ATE125254T1 - Verfahren zur racematspaltung von 5-alkoxy- substituierten (+/-)-1,3- dimethyloxindolylethylaminen. - Google Patents
Verfahren zur racematspaltung von 5-alkoxy- substituierten (+/-)-1,3- dimethyloxindolylethylaminen.Info
- Publication number
- ATE125254T1 ATE125254T1 AT90117821T AT90117821T ATE125254T1 AT E125254 T1 ATE125254 T1 AT E125254T1 AT 90117821 T AT90117821 T AT 90117821T AT 90117821 T AT90117821 T AT 90117821T AT E125254 T1 ATE125254 T1 AT E125254T1
- Authority
- AT
- Austria
- Prior art keywords
- tartaric acid
- enantiomers
- acid
- dimethyloxindolylethylamines
- racemat
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000002244 precipitate Substances 0.000 abstract 3
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- WMJNKBXKYHXOHC-PMACEKPBSA-N (2S,3S)-2,3-dihydroxy-2,3-bis(2-methylbenzoyl)butanedioic acid Chemical compound C=1(C(=CC=CC1)C(=O)[C@]([C@](C(=O)O)(O)C(=O)C=1C(=CC=CC1)C)(O)C(=O)O)C WMJNKBXKYHXOHC-PMACEKPBSA-N 0.000 abstract 1
- XEEBADQXIMNBQG-UHFFFAOYSA-N 3-(2-aminoethyl)-5-methoxy-1,3-dimethyl-2-indolone Chemical compound COC1=CC=C2N(C)C(=O)C(C)(CCN)C2=C1 XEEBADQXIMNBQG-UHFFFAOYSA-N 0.000 abstract 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229960001270 d- tartaric acid Drugs 0.000 abstract 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 abstract 1
- 229960001697 physostigmine Drugs 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40921389A | 1989-09-19 | 1989-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE125254T1 true ATE125254T1 (de) | 1995-08-15 |
Family
ID=23619520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT90117821T ATE125254T1 (de) | 1989-09-19 | 1990-09-15 | Verfahren zur racematspaltung von 5-alkoxy- substituierten (+/-)-1,3- dimethyloxindolylethylaminen. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5387695A (de) |
| EP (1) | EP0418770B1 (de) |
| JP (1) | JPH0757746B2 (de) |
| KR (1) | KR0165670B1 (de) |
| AT (1) | ATE125254T1 (de) |
| AU (1) | AU626458B2 (de) |
| CA (1) | CA2025593A1 (de) |
| DE (1) | DE69020989T2 (de) |
| DK (1) | DK0418770T3 (de) |
| ES (1) | ES2075102T3 (de) |
| FI (1) | FI95030C (de) |
| IE (1) | IE67640B1 (de) |
| IL (1) | IL95717A (de) |
| NO (1) | NO174252C (de) |
| NZ (1) | NZ235333A (de) |
| PT (1) | PT95340B (de) |
| ZA (1) | ZA907424B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
| DE69032595T2 (de) * | 1990-01-22 | 1999-03-25 | Hoechst Marion Roussel, Inc., Kansas City, Mo. 64137 | Verfahren zur enantioselektiven Synthese alkylierter Oxindole zur Verwendung als Zwischenprodukte bei der Herstellung von Physostigminen |
| US5521320A (en) * | 1990-01-22 | 1996-05-28 | Hoechst-Roussel Pharmaceuticals Incorporated | Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine |
| US5840915A (en) * | 1990-01-22 | 1998-11-24 | Hoechst Marion Roussel, Inc. | Process for the enatioselective synthesis of intermediates used |
| US5665880A (en) * | 1996-10-31 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseretholes |
| US5677457A (en) * | 1996-12-19 | 1997-10-14 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseroline ethers |
| JP6687596B2 (ja) | 2015-02-17 | 2020-04-22 | アモーレパシフィック コーポレーションＡｍｏｒｅｐａｃｉｆｉｃ Ｃｏｒｐｏｒａｔｉｏｎ | Ｎ−［４−（１−アミノエチル）−フェニル］−スルホンアミド誘導体のキラル分割方法 |
| CN116903633B (zh) * | 2022-10-10 | 2025-11-18 | 福建医科大学 | 基于手性有机酸分离的高纯钩吻素子及其药学可接受盐的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
| US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
| 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 |
| DE69032595T2 (de) * | 1990-01-22 | 1999-03-25 | Hoechst Marion Roussel, Inc., Kansas City, Mo. 64137 | Verfahren zur enantioselektiven Synthese alkylierter Oxindole zur Verwendung als Zwischenprodukte bei der Herstellung von Physostigminen |
-
1990
- 1990-09-15 EP EP90117821A patent/EP0418770B1/de not_active Expired - Lifetime
- 1990-09-15 AT AT90117821T patent/ATE125254T1/de not_active IP Right Cessation
- 1990-09-15 DE DE69020989T patent/DE69020989T2/de not_active Expired - Fee Related
- 1990-09-15 DK DK90117821.0T patent/DK0418770T3/da active
- 1990-09-15 ES ES90117821T patent/ES2075102T3/es not_active Expired - Lifetime
- 1990-09-17 IL IL9571790A patent/IL95717A/en not_active IP Right Cessation
- 1990-09-17 FI FI904562A patent/FI95030C/fi not_active IP Right Cessation
- 1990-09-17 NZ NZ235333A patent/NZ235333A/en unknown
- 1990-09-18 CA CA002025593A patent/CA2025593A1/en not_active Abandoned
- 1990-09-18 PT PT95340A patent/PT95340B/pt not_active IP Right Cessation
- 1990-09-18 AU AU62629/90A patent/AU626458B2/en not_active Ceased
- 1990-09-18 ZA ZA907424A patent/ZA907424B/xx unknown
- 1990-09-18 IE IE337490A patent/IE67640B1/en not_active IP Right Cessation
- 1990-09-18 KR KR1019900014730A patent/KR0165670B1/ko not_active Expired - Fee Related
- 1990-09-18 NO NO904067A patent/NO174252C/no not_active IP Right Cessation
- 1990-09-18 JP JP2246409A patent/JPH0757746B2/ja not_active Expired - Lifetime
-
1993
- 1993-02-17 US US08/022,605 patent/US5387695A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0418770A3 (en) | 1991-11-27 |
| IL95717A (en) | 1994-10-21 |
| EP0418770A2 (de) | 1991-03-27 |
| ZA907424B (en) | 1991-06-26 |
| KR910006229A (ko) | 1991-04-27 |
| US5387695A (en) | 1995-02-07 |
| PT95340A (pt) | 1991-05-22 |
| KR0165670B1 (ko) | 1999-01-15 |
| NO174252B (no) | 1993-12-27 |
| DE69020989D1 (de) | 1995-08-24 |
| IE903374A1 (en) | 1991-04-10 |
| FI95030B (fi) | 1995-08-31 |
| PT95340B (pt) | 1997-06-30 |
| NZ235333A (en) | 1992-03-26 |
| NO904067L (no) | 1991-03-20 |
| FI904562A0 (fi) | 1990-09-17 |
| JPH0757746B2 (ja) | 1995-06-21 |
| IL95717A0 (en) | 1991-06-30 |
| FI95030C (fi) | 1995-12-11 |
| JPH03167172A (ja) | 1991-07-19 |
| AU6262990A (en) | 1991-03-28 |
| NO174252C (no) | 1994-04-06 |
| NO904067D0 (no) | 1990-09-18 |
| ES2075102T3 (es) | 1995-10-01 |
| DK0418770T3 (da) | 1995-10-30 |
| IE67640B1 (en) | 1996-04-17 |
| EP0418770B1 (de) | 1995-07-19 |
| DE69020989T2 (de) | 1996-02-08 |
| AU626458B2 (en) | 1992-07-30 |
| CA2025593A1 (en) | 1991-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |