NO982712L - Methods and intermediates for the preparation of 1-benzyl-4 - ((5,6-dimethoxy-1-indanone) -2-yl) methylpiperidine - Google Patents
Methods and intermediates for the preparation of 1-benzyl-4 - ((5,6-dimethoxy-1-indanone) -2-yl) methylpiperidineInfo
- Publication number
- NO982712L NO982712L NO982712A NO982712A NO982712L NO 982712 L NO982712 L NO 982712L NO 982712 A NO982712 A NO 982712A NO 982712 A NO982712 A NO 982712A NO 982712 L NO982712 L NO 982712L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compound
- formula
- trifluoromethyl
- alkoxy
- Prior art date
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
Abstract
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av en forbindelse med formel l hvor R1 er R2O(C=0)- eller R3(C=O)-, R2 er (C,-C4)alkyl og R' er (C,-C4) alkyl eller fenyl, eventuelt substituert med fra en til tre substituenter uavhengig av hverandre valgt fra (C^C^alkyl, (C^C^alkoksy, halogen eller trifluormetyl, omfattende a) omsetning av en forbindelse med formel III hvor R1 er R2O(C=O)- eller R3(C=O)-, R2 er (C^COalkyl og Rs er (C,-C,) alkyl eller fenyl, eventuelt substituert med fra en til tre substituenter uavhengig av hverandre valgt fra (C,-C,)alkyl, (C,-C4)alkoksy, halogen eller trifluormetyl med et metenyleringsmiddel for fremstilling av en forbindelse med formel II hvor R' er R2O(C=O)- eller R3(C=0)-, R2 er (C,-CJalkyl og R3 er (C,-C4) alkyl eller fenyl, eventuelt substituert med fra en til tre substituenter uavhengig av hverandre valgt fra (C,-C<)alkyl, (C,-C4)alkoksy, halogen eller trifluormetyl og; b) omsetning av nevnte forbindelse med formel II med en sterk syre. Oppfinnelsen innbefatter videre et ytterligere trinn hvor forbindelsen med formel l reageres med hydroksyd for fremstilling av en forbindelse med formel VI, og omsetning av nevnte således dannede forbindelse med formel VI med et benzylhalogenid og en base for fremstilling av en forbindelse med formel VII. Foreliggende oppfinnelse angår også de nye mellomproduktene med formlene (l), (11) og (III).The present invention relates to a process for preparing a compound of formula I wherein R 1 is R 2 O (C = O) - or R 3 (C = O) -, R 2 is (C 1 -C 4) alkyl and R 1 is (C 1 -C 4 ) alkyl or phenyl, optionally substituted with from one to three substituents independently selected from (C 1 -C 4 alkyl, (C 1 -C 3 alkoxy, halogen or trifluoromethyl, comprising a) reacting a compound of formula III wherein R 1 is R 2 (C = O) - or R3 (C = O) -, R 2 is (C 1 -C 4 alkyl and R 5 is (C 1 -C 2) alkyl or phenyl, optionally substituted with from one to three substituents independently selected from (C , -C1) alkyl, (C1-C4) alkoxy, halogen or trifluoromethyl with a methenylating agent to prepare a compound of formula II wherein R 'is R2O (C = O) - or R3 (C = O) -, R2 is (C 1 -C 4 alkyl and R 3 is (C 1 -C 4) alkyl or phenyl, optionally substituted with from one to three substituents independently selected from (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, halogen or trifluoromethyl and; b) reacting said compound of formula II with a s dry acid. The invention further includes a further step wherein the compound of formula I is reacted with hydroxide to prepare a compound of formula VI, and reacting said compound of formula VI thus formed with a benzyl halide and a base for preparing a compound of formula VII. The present invention also relates to the novel intermediates of formulas (1), (11) and (III).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US875395P | 1995-12-15 | 1995-12-15 | |
| PCT/IB1996/001076 WO1997022584A1 (en) | 1995-12-15 | 1996-10-11 | Processes and intermediates for preparing 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO982712L true NO982712L (en) | 1998-06-12 |
| NO982712D0 NO982712D0 (en) | 1998-06-12 |
Family
ID=21733469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO982712A NO982712D0 (en) | 1995-12-15 | 1998-06-12 | Methods and intermediates for the preparation of 1-benzyl-4 - ((5,6-dimethoxy-1-indanone) -2-yl) methylpiperidine |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0883607A1 (en) |
| JP (1) | JP3066083B2 (en) |
| KR (1) | KR20000064387A (en) |
| AP (1) | AP708A (en) |
| AR (1) | AR004368A1 (en) |
| AU (1) | AU716462B2 (en) |
| BG (1) | BG102525A (en) |
| BR (1) | BR9612018A (en) |
| CA (1) | CA2237647A1 (en) |
| CO (1) | CO4750831A1 (en) |
| CZ (1) | CZ180898A3 (en) |
| DZ (1) | DZ2141A1 (en) |
| GT (1) | GT199600092A (en) |
| HN (1) | HN1996000065A (en) |
| HR (1) | HRP960592A2 (en) |
| HU (1) | HUP9904275A3 (en) |
| IL (3) | IL124452A0 (en) |
| IS (1) | IS4752A (en) |
| MA (1) | MA24032A1 (en) |
| NO (1) | NO982712D0 (en) |
| NZ (1) | NZ318843A (en) |
| OA (1) | OA10694A (en) |
| PE (1) | PE25698A1 (en) |
| PL (1) | PL197306B1 (en) |
| RO (1) | RO121382B1 (en) |
| RU (1) | RU2160731C2 (en) |
| SK (1) | SK75498A3 (en) |
| TN (1) | TNSN96153A1 (en) |
| TW (1) | TW414787B (en) |
| UY (1) | UY24401A1 (en) |
| WO (1) | WO1997022584A1 (en) |
| YU (1) | YU49486B (en) |
| ZA (1) | ZA9610533B (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2237078T3 (en) | 1998-01-16 | 2005-07-16 | Eisai Co., Ltd. | PROCEDURE TO PRODUCE DERIVATIVES OF DONEPEZILO. |
| 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 the preparation of donepezil |
| 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) |
| WO2004082685A1 (en) * | 2003-03-21 | 2004-09-30 | Ranbaxy Laboratories Limited | Process for the preparation of donepezil and derivatives thereof |
| WO2004099142A1 (en) * | 2003-05-05 | 2004-11-18 | Ranbaxy Laboratories Limited | Hydrobromide salt of benzyl-piperidylmethyl-indanone and its polymorphs |
| US7446203B2 (en) | 2003-07-01 | 2008-11-04 | Hetero Drugs Limited | Preparation of intermediates for acetycholinesterase inhibitors |
| CN1280273C (en) | 2003-11-05 | 2006-10-18 | 天津和美生物技术有限公司 | Synthesis of donepizin and its derivative |
| WO2006035433A2 (en) | 2004-09-29 | 2006-04-06 | Chemagis Ltd. | Use of purified donepezil maleate for preparing pharmaceutically pure amorphous donepezil hydrochloride |
| CN100436416C (en) * | 2005-07-29 | 2008-11-26 | 西南合成制药股份有限公司 | Novel donepezil synthesis process |
| GB0515803D0 (en) | 2005-07-30 | 2005-09-07 | Pliva Hrvatska D O O | Intermediate compounds |
| AR057910A1 (en) | 2005-11-18 | 2007-12-26 | Synthon Bv | PROCESS TO PREPARE DONEPEZILO |
| AU2007203969B2 (en) | 2006-01-04 | 2012-04-05 | Cipla Limited | Process and intermediate for preparation of donepezil |
| US8247563B2 (en) * | 2006-12-11 | 2012-08-21 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using indanone based cholinesterase inhibitors |
| WO2013078608A1 (en) * | 2011-11-29 | 2013-06-06 | Ziqiang Gu | Donepezil pamoate and methods of making and using the same |
| ES2888074T3 (en) | 2013-08-16 | 2021-12-30 | Univ Maastricht | Treatment of cognitive impairment with PDE4 inhibitor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI95572C (en) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Process for the preparation of a medicament useful as a piperidine derivative or its pharmaceutical salt |
| FR2642069B1 (en) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | NOVEL BENZOPYRAN DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| DE4439822A1 (en) * | 1994-11-08 | 1996-08-29 | Bayer Ag | Process for the preparation of benzyl-piperidylmethyl-indanones |
-
1996
- 1996-10-11 IL IL12445296A patent/IL124452A0/en unknown
- 1996-10-11 CA CA002237647A patent/CA2237647A1/en not_active Abandoned
- 1996-10-11 WO PCT/IB1996/001076 patent/WO1997022584A1/en not_active Application Discontinuation
- 1996-10-11 RU RU98111204/04A patent/RU2160731C2/en not_active IP Right Cessation
- 1996-10-11 PL PL327512A patent/PL197306B1/en not_active IP Right Cessation
- 1996-10-11 IL IL13642096A patent/IL136420A0/en unknown
- 1996-10-11 BR BR9612018A patent/BR9612018A/en not_active Application Discontinuation
- 1996-10-11 CZ CZ981808A patent/CZ180898A3/en unknown
- 1996-10-11 NZ NZ318843A patent/NZ318843A/en unknown
- 1996-10-11 EP EP96931937A patent/EP0883607A1/en not_active Withdrawn
- 1996-10-11 JP JP9522607A patent/JP3066083B2/en not_active Expired - Lifetime
- 1996-10-11 HU HU9904275A patent/HUP9904275A3/en unknown
- 1996-10-11 SK SK754-98A patent/SK75498A3/en unknown
- 1996-10-11 RO RO98-01070A patent/RO121382B1/en unknown
- 1996-10-11 AU AU70925/96A patent/AU716462B2/en not_active Ceased
- 1996-10-11 IL IL13642196A patent/IL136421A0/en unknown
- 1996-10-11 KR KR1019980704423A patent/KR20000064387A/en not_active Application Discontinuation
- 1996-10-14 TW TW085112515A patent/TW414787B/en not_active IP Right Cessation
- 1996-10-15 HN HN1996000065A patent/HN1996000065A/en unknown
- 1996-11-18 GT GT199600092A patent/GT199600092A/en unknown
- 1996-12-09 PE PE1996000883A patent/PE25698A1/en not_active Application Discontinuation
- 1996-12-10 AR ARP960105577A patent/AR004368A1/en unknown
- 1996-12-11 YU YU66096A patent/YU49486B/en unknown
- 1996-12-11 MA MA24424A patent/MA24032A1/en unknown
- 1996-12-11 TN TNTNSN96153A patent/TNSN96153A1/en unknown
- 1996-12-11 DZ DZ960186A patent/DZ2141A1/en active
- 1996-12-12 AP APAP/P/1996/000892A patent/AP708A/en active
- 1996-12-12 UY UY24401A patent/UY24401A1/en not_active IP Right Cessation
- 1996-12-12 CO CO96065334A patent/CO4750831A1/en unknown
- 1996-12-13 ZA ZA9610533A patent/ZA9610533B/en unknown
- 1996-12-13 HR HR60/008,753A patent/HRP960592A2/en not_active Application Discontinuation
-
1998
- 1998-05-22 IS IS4752A patent/IS4752A/en unknown
- 1998-06-05 OA OA9800076A patent/OA10694A/en unknown
- 1998-06-09 BG BG102525A patent/BG102525A/en unknown
- 1998-06-12 NO NO982712A patent/NO982712D0/en not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application |