3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)

Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2...

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1. Verfasser: PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER
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description Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride. NOUVEAUX DERIVES DU B-AMINO-3 NOR-TROPANE.ILS REPONDENT A LA FORMULE:(CF DESSIN DANS BOPI)DANS LAQUELLE R REPRESENTE:-SOIT UN ATOME D'HYDROGENE, Y REPRESENTANT ALORS UN GROUPE ACETYLE,-SOIT UN GROUPE BENZYLE, FLUORO-2 BENZYLE, CHLORO-3 BENZYLE, FLUORO-3 BENZYLE, FLUORO-4 BENZYLE, NITRO-3 BENZYLE, NITRO-4 BENZYLE, METHYL-2 BENZYLE, CHLORO-4 BENZYLE, METHOXY-4 BENZYLE, METHYL-3 BENZYLE, METHYL-4 BENZYLE OU CYCLOHEXYLMETHYLE, Y ETANT ALORS UN ATOME D'HYDROGENE OU UN GROUPE ACETYLE.INTERMEDIAIRES DE SYNTHESE POUR LA PREPARATION DE MEDICAMENTS.
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In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride. NOUVEAUX DERIVES DU B-AMINO-3 NOR-TROPANE.ILS REPONDENT A LA FORMULE:(CF DESSIN DANS BOPI)DANS LAQUELLE R REPRESENTE:-SOIT UN ATOME D'HYDROGENE, Y REPRESENTANT ALORS UN GROUPE ACETYLE,-SOIT UN GROUPE BENZYLE, FLUORO-2 BENZYLE, CHLORO-3 BENZYLE, FLUORO-3 BENZYLE, FLUORO-4 BENZYLE, NITRO-3 BENZYLE, NITRO-4 BENZYLE, METHYL-2 BENZYLE, CHLORO-4 BENZYLE, METHOXY-4 BENZYLE, METHYL-3 BENZYLE, METHYL-4 BENZYLE OU CYCLOHEXYLMETHYLE, Y ETANT ALORS UN ATOME D'HYDROGENE OU UN GROUPE ACETYLE.INTERMEDIAIRES DE SYNTHESE POUR LA PREPARATION DE MEDICAMENTS.</description><language>eng ; fre</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1982</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=19820813&amp;DB=EPODOC&amp;CC=FR&amp;NR=2499570A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76290</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=19820813&amp;DB=EPODOC&amp;CC=FR&amp;NR=2499570A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER</creatorcontrib><title>3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)</title><description>Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride. NOUVEAUX DERIVES DU B-AMINO-3 NOR-TROPANE.ILS REPONDENT A LA FORMULE:(CF DESSIN DANS BOPI)DANS LAQUELLE R REPRESENTE:-SOIT UN ATOME D'HYDROGENE, Y REPRESENTANT ALORS UN GROUPE ACETYLE,-SOIT UN GROUPE BENZYLE, FLUORO-2 BENZYLE, CHLORO-3 BENZYLE, FLUORO-3 BENZYLE, FLUORO-4 BENZYLE, NITRO-3 BENZYLE, NITRO-4 BENZYLE, METHYL-2 BENZYLE, CHLORO-4 BENZYLE, METHOXY-4 BENZYLE, METHYL-3 BENZYLE, METHYL-4 BENZYLE OU CYCLOHEXYLMETHYLE, Y ETANT ALORS UN ATOME D'HYDROGENE OU UN GROUPE ACETYLE.INTERMEDIAIRES DE SYNTHESE POUR LA PREPARATION DE MEDICAMENTS.</description><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS</subject><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1982</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNyrsKwjAUANAuDqL-wx11SGhtpelYxOIgDiI4lku81UCahDyE_L2LH-B0lrMsHjXrZdY4K2OZYOiznim-s2bG-uitQ0PwJK8-gQODFGhKGjCAoeStJheVBHyRiQG21wtUgrdclLt1sZhQB9r8XBUwnO7HMyNnRwoOJRmK43DbN113aMu-qv8oX-kuNw4</recordid><startdate>19820813</startdate><enddate>19820813</enddate><creator>PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER</creator><scope>EVB</scope></search><sort><creationdate>19820813</creationdate><title>3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)</title><author>PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_FR2499570A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; fre</language><creationdate>1982</creationdate><topic>ACYCLIC OR CARBOCYCLIC COMPOUNDS</topic><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>PHILIPPE DOSTERT, THIERRY IMBERT ET BERNARD BUCHER</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)</title><date>1982-08-13</date><risdate>1982</risdate><abstract>Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride. NOUVEAUX DERIVES DU B-AMINO-3 NOR-TROPANE.ILS REPONDENT A LA FORMULE:(CF DESSIN DANS BOPI)DANS LAQUELLE R REPRESENTE:-SOIT UN ATOME D'HYDROGENE, Y REPRESENTANT ALORS UN GROUPE ACETYLE,-SOIT UN GROUPE BENZYLE, FLUORO-2 BENZYLE, CHLORO-3 BENZYLE, FLUORO-3 BENZYLE, FLUORO-4 BENZYLE, NITRO-3 BENZYLE, NITRO-4 BENZYLE, METHYL-2 BENZYLE, CHLORO-4 BENZYLE, METHOXY-4 BENZYLE, METHYL-3 BENZYLE, METHYL-4 BENZYLE OU CYCLOHEXYLMETHYLE, Y ETANT ALORS UN ATOME D'HYDROGENE OU UN GROUPE ACETYLE.INTERMEDIAIRES DE SYNTHESE POUR LA PREPARATION DE MEDICAMENTS.</abstract><oa>free_for_read</oa></addata></record>
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CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
title 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)
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