NO325949B1 - Fremgangsmate ved fremstilling av hovedsakelig enkelt-enantiomer narwedin - Google Patents
Fremgangsmate ved fremstilling av hovedsakelig enkelt-enantiomer narwedin Download PDFInfo
- Publication number
- NO325949B1 NO325949B1 NO19994928A NO994928A NO325949B1 NO 325949 B1 NO325949 B1 NO 325949B1 NO 19994928 A NO19994928 A NO 19994928A NO 994928 A NO994928 A NO 994928A NO 325949 B1 NO325949 B1 NO 325949B1
- Authority
- NO
- Norway
- Prior art keywords
- narwedine
- enantiomer
- preparation
- solvent
- amine base
- Prior art date
Links
- QENVUHCAYXAROT-UHFFFAOYSA-N Galanthaminon Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(=O)C=C2 QENVUHCAYXAROT-UHFFFAOYSA-N 0.000 title claims abstract description 40
- QENVUHCAYXAROT-YOEHRIQHSA-N Narwedine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1CC(=O)C=C2 QENVUHCAYXAROT-YOEHRIQHSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 21
- WCRYNEMFWLZAAZ-WMLDXEAASA-N Narwedine Natural products COc1ccc2CCCC[C@@]34C=CC(=O)C[C@@H]3Oc1c24 WCRYNEMFWLZAAZ-WMLDXEAASA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 8
- 229960003980 galantamine Drugs 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000010899 nucleation Methods 0.000 abstract 1
- VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 abstract 1
- 230000006340 racemization Effects 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- 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 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 241000234479 Narcissus Species 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ASUTZQLVASHGKV-SUYBPPKGSA-N ent-galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@@]23[C@H]1C[C@H](O)C=C2 ASUTZQLVASHGKV-SUYBPPKGSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9707413.2A GB9707413D0 (en) | 1997-04-11 | 1997-04-11 | Process |
| PCT/GB1998/001029 WO1998046610A1 (fr) | 1997-04-11 | 1998-04-08 | Procede de preparation de narwedine possedant un seul enantiomere |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994928L NO994928L (no) | 1999-10-08 |
| NO994928D0 NO994928D0 (no) | 1999-10-08 |
| NO325949B1 true NO325949B1 (no) | 2008-08-25 |
Family
ID=10810680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994928A NO325949B1 (no) | 1997-04-11 | 1999-10-08 | Fremgangsmate ved fremstilling av hovedsakelig enkelt-enantiomer narwedin |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6392038B1 (fr) |
| EP (1) | EP0971930B1 (fr) |
| JP (1) | JP4322317B2 (fr) |
| KR (1) | KR100523125B1 (fr) |
| AT (1) | ATE253579T1 (fr) |
| AU (1) | AU726812B2 (fr) |
| CA (1) | CA2284976C (fr) |
| DE (1) | DE69819479T2 (fr) |
| DK (1) | DK0971930T3 (fr) |
| ES (1) | ES2209125T3 (fr) |
| GB (1) | GB9707413D0 (fr) |
| NO (1) | NO325949B1 (fr) |
| NZ (1) | NZ337962A (fr) |
| PT (1) | PT971930E (fr) |
| WO (1) | WO1998046610A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1875004B (zh) * | 2003-09-26 | 2010-06-23 | 台湾神隆股份有限公司 | 那维啶酰胺衍生物的拆分 |
| CA2551946A1 (fr) * | 2003-12-31 | 2005-07-21 | Actavis Group Hf | Formulations de galantamine |
| CA2552114A1 (fr) * | 2003-12-31 | 2005-07-21 | Actavis Group Hf | Formulations solides d'administration de galantamine |
| WO2006046096A2 (fr) * | 2004-08-16 | 2006-05-04 | Ranbaxy Laboratories Limited | Forme polymorphe de la narwedine et son utilisation dans la synthese de la galantamine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5428159A (en) * | 1994-04-08 | 1995-06-27 | Ciba-Geigy Corporation | Method of manufacture of (-)-galanthamine in high yield and purity substantially free of epigalanthamine |
| CA2203183C (fr) * | 1994-10-21 | 2008-04-08 | Laszlo Czollner | Procede de preparation de derives de 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine |
-
1997
- 1997-04-11 GB GBGB9707413.2A patent/GB9707413D0/en active Pending
-
1998
- 1998-04-08 EP EP98915005A patent/EP0971930B1/fr not_active Expired - Lifetime
- 1998-04-08 JP JP54359598A patent/JP4322317B2/ja not_active Expired - Lifetime
- 1998-04-08 AU AU69296/98A patent/AU726812B2/en not_active Expired
- 1998-04-08 US US09/402,722 patent/US6392038B1/en not_active Expired - Lifetime
- 1998-04-08 PT PT98915005T patent/PT971930E/pt unknown
- 1998-04-08 DE DE69819479T patent/DE69819479T2/de not_active Expired - Lifetime
- 1998-04-08 WO PCT/GB1998/001029 patent/WO1998046610A1/fr active IP Right Grant
- 1998-04-08 AT AT98915005T patent/ATE253579T1/de active
- 1998-04-08 KR KR10-1999-7009195A patent/KR100523125B1/ko not_active IP Right Cessation
- 1998-04-08 NZ NZ337962A patent/NZ337962A/en not_active IP Right Cessation
- 1998-04-08 ES ES98915005T patent/ES2209125T3/es not_active Expired - Lifetime
- 1998-04-08 DK DK98915005T patent/DK0971930T3/da active
- 1998-04-08 CA CA002284976A patent/CA2284976C/fr not_active Expired - Lifetime
-
1999
- 1999-10-08 NO NO19994928A patent/NO325949B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO994928L (no) | 1999-10-08 |
| JP2001518911A (ja) | 2001-10-16 |
| ES2209125T3 (es) | 2004-06-16 |
| EP0971930B1 (fr) | 2003-11-05 |
| PT971930E (pt) | 2004-02-27 |
| US6392038B1 (en) | 2002-05-21 |
| JP4322317B2 (ja) | 2009-08-26 |
| CA2284976A1 (fr) | 1998-10-22 |
| AU6929698A (en) | 1998-11-11 |
| EP0971930A1 (fr) | 2000-01-19 |
| CA2284976C (fr) | 2006-10-17 |
| NZ337962A (en) | 2001-05-25 |
| KR100523125B1 (ko) | 2005-10-19 |
| WO1998046610A1 (fr) | 1998-10-22 |
| GB9707413D0 (en) | 1997-05-28 |
| AU726812B2 (en) | 2000-11-23 |
| ATE253579T1 (de) | 2003-11-15 |
| DK0971930T3 (da) | 2004-01-26 |
| NO994928D0 (no) | 1999-10-08 |
| DE69819479T2 (de) | 2004-08-26 |
| DE69819479D1 (de) | 2003-12-11 |
| KR20010006117A (ko) | 2001-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2351594C2 (ru) | Способ получения дулоксетина и используемые при этом промежуточные соединения | |
| NO314581B1 (no) | Opplösning av aminer | |
| EP0441160B1 (fr) | Procédé pour la préparation de lévo- et dextrofenfluramine | |
| US6806373B2 (en) | Process for preparing leflunomide form I | |
| US20080167477A1 (en) | Novel polymorphic forms of carvedilol dihydrogen phosphate and process for preparing the same | |
| CZ293546B6 (cs) | Způsob štěpení racemátů ketaminu | |
| NO325949B1 (no) | Fremgangsmate ved fremstilling av hovedsakelig enkelt-enantiomer narwedin | |
| AU2014393488B2 (en) | Process for obtaining optically active pirlindole enantiomers and salts thereof | |
| NO309035B1 (no) | Ny fremgangsmÕte for fremstilling av ropivacainhydrokloridmonohydrat | |
| JPS6187667A (ja) | 光学的活性アミンの製造方法 | |
| US20100081839A1 (en) | Process for preparation of crystalline clopidogrel hydrogen sulphate form i | |
| WO2010111844A1 (fr) | Procédé de préparation de sibutramine optiquement pure et de ses sels dérivés | |
| KR100612183B1 (ko) | Ｒ-(+)-6-카르복사미도-3-ｎ-메틸아미노-1,2,3,4-테트라히드로카르바졸의 제조 방법 | |
| US20020082277A1 (en) | Tosylate salts of 4-(p-fluorophenyl)-piperidine -3-carbinols | |
| CN115819171B (zh) | 一种mor受体激动剂合成路线中关键中间体的手性拆分方法 | |
| KR100863922B1 (ko) | 피페리돈 유도체의 목적하는 에난티오머를 분리하는 동시에 동일 반응계에서 목적하지 않는 에난티오머를 라세미화시키는 방법 | |
| CN118580235A (zh) | 一种内磺酰胺化合物的制备方法 | |
| US6495694B2 (en) | Efficient separation of enantiomers of piperidone derivatives by precipitation of the desired eantiomer during in situ racemization of the unwanted enantiomer | |
| CN118206501A (zh) | 一种卢吗哌酮的制备方法 | |
| MXPA99009247A (en) | Process for preparing single enantiomer narwedine | |
| JPH07157475A (ja) | （＋）−３−フェニル−５−｛２−（１−ピロリジニルメチル）ブチリル｝イソオキサゾール及びその塩の分割法 | |
| JPH07215922A (ja) | １−アミノ−２−インダノール類の光学分割法 | |
| AU2005202109A1 (en) | Novel processes for making- and a new crystalline form of- leflunomide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |