CA2237647A1 - Procedes de preparation de 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine et intermediaires utilises a cet effet - Google Patents
Procedes de preparation de 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine et intermediaires utilises a cet effet Download PDFInfo
- Publication number
- CA2237647A1 CA2237647A1 CA002237647A CA2237647A CA2237647A1 CA 2237647 A1 CA2237647 A1 CA 2237647A1 CA 002237647 A CA002237647 A CA 002237647A CA 2237647 A CA2237647 A CA 2237647A CA 2237647 A1 CA2237647 A1 CA 2237647A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- formula
- halo
- trifluoromethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Cette invention a trait à un procédé de préparation d'un composé répondant à la formule (I) dans laquelle R?1¿ représente R?2¿O(C=O)- ou R?3¿(C=O)-, R?2¿ représente un alkyle comportant de 1 à 4 atomes de carbone et R?3¿ représente un alkyle comportant de 1 à 4 atomes de carbone ou un phényle éventuellement substitué par des substituants, de un à trois, sélectionnés de manière indépendante entre un alkyle comportant de 1 à 4 atomes de carbone, un alcoxy comportant de 1 à 4 atomes de carbone, un halo ou un trifluorométhyle. Le procédé consiste a), à faire réagir un composé répondant à la formule (III) dans laquelle R?1¿ représente R?2¿O(C=O)- ou R?3¿(C=O)-, R?2¿ représente un alkyle comportant de 1 à 4 atomes de carbone et R?3¿ représente un alkyle comportant de 1 à 4 atomes de carbone ou un phényle éventuellement substitué par des substituants, de un à trois, sélectionnés de manière indépendante entre un alkyle comportant de 1 à 4 atomes de carbone, un alcoxy comportant de 1 à 4 atomes de carbone, un halo ou un trifluorométhyle, avec un agent de méthénylation afin de constituer un composé répondant à la formule (II) dans laquelle R?1¿ représente R?2¿O(C=O)- ou R?3¿(C=O)-, R?2¿ représente un alkyle comportant de 1 à 4 atomes de carbone et R?3¿ représente un alkyle comportant de 1 à 4 atomes de carbone ou un phényle éventuellement substitué par des substituants, de un à trois, sélectionnés de manière indépendante entre un alkyle comportant de 1 à 4 atomes de carbone, un alcoxy comportant de 1 à 4 atomes de carbone, un halo ou un trifluorométhyle et b), à faire réagir le composé, ainsi obtenu, répondant à la formule (II) avec un acide fort. Cette invention comporte également une autre étape consistant à faire réagir le composé répondant à la formule (I) avec un hydroxyde afin de constituer un composé répondant à la formule (VI) puis à faire réagir ce composé, ainsi obtenu, répondant à la formule (VI) avec un halogénure de benzyle et une base afin de constituer un composé répondant à la formule (VII). L'invention porte également sur de nouveaux intermédiaires des formules (I), (II) et (III).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US875395P | 1995-12-15 | 1995-12-15 | |
| US60/008,753 | 1995-12-15 | ||
| PCT/IB1996/001076 WO1997022584A1 (fr) | 1995-12-15 | 1996-10-11 | Procedes de preparation de 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine et intermediaires utilises a cet effet |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2237647A1 true CA2237647A1 (fr) | 1997-06-26 |
Family
ID=21733469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002237647A Abandoned CA2237647A1 (fr) | 1995-12-15 | 1996-10-11 | Procedes de preparation de 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine et intermediaires utilises a cet effet |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0883607A1 (fr) |
| JP (1) | JP3066083B2 (fr) |
| KR (1) | KR20000064387A (fr) |
| AP (1) | AP708A (fr) |
| AR (1) | AR004368A1 (fr) |
| AU (1) | AU716462B2 (fr) |
| BG (1) | BG102525A (fr) |
| BR (1) | BR9612018A (fr) |
| CA (1) | CA2237647A1 (fr) |
| CO (1) | CO4750831A1 (fr) |
| CZ (1) | CZ180898A3 (fr) |
| DZ (1) | DZ2141A1 (fr) |
| GT (1) | GT199600092A (fr) |
| HN (1) | HN1996000065A (fr) |
| HR (1) | HRP960592A2 (fr) |
| HU (1) | HUP9904275A3 (fr) |
| IL (3) | IL124452A0 (fr) |
| IS (1) | IS4752A (fr) |
| MA (1) | MA24032A1 (fr) |
| NO (1) | NO982712D0 (fr) |
| NZ (1) | NZ318843A (fr) |
| OA (1) | OA10694A (fr) |
| PE (1) | PE25698A1 (fr) |
| PL (1) | PL197306B1 (fr) |
| RO (1) | RO121382B1 (fr) |
| RU (1) | RU2160731C2 (fr) |
| SK (1) | SK75498A3 (fr) |
| TN (1) | TNSN96153A1 (fr) |
| TW (1) | TW414787B (fr) |
| UY (1) | UY24401A1 (fr) |
| WO (1) | WO1997022584A1 (fr) |
| YU (1) | YU49486B (fr) |
| ZA (1) | ZA9610533B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999036405A1 (fr) | 1998-01-16 | 1999-07-22 | Eisai Co., Ltd. | Procede de production de derive de donepezil |
| IL125809A (en) | 1998-08-17 | 2005-08-31 | Finetech Lab Ltd | Process and intermediates for production of donepezil and related compounds |
| US7148354B2 (en) * | 2002-07-24 | 2006-12-12 | Dr. Reddy's Laboratories Limited | Process for preparation of donepezil |
| IL150982A (en) | 2002-07-30 | 2007-02-11 | Ori Lerman | Process for making Donafzil |
| IL151253A0 (en) * | 2002-08-14 | 2003-04-10 | Finetech Lab Ltd | Process for production of highly pure donepezil hydrochloride |
| US6649765B1 (en) | 2003-02-12 | 2003-11-18 | Usv Limited, Bsd Marg. | Process for the preparation of 1-benzyl-4(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCL) |
| US6953856B2 (en) | 2003-02-12 | 2005-10-11 | Usv, Limited | Process for the preparation of 1-benzyl-4-(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCI) |
| EP1608371A1 (fr) * | 2003-03-21 | 2005-12-28 | Ranbaxy Laboratories, Ltd. | Procede de preparation de donepezil et de ses derives |
| WO2004099142A1 (fr) * | 2003-05-05 | 2004-11-18 | Ranbaxy Laboratories Limited | Sel de bromhydrate de benzyl-piperidylmethyl-indanone et ses polymorphes |
| EP1654230A1 (fr) | 2003-07-01 | 2006-05-10 | Hetero Drugs Limited | Preparation d'intermediaires pour inhibiteurs de l'acetyl cholinesterase |
| CN1280273C (zh) * | 2003-11-05 | 2006-10-18 | 天津和美生物技术有限公司 | 合成多奈哌齐及其衍生物的方法 |
| AU2005288521A1 (en) | 2004-09-29 | 2006-04-06 | Chemagis Ltd. | Use of purified donepezil maleate for preparing pharmaceutically pure amorphous donepezil hydrochloride |
| CN100436416C (zh) * | 2005-07-29 | 2008-11-26 | 西南合成制药股份有限公司 | 盐酸多奈哌齐合成工艺 |
| GB0515803D0 (en) | 2005-07-30 | 2005-09-07 | Pliva Hrvatska D O O | Intermediate compounds |
| AR057910A1 (es) | 2005-11-18 | 2007-12-26 | Synthon Bv | Proceso para preparar donepezilo |
| KR20080085195A (ko) * | 2006-01-04 | 2008-09-23 | 씨아이피엘에이 엘티디. | 도네페질의 제조방법 및 중간체 |
| EP2114166A4 (fr) * | 2006-12-11 | 2011-05-25 | Reviva Pharmaceuticals Inc | Compositions, synthèse et procédés d'utilisation d'inhibiteurs de cholinestérase à base d'indanone |
| WO2013078608A1 (fr) | 2011-11-29 | 2013-06-06 | Ziqiang Gu | Pamoate de donepezil et ses procédés de fabrication et d'utilisation |
| ES2888074T3 (es) | 2013-08-16 | 2021-12-30 | Univ Maastricht | Tratamiento del deterioro cognitivo con inhibidor de PDE4 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| FR2642069B1 (fr) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les compositions pharmaceutiques qui les contiennent |
| DE4439822A1 (de) * | 1994-11-08 | 1996-08-29 | Bayer Ag | Verfahren zur Herstellung von Benzyl-piperidylmethyl-indanonen |
-
1996
- 1996-10-11 AU AU70925/96A patent/AU716462B2/en not_active Ceased
- 1996-10-11 EP EP96931937A patent/EP0883607A1/fr not_active Withdrawn
- 1996-10-11 CA CA002237647A patent/CA2237647A1/fr not_active Abandoned
- 1996-10-11 BR BR9612018A patent/BR9612018A/pt not_active Application Discontinuation
- 1996-10-11 IL IL12445296A patent/IL124452A0/xx unknown
- 1996-10-11 WO PCT/IB1996/001076 patent/WO1997022584A1/fr not_active Ceased
- 1996-10-11 HU HU9904275A patent/HUP9904275A3/hu unknown
- 1996-10-11 KR KR1019980704423A patent/KR20000064387A/ko not_active Ceased
- 1996-10-11 NZ NZ318843A patent/NZ318843A/xx unknown
- 1996-10-11 RO RO98-01070A patent/RO121382B1/ro unknown
- 1996-10-11 RU RU98111204/04A patent/RU2160731C2/ru not_active IP Right Cessation
- 1996-10-11 PL PL327512A patent/PL197306B1/pl not_active IP Right Cessation
- 1996-10-11 IL IL13642196A patent/IL136421A0/xx unknown
- 1996-10-11 CZ CZ981808A patent/CZ180898A3/cs unknown
- 1996-10-11 JP JP9522607A patent/JP3066083B2/ja not_active Expired - Lifetime
- 1996-10-11 IL IL13642096A patent/IL136420A0/xx unknown
- 1996-10-11 SK SK754-98A patent/SK75498A3/sk unknown
- 1996-10-14 TW TW085112515A patent/TW414787B/zh not_active IP Right Cessation
- 1996-10-15 HN HN1996000065A patent/HN1996000065A/es unknown
- 1996-11-18 GT GT199600092A patent/GT199600092A/es unknown
- 1996-12-09 PE PE1996000883A patent/PE25698A1/es not_active Application Discontinuation
- 1996-12-10 AR ARP960105577A patent/AR004368A1/es unknown
- 1996-12-11 DZ DZ960186A patent/DZ2141A1/fr active
- 1996-12-11 TN TNTNSN96153A patent/TNSN96153A1/fr unknown
- 1996-12-11 MA MA24424A patent/MA24032A1/fr unknown
- 1996-12-11 YU YU66096A patent/YU49486B/sh unknown
- 1996-12-12 CO CO96065334A patent/CO4750831A1/es unknown
- 1996-12-12 UY UY24401A patent/UY24401A1/es not_active IP Right Cessation
- 1996-12-12 AP APAP/P/1996/000892A patent/AP708A/en active
- 1996-12-13 ZA ZA9610533A patent/ZA9610533B/xx unknown
- 1996-12-13 HR HR60/008,753A patent/HRP960592A2/xx not_active Application Discontinuation
-
1998
- 1998-05-22 IS IS4752A patent/IS4752A/is unknown
- 1998-06-05 OA OA9800076A patent/OA10694A/en unknown
- 1998-06-09 BG BG102525A patent/BG102525A/xx unknown
- 1998-06-12 NO NO982712A patent/NO982712D0/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |