EP1313742A1 - Procede de preparation d'hydrates d'olanzapine et de conversion de ceux-ci en formes cristallines d'olanzapine - Google Patents
Procede de preparation d'hydrates d'olanzapine et de conversion de ceux-ci en formes cristallines d'olanzapineInfo
- Publication number
- EP1313742A1 EP1313742A1 EP01916449A EP01916449A EP1313742A1 EP 1313742 A1 EP1313742 A1 EP 1313742A1 EP 01916449 A EP01916449 A EP 01916449A EP 01916449 A EP01916449 A EP 01916449A EP 1313742 A1 EP1313742 A1 EP 1313742A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- olanzapine
- methyl
- thieno
- dichloromethane
- process according
- 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.)
- Withdrawn
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 90
- 229960005017 olanzapine Drugs 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 title abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 150000004677 hydrates Chemical class 0.000 title abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 99
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- XBWAZCLHZCFCGK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3,4-dihydro-2h-1,4-benzodiazepin-1-ium;chloride Chemical compound [Cl-].C12=CC(Cl)=CC=C2[NH+](C)CCN=C1C1=CC=CC=C1 XBWAZCLHZCFCGK-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 9
- 229940049706 benzodiazepine Drugs 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 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 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 2
- FDWMAKNNNPSUTL-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine hydrochloride Chemical compound Cl.N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 FDWMAKNNNPSUTL-UHFFFAOYSA-N 0.000 claims 1
- DQHIXWWYDHOZKI-UHFFFAOYSA-N 2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine hydrate Chemical compound O.CN1CCN(CC1)C1=Nc2ccccc2Nc2sc(C)cc12 DQHIXWWYDHOZKI-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000001757 thermogravimetry curve Methods 0.000 description 6
- 150000004683 dihydrates Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- -1 Dihydrate B Chemical compound 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 239000002253 acid Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent 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
-
- 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
-
- 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
- A61P25/22—Anxiolytics
Definitions
- the present invention relates to a method for the preparation of hydrates of 2- methyl-4-(4-methyl-l-piperazinyl)-10H-thieno [2,3-b] [1,5] benzodiazepine (hereinafter referred to as Olanzapine).
- the present invention also relates to a process for conversion of these hydrates into a pure crystalline form of olanzapine referred to as form-I.
- the present invention also relates to a method of converting Olanzapine Form-2 to Form-1.
- This invention more particularly relates to the preparation of hydrates of olanzapine and their conversion into crystalline form of Olanzapine Form-1 through recrystallization from a solvent.
- Olanzapine is represented by the following structure.
- Olanzapine is useful for treating psychotic patients and mild anxiety states.
- Preparation of Olanzapine and its acid salts, having pharmaceutical properties particularly in the treatment of disorders ofthe central nervous system has been discussed in U.S. Patent No. 5,229,382.
- U.S. Patent No. 5,229,382 does not refer to any specific polymorphic crystalline form of Olanzapine.
- European patent specification No. 733635A1 claims Form-2 of Olanzapine. The process under this patent describes preparation of Form-2 from ethyl acetate. This patent also designated the product obtained according to the process described in U.S. Patent No. 5,229,382 as Form-1.
- EP 733635 Al discloses the d values for Form-1 and Form-2 from their X-ray Diffractograms. The values are: d value d value
- EP 0 831 098 A2 discloses the preparation of a series of dihydrates of olanzapine namely Dihydrate B, Dihydrate D and Dihydrate E.
- the compound was dried to a constant weight in an oven (51.6g).
- the present invention provides a novel method for preparation of hydrates of olanzapine, which are different from those reported in the literature. These hydrates are named Olanzapine monohydrate-I and Olanzapine dihydrate-I for convenience.
- the present invention also provides a novel method for preparation of Olanzapine Form-1 by recrystallization of olanzapine or its hydrates in dichloromethane .
- the present invention also provides a novel method for converting Olanzapine
- the process for the preparation of olanzapine monohydrate-I comprises: a) refluxing a mixture of 4-amino-2-methyl-10H-thieno-[2,3-b] [l,5]benzodiazepine hydrochloride, N-methyl piperazine, dimethyl sulfoxide (DMSO) and toluene for 5 to 20 hours; b) cooling the mixture to 20 to 90°C; c) adding water; d) cooling the mixture to -5 to 25°C and stirring for 2-10 hours; e) filtering the mixture and washing with water; and f) drying at 30 to 50°C to a constant weight.
- DMSO dimethyl sulfoxide
- the process for the preparation of olanzapine dihydrate -I comprises: a) refluxing a mixture of 4-amino-2-methyl- 10H-thieno-[2,3-b] [l,5]benzodiazepine hydrochloride, N-methyl piperazine, dimethyl sulfoxide (DMSO) and toluene for 5 to 20 hours; b) cooling the mixture to 20 to 90°C; c) adding water; d) cooling the mixture to -5 to 25°C and stirring for 2-10 hours; e) filtering the mixture and washing with water; and f) drying at ambient temperature to a constant weight.
- DMSO dimethyl sulfoxide
- Olanzapine Form -I is prepared by heating to reflux a suspension of olanzapine or its hydrates in dichloromethane wherein the amount of dichloro-methane used is 4.5 to 13 volume/weight of Olanzapine to obtain a clear solution. The resultant solution is then treated with carbon followed by filtration. Upon completion of this step the filtrate is cooled to 0 to 5°C and stirred at the same temperature for 60-90 minutes. The separated solid was filtered and washed with dichloromethane.
- the product obtained on drying in an oven at 60-70°C to a constant weight is Form-1 of Olanzapine.
- the process described in U.S. 5,229,382 was used to prepare olanzapine crude and the process described in EP 733 635 Al was used to prepare olanzapine Form-2 for our studies.
- other methods may be used to prepare olanzapine crude and olanzapine Form-2 and any other methods that can be used to prepare olanzapine crude and olanzapine Form 2 can be used in the processes of this invention.
- Fig.l is a characteristic X-ray powder diffraction pattern of Form-2 obtained on recrystallization with acetonitrile (Nertical axis: Intensity (CPS); Horizontal axis:
- Fig. 2 is a characteristic X-ray powder diffraction pattern of Olanzapine monohydrate-I (Nertical axis: Intensity (CPS); Horizontal axis: Two Theta (degrees)).
- Fig. 3 is a characteristic infrared absorption spectrum in potassium bromide of
- Olanzapine monohydrate-I (Nertical axis, Tramission (%); Horizontal axis: Wave number (cm )).
- Fig. 4 is a characteristic of differential scanning calorimetry thermogram of Olanzapine monohydrate-I. (Nertical axis: mW; Horizontal axis: Temperature (°C)).
- Fig. 5 is a characteristic X-ray powder diffraction pattern of Olanzapine dihydrate-I (Nertical axis: Intensity (CPS); Horizontal axis: Two Theta (degrees)).
- Fig. 6 is a characteristic infrared absorption spectrum in potassium bromide of
- Olanzapine dihydrate-I (Nertical axis, Tramission (%); Horizontal axis: Wave number (cm " )).
- Fig. 7 is a characteristic of differential scanning calorimetry thermogram of
- Fig. 8 is a characteristic X-ray powder diffraction pattern of Form-1 produced by recrystallizing crude Olanzapine in dichloromethane. (Nertical axis: Intensity
- Fig.9 is a characteristic infrared absorption spectrum in potassium bromide of Form-1 produced by recrystallizing crude Olanzapine in dichloromethane. (Nertical axis, Tramission (%); Horizontal axis: Wave number (cm "1 )).
- Fig.10 is a characteristic of differential scanning calorimetry thermogram of Form-1 produced by recrystallizing crude Olanzapine in dichloromethane. [Nertical axis: mW; Horizontal axis: Temperature (°C))].
- Fig.11 is a characteristic X-ray powder diffraction pattern of Form-I obtained on conversion of Form-2 to Form-1 Olanzapine in dichloromethane (Nertical axis: Intensity (CPS); Horizontal axis: Two Theta (degrees)).
- Fig.12 is a characteristic infrared absorption spectrum in potassium bromide of Form-1 obtained on conversion of Form-2 to Form-1 Olanzapine in dichloromethane (Nertical axis, Tramission (%); Horizontal axis: Wave number (cm "1 ))].
- Fig.13 is a characteristic of differential scanning calorimetry thermogram of Form-1 obtained on conversion of Form-2 to Form-1 Olanzapine in dichloromethane (Nertical axis: mW; Horizontal axis: Temperature (°C))].
- Fig.14 is a characteristic X-ray powder diffraction pattern of Form-1 obtained on conversion of olanzapine monohydrate-I to Form-1 Olanzapine in dichloromethane (Nertical axis: Intensity (CPS); Horizontal axis: Two Theta (degrees)).
- Fig.15 is a characteristic infrared absorption spectrum in potassium bromide of Form-1 obtained on conversion of olanzapine monohydrate-I to Form-1 Olanzapine in dichloromethane (Nertical axis, Tramission (%); Horizontal axis: Wave number (cm "1 )).
- Fig.16 is a characteristic of differential scanning calorimetry thermogram of
- Form-1 obtained on conversion of olanzapine monohydrate-I to Form-1
- Fig.17 is a characteristic X-ray powder diffraction pattern of Form-1 obtained on conversion of olanzapine dihydrate-I to Form-1 Olanzapine in dichloromethane
- Fig.18 is a characteristic infrared absorption spectrum in potassium bromide of Form-1 obtained on conversion of olanzapine dihydrate-I to Form-1 Olanzapine in dichloromethane. ([Vertical axis, Tramission (%); Horizontal axis: Wave number
- Fig.19 is a characteristic of differential scanning calorimetry thermogram of Form-1 obtained on conversion of olanzapine dihydrate-I to Form-1 Olanzapine in dichloromethane. (Nertical axis: mW; Horizontal axis: Temperature (°C)).
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne un procédé de préparation d'hydrates de 2-méthyl-4-(4-méthyl-1-pipérazinyl)-10H-thiéno [2,3-b] [1,5] benzodiazépine (ci-après dénommés olanzapine), ainsi qu'un procédé de conversion de ces hydrates en une forme cristalline pure dénommée forme 1. L'invention concerne encore un procédé de conversion d'olanzapine forme 2 en Olanzapine forme 1.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
INMU070900 | 2000-08-31 | ||
INMU071100 | 2000-08-31 | ||
IN711CH2000 | 2000-08-31 | ||
IN709CH2000 | 2000-08-31 | ||
PCT/US2001/007258 WO2002018390A1 (fr) | 2000-08-31 | 2001-03-07 | Procede de preparation d'hydrates d'olanzapine et de conversion de ceux-ci en formes cristallines d'olanzapine |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1313742A1 true EP1313742A1 (fr) | 2003-05-28 |
Family
ID=26324874
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01916449A Withdrawn EP1313742A1 (fr) | 2000-08-31 | 2001-03-07 | Procede de preparation d'hydrates d'olanzapine et de conversion de ceux-ci en formes cristallines d'olanzapine |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP1313742A1 (fr) |
JP (1) | JP2004507548A (fr) |
AU (1) | AU2001243475A1 (fr) |
BR (1) | BR0114031A (fr) |
CA (1) | CA2420987A1 (fr) |
CZ (1) | CZ2003566A3 (fr) |
HU (1) | HUP0300875A3 (fr) |
IL (1) | IL154688A0 (fr) |
NO (1) | NO20030926L (fr) |
RU (1) | RU2003108745A (fr) |
SK (1) | SK2502003A3 (fr) |
WO (1) | WO2002018390A1 (fr) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2464306A1 (fr) * | 2001-10-29 | 2003-05-08 | Dr. Reddy's Laboratories Ltd. | Dihydrate-ii d'olanzapine: son procede de preparation et son utilisation |
WO2003091260A1 (fr) * | 2002-04-23 | 2003-11-06 | Dr. Reddy's Laboratories Limited | Nouvelle forme vi polymorphe cristalline d'olanzapine et procede de preparation |
WO2003090730A1 (fr) * | 2002-04-25 | 2003-11-06 | Generics [Uk] Limited | Nouvelles formes cristallines de celecoxib et d'autres composes |
PL196814B1 (pl) | 2002-05-17 | 2008-02-29 | Inst Farmaceutyczny | Sposób wytwarzania odmiany polimorficznej I olanzapiny i jej solwaty |
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 |
PL202856B1 (pl) * | 2002-12-20 | 2009-07-31 | Adamed Spo & Lstrok Ka Z Ogran | Sposób otrzymywania farmaceutycznie czystej polimorficznej postaci I olanzapiny |
US7323459B2 (en) | 2002-12-24 | 2008-01-29 | Teva Pharmaceutical Industries Ltd. | Crystal forms, methods for their preparation and method for preparation of olanzapine |
CA2551806A1 (fr) | 2003-12-22 | 2005-07-14 | Teva Pharmaceutical Industries, Ltd. | Methodes de preparation de l'olanzapine |
WO2005070937A1 (fr) * | 2004-01-27 | 2005-08-04 | Synthon B.V. | Procede de fabrication d'olanzapine sous forme polymorphe i |
AR047459A1 (es) | 2004-01-27 | 2006-01-18 | Synthon Bv | Sales estables de 2-metil-4-(4-metil-1-piperazinil)-10h-tieno[2,3-b][1,5]benzodiazepina (olanzapina) |
WO2005080401A1 (fr) * | 2004-02-19 | 2005-09-01 | Neuland Laboratories Limited | Procede ameliore de preparation de la forme 1 de l'olanzapine utile en tant que medicament psychotique |
WO2005107375A2 (fr) * | 2004-05-06 | 2005-11-17 | Matrix Laboratories Ltd | Procede pour la preparation de forme i d'olanzapine |
ES2289974T1 (es) * | 2004-07-14 | 2008-02-16 | Shasun Chemicals And Drugs Limited | Metodo mejorado para producir la forma i de la olanzapina. |
WO2006006180A1 (fr) | 2004-07-14 | 2006-01-19 | Jubilant Organosys Limited | Procede permettant de produire une forme pure de 2-methyl-4-(4-methyl-1-piperazinyl)-10h-thieno[2,3-b][1,5]benzodiazepine |
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. |
WO2006025065A1 (fr) * | 2004-08-31 | 2006-03-09 | Lee Pharma Private Limited | Procédé pour la préparation de chlorhydrate d'olanzapine anhydre de forme 1 |
DE112005000641T5 (de) | 2004-09-06 | 2007-09-06 | Shasun Chemicals and Drugs Ltd., Chennai | Neues Verfahren zur Herstellung einer pharmazeutisch reinen polymorphen Form I von Olanzapin |
WO2006073886A1 (fr) * | 2005-01-05 | 2006-07-13 | Eli Lilly And Company | Dihydrate d'olanzapine pamoate |
BRPI0608484E2 (pt) * | 2005-03-21 | 2014-10-29 | Reddys Lab Ltd Dr | Processo de preparação da forma i cristalina de olanzapina |
HUP0501046A2 (en) * | 2005-11-11 | 2007-08-28 | Egis Gyogyszergyar Nyilvanosan | Process for the preparation of olanzapine |
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 |
PL381564A1 (pl) | 2007-01-22 | 2008-08-04 | Koźluk Tomasz Nobilus Ent | Sposób wytwarzania zasadniczo czystej odmiany polimorficznej I olanzapiny |
CA2687143A1 (fr) * | 2007-05-15 | 2008-11-20 | Generics [Uk] Limited | Procede de purification d'olanzapine |
EP2292624A1 (fr) | 2009-07-20 | 2011-03-09 | LEK Pharmaceuticals d.d. | Processus de purification d'olanzapine |
CN102093386B (zh) * | 2011-01-05 | 2016-06-01 | 浙江华海药业股份有限公司 | 一种制备奥兰扎平晶型ⅱ的方法 |
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 |
KR102543559B1 (ko) | 2016-05-31 | 2023-06-13 | 다이호야쿠힌고교 가부시키가이샤 | 설폰아미드화합물 또는 이의 염 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0454436B1 (fr) | 1990-04-25 | 1995-09-13 | Lilly Industries Limited | Composés pharmaceutiques |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EG23659A (en) * | 1995-03-24 | 2007-03-26 | Lilly Co Eli | Process and crystal forms of methyl-thieno-benzodiazepine |
ZA978515B (en) * | 1996-09-23 | 1999-03-23 | Lilly Co Eli | Intermediates and process for preparing olanzapine |
CA2266444C (fr) * | 1996-09-23 | 2007-01-09 | Eli Lilly And Company | Dihydrate d d'olanzapine |
-
2001
- 2001-03-07 IL IL15468801A patent/IL154688A0/xx unknown
- 2001-03-07 RU RU2003108745/04A patent/RU2003108745A/ru not_active Application Discontinuation
- 2001-03-07 SK SK250-2003A patent/SK2502003A3/sk unknown
- 2001-03-07 EP EP01916449A patent/EP1313742A1/fr not_active Withdrawn
- 2001-03-07 WO PCT/US2001/007258 patent/WO2002018390A1/fr not_active Application Discontinuation
- 2001-03-07 CZ CZ2003566A patent/CZ2003566A3/cs unknown
- 2001-03-07 AU AU2001243475A patent/AU2001243475A1/en not_active Abandoned
- 2001-03-07 JP JP2002523905A patent/JP2004507548A/ja active Pending
- 2001-03-07 HU HU0300875A patent/HUP0300875A3/hu unknown
- 2001-03-07 BR BR0114031-0A patent/BR0114031A/pt not_active IP Right Cessation
- 2001-03-07 CA CA002420987A patent/CA2420987A1/fr not_active Abandoned
-
2003
- 2003-02-27 NO NO20030926A patent/NO20030926L/no not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0454436B1 (fr) | 1990-04-25 | 1995-09-13 | Lilly Industries Limited | Composés pharmaceutiques |
Non-Patent Citations (3)
Title |
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BREWSTER R.Q.; VANDERWERF C.A.; MCEWEN W.E.: "Initized Experiments in Organic Chemistry", vol. 2, June 1965, D. VAN NOSTRAND COMPANY, INC., TORONTO, article "EXPERIMENT 4 - Chrystallization", pages: 18 - 23, XP002970932 |
FIESER L.F.: "ORGANIC EXPERIMENTS", part 7 1964, D.C. HEATH AND COMPANY, BOSTON, article "Crystallization", pages: 41 - 51, XP002970931 |
See also references of WO0218390A1 |
Also Published As
Publication number | Publication date |
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WO2002018390A1 (fr) | 2002-03-07 |
BR0114031A (pt) | 2003-09-09 |
CZ2003566A3 (cs) | 2004-01-14 |
SK2502003A3 (en) | 2004-03-02 |
HUP0300875A3 (en) | 2005-09-28 |
NO20030926D0 (no) | 2003-02-27 |
CA2420987A1 (fr) | 2002-03-07 |
AU2001243475A1 (en) | 2002-03-13 |
NO20030926L (no) | 2003-04-24 |
JP2004507548A (ja) | 2004-03-11 |
IL154688A0 (en) | 2003-09-17 |
RU2003108745A (ru) | 2005-01-10 |
HUP0300875A2 (hu) | 2003-12-29 |
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