GT201200182A - Procedimiento de síntesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmacéuticas que la contienen - Google Patents

Procedimiento de síntesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmacéuticas que la contienen

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Publication number
GT201200182A
GT201200182A GT201200182A GT201200182A GT201200182A GT 201200182 A GT201200182 A GT 201200182A GT 201200182 A GT201200182 A GT 201200182A GT 201200182 A GT201200182 A GT 201200182A GT 201200182 A GT201200182 A GT 201200182A
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GT
Guatemala
Prior art keywords
formula compound
hexahydrociclopenta
propoxi
pirrol
cis
Prior art date
Application number
GT201200182A
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English (en)
Inventor
Nicolas Robert
Jean-Pierre Lecouve
Jean-Michel Lerestif
Marina Gaillard
Julie Raymonde Laurence Delcroix
Phillippe Letellier
Mathieu Boiret
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Publication date
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Publication of GT201200182A publication Critical patent/GT201200182A/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Abstract

PROCESO PARA LA SÍNTESIS INDUSTRIAL DEL COMPUESTO DE FÓRMULA (I) (4 - {3 - [CIS-HEXAHIDROCICLOPENTA [C] PIRROL-2 (1H)-IL] PROPOXI} BENZAMIDA), CARACTERIZADO PORQUE EL COMPUESTO DE FÓRMULA (II) SE HACE REACCIONAR CON AMONIACO A UNA TEMPERATURA SUPERIOR A 100 GRADOS C PARA FORMAR EL COMPUESTO DE FÓRMULA (III) QUE SE REDUCE PARA PRODUCIR LA AMINA BICÍCLICO DE FÓRMULA (IV), QUE ESTE ÚLTIMO COMPUESTO SE SOMETE POSTERIORMENTE A - YA SEA A UNA REACCIÓN DE ACOPLAMIENTO, EN CONDICIONES BÁSICAS CONDICIONES EN UN MEDIO POLAR, CON UN COMPUESTO DE FÓRMULA (V) EN LA QUE LOS SUSTITUYENTES SON COMO SE DESCRIBE EN LA ESPECIFICACIÓN, - O AMINACIÓN REDUCTORA, EN UN MEDIO ÁCIDO, CON UN COMPUESTO DE FÓRMULA (V ') EN DONDE LOS SUSTITUYENTES SON COMO SE DESCRIBE EN LA ESPECIFICACIÓN, - O A AMINACIÓN REDUCTORA CON EL COMPUESTO DE FÓRMULA (V ") PARA DAR LA BASE LIBRE DEL COMPUESTO DE FÓRMULA (I), QUE SE COLOCA EN PRESENCIA DE HCL (ÁCIDO CLORHÍDRICO) PARA FORMAR EL COMPUESTO DE FÓRMULA (I), QUE SE AÍSLA EN FORMA DE UN SÓLIDO.
GT201200182A 2011-06-08 2012-06-07 Procedimiento de síntesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmacéuticas que la contienen GT201200182A (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1101746A FR2976285B1 (fr) 2011-06-08 2011-06-08 Procede de synthese et forme cristalline du chlorhydrate de 4-{3-[cis-hexahydrocypenta[c]pyrrol-2(1h)-yl]propoxy}benzamide ainsi que les compositions pharmaceutiques qui la contiennent

Publications (1)

Publication Number Publication Date
GT201200182A true GT201200182A (es) 2014-09-18

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GT201200182A GT201200182A (es) 2011-06-08 2012-06-07 Procedimiento de síntesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmacéuticas que la contienen

Country Status (43)

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US (3) US8664408B2 (es)
EP (1) EP2532651B1 (es)
JP (2) JP5680022B2 (es)
KR (2) KR20120136296A (es)
CN (1) CN102816102A (es)
AP (1) AP2012006280A0 (es)
AR (1) AR086848A1 (es)
AU (1) AU2012203062B2 (es)
BR (1) BR102012013573A2 (es)
CA (1) CA2779045C (es)
CL (1) CL2012001500A1 (es)
CO (1) CO6580197A1 (es)
CR (1) CR20120274A (es)
CU (1) CU20120087A7 (es)
CY (1) CY1116739T1 (es)
DK (1) DK2532651T3 (es)
EA (1) EA022741B1 (es)
EC (1) ECSP12011941A (es)
ES (1) ES2554933T3 (es)
FR (1) FR2976285B1 (es)
GE (1) GEP20156395B (es)
GT (1) GT201200182A (es)
HR (1) HRP20151073T1 (es)
HU (1) HUE028050T2 (es)
IL (1) IL219925A0 (es)
MA (1) MA33883B1 (es)
MD (1) MD4345C1 (es)
ME (1) ME02346B (es)
MX (1) MX2012006525A (es)
NI (1) NI201200102A (es)
PE (1) PE20130046A1 (es)
PL (1) PL2532651T3 (es)
PT (1) PT2532651E (es)
RS (1) RS54279B1 (es)
RU (1) RU2013158817A (es)
SG (1) SG186546A1 (es)
SI (1) SI2532651T1 (es)
SV (1) SV2012004237A (es)
TN (1) TN2012000254A1 (es)
TW (1) TWI499584B (es)
UY (1) UY34110A (es)
WO (1) WO2012168657A1 (es)
ZA (1) ZA201204183B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3003466B1 (fr) 2013-03-22 2015-08-07 Servier Lab Utilisation du 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide pour le traitement des douleurs neuropathiques
CN103601666B (zh) * 2013-11-28 2015-09-02 遵义医学院 八氢环戊烷[c]吡咯的制备方法
CN104387313B (zh) * 2014-10-22 2015-12-30 滨海博大化工有限公司 一种1,2-环戊二甲酰亚胺的制备方法
KR101966221B1 (ko) * 2017-06-14 2019-04-12 최상근 유해가스 처리 장치
CN115232058A (zh) * 2022-08-01 2022-10-25 上海巽田科技股份有限公司 一种格列齐特中间体1,2-环戊二甲酰胺的合成方法

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US756120A (en) * 1902-07-28 1904-03-29 Krupp Gmbh Recoil-gun with special devices for protecting the slide-tracks from dust.
NL132376C (es) * 1966-02-10
US4895840A (en) * 1987-06-10 1990-01-23 A. H. Robins Company, Incorporated N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines
CN1314340A (zh) * 2000-03-21 2001-09-26 山东省医药工业研究所 环戊烷酰亚胺的制备方法
FR2866647B1 (fr) * 2004-02-20 2006-10-27 Servier Lab Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CN100424077C (zh) * 2005-06-07 2008-10-08 台州市四维化工厂 一种环戊烷1，2-二酰亚胺的制备方法
FR2937251B1 (fr) * 2008-10-16 2011-03-18 Servier Lab Utilisation du 4-{3-°hexahydrocyclopenta°c!pyrrol-2(1h)-yl! propoxy}benzamide pour l'obtention de medicaments destines au traitement des troubles du sommeil
KR20110091784A (ko) * 2008-11-26 2011-08-12 아보트 러보러터리즈 칼슘 채널 차단제로서의 치환된 옥타하이드로사이클로펜타［ｃ］피롤­4­아민
FR2953515B1 (fr) * 2009-12-09 2011-12-23 Servier Lab Nouveaux derives du type hexahydrocyclopenta[b]pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2974729B1 (fr) * 2011-05-02 2013-04-19 Servier Lab Nouvelle association entre le 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide et un inhibiteur de l'acetylcholinesterase et les compositions pharmaceutiques qui la contiennent

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Publication number Publication date
US8952179B2 (en) 2015-02-10
ECSP12011941A (es) 2012-07-31
EP2532651B1 (fr) 2015-08-05
CN102816102A (zh) 2012-12-12
PL2532651T3 (pl) 2016-01-29
HUE028050T2 (en) 2016-11-28
GEP20156395B (en) 2015-11-10
FR2976285A1 (fr) 2012-12-14
JP2015044840A (ja) 2015-03-12
EA022741B1 (ru) 2016-02-29
FR2976285B1 (fr) 2013-05-24
NI201200102A (es) 2012-08-20
TN2012000254A1 (fr) 2013-12-12
SI2532651T1 (sl) 2015-10-30
AU2012203062B2 (en) 2015-05-07
CO6580197A1 (es) 2012-12-17
MA33883B1 (fr) 2013-01-02
TWI499584B (zh) 2015-09-11
AP2012006280A0 (en) 2012-06-30
NZ600474A (en) 2013-12-20
WO2012168657A1 (fr) 2012-12-13
CL2012001500A1 (es) 2014-09-05
MD20120049A2 (en) 2012-12-31
MX2012006525A (es) 2013-01-09
SV2012004237A (es) 2013-01-04
DK2532651T3 (en) 2015-11-09
PE20130046A1 (es) 2013-02-10
UY34110A (es) 2013-01-03
MD4345C1 (ro) 2015-11-30
MD4345B1 (ro) 2015-04-30
JP2012254982A (ja) 2012-12-27
ZA201204183B (en) 2013-02-27
US8664408B2 (en) 2014-03-04
KR20140079346A (ko) 2014-06-26
ES2554933T3 (es) 2015-12-28
RS54279B1 (en) 2016-02-29
US20140100374A1 (en) 2014-04-10
RU2013158817A (ru) 2015-07-20
ME02346B (me) 2016-06-20
EA201200726A1 (ru) 2013-04-30
CA2779045C (fr) 2016-06-21
CY1116739T1 (el) 2017-03-15
CA2779045A1 (fr) 2012-12-08
HRP20151073T1 (hr) 2015-11-06
CU20120087A7 (es) 2014-01-29
US20120316214A1 (en) 2012-12-13
PT2532651E (pt) 2015-10-15
TW201302702A (zh) 2013-01-16
IL219925A0 (en) 2012-10-31
CR20120274A (es) 2013-01-11
JP5680022B2 (ja) 2015-03-04
KR20120136296A (ko) 2012-12-18
AU2012203062A1 (en) 2013-01-10
BR102012013573A2 (pt) 2013-07-02
SG186546A1 (en) 2013-01-30
AR086848A1 (es) 2014-01-29
EP2532651A1 (fr) 2012-12-12
US20140155453A1 (en) 2014-06-05

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