BR9712719A - Médoto de preparação de derivados de carbamato de fisostigmina a partir de eseretóis - Google Patents
Médoto de preparação de derivados de carbamato de fisostigmina a partir de eseretóisInfo
- Publication number
- BR9712719A BR9712719A BR9712719-1A BR9712719A BR9712719A BR 9712719 A BR9712719 A BR 9712719A BR 9712719 A BR9712719 A BR 9712719A BR 9712719 A BR9712719 A BR 9712719A
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- lower alkyl
- compound
- hydrogen
- cycloalkyl
- Prior art date
Links
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 title abstract 2
- 229960001697 physostigmine Drugs 0.000 title abstract 2
- -1 physostigmine carbamate derivatives Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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
Patente de Invenção: <B>"MéTODO DE PREPARAçãO DE DERIVADOS DE CARBAMATO DE FISOSTIGMINA A PARTIR DE ESERETóIS''<D>. A invenção refere-se a um processo para preparação de um composto de fórmula: onde R é alquila inferior; R~ 1~ é hidrogênio, alquila inferior, cicloalquila inferior, cicloalquila inferior alquila inferior, bicicloalquila inferior, arila ou alquilarila inferior; R~ 2~ é alquila inferior, cicloalquila inferior, cicloalquila inferior alquila inferior, bicicloalquila inferior, arila ou alquilarila inferior; ou R~ 1~ e R~ 2~ tomados juntos com o átomo de nitrogênio ao qual estão ligados formam um grupo de fórmula (Ia): onde Y é hidrogênio ou alquila inferior e Z é hidrogênio, alquila inferior, halogênio, alcóxi inferior ou hidróxi; X é alquila inferior, alcóxi inferior, halogênio ou trifluormetila; e m é 0, 1 ou 2; ou um sal farmaceuticamente aceitável do mesmo; cujo processo compreende: (a) colocar em contato um composto de fórmula (II) como aqui definido com brometo de hidrogênio concentrado para produzir um composto de fórmula (III) como aqui definido; (b) colocar em contato a mistura reacional contendo o composto de fórmula (III) com: um isocianato de fórmula R~ 1~NCO, ou um composto de fórmula (IV), como definido para produzir um composto de fórmula (V) como aqui definido, e (c) colocar em contato a mistura reacional contendo o composto de fórmula (V), com uma amina de fórmula: R~ 1~R~ 2~NH na presença de um ácido carboxílico de fórmula: R~ 5~COOH e formando e isolando o produto de fórmula (I).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/739,402 US5665880A (en) | 1996-10-31 | 1996-10-31 | Method of preparation of physostigmine carbamate derivatives from eseretholes |
| PCT/US1997/012370 WO1998018799A1 (en) | 1996-10-31 | 1997-07-21 | Method of preparation of physostigmine carbamate derivatives from eseretholes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR9712719A true BR9712719A (pt) | 1999-10-26 |
Family
ID=24972126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9712719-1A BR9712719A (pt) | 1996-10-31 | 1997-07-21 | Médoto de preparação de derivados de carbamato de fisostigmina a partir de eseretóis |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5665880A (pt) |
| EP (1) | EP0937080A1 (pt) |
| JP (1) | JP2001503049A (pt) |
| KR (1) | KR20000052891A (pt) |
| CN (1) | CN1235607A (pt) |
| AR (1) | AR009300A1 (pt) |
| AU (1) | AU712493B2 (pt) |
| BR (1) | BR9712719A (pt) |
| CA (1) | CA2268150A1 (pt) |
| HU (1) | HUP9904284A3 (pt) |
| IL (1) | IL129661A0 (pt) |
| NO (1) | NO992058L (pt) |
| WO (1) | WO1998018799A1 (pt) |
| ZA (1) | ZA976712B (pt) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19956920A1 (de) | 1999-11-26 | 2001-05-31 | Bayer Ag | Verfahren zur Herstellung von 2-(2-Hydrodyphenyl)-2-(alkoxyimino)-N-methyl-acetamid-Derivaten |
| US6495700B1 (en) | 2002-01-09 | 2002-12-17 | Axonyx, Inc. | Process for producing phenserine and its analog |
| WO2005042475A2 (en) * | 2003-10-21 | 2005-05-12 | Sention, Inc. | Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents |
| JP2007519733A (ja) * | 2004-01-26 | 2007-07-19 | コーテックス ファーマシューティカルズ インコーポレーティッド | アンパカインにより誘導されるシナプス応答促通のコリンエステラーゼ阻害剤による増強方法 |
| JP2010518010A (ja) * | 2007-02-02 | 2010-05-27 | コルシド・ファーマシューティカルズ・インコーポレイテッド | コリンエステラーゼを阻害する化合物 |
| CN101121717B (zh) * | 2007-05-17 | 2010-07-28 | 四川大学 | 抗老年痴呆疾病的天然药物毒扁豆碱及其衍生物苯胺基甲酸酯毒扁豆酚碱的合成 |
| SE531698C2 (sv) | 2007-07-12 | 2009-07-07 | Respiratorius Ab | Nya bronkdilaterande a,b-omättade amider |
| US20090048229A1 (en) * | 2007-07-18 | 2009-02-19 | Rupniak Nadia M J | 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 (25)
| 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 |
| US4652635A (en) * | 1983-05-02 | 1987-03-24 | Polaroid Corporation | Method for converting ether groups to hydroxyl groups and ester groups to acid groups |
| 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 |
| ATE125254T1 (de) * | 1989-09-19 | 1995-08-15 | 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 |
| 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 |
| 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 |
| MC2287A1 (fr) * | 1990-06-27 | 1993-07-14 | Hoechst Roussel Pharma | Tetrahydroisoquinoleinylcarbamates de 1,2,3,3a,8,8a-hexahydro-1,31,8-trimethylpyrrolo(2,3,-b)indole |
| 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 |
| 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 |
| US5302721A (en) * | 1992-07-21 | 1994-04-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of preparation of physostigmine carbamate derivatives from eseretholes |
| FI933264A (fi) * | 1992-07-21 | 1994-01-22 | Hoechst Roussel Pharma | Foerfarande foer framstaellning av fysostigminkarbamatderivat fraon fysostigmin |
| US5350762A (en) * | 1993-03-08 | 1994-09-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Tetrahydrocyclopent[B]indole methanamines and related compounds |
-
1996
- 1996-10-31 US US08/739,402 patent/US5665880A/en not_active Expired - Fee Related
-
1997
- 1997-05-20 US US08/858,987 patent/US5734062A/en not_active Expired - Fee Related
- 1997-07-21 BR BR9712719-1A patent/BR9712719A/pt not_active Application Discontinuation
- 1997-07-21 AU AU38010/97A patent/AU712493B2/en not_active Ceased
- 1997-07-21 CA CA002268150A patent/CA2268150A1/en not_active Abandoned
- 1997-07-21 IL IL12966197A patent/IL129661A0/xx unknown
- 1997-07-21 JP JP10520434A patent/JP2001503049A/ja active Pending
- 1997-07-21 KR KR1019990703755A patent/KR20000052891A/ko not_active Application Discontinuation
- 1997-07-21 WO PCT/US1997/012370 patent/WO1998018799A1/en not_active Application Discontinuation
- 1997-07-21 EP EP97934964A patent/EP0937080A1/en not_active Withdrawn
- 1997-07-21 HU HU9904284A patent/HUP9904284A3/hu unknown
- 1997-07-21 CN CN97199271A patent/CN1235607A/zh active Pending
- 1997-07-28 ZA ZA9706712A patent/ZA976712B/xx unknown
- 1997-08-22 AR ARP970103813A patent/AR009300A1/es unknown
-
1999
- 1999-04-29 NO NO992058A patent/NO992058L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2268150A1 (en) | 1998-05-07 |
| KR20000052891A (ko) | 2000-08-25 |
| EP0937080A1 (en) | 1999-08-25 |
| IL129661A0 (en) | 2000-02-29 |
| ZA976712B (en) | 1998-04-30 |
| HUP9904284A2 (hu) | 2000-05-28 |
| NO992058D0 (no) | 1999-04-29 |
| CN1235607A (zh) | 1999-11-17 |
| AU3801097A (en) | 1998-05-22 |
| US5734062A (en) | 1998-03-31 |
| AU712493B2 (en) | 1999-11-11 |
| NO992058L (no) | 1999-04-29 |
| AR009300A1 (es) | 2000-04-12 |
| HUP9904284A3 (en) | 2000-09-28 |
| US5665880A (en) | 1997-09-09 |
| JP2001503049A (ja) | 2001-03-06 |
| WO1998018799A1 (en) | 1998-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA10 | Dismissal: dismissal - article 33 of industrial property law | ||
| B11Y | Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette] |