NO992058L - FremgangsmÕte for fremstilling av fysostigminkarbamatderivater fra eseretoler - Google Patents
FremgangsmÕte for fremstilling av fysostigminkarbamatderivater fra eseretolerInfo
- Publication number
- NO992058L NO992058L NO992058A NO992058A NO992058L NO 992058 L NO992058 L NO 992058L NO 992058 A NO992058 A NO 992058A NO 992058 A NO992058 A NO 992058A NO 992058 L NO992058 L NO 992058L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- lower alkyl
- compound
- aryl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 title 1
- 229960001697 physostigmine Drugs 0.000 title 1
- -1 physostigmine carbamate derivatives Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 6
- 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
- 125000000753 cycloalkyl group 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 group 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
- 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
Foreliggende oppfinnelse an- går en fremgangsmåte for fremstilling av et produkt av formel (I) (D (X)m hvori R er lavere alkyl; Rx er hydro- gen, lavere alkyl, lavere sykloalkyl, lavere sykloalkyl-lavere alkyl, lavere bisykloalkyl, aryl eller aryl-lavere alkyl; R2 er lavere alkyl, lavere syk- loalkyl, lavere sykloalkyl-lavere alkyl, lavere bisykloalkyl, aryl eller aryl-lavere alkyl; eller Rx og R2 tatt sammen med nitrogenatomet til hvilket de er bundet, danner en gruppe av for- mel (la) hvori Y er hydrogen eller lavere alkyl, og Z er hydrogen, lavere alkyl, halo- gen, lavere alkoksy eller hydroksy; X er lavere alkyl, lavere alkoksy, halogen eller trifluormetyl; og m er O, l eller 2; eller et farmasøytisk aksep- tabelt salt derav; hvilken fremgangs- måte omfatter: (a) en forbindelse av formel (II) som her definert, bringes i kontakt med forsterket hydrogenbromid for å gi en forbindelse av formel (III) som her definert; (b) reaksjonsblandin- gen inneholdende en forbindelse av for- mel (III), bringes i kontakt med enten: (1) et isocyanat av formel RjNCO, eller (2) en forbindelse av formel (IV) som definert, for å gi en forbindelse av formel (V) som her definert, og (c) reaksjonsblandingen inneholdende for- bindelsen av formel (V), bringes i kon- takt med et amin av formel R^NH i nær- vær av en karboksylsyre av formel R5COOH, og dannelse og isolering av produktet av formel (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 (2)
| Publication Number | Publication Date |
|---|---|
| NO992058L true NO992058L (no) | 1999-04-29 |
| NO992058D0 NO992058D0 (no) | 1999-04-29 |
Family
ID=24972126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO992058A NO992058D0 (no) | 1996-10-31 | 1999-04-29 | FremgangsmÕte for fremstilling av fysostigminkarbamatderivater fra eseretoler |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5665880A (no) |
| EP (1) | EP0937080A1 (no) |
| JP (1) | JP2001503049A (no) |
| KR (1) | KR20000052891A (no) |
| CN (1) | CN1235607A (no) |
| AR (1) | AR009300A1 (no) |
| AU (1) | AU712493B2 (no) |
| BR (1) | BR9712719A (no) |
| CA (1) | CA2268150A1 (no) |
| HU (1) | HUP9904284A3 (no) |
| IL (1) | IL129661A0 (no) |
| NO (1) | NO992058D0 (no) |
| WO (1) | WO1998018799A1 (no) |
| ZA (1) | ZA976712B (no) |
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 |
| JP4676961B2 (ja) * | 2003-10-21 | 2011-04-27 | 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し、薬理活性物質を放出するカルバモイルエステル類 |
| US20050228019A1 (en) * | 2004-01-26 | 2005-10-13 | Cortex Pharmaceuticals, Inc. | Enhancement of ampakine-Induced facilitation of synaptic responses by cholinesterase inhibitors |
| MX2009008288A (es) * | 2007-02-02 | 2009-12-01 | Colucid Pharmaceuticals Inc | Compuestos que inhiben la colinesterasa. |
| 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 |
| JP2010533717A (ja) * | 2007-07-18 | 2010-10-28 | 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 | 覚醒を促進する方法 |
| 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 |
| ES2075102T3 (es) * | 1989-09-19 | 1995-10-01 | Hoechst Roussel Pharma | Procedimiento para la resolucion quimica de (+/-)-1,3-dimetiloxiindoliletilaminas 5-alcoxi sustituidas. |
| US4937341A (en) * | 1989-09-28 | 1990-06-26 | Hoechst-Roussel Pharmaceuticals Inc. | Process for preparing N-aminocarbarbamates related to physostigmine |
| US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
| 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 |
| US4983616A (en) * | 1990-02-01 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Hexahydropyrrolo(2,3-B)indole carbamates, ureas, amides and related compounds |
| US5091541A (en) * | 1990-02-01 | 1992-02-25 | 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 |
| RO110501B1 (ro) * | 1990-06-27 | 1996-01-30 | Hoechst Roussel Pharma | Derivati de tetrahidroizochinolinil carbamati |
| 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 |
| 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
- 1996-10-31 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 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 Withdrawn
- 1997-07-21 EP EP97934964A patent/EP0937080A1/en not_active Withdrawn
- 1997-07-21 WO PCT/US1997/012370 patent/WO1998018799A1/en not_active Ceased
- 1997-07-21 AU AU38010/97A patent/AU712493B2/en not_active Ceased
- 1997-07-21 HU HU9904284A patent/HUP9904284A3/hu unknown
- 1997-07-21 BR BR9712719-1A patent/BR9712719A/pt not_active Application Discontinuation
- 1997-07-21 CN CN97199271A patent/CN1235607A/zh active Pending
- 1997-07-21 CA CA002268150A patent/CA2268150A1/en not_active Abandoned
- 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/NO992058D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US5665880A (en) | 1997-09-09 |
| KR20000052891A (ko) | 2000-08-25 |
| JP2001503049A (ja) | 2001-03-06 |
| AU3801097A (en) | 1998-05-22 |
| CN1235607A (zh) | 1999-11-17 |
| ZA976712B (en) | 1998-04-30 |
| HUP9904284A3 (en) | 2000-09-28 |
| US5734062A (en) | 1998-03-31 |
| AU712493B2 (en) | 1999-11-11 |
| HUP9904284A2 (hu) | 2000-05-28 |
| EP0937080A1 (en) | 1999-08-25 |
| BR9712719A (pt) | 1999-10-26 |
| AR009300A1 (es) | 2000-04-12 |
| IL129661A0 (en) | 2000-02-29 |
| WO1998018799A1 (en) | 1998-05-07 |
| NO992058D0 (no) | 1999-04-29 |
| CA2268150A1 (en) | 1998-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application |