ethoxy-phenyl)-acetamide N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-(4-hydroxy-phenyl)-acetamide 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-methyl-3-(4-butoxy-phenyl)-uree 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-methyl-3-(4-methoxy-phenyl)-uree 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-methyl-3-(4-ethoxy-phenyl)-uree 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-1-methyl-3-(4-hydroxy-phenyl)-uree Acide (S)-2-ethoxy-3-(3'-{[methyl-(1-(4-butoxy)-phenylmethanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-ethoxy-3-(3'-{[methyl-(1-(4-methoxy)-phenylmethanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-ethoxy-3-(3'-{[methyl-(1-(4-ethoxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-ethoxy-3-(3'-{[methyl-(1-(4-hydroxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-(3'-{[methyl-(1-(4-butoxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-(3'-{[methyl-(1-(4-methoxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-(3'-{[methyl-(1-(4-ethoxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-(3'-{[methyl-(1-(4-hydroxy-phenyl)-methanoyl)-amino]-methyl}biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-(3'-{[methyl-(1-phenyl-methanoyl)-amino]-methyl}-biphenyl-4-yl)-propionique Acide (S)-2-phenoxy-3-{3'-[(methyl-octanoyl-amino)-methyl]-biphenyl-4-yl}-propionique 5-{3'-[Methyl-(2-oxo-2-phenyl-ethyl)-amino]-biphenyl-4-ylmethyl}-thiazolidine-2,4-dione 5-[3'-(Methyl-phenethyl-amino)-biphenyl-4-ylmethyl]-thiazolidine-2,4-dione [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-methyl-carbamate de phenyle [4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-methyl-carbamate de tert-butyle Selon la présente invention les composés de formule (I) plus particulièrement préférés sont ceux qui présentent l'une au moins des caractéristiques suivantes : R 1 représente le radical de formule (a) ou le radical de formule (b) où R 5 représente un radical hydroxy et R 6 représente le radical OR 10, X représente une liaison de structure choisie parmi -CH 2 -N(R 12 )-CO-, ou -NR12-(CO)-NR13, ou -NR12-(CO)-CH2-, ces liaisons étant lues de gauche à droite ou inversement.

English

DETAILED DESCRIPTION OF BEST MODE AND SPECIFIC/PREFERRED EMBODIMENTS OF THE INVENTION Among the compounds of formula (I) above falling within the context of the present invention, mention may be made in particular of the following (alone or as a mixture): N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl[-N-methylbenzamide; 5-{3′-[(Methylpyrid-2-ylamino)methyl]biphenyl-4-yl-methyl}thiazolidine-2,4-dione; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]benzamide; Ethyl 3-{3′-[(Benzoylmethylamino)methyl]biphenyl-4-yl}-2-methylpropionate; 2-Methyl-3-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-yl)propionic acid; N-[4′-(2-Carbamoylpropyl)biphenyl-3-ylmethyl]-N-methylbenzamide; N-Methyl-N-[4′-(2-phenylcarbamoylpropyl)biphenyl-3-ylmethyl]benzamide; N-[4′-(2-Hydroxycarbamoylpropyl)biphenyl-3-ylmethyl]-N-methylbenzamide; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3-phenylurea; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-1-methyl-3-phenylurea; tert-Butyl [4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]methylcarbamate; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylnonanamide; (S)-2-Ethoxy-3-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-yl)propionic acid; Monomethyl 2-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-ylmethyl)malonate; Dimethyl 2-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-ylmethyl)malonate; Methyl 2-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-ylmethyl)malonamate; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-ethylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-pentylbenzamide; tert-Butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]ethylcarbamate; tert-Butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]propylcarbamate; 9H-Fluoren-9-ylmethyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamate; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2,2,N-trimethylpropionamide; N-Octyl-4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-carboxamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl-N-methyl]-3-phenylpropionamide; 2-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-N-phenylacetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-propylbenzamide; tert-Butyl [4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]carbamate; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3,4-diethoxy-N-methylbenzamide; 2-(3′-{[Methyl-(1-phenylmethanoyl)amino]methyl}-biphenyl-4-ylmethyl)malonamic acid; N-Benzyl-N-methyl-4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-carboxamide; N-Benzyl-4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-carboxamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyldecanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-2-phenylacetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyloctanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylheptanamide; N-Hydroxy-2-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-ylmethyl)malonamic acid; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-methoxy-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3-methoxy-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-3,N-dimethylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyl-4-propylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4,N-dimethylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylisoxazole-5-carboxamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-ethoxy N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-fluoro-N-methylbenzamide; 4-Dimethylamino-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylnicotinamide; 3,5-Dichloro-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-2-carboxamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylhexanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2-methoxy-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylpyridine-2-carboxamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylfuran-2-carboxamide; 4-Butoxy-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylthiophene-3-carboxamide; 4-{[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}phenyl acetate; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-hydroxy-N-methylbenzamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-2N-dimethylbenzamide; 2-Butyl-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide; 4-Acetylamino-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide; Hexyl N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylcarbamate; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-3-phenylurea; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-phenylacetamide; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-methyl-3-phenylurea; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-3-heptyl-1-methylurea; 4-Monomethyl ester of 2-{3′-[(heptanoylmethylamino)-methyl]biphenyl-4-ylmethyl)succinic acid; 2-{3′-[(Methyloctanoylamino)methyl]biphenyl-4-yl-methyl}succinic acid; N-[4′-(2,5-Dioxopyrrolidin-3-ylmethyl)biphenyl-3-yl-methyl]-N-methylheptanamide; 3-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)]biphenyl N-phenylcarbamate; 3-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)]biphenyl N-heptylcarbamate; 3-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)]biphenyl phenylacetate; 3-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)]biphenyl nonanoate; 3-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)]biphenyl N-heptylcarbamate; 3-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)]biphenyl N-phenylcarbamate; N-[6-Benzyloxy-4′-(2,4-dioxothiazolidin-5-ylidene-methyl)biphenyl-3-ylmethyl]-N-methyloctanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-6-hydroxybiphenyl-3-ylmethyl]-N-methyloctanamide; N-[4-Benzyloxy-4′-(2,4-dioxothiazolidin-5-ylidene-methyl)biphenyl-3-ylmethyl]-N-methyloctanamide; N-[4″-(2,4-Dioxothiazolidin-5-ylmethyl)-[1,1′;3′,1″]terphenyl-5′-ylmethyl]-N-methyloctanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-2′-methylbiphenyl-3-ylmethyl]-N-methyloctanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-3′-methylbiphenyl-3-ylmethyl]-N-methyloctanamide; (S)-2-Ethoxy-3-{3′-[(methyloctanoylamino)methyl]-biphenyl-4-yl}propionic acid; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-ethyl-3-phenylurea; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyldecanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methylnonanamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-(4-butoxyphenyl)acetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-(4-methoxyphenyl)acetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-(4-ethoxyphenyl)acetamide; N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-(4-hydroxy phenyl)acetamide; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-methyl-3-(4-butoxyphenyl)urea; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-methyl-3-(4-methoxyphenyl)urea; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-methyl-3-(4-ethoxyphenyl)urea; 1-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-1-methyl-3-(4-hydroxy phenyl)urea; (S)-2-Ethoxy-3-(3′-{[methyl-(1-(4-butoxy)phenyl-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Ethoxy-3-(3′-{[methyl-(1-(4-methoxy)phenyl-methanoyl)amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Ethoxy-3-(3′-{[methyl-(1-(4-ethoxyphenyl)-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Ethoxy-3-(3′-{[methyl-(1-(4-hydroxy phenyl)-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-(3′-{[methyl-(1-(4-butoxyphenyl)-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-(3′-{[methyl-(1-(4-methoxyphenyl)-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-(3′-{[methyl-(1-(4-ethoxyphenyl)-methanoyl)amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-(3′-{[methyl-(1-(4-hydroxy phenyl)-methanoyl) amino]methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-yl)propionic acid; (S)-2-Phenoxy-3-{3′-[(methyloctanoylamino)methyl]-biphenyl-4-yl}propionic acid; 5-{3′-[Methyl-(2-oxo-2-phenyl ethyl)amino]biphenyl-4-ylmethyl}thiazolidine-2,4-dione; 5-[3′-(Methylphenethylamino)biphenyl-4-ylmethyl]-thiazolidine-2,4-dione; Phenyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]methylcarbamate; and tert-Butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]methylcarbamate.

Last Update: 2014-12-03
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French

On obtient 100 mg (65%) du produit attendu de point de fusion 137-8°C. EXEMPLE 24 N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-3-phenyl-propionamide (a) N -[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methyl-3-phenyl-propionamide De manière analogue à l'exemple 1(d) par réaction de 500 mg (0,9 mmol) de 5-(3'-Methylaminomethyl-biphenyl-4-ylmethylene)-thiazolidine-2,4-dione ( préparé en 10(c)) avec 0,35 ml (2,3 mmol) de chlorure de 3-phenyl-propionyle, on obtient 220 mg (54%) de produit attendu. (b) N -[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]- N -methyl-3-phenyl-propionamide De manière analogue à l'exemple 1(g) à partir de 210 mg (0,45 mmol) de N -[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methyl-3-phenyl-propionamide dans 15 ml de tétrahydrofuranne, on obtient 95 mg (45%) du produit voulu de point de fusion 325°C. EXEMPLE 25 2-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-N-phenylacetamide (a) 2-(3-Bromo-phenyl)- N -methyl- N -phenyl-acetamide Dans un tricol sous courant d'azote, on introduit 6 g (28 mmol) d'acide (3-Bromo-phenyl)-acétique dans 50 ml de dichlorométhane.

English

100 mg (65%) of the expected product, with a melting point of 137-138° C., are obtained. EXAMPLE 24 N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyl-3-phenylpropionamide (a) N-[4′-(2,4-Dioxothiazolidin-5-ylidene-methyl)biphenyl-3-ylmethyl]-N-methyl-3-phenyl-propionamide In a manner similar to that of Example 1(d), by reacting 500 mg (0.9 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethylene)thiazolidine-2,4-dione (prepared in Example 10(c)) with 0.35 ml (2.3 mmol) of 3-phenylpropionyl chloride, 220 mg (54%) of the expected product are obtained. (b) N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-3-phenylpropionamide In a manner similar to that of Example 1(g), starting with 210 mg (0.45 mmol) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-methyl-3-phenylpropionamide in 15 ml of tetrahydrofuran, 95 mg (45%) of the desired product, with a melting point of 325° C., are obtained. EXAMPLE 25 2-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-3-phenylacetamide (a) 2-(3-Bromophenyl)-N-methyl-N-phenylacetamide 6 g (28 mmol) of (3-bromophenyl)acetic acid in 50 ml of dichloromethane are introduced into a three-necked flask under a stream of nitrogen.

Last Update: 2014-12-03
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French

On recueille après évaporation des solvants 150 mg (33%) de 1-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-phenyl-uree sous la forme d'un solide blanc de point de fusion 185°C. EXEMPLE 63 N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-N-methyl-2-phenylacetamide (a) (3-Bromo-phenyl)-methyl-amine Dans un tricol et sous azote, on introduit 10 g (58 mmol) de 3-bromoaniline et 34 ml (203 mmol) de triéthylorthoformate.

English

After evaporation of the solvents, 150 mg (33%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]-3-phenylurea are obtained in the form of a white solid with a melting point of 185° C. EXAMPLE 63 N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-N-methyl-2-phenylacetamide (a) (3-Bromophenyl)methylamine 10 g (58 mmol) of 3-bromoaniline and 34 ml (203 mmol) of triethylorthoformate are introduced into a three-necked flask under nitrogen.

Last Update: 2014-12-03
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French

On obtient 5, 7 g (67%) du produit voulu de point de fusion 60°C. (b) 2-(4'-Acetyl-biphenyl-3-yl)- N -methyl- N -phenyl-acetamide De manière analogue à l'exemple 1 (e) par réaction de 2,9 g (9,5 mmol) de 2-(3-Bromo-phenyl)- N -methyl- N -phenyl-acetamide avec 2,2 g (14,2 mmol) d'acide 4-formylbenzèneboronique, on obtient 2,25 g (95%) de produit attendu. (c) 2-[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]- N -methyl- N -phenyl-acetamide De manière analogue à l'exemple 1 (f) par réaction de 1 g (4 mmol) de 2-(4'-Acetyl-biphenyl-3-yl)- N -methyl- N -phenyl-acetamide avec 460 mg (4 mmol) de 2,4-thiazolidinedione, on obtient 1,2 g (71 %) de produit attendu. (d) 2-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]- N -methyl- N -phenylacetamide De manière analogue à l'exemple 1(g) à partir de 1,1 g (2,6 mmol) de 2-[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]- N -methyl- N -phenyl-acetamide dans 20 ml d'acétate d'éthyle et 20 ml d'éthanol, on obtient 660 mg (60%) du produit voulu de point de fusion 158°C. EXEMPLE 26 N-[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-propylbenzamide (a) (3-Bromo-benzyl)-propyl-carbamate de tert-butyle De manière analogue à l'exemple 17(d) à partir de 3 g (10,5 mmol) de (3-Bromo-benzyl)-carbamate de tert-butyle et de 1,15 ml (11,5 mmol) d'iodopropane, on obtient 3,35 g (97%) de produit voulu. (b) (3-Bromo-benzyl)-propyl-amine De manière analogue à l'exemple 10(c) à partir de 2 g (6 mmol) de (3-Bromo-benzyl)-propyl-carbamate de tert-butyle, on obtient 1,3 g (92%) du produit voulu. (c) N -(3-Bromo-benzyl)- N -propyl-benzamide De manière analogue à l'exemple 1(d) par réaction de 1,3 g (5,6 mmol) de (3-Bromo-benzyl)-propyl-amine avec 700 µl (6,2 mmol) de chlorure de benzoyle, on obtient 1,4 g (74%) de produit attendu. (d) N -(4'-Formyl-biphenyl-3-ylmethyl)- N -propyl-benzamide De manière analogue à l'exemple 1 (e) par réaction de 1,4 g (4,2 mmol) de N -(3-Bromo-benzyl)- N -propyl-benzamide avec 940 mg (6,2 mmol) d'acide 4-formylbenzèneboronique, on obtient 780 mg (53%) de produit attendu. (e) N-[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-propyl-benzamide De manière analogue à l'exemple 1(f) par réaction de 580 mg (1,6 mmol) de N -(4'-Formyl-biphenyl-3-ylmethyl)- N -propyl-benzamide avec 190 mg (1,6 mmol) de 2,4-thiazolidinedione, on obtient 530 mg (72%) de produit attendu de point de fusion 250-1°C. EXEMPLE 27 [4'-(2,4-dioxo-thiazolidin-5-ylméthyl)-biphenyl-3-yl]-carbamate de tert-butyle (a) (3-Bromo-phenyl)-carbamate de tert -butyle Dans un tricol sous courant d'azote, on introduit 19 ml de 3-bromoaniline dans 300 ml de tétrahydrofuranne.

English

5.7 g (67%) of the desired product, with a melting point of 60° C., are obtained. (b) 2-(4′-Acetylbiphenyl-3-yl)-N-methyl-N-phenylacetamide In a manner similar to that of Example 1(e), by reacting 2.9 g (9.5 mmol) of 2-(3-bromophenyl)-N-methyl-N-phenylacetamide with 2.2 g (14.2 mmol) of 4-formylbenzene boronic acid, 2.25 g (95%) of the expected product are obtained. (c) 2-[4′-(2,4-Dioxothiazolidin-5-ylidene-methyl)biphenyl-3-yl]-N-methyl-N-phenylacetamide In a manner similar to that of Example 1(f), by reacting 1 g (4 mmol) of 2-(4′-acetylbiphenyl-3-yl)-N-methyl-N-phenylacetamide with 460 mg (4 mmol) of 2,4-thiazolidine dione, 1.2 g (71%) of the expected product are obtained. (d) 2-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl)-N-methyl-N-phenylacetamide In a manner similar to that of Example 1(g), starting with 1.1 g (2.6 mmol) of 2-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]-N-methyl-N-phenylacetamide in 20 ml of ethyl acetate and 20 ml of ethanol, 660 mg (60%) of the desired product, with a melting point of 158° C., are obtained. EXAMPLE 26 N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-propylbenzamide (a) tert-Butyl (3-bromo benzyl)propylcarbamate In a manner similar to that of Example 17(d), starting with 3 g (10.5 mmol) of tert-butyl (3-bromo-benzyl) carbamate and 1.15 ml (11.5 mmol) of iodopropane, 3.35 g (97%) of the desired product are obtained. (b) (3-Bromo benzyl)propylamine In a manner similar to that of Example 10(c), starting with 2 g (6 mmol) of tert-butyl (3-bromo-benzyl)propylcarbamate, 1.3 g (92%) of the desired product are obtained. (c) N-(3-Bromo benzyl)-N-propylbenzamide In a manner similar to that of Example 1(d), by reacting 1.3 g (5.6 mmol) of (3-bromo benzyl)propylamine with 700 μl (6.2 mmol) of benzoyl chloride, 1.4 g (74%) of the expected product are obtained. (d) N-(4′-Formylbiphenyl-3-ylmethyl)-N-propylbenzamide In a manner similar to that of Example 1(e), by reacting 1.4 g (4.2 mmol) of N-(3-bromo benzyl)-N-propylbenzamide with 940 mg (6.2 mmol) of 4-formylbenzene boronic acid, 780 mg (53%) of the expected product are obtained. (e) N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-propylbenzamide In a manner similar to that of Example 1(f), by reacting 580 mg (1.6 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-propylbenzamide with 190 mg (1.6 mmol) of 2,4-thiazolidine dione, 530 mg (72%) of the expected product, with a melting point of 250-251° C., are obtained. EXAMPLE 27 tert-Butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-yl]carbamate (a) tert-Butyl (3-bromophenyl)carbamate ml of 3-bromoaniline in 300 ml of tetrahydrofuran are introduced into a three-necked flask under a stream of nitrogen.

Last Update: 2014-12-03
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French

EXEMPLE 33 N-[4'-(2,4-Dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-yl]-2-phenyl-acetamide (a) 5-(3'-Amino-biphenyl-4-ylmethylene)-thiazolidine-2,4-dione De manière analogue à 10c, à partir de 5 g (13 mmol) de [4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-carbamate de tert -butyle ( préparé en 27(c) ), on obtient 5,2 g (100%) du produit attendu. (b) N -[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-2-phenylacetamide De manière analogue à l'exemple 1 (d) par réaction de 1,2 g (2,3 mmol) de 5-(3'-Amino-biphenyl-4-ylmethylene)-thiazolidine-2,4-dione avec 430 µl (3 mmol) de chlorure de phénylacétyle, on obtient 920 mg (97%) de produit attendu. (c) N -[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-2-phenylacetamide De manière analogue à l'exemple 1 (g) à partir de 580 mg (1,4 mmol) de N -[4'-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-2-phenyl-acetamide dans 10 ml d'un mélange dioxanne-méthanol (50-50) sous 3 atm, on obtient 140 mg (15%) du produit voulu de point de fusion 165°C. EXEMPLE 34 N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide (a) N -[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methyloctanamide De manière analogue à l'exemple 1(d) par réaction de 500 mg (0,9 mmol) de 5-(3'-Methylaminomethyl-biphenyl-4-ylidenemethyl)-thiazolidine-2,4-dione préparé en 10c avec 170 µl (1 mmol) de chlorure d'octanoyle, on obtient 250 mg (62%) de produit attendu. (b) N -[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]- N -methyloctanamide De manière analogue à l'exemple 1 (g) à partir de 220 mg (0,5 mmol) de N -[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methyloctanamide dans 10 ml de dioxanne, on obtient 120 mg (53%) du produit voulu de point de fusion 36°C. EXEMPLE 35 N-[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylheptanamide (a) N -[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methylheptanamide De manière analogue à l'exemple 1(d) par réaction de 1 g (1,8 mmol) de 5-(3'-Methylaminomethyl-biphenyl-4-ylidenemethyl)-thiazolidine-2,4-dione ( préparé en 10(c) )avec 300 µl (2 mmol) de chlorure d'heptanoyle, on obtient 450 mg (57%) du produit attendu. (b) N -[4'-(2,4-dioxo-thiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]- N -methylheptanamide De manière analogue à l'exemple 1(g) à partir de 360 mg (0,8 mmol) de N -[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]- N -methylheptanamide dans 15 ml de dioxanne, sous 3 atm, on obtient 230 mg (66%) du produit voulu sous la forme d'un film incolore.

English

EXAMPLE 33 N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-2-phenylacetamide (a) 5-(3′-Aminobiphenyl-4-ylmethylene)-thiazolidine-2,4-dione In a manner similar to that of Example 10c, starting with 5 g (13 mmol) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]carbamate (prepared in Example 27(c)), 5.2 g (100%) of the expected product are obtained. (b) N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-2-phenylacetamide In a manner similar to that of Example 1(d), by reacting 1.2 g (2.3 mmol) of 5-(3′-aminobiphenyl-4-ylmethylene)thiazolidine-2,4-dione with 430 μl (3 mmol) of phenylacetyl chloride, 920 mg (97%) of the expected product are obtained. (c) N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-2-phenylacetamide In a manner similar to that of Example 1(g), starting with 580 mg (1.4 mmol) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]-2-phenylacetamide in 10 ml of a dioxane/methanol mixture (50/50) under 3 atm, 140 mg (15%) of the desired product, with a melting point of 165° C., are obtained. EXAMPLE 34 N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyloctanamide (a) N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide In a manner similar to that of Example 1(d), by reacting 500 mg (0.9 mmol) of 5-(3′-methylamino-methylbiphenyl-4-ylidenemethyl)thiazolidine-2,4-dione prepared in Example 10c with 170 μl (1 mmol) of octanoyl chloride, 250 mg (62%) of the expected product are obtained. (b) N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyloctanamide In a manner similar to that of Example 1(g), starting with 220 mg (0.5 mmol) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-methyloctanamide in 10 ml of dioxane, 120 mg (53%) of the desired product, with a melting point of 36° C., are obtained. EXAMPLE 35 N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylheptanamide (a) N-[4′-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-ylmethyl]-N-methylheptanamide In a manner similar to that of Example 1(d), by reacting 1 g (1.8 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylidenemethyl)thiazolidine-2,4-dione (prepared in Example 10(c)) with 300 μl (2 mmol) of heptanoyl chloride, 450 mg (57%) of the expected product are obtained. (b) N-[4′-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylheptanamide In a manner similar to that of Example 1(g), starting with 360 mg (0.8 mmol) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-methylheptanamide in 15 ml of dioxane, under 3 atm, 230 mg (66%) of the desired product are obtained in the form of a colorless film.

Last Update: 2014-12-03
Usage Frequency: 1
Quality:

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