AR086848A1 - Procedimiento de sintesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2-(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienen - Google Patents

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

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Publication number
AR086848A1
AR086848A1 ARP120102010A ARP120102010A AR086848A1 AR 086848 A1 AR086848 A1 AR 086848A1 AR P120102010 A ARP120102010 A AR P120102010A AR P120102010 A ARP120102010 A AR P120102010A AR 086848 A1 AR086848 A1 AR 086848A1
Authority
AR
Argentina
Prior art keywords
formula
compound
group
hexahydrociclopenta
propoxi
Prior art date
Application number
ARP120102010A
Other languages
English (en)
Inventor
Nicolas Robert
Jean Lecouve
Marina Pierre-Gaillard
Loc Meunier
Mathieu Boiret
Jean Lerestif
Philippe Michel-Letellier
Original Assignee
Servier Lab
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Servier Lab filed Critical Servier Lab
Publication of AR086848A1 publication Critical patent/AR086848A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic 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
    • A61K31/403Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42Carboxylic 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
    • C07C235/44Carboxylic 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
    • C07C235/46Carboxylic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10Heterocyclic 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
    • C07D317/14Heterocyclic 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
    • C07D317/18Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D319/00Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/041,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/061,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

Abstract

Medicamentos.Reivindicación 1: Procedimiento de síntesis industrial del compuesto de fórmula (1), caracterizado porque el compuesto de fórmula (2) reacciona con el amoniaco a una temperatura superior a 100ºC para formar el compuesto de fórmula (3) que se reduce para dar lugar a la amina bicíclica de fórmula (4); este último compuesto se somete posteriormente: bien a una reacción de acoplamiento en condición básica en un medio polar con un compuesto de fórmula (5), en la que Y representa un -CH2-Hal en el que Hal es un halógeno, o un grupo -CH2-OSO2-R en el que R es un grupo alquilo C1-6 o un grupo -C6H4-CH3; bien a una aminación reductora en medio ácido con un compuesto de fórmula (6), en la que R’ y R’’ representan independientemente el uno del otro un grupo alquilo C1-6 o bien R’ y R’’ forman juntos un grupo -(CH2)n- en el que n = 2 - 3, o bien uno de los grupos R’ o R’’ representan un átomo de hidrógeno y el otro un grupo alquilo C1-6; bien a una aminación reductora con un compuesto de fórmula (7), para dar lugar a la base libre del compuesto de fórmula (1), la cual se pone en presencia de ácido clorhídrico para formar el compuesto de fórmula (1) que se aísla en la forma de un sólido.
ARP120102010A 2011-06-08 2012-06-07 Procedimiento de sintesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2-(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienen AR086848A1 (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
AR086848A1 true AR086848A1 (es) 2014-01-29

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
ARP120102010A AR086848A1 (es) 2011-06-08 2012-06-07 Procedimiento de sintesis y forma cristalina del hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2-(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienen

Country Status (43)

Country Link
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

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Also Published As

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
GT201200182A (es) 2014-09-18
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
EP2532651A1 (fr) 2012-12-12
US20140155453A1 (en) 2014-06-05

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