AR009311A1 - Procedimiento para la preparacion de carbamato de fisostigmina a partir de eteres de eserolina y procedimiento de obtencion de un intermediario en dichoprocedimiento - Google Patents
Procedimiento para la preparacion de carbamato de fisostigmina a partir de eteres de eserolina y procedimiento de obtencion de un intermediario en dichoprocedimientoInfo
- Publication number
- AR009311A1 AR009311A1 ARP970103837A ARP970103837A AR009311A1 AR 009311 A1 AR009311 A1 AR 009311A1 AR P970103837 A ARP970103837 A AR P970103837A AR P970103837 A ARP970103837 A AR P970103837A AR 009311 A1 AR009311 A1 AR 009311A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- procedure
- alkyl
- compound
- cycloalkyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Se obtienen compuestos de formula (I) donde R es alquilo; R1 es hidrogeno, alquilo, cicloalquilo, cicloalquil alquilo, bicicloalquilo, arilo oarilalquilo; R2 es alquilo, cicloalquilo, cicloalquil alquilo, bicicloalquilo, arilo o arilalquilo; o R1 yR2, tomados junto con el átomo de nitrogeno al queestán unidos, forman un grupo de formula (Ia), donde Y es hidrogeno o alquilo y Z es hidrogeno, alquilo, halogeno, alcoxi o hidroxi; X es alquilo inferior,alcoxi, halogeno o trifluorometilo, y m es 0, 1 o 2, o una sal del mismo farmacéuticamente aceptable. El procedimiento consiste en (a) poner en contactoun compuesto de formula (II) segun se ha definido aquí con bromuro de hidrogeno acuoso y haluro de litio para obtener un compuesto de formula (III)segun se ha definido aquí; poner en contacto la mezcla de reaccion que contiene un compuesto de formula (III) con (1) un isocianato de formula R1NCO o (2) uncompuesto de formula (IV) segun se ha definido para obtener un compuesto de formula (V) segun se ha definido aquí y poner en contacto la mezcla de reaccionque contiene el compuesto de formula (V) con una amina de formula R1R2NH aquí en presencia de un ácido carboxílico de formula R5COOH y formar y aislar elproducto de formula (I). También se describe un procedimiento para la obtencion de los compuestos de formula (III).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/769,409 US5677457A (en) | 1996-12-19 | 1996-12-19 | Method of preparation of physostigmine carbamate derivatives from eseroline ethers |
Publications (1)
Publication Number | Publication Date |
---|---|
AR009311A1 true AR009311A1 (es) | 2000-04-12 |
Family
ID=25085359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP970103837A AR009311A1 (es) | 1996-12-19 | 1997-08-25 | Procedimiento para la preparacion de carbamato de fisostigmina a partir de eteres de eserolina y procedimiento de obtencion de un intermediario en dichoprocedimiento |
Country Status (13)
Country | Link |
---|---|
US (1) | US5677457A (es) |
EP (1) | EP0946560A1 (es) |
JP (1) | JP2001506259A (es) |
KR (1) | KR20000062263A (es) |
AR (1) | AR009311A1 (es) |
AU (1) | AU715483B2 (es) |
BR (1) | BR9714046A (es) |
CA (1) | CA2273180C (es) |
HU (1) | HUP0000046A3 (es) |
IL (1) | IL130460A0 (es) |
NO (1) | NO993011L (es) |
WO (1) | WO1998027096A1 (es) |
ZA (1) | ZA976713B (es) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9815237A (pt) * | 1997-10-10 | 2000-10-31 | Chiesi Farma Spa | Processo para preparação de derivados de aminocarbonil de geneserolina que possuem atividade anticolinesterase seletiva no cérebro |
US6495700B1 (en) | 2002-01-09 | 2002-12-17 | Axonyx, Inc. | Process for producing phenserine and its analog |
AU2004285893B2 (en) * | 2003-10-21 | 2011-12-15 | Colucid Pharmaceuticals, Inc. | Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents |
CA2677241A1 (en) * | 2007-02-02 | 2008-08-14 | Colucid Pharmaceuticals, Inc. | Compounds that inhibit cholinesterase |
SE531698C2 (sv) | 2007-07-12 | 2009-07-07 | Respiratorius Ab | Nya bronkdilaterande a,b-omättade amider |
CA2693110A1 (en) * | 2007-07-18 | 2009-01-22 | Colucid Pharmaceuticals, Inc. | Methods for promoting wakefulness |
US8593728B2 (en) * | 2009-02-19 | 2013-11-26 | Toyota Motor Engineering & Manufacturing North America, Inc. | Multilayer photonic structures |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2905054C3 (de) * | 1979-02-08 | 1982-04-29 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 4-Hydroxyindolen |
IT1199076B (it) * | 1984-03-01 | 1988-12-30 | Consiglio Nazionale Ricerche | Derivati della fisostigmina con proprieta'di inibizione della aceticolinesterasi e relativo procedimento di produzione |
US4791107A (en) * | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
US5187165A (en) * | 1987-05-15 | 1993-02-16 | Hoechst-Roussel Pharmaceuticals Inc. | Memory enhancing and analgesic 1,2,3a,8,8a-hexahydro-3a,8(and 1,3a,8)-di(and tri)methylpyrrolo[2,3-b]indoles |
US4971992A (en) * | 1989-03-27 | 1990-11-20 | Hoechst-Roussel Pharmaceuticals Inc. | Carbonate derivatives of eseroline |
DE69020989T2 (de) * | 1989-09-19 | 1996-02-08 | Hoechst Roussel Pharma | Verfahren zur Racematspaltung von 5-alkoxy-substituierten (+/-)-1,3-dimethyloxindolylethylaminen. |
US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
US4937341A (en) * | 1989-09-28 | 1990-06-26 | Hoechst-Roussel Pharmaceuticals Inc. | Process for preparing N-aminocarbarbamates related to physostigmine |
US5260452A (en) * | 1989-11-03 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Inc. | 4- and 6-carbamates related to physostigmine and intermediates for the preparation thereof |
US5077289A (en) * | 1989-11-30 | 1991-12-31 | Hoechst Roussel Pharmaceuticals Inc. | Memory enhancing and analgesic aminocarbonylcarbamates related to physostigmine |
US5177101A (en) * | 1989-11-30 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Memory enhancing and analgesic aminocarbonylcarbamates related to physostigmine |
US5274117A (en) * | 1990-01-22 | 1993-12-28 | Hoechst-Roussel Pharmaceuticals, Inc. | Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine |
US5091541A (en) * | 1990-02-01 | 1992-02-25 | Hoechst-Roussel Pharmaceuticals Inc. | Hexahydropyrrolo(2,3-B)indole carbamates, ureas, amides and related compounds |
US4983616A (en) * | 1990-02-01 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Hexahydropyrrolo(2,3-B)indole carbamates, ureas, amides and related compounds |
US5216017A (en) * | 1990-05-11 | 1993-06-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Pyrrolo[2,3-b]indole-ketones and analogs |
US5173497A (en) * | 1990-05-17 | 1992-12-22 | Hoechst-Roussel Pharmaceuticals Incorporated | Alpha-oxopyrrolo[2,3-B]indole acetic acids, esters, amides and related analogs |
US5264587A (en) * | 1990-05-17 | 1993-11-23 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of preparing α-oxopyrrolo[2,3-b]indole acetic acids and derivatives |
DE69032046T2 (de) * | 1990-06-27 | 1998-08-27 | Hoechst Marion Roussel Inc | Tetrahydroisochinolinylcarbamate von 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo [2,3-b] indol |
US5234941A (en) * | 1991-10-01 | 1993-08-10 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
US5231093A (en) * | 1991-10-01 | 1993-07-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
US5153193A (en) * | 1991-10-01 | 1992-10-06 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
US5302721A (en) * | 1992-07-21 | 1994-04-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of preparation of physostigmine carbamate derivatives from eseretholes |
NZ248180A (en) * | 1992-07-21 | 1995-02-24 | Hoechst Roussel Pharma | Process for the preparation of physostigmine carbamate derivatives |
US5350762A (en) * | 1993-03-08 | 1994-09-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Tetrahydrocyclopent[B]indole methanamines and related compounds |
-
1996
- 1996-12-19 US US08/769,409 patent/US5677457A/en not_active Expired - Fee Related
-
1997
- 1997-07-21 EP EP97934961A patent/EP0946560A1/en not_active Withdrawn
- 1997-07-21 KR KR1019997005614A patent/KR20000062263A/ko not_active Application Discontinuation
- 1997-07-21 CA CA002273180A patent/CA2273180C/en not_active Expired - Fee Related
- 1997-07-21 JP JP52766298A patent/JP2001506259A/ja active Pending
- 1997-07-21 IL IL13046097A patent/IL130460A0/xx unknown
- 1997-07-21 AU AU38008/97A patent/AU715483B2/en not_active Ceased
- 1997-07-21 HU HU0000046A patent/HUP0000046A3/hu unknown
- 1997-07-21 BR BR9714046-5A patent/BR9714046A/pt not_active IP Right Cessation
- 1997-07-21 WO PCT/US1997/012367 patent/WO1998027096A1/en not_active Application Discontinuation
- 1997-07-28 ZA ZA9706713A patent/ZA976713B/xx unknown
- 1997-08-25 AR ARP970103837A patent/AR009311A1/es unknown
-
1999
- 1999-06-18 NO NO993011A patent/NO993011L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
BR9714046A (pt) | 2000-05-09 |
IL130460A0 (en) | 2000-06-01 |
KR20000062263A (ko) | 2000-10-25 |
CA2273180A1 (en) | 1998-06-25 |
JP2001506259A (ja) | 2001-05-15 |
US5677457A (en) | 1997-10-14 |
WO1998027096A1 (en) | 1998-06-25 |
AU715483B2 (en) | 2000-02-03 |
HUP0000046A2 (hu) | 2000-06-28 |
ZA976713B (en) | 1998-06-19 |
AU3800897A (en) | 1998-07-15 |
EP0946560A1 (en) | 1999-10-06 |
NO993011D0 (no) | 1999-06-18 |
NO993011L (no) | 1999-08-18 |
HUP0000046A3 (en) | 2000-09-28 |
CA2273180C (en) | 2002-10-29 |
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