CA2265712C - Intermediates and process for preparing olanzapine - Google Patents
Intermediates and process for preparing olanzapine Download PDFInfo
- Publication number
- CA2265712C CA2265712C CA002265712A CA2265712A CA2265712C CA 2265712 C CA2265712 C CA 2265712C CA 002265712 A CA002265712 A CA 002265712A CA 2265712 A CA2265712 A CA 2265712A CA 2265712 C CA2265712 C CA 2265712C
- Authority
- CA
- Canada
- Prior art keywords
- dihydrate
- olanzapine
- dehydrate
- ray powder
- powder diffraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229960005017 olanzapine Drugs 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000000543 intermediate Substances 0.000 title abstract description 12
- 150000004683 dihydrates Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- FUOBHGGXKJHKDF-UHFFFAOYSA-N 2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine dihydrate Chemical compound O.O.C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 FUOBHGGXKJHKDF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 101100001673 Emericella variicolor andH gene Proteins 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- -1 dihydrate compound Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2648796P | 1996-09-23 | 1996-09-23 | |
| US60/026,487 | 1996-09-23 | ||
| PCT/US1997/016499 WO1998012199A1 (en) | 1996-09-23 | 1997-09-18 | Intermediates and process for preparing olanzapine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2265712A1 CA2265712A1 (en) | 1998-03-26 |
| CA2265712C true CA2265712C (en) | 2006-10-31 |
Family
ID=21832120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002265712A Expired - Lifetime CA2265712C (en) | 1996-09-23 | 1997-09-18 | Intermediates and process for preparing olanzapine |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6020487A (h) |
| EP (1) | EP0831098B1 (h) |
| JP (2) | JP2001500877A (h) |
| KR (1) | KR100560015B1 (h) |
| CN (1) | CN1122036C (h) |
| AR (1) | AR013838A1 (h) |
| AT (1) | ATE209208T1 (h) |
| AU (1) | AU719441B2 (h) |
| BR (1) | BR9712100A (h) |
| CA (1) | CA2265712C (h) |
| CO (1) | CO4910140A1 (h) |
| CZ (1) | CZ299248B6 (h) |
| DE (1) | DE69708428T2 (h) |
| DK (1) | DK0831098T3 (h) |
| EA (1) | EA001642B1 (h) |
| EG (1) | EG23861A (h) |
| ES (1) | ES2166051T3 (h) |
| HU (1) | HU226484B1 (h) |
| ID (1) | ID27275A (h) |
| IL (1) | IL128962A (h) |
| IN (1) | IN187156B (h) |
| MY (1) | MY125565A (h) |
| NO (1) | NO323980B1 (h) |
| NZ (1) | NZ334448A (h) |
| PE (1) | PE110398A1 (h) |
| PL (3) | PL196069B1 (h) |
| PT (1) | PT831098E (h) |
| RS (1) | RS49598B (h) |
| SI (1) | SI0831098T1 (h) |
| SV (1) | SV1997000081A (h) |
| TR (1) | TR199900640T2 (h) |
| TW (1) | TW470746B (h) |
| UA (1) | UA59371C2 (h) |
| WO (1) | WO1998012199A1 (h) |
| ZA (1) | ZA978515B (h) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0300875A3 (en) * | 2000-08-31 | 2005-09-28 | Reddy S Lab Ltd Hyderabad Dr | Process for preparation of hydrates of olanzapine and their conversion into crystalline forms of olanzapine |
| US6740753B2 (en) * | 2001-01-04 | 2004-05-25 | Geneva Pharmaceuticals, Inc. | Olanzapine crystal modification |
| AU2002340328A1 (en) * | 2001-10-29 | 2003-05-12 | Janet I. Cord | Olanzapine dihydrate-ii a process for its preparation and use thereof |
| CA2471341C (en) | 2001-12-24 | 2012-01-24 | Sun Pharmaceutical Industries Limited | Crystalline form i of 2-methyl-4-(4-methyl-1-piperazinyl) 10h thieno [2,3-b][1,5]benzodiazepine |
| WO2003091260A1 (en) * | 2002-04-23 | 2003-11-06 | Dr. Reddy's Laboratories Limited | Novel crystalline polymorph form-vi of olanzapine and a process for preparation thereof |
| ATE500258T1 (de) * | 2002-05-31 | 2011-03-15 | Sandoz Ag | Verfahren zur herstellung von olanzapin form i |
| SI21270A (sl) | 2002-07-15 | 2004-02-29 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Kristalne oblike olanzapina in postopki za njihovo pripravo |
| AU2003300324A1 (en) * | 2002-12-24 | 2004-07-22 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of olanzapine, methods for their preparation and method for the preparation of known olanzapine crystal forms |
| US20070148218A1 (en) * | 2003-11-18 | 2007-06-28 | Gordon Ryan D | Olanzapine containing transdermal drug delivery compositions |
| CN1906201A (zh) * | 2003-12-22 | 2007-01-31 | 特瓦制药工业有限公司 | 合成奥氮平的方法 |
| DE602005027308D1 (de) | 2004-01-27 | 2011-05-19 | Synthon Bv | Stabile salze von olanzapin |
| EP1716154A1 (en) * | 2004-02-19 | 2006-11-02 | Neuland Laboratories Ltd | Process for the preparation of olanzapine form 1 useful as antipsychotic drug |
| US20080009481A1 (en) * | 2004-07-14 | 2008-01-10 | Shasun Chemicals And Drugs Limited | Process For Making Form I Of Olanzapine |
| ES2253091B1 (es) | 2004-07-27 | 2007-02-01 | Inke, S.A. | Solvato mixto de olanzapina, procedimiento para su obtencion y procedimiento de obtencion de la forma i de olanzapina a partir del mismo. |
| US7829700B2 (en) | 2004-09-06 | 2010-11-09 | Shasun Chemicals And Drugs Limited | Process for preparation of a pharmaceutically pure polymorphic form I of Olanzapine |
| KR20130030305A (ko) * | 2004-11-16 | 2013-03-26 | 엘란 파마 인터내셔널 리미티드 | 주사가능한 나노입자형 올란자핀 제형 |
| US7834176B2 (en) | 2006-01-26 | 2010-11-16 | Sandoz Ag | Polymorph E of Olanzapine and preparation of anhydrous non-solvated crystalline polymorphic Form I of 2-methyl-4(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine (Olanzapine Form I) from the polymorphic Olanzapine Form E |
| CA2591644A1 (en) * | 2007-06-14 | 2008-12-14 | Apotex Pharmachem Inc. | Novel processes to form-i of olanzapine |
| EP2486913A1 (en) | 2011-02-14 | 2012-08-15 | Labtec GmbH | Rapidly disintegrating oral film formulation for Olanzapin |
| JP6008734B2 (ja) * | 2012-12-20 | 2016-10-19 | 株式会社トクヤマ | オランザピンｉｉ型結晶の製造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5302716A (en) * | 1986-01-16 | 1994-04-12 | Schering Corporation | Fused benzazepines |
| CA2002596A1 (en) * | 1988-11-14 | 1990-05-14 | Thomas M. Eckrich | Hydrates of b-lactam antibiotic |
| GB9009229D0 (en) * | 1990-04-25 | 1990-06-20 | Lilly Industries Ltd | Pharmaceutical compounds |
| US5229382A (en) * | 1990-04-25 | 1993-07-20 | Lilly Industries Limited | 2-methyl-thieno-benzodiazepine |
| EP0582368B1 (en) * | 1992-05-29 | 2001-01-24 | Eli Lilly And Company Limited | Thienobenzodiazepine derivatives for treatment of CNS disorders |
| US5550231A (en) * | 1993-06-15 | 1996-08-27 | Eli Lilly And Company | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
| US5602124A (en) * | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | 5-HT2 receptor ligands |
| US5631250A (en) * | 1995-03-24 | 1997-05-20 | Eli Lilly And Company | Process and solvate of 2-methyl-thieno-benzodiazepine |
| US5637584A (en) * | 1995-03-24 | 1997-06-10 | Eli Lilly And Company | Solvate of olanzapine |
| EG23659A (en) * | 1995-03-24 | 2007-03-26 | Lilly Co Eli | Process and crystal forms of methyl-thieno-benzodiazepine |
| EG24221A (en) * | 1995-03-24 | 2008-11-10 | Lilly Co Eli | Process for preparing olanzapine |
| RS49597B (sr) * | 1996-09-23 | 2007-06-04 | Eli Lilly And Company, | Olanzapin dihidrat d |
-
1997
- 1997-09-02 ZA ZA978515A patent/ZA978515B/xx unknown
- 1997-09-18 TR TR1999/00640T patent/TR199900640T2/xx unknown
- 1997-09-18 CA CA002265712A patent/CA2265712C/en not_active Expired - Lifetime
- 1997-09-18 WO PCT/US1997/016499 patent/WO1998012199A1/en not_active Application Discontinuation
- 1997-09-18 UA UA99031635A patent/UA59371C2/uk unknown
- 1997-09-18 PL PL381478A patent/PL196069B1/pl unknown
- 1997-09-18 IL IL12896297A patent/IL128962A/xx not_active IP Right Cessation
- 1997-09-18 AU AU44841/97A patent/AU719441B2/en not_active Expired
- 1997-09-18 EA EA199900326A patent/EA001642B1/ru not_active IP Right Cessation
- 1997-09-18 HU HU0000066A patent/HU226484B1/hu unknown
- 1997-09-18 RS YUP-155/99A patent/RS49598B/sr unknown
- 1997-09-18 KR KR1019997002424A patent/KR100560015B1/ko not_active Expired - Lifetime
- 1997-09-18 CN CN97198137A patent/CN1122036C/zh not_active Expired - Lifetime
- 1997-09-18 CZ CZ0099099A patent/CZ299248B6/cs not_active IP Right Cessation
- 1997-09-18 NZ NZ334448A patent/NZ334448A/en not_active IP Right Cessation
- 1997-09-18 PL PL381479A patent/PL196068B1/pl unknown
- 1997-09-18 BR BR9712100-2A patent/BR9712100A/pt not_active Application Discontinuation
- 1997-09-18 ID IDW990058D patent/ID27275A/id unknown
- 1997-09-18 PL PL97332482A patent/PL194565B1/pl unknown
- 1997-09-18 JP JP10514842A patent/JP2001500877A/ja not_active Withdrawn
- 1997-09-19 IN IN1736CA1997 patent/IN187156B/en unknown
- 1997-09-22 MY MYPI97004392A patent/MY125565A/en unknown
- 1997-09-22 DK DK97307383T patent/DK0831098T3/da active
- 1997-09-22 PT PT97307383T patent/PT831098E/pt unknown
- 1997-09-22 SI SI9730288T patent/SI0831098T1/xx unknown
- 1997-09-22 EP EP97307383A patent/EP0831098B1/en not_active Expired - Lifetime
- 1997-09-22 AT AT97307383T patent/ATE209208T1/de active
- 1997-09-22 ES ES97307383T patent/ES2166051T3/es not_active Expired - Lifetime
- 1997-09-22 SV SV1997000081A patent/SV1997000081A/es not_active Application Discontinuation
- 1997-09-22 CO CO97055061A patent/CO4910140A1/es unknown
- 1997-09-22 DE DE69708428T patent/DE69708428T2/de not_active Expired - Lifetime
- 1997-09-23 PE PE1997000855A patent/PE110398A1/es active IP Right Grant
- 1997-09-23 AR ARP970104362A patent/AR013838A1/es not_active Application Discontinuation
- 1997-09-23 US US08/935,884 patent/US6020487A/en not_active Expired - Lifetime
- 1997-09-23 EG EG98697A patent/EG23861A/xx active
-
1998
- 1998-02-27 TW TW086113832A patent/TW470746B/zh not_active IP Right Cessation
-
1999
- 1999-03-22 NO NO19991382A patent/NO323980B1/no not_active IP Right Cessation
-
2009
- 2009-06-05 JP JP2009135901A patent/JP2009242407A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170918 |