EA199900382A1 - Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана и l-винно-кислой соли производного - Google Patents
Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана и l-винно-кислой соли производногоInfo
- Publication number
- EA199900382A1 EA199900382A1 EA199900382A EA199900382A EA199900382A1 EA 199900382 A1 EA199900382 A1 EA 199900382A1 EA 199900382 A EA199900382 A EA 199900382A EA 199900382 A EA199900382 A EA 199900382A EA 199900382 A1 EA199900382 A1 EA 199900382A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- mol
- derivative
- heptane
- azadihydroxybicyclo
- formula
- Prior art date
Links
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 150000003951 lactams Chemical class 0.000 abstract 2
- 239000012285 osmium tetroxide Substances 0.000 abstract 2
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 238000006359 acetalization reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical class C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000001172 regenerating effect Effects 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
-
- 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
- C07D209/52—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 condensed with a ring other than six-membered
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Предлагаемый способ относится к способу получения производного 2-азадигидроксибицикло [2.2.1] гептана формулы (I) или (I')где * обозначает R-хиральность и *' обозначает S-хиральность, R представляет водород или соответственно группу формулы (II) или (II'), где Rпредставляет алкил и Ar представляет необязательно замещенный арил, включающему в себя бисгидроксилирование производного бицикло [2.2.1] гептена формулы (III) или (III'), где *, *' и R такие, как определено выше, в присутствии от около 0,1 мол.% до около 5 мол.% осмата металла или от около 0,06 мол.% до около 0,07 мол.% тетроксида осмия и окислителя, способного регенерировать тетроксид осмия. Кроме того изобретение относится к обработке (1R) диастереомера производного (I) 2-азадигидроксибицикло [2.2.1] гептана, где R представляет группу формулы (II), L-винной кислотой, и к L-винно-кислому солевому продукту ее. Кроме того изобретение относится к использованию (1R) диастереомера производного 2-азадигидроксибицикло [2.2.1] гептана в катализируемой кислотой реакции ацетализации или кетализации, которая приводит к защите дигидрокси частей его в изопропаноле. Кроме того, изобретение относится к окислению бис-О-защищенного производного (1R) диастереомера производного 2-азадигидроксибицикло [2.2.1] гептана в соответствующий лактам в присутствии от около 0,01 мол. % до 1 мол. % RuOприблизительно 3 эквивалентами окислителя с образованием лактама с энантиомерным избытком ("эи") большим или равным около 95%.Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/732,024 US5684159A (en) | 1995-05-30 | 1996-10-16 | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
| PCT/US1997/018365 WO1998016510A1 (en) | 1996-10-16 | 1997-10-15 | Process for preparing 2-azadihydroxybicyclo[2.2.1]heptane compounds and the l-tartaric acid salt of the compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199900382A1 true EA199900382A1 (ru) | 1999-10-28 |
| EA002438B1 EA002438B1 (ru) | 2002-04-25 |
Family
ID=24941881
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200100661A EA200100661A1 (ru) | 1996-10-16 | 1997-10-15 | Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана |
| EA200100660A EA200100660A1 (ru) | 1996-10-16 | 1997-10-15 | Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана |
| EA199900382A EA002438B1 (ru) | 1996-10-16 | 1997-10-15 | Способ получения производных 2-азадигидроксибицикло[2.2.1]гептана и l-виннокислой соли производного |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200100661A EA200100661A1 (ru) | 1996-10-16 | 1997-10-15 | Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана |
| EA200100660A EA200100660A1 (ru) | 1996-10-16 | 1997-10-15 | Способ получения производных 2-азадигидроксибицикло [2.2.1] гептана |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US5684159A (ru) |
| EP (1) | EP0934268A4 (ru) |
| JP (1) | JP2001502329A (ru) |
| KR (1) | KR20000049195A (ru) |
| CN (2) | CN1094927C (ru) |
| AP (1) | AP942A (ru) |
| AU (1) | AU721965B2 (ru) |
| BG (2) | BG64733B1 (ru) |
| BR (1) | BR9711910A (ru) |
| CA (1) | CA2268652A1 (ru) |
| CZ (1) | CZ291387B6 (ru) |
| EA (3) | EA200100661A1 (ru) |
| HU (1) | HUP9903583A3 (ru) |
| IL (1) | IL129231A (ru) |
| NO (2) | NO320332B1 (ru) |
| OA (1) | OA11112A (ru) |
| PL (1) | PL332827A1 (ru) |
| SK (1) | SK43799A3 (ru) |
| UA (1) | UA52702C2 (ru) |
| WO (1) | WO1998016510A1 (ru) |
| ZA (1) | ZA979268B (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5684159A (en) * | 1995-05-30 | 1997-11-04 | Rhone-Poulenc Rorer S.A. | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
| ES2216252T3 (es) * | 1997-12-25 | 2004-10-16 | Kuraray Co., Ltd. | Procedimiento de preparacion y metodo de cristalizacion de 2-azabiciclo (2.2.1) hepta-5-en-3-ona. |
| TW396337B (en) * | 1998-02-13 | 2000-07-01 | Mediatek Inc | The automatic regulating device of cdrom optimum focusing spot and the method thereof |
| US5952339A (en) * | 1998-04-02 | 1999-09-14 | Bencherif; Merouane | Pharmaceutical compositions and methods of using nicotinic antagonists for treating a condition or disorder characterized by alteration in normal neurotransmitter release |
| US6057446A (en) | 1998-04-02 | 2000-05-02 | Crooks; Peter Anthony | Certain 1-aza-tricyclo [3.3.1-13,7 ] decane compounds |
| US5986100A (en) | 1998-04-02 | 1999-11-16 | Crooks; Peter Anthony | Pharmaceutical compositions and methods for use |
| DK1140933T3 (da) | 1998-12-31 | 2004-12-20 | Aventis Pharma Inc | Fremgangsmåde til fremstilling af N6-substituerede deaza-adenosinderivater |
| US6387033B1 (en) * | 2000-11-22 | 2002-05-14 | Council Of Scientific And Industrial Research | Preparation of new layered double hydroxides exchanged with osmate for asymmetric dihydroxylation of olefins to vicinal diols |
| WO2002091988A2 (en) * | 2001-05-10 | 2002-11-21 | Aventis Pharma Deutschland Gmbh | Novel processes for the preparation of adenosine compounds and intermediates thereto |
| EP1574508A1 (de) * | 2004-01-30 | 2005-09-14 | Lonza AG | Verfahren zur Herstellung von Acetalen und Ketalen von 3-Amino-5-(hydroxymethyl)-cyclopentan-1,2-diolen, sowie deren Derivaten und Salzen |
| ATE537148T1 (de) * | 2006-10-11 | 2011-12-15 | Nippon Soda Co | Verfahren zur herstellung eines azabicycloalkanolderivats |
| CN102311440B (zh) * | 2010-07-02 | 2015-01-07 | 无锡药明康德生物技术有限公司 | 1-甲氧羰基-3-苄基-8-叔丁氧羰基-3,8-二氮杂双环[3.2.1]辛烷及制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK532575A (da) * | 1974-12-13 | 1976-06-14 | Merck & Co Inc | Fremgangsmade til racematspaltning af organiske forbindelser |
| US4508911A (en) * | 1982-06-21 | 1985-04-02 | The Upjohn Company | Amine intermediates for analgesic compounds |
| US5284769A (en) * | 1989-10-16 | 1994-02-08 | Chiros Ltd. | Process for preparing a single enantiomer of a lactam using lactamase |
| AU641712B2 (en) * | 1989-12-13 | 1993-09-30 | Noristan Holdings Limited | Polycyclic nitrile compounds and pharmaceutical compositions thereof |
| JP2891740B2 (ja) * | 1990-03-30 | 1999-05-17 | 塩野義製薬株式会社 | 光学活性ノルボルナン系アミン誘導体の製造方法 |
| SG80526A1 (en) * | 1990-09-25 | 2001-05-22 | Rhone Poulenc Rorer Int | Compounds having antihypertensive and anti- ischemic properies |
| US5700895A (en) * | 1993-08-23 | 1997-12-23 | Sumitomo Chemical Company, Limited | Ethylene-α-olefin copolymer and molded article thereof |
| US5670649A (en) * | 1995-05-30 | 1997-09-23 | Rhone-Poulenc Rorer S.A. | Derivatives of 2-azabicyclo 2.2.1!heptane, their preparation and their application |
| US5684159A (en) * | 1995-05-30 | 1997-11-04 | Rhone-Poulenc Rorer S.A. | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
| FR2734822B1 (fr) * | 1995-05-30 | 1997-07-04 | Rhone Poulenc Rorer Sa | Nouveaux derives du 2-azabicyclo(2.2.1)heptane, leur preparation et leur application |
| US5856497A (en) * | 1995-12-11 | 1999-01-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Asymmetric synthesis of α-cycloalkylalkyl substituted methanamines |
-
1996
- 1996-10-16 US US08/732,024 patent/US5684159A/en not_active Expired - Fee Related
-
1997
- 1997-06-10 US US08/873,285 patent/US5808093A/en not_active Expired - Fee Related
- 1997-06-10 US US08/873,096 patent/US5886192A/en not_active Expired - Fee Related
- 1997-06-10 US US08/873,284 patent/US5831096A/en not_active Expired - Fee Related
- 1997-10-15 CN CN97198783A patent/CN1094927C/zh not_active Expired - Fee Related
- 1997-10-15 AU AU48160/97A patent/AU721965B2/en not_active Ceased
- 1997-10-15 SK SK437-99A patent/SK43799A3/sk unknown
- 1997-10-15 UA UA99052680A patent/UA52702C2/ru unknown
- 1997-10-15 EP EP97910894A patent/EP0934268A4/en not_active Withdrawn
- 1997-10-15 JP JP10518472A patent/JP2001502329A/ja not_active Ceased
- 1997-10-15 HU HU9903583A patent/HUP9903583A3/hu unknown
- 1997-10-15 BR BR9711910A patent/BR9711910A/pt not_active Application Discontinuation
- 1997-10-15 PL PL97332827A patent/PL332827A1/xx not_active IP Right Cessation
- 1997-10-15 CZ CZ19991312A patent/CZ291387B6/cs not_active IP Right Cessation
- 1997-10-15 EA EA200100661A patent/EA200100661A1/ru unknown
- 1997-10-15 AP APAP/P/1999/001486A patent/AP942A/en active
- 1997-10-15 CA CA002268652A patent/CA2268652A1/en not_active Abandoned
- 1997-10-15 WO PCT/US1997/018365 patent/WO1998016510A1/en not_active Application Discontinuation
- 1997-10-15 KR KR1019990703293A patent/KR20000049195A/ko not_active Abandoned
- 1997-10-15 EA EA200100660A patent/EA200100660A1/ru unknown
- 1997-10-15 EA EA199900382A patent/EA002438B1/ru not_active IP Right Cessation
- 1997-10-15 IL IL12923197A patent/IL129231A/xx unknown
- 1997-10-16 ZA ZA979268A patent/ZA979268B/xx unknown
-
1999
- 1999-03-30 BG BG108906A patent/BG64733B1/bg unknown
- 1999-03-30 BG BG103296A patent/BG64701B1/bg unknown
- 1999-04-09 OA OA9900080A patent/OA11112A/en unknown
- 1999-04-15 NO NO19991800A patent/NO320332B1/no unknown
-
2002
- 2002-06-05 CN CN02122409A patent/CN1385422A/zh active Pending
-
2005
- 2005-04-08 NO NO20051757A patent/NO20051757D0/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC4A | Change in name of a patent proprietor in a eurasian patent |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |