JP2008508254A - オランザピンの混合溶媒和物、その製造方法、およびそれからオランザピンのi型の製造方法 - Google Patents
オランザピンの混合溶媒和物、その製造方法、およびそれからオランザピンのi型の製造方法 Download PDFInfo
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- JP2008508254A JP2008508254A JP2007523170A JP2007523170A JP2008508254A JP 2008508254 A JP2008508254 A JP 2008508254A JP 2007523170 A JP2007523170 A JP 2007523170A JP 2007523170 A JP2007523170 A JP 2007523170A JP 2008508254 A JP2008508254 A JP 2008508254A
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- olanzapine
- tetrahydrofuran
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- 229960005017 olanzapine Drugs 0.000 title claims abstract description 62
- 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 61
- 239000012453 solvate Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 12
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000004807 desolvation Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 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 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 101100438156 Arabidopsis thaliana CAD7 gene Proteins 0.000 description 1
- 101150071647 CAD4 gene Proteins 0.000 description 1
- 101100322652 Catharanthus roseus ADH13 gene Proteins 0.000 description 1
- 101100087088 Catharanthus roseus Redox1 gene Proteins 0.000 description 1
- 0 Cc1cc(C(N)=Nc2ccccc2*2)c2[s]1 Chemical compound Cc1cc(C(N)=Nc2ccccc2*2)c2[s]1 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000003453 histamine agonist Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
本発明は、オランザピンの新規な混合溶媒和物に関する。詳細には、本発明は、1:1:1/2の比のオランザピン/水/テトラヒドロフランの混合溶媒和物に関する。
オランザピンは、ドパミンD1、D2、D3、D4およびD5、セロトニン5-HT2および5HT3、α-1-アドレナリン作動薬、コリン作動薬およびH1ヒスタミン作用薬の受容体に対する拮抗薬として作用する式(I):
本発明の目的は、オランザピンの新規な混合溶媒和物をその製造方法と共に提供することである。
本発明の新規な混合溶媒和物という対象は、その粉体X線回折パターンによって確認されている。
4-アミノ-2-メチル-10H-チエノ[2,3-b][1,5]ベンゾジアゼピン塩酸50g(0.188モル)とN-メチルピペラジン125ml(1.127モル)からなる混合物を、若干の窒素流を継続しながら還流温度(内部温度140℃)に加熱する。2時間経過したならば、反応を停止して、混合物を70℃に冷却する。次に、N-メチルピペラジン40mlを70℃で真空(40mmHg)にて蒸留し、テトラヒドロフラン/水 1:4(v/v)混合物125mlを加える。混合物を70℃にて15 分間攪拌継続し、20-25℃に冷却し、この温度で1時間放置する。混合物を濾過し、固形物をテトラヒドロフラン/水1:4(v/v)混合物50mlおよび水100mlで2回洗浄する。得られた固形物を42℃のエアオーブンで一定重量になるまで乾燥し、オランザピン/水/テトラヒドロフランの比が1:1:1/2の混合溶媒和物65.1g (94.4%)を得る。
水分測定(KF): 4.9%
オランザピン/テトラヒドロフランのモル比が1:1/2であることは、1H NMRによって確認した(図5)。
THF100ml、水25ml、および欧州特許第0454436B1号明細書に記載の方法に従って得た粗製の無水オランザピン25gからなる混合物を、50℃で30分間加熱する。最初に20-25℃まで1時間、次いで0℃まで更に1時間冷却した後、固形物を濾過し、42℃のエアオーブンで一定重量になるまで乾燥し、オランザピン/水/テトラヒドロフランの比が1:1:1/2の混合溶媒和物24.9g(85%)を得る。
(1) オランザピン/水/テトラヒドロフランの比が1:1:1/2の混合溶媒和物1gを、油ポンプ真空(1mmHg)下にてテトラヒドロフランの痕跡が1H NMRによって観察されなくなるまで4-5時間乾燥する。得られた固形物は、オランザピンI型の特徴的なX線回折パターンを示す。融点195℃。
Claims (14)
- KBr錠剤で記録したIRスペクトルにおいて下記の波長(cm-1): 3390, 3240, 2930, 2830, 1595, 1560, 1465, 1410, 1270, 1220, 1140, 965, 755に吸収を有することを特徴とする、請求項1または2に記載の溶媒和物。
- 粗製の無水オランザピンをテトラヒドロフラン/水の比が1:10-10:1(v/v)の混合物で20-80℃の範囲の温度で溶媒和することを含む、請求項1-3のいずれか一項に記載の混合溶媒和物の製造方法。
- 上記温度が40-60℃の範囲である、請求項4に記載の方法。
- 上記テトラヒドロフラン/水の比が1:5-5:1(v/v)の範囲である、請求項4または5に記載の方法。
- 上記段階c)において、テトラヒドロフランと水の比が1:5-5:1(v/v)の範囲である、請求項7に記載の方法。
- 段階c)で得られる沈澱を精製する、請求項7に記載の方法。
- 上記N-メチルピペラジンの過剰量が6-8当量の範囲である、請求項7-9のいずれか一項に記載の方法。
- 請求項1-3のいずれか一項に記載のオランザピンのテトラヒドロフランとH2Oの混合溶媒和物を1-40mmHgの範囲の圧力の真空で10-50℃の範囲の温度にて乾燥することを含む、オランザピンのI型の製造方法。
- 上記圧力が1-20mmHgの範囲である、請求項11に記載の方法。
- 上記温度が20-40℃の範囲である、請求項12に記載の方法。
- 上記溶媒和物を乾燥手続中に攪拌下に保持する、請求項11-13のいずれか一項に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200401850A ES2253091B1 (es) | 2004-07-27 | 2004-07-27 | Solvato mixto de olanzapina, procedimiento para su obtencion y procedimiento de obtencion de la forma i de olanzapina a partir del mismo. |
PCT/IB2005/002209 WO2006013435A1 (en) | 2004-07-27 | 2005-07-07 | Mixed solvate of olanzapine, method for preparing it and method for preparing form i of olanzapine therefrom |
Publications (1)
Publication Number | Publication Date |
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JP2008508254A true JP2008508254A (ja) | 2008-03-21 |
Family
ID=35064845
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007523170A Pending JP2008508254A (ja) | 2004-07-27 | 2005-07-07 | オランザピンの混合溶媒和物、その製造方法、およびそれからオランザピンのi型の製造方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US7759484B2 (ja) |
EP (1) | EP1773841B1 (ja) |
JP (1) | JP2008508254A (ja) |
KR (1) | KR20070063496A (ja) |
AR (1) | AR050359A1 (ja) |
AT (1) | ATE380191T1 (ja) |
DE (1) | DE602005003678T2 (ja) |
ES (2) | ES2253091B1 (ja) |
PL (1) | PL1773841T3 (ja) |
PT (1) | PT1773841E (ja) |
TW (1) | TWI295993B (ja) |
WO (1) | WO2006013435A1 (ja) |
ZA (1) | ZA200700670B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014065679A (ja) * | 2012-09-26 | 2014-04-17 | Tokuyama Corp | オランザピンの製造方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1575962A1 (en) | 2002-12-24 | 2005-09-21 | Teva Pharmaceutical Industries Limited | Novel crystal forms of olanzapine, methods for their preparation and method for the preparation of known olanzapine crystal forms |
EP1778649A4 (en) * | 2004-07-14 | 2008-09-10 | Jubilant Organosys Ltd | PROCESS FOR PREPARING A PURE FORM OF 2-METHYL-4- (4-METHYL-1-PIPERAZINYL) -10H-THIENO [2,3-B] [1,5] BENZODIAZEPINE |
ES2292333B1 (es) * | 2004-07-27 | 2008-12-16 | Inke, S.A. | Mejoras en el objeto de la patente principal n. 200401850, por "solvato mixto de olanzapina, procedimiento para su obtencion y procedimiento de obtencion de la forma i de olanzapina a partir del mismo". |
ES2279715B1 (es) | 2005-12-26 | 2008-06-01 | Laboratorios Lesvi, S.L. | Formulacion oral de olanzapina. |
PT1968983E (pt) * | 2006-01-05 | 2011-03-01 | Inke Sa | Processo para a preparação de um solvato misto de olanzapina |
CN102532158A (zh) * | 2010-12-17 | 2012-07-04 | 北大方正集团有限公司 | 一种合成奥氮平的方法 |
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JP2002525330A (ja) * | 1998-09-30 | 2002-08-13 | イーライ・リリー・アンド・カンパニー | 2−メチル−チエノ−ベンゾジアゼピン製剤 |
WO2003097650A1 (en) * | 2002-05-17 | 2003-11-27 | Institut Farmaceutyczny | Methods for preparation of olanzapine polymorphic form i |
WO2004006933A2 (en) * | 2002-07-15 | 2004-01-22 | Krka, D.D., Novo Mesto | Crystal forms of olanzapine and processes for their preparation |
WO2004058773A1 (en) * | 2002-12-24 | 2004-07-15 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of olanzapine, methods for their preparation and method for the preparation of known olanzapine crystal forms |
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GB9009229D0 (en) * | 1990-04-25 | 1990-06-20 | Lilly Industries Ltd | Pharmaceutical compounds |
EG23659A (en) * | 1995-03-24 | 2007-03-26 | Lilly Co Eli | Process and crystal forms of methyl-thieno-benzodiazepine |
US5631250A (en) * | 1995-03-24 | 1997-05-20 | Eli Lilly And Company | Process and solvate of 2-methyl-thieno-benzodiazepine |
CR5278A (es) * | 1995-03-24 | 1996-07-04 | Lilly Co Eli | Formulacion oral de 2-metil-tieno-benzodiacepina |
US5637584A (en) | 1995-03-24 | 1997-06-10 | Eli Lilly And Company | Solvate of olanzapine |
EG24221A (en) | 1995-03-24 | 2008-11-10 | Lilly Co Eli | Process for preparing olanzapine |
ZA978515B (en) | 1996-09-23 | 1999-03-23 | Lilly Co Eli | Intermediates and process for preparing olanzapine |
WO2002018390A1 (en) | 2000-08-31 | 2002-03-07 | Dr. Reddy's Laboratories Ltd. | Process for preparation of hydrates of olanzapine and their conversion into crystalline forms of olanzapine |
JP4530664B2 (ja) | 2001-12-24 | 2010-08-25 | サン・ファーマシューティカル・インダストリーズ・リミテッド | 2−メチル−4−(4−メチル−1−ピペラジニル)−10H−チエノ[2,3−b][1,5]ベンゾジアゼピンの結晶形I、この結晶形Iの製造方法、及び医薬組成物 |
SI1513846T1 (sl) | 2002-05-31 | 2011-11-30 | Sandoz Ag | Postopek za pripravo olanzapina form I |
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2004
- 2004-07-27 ES ES200401850A patent/ES2253091B1/es not_active Expired - Fee Related
-
2005
- 2005-07-07 DE DE602005003678T patent/DE602005003678T2/de active Active
- 2005-07-07 ZA ZA200700670A patent/ZA200700670B/xx unknown
- 2005-07-07 PL PL05759149T patent/PL1773841T3/pl unknown
- 2005-07-07 ES ES05759149T patent/ES2299049T3/es active Active
- 2005-07-07 KR KR1020077002091A patent/KR20070063496A/ko not_active Application Discontinuation
- 2005-07-07 PT PT05759149T patent/PT1773841E/pt unknown
- 2005-07-07 WO PCT/IB2005/002209 patent/WO2006013435A1/en active IP Right Grant
- 2005-07-07 EP EP05759149A patent/EP1773841B1/en active Active
- 2005-07-07 JP JP2007523170A patent/JP2008508254A/ja active Pending
- 2005-07-07 US US11/568,021 patent/US7759484B2/en not_active Expired - Fee Related
- 2005-07-07 AT AT05759149T patent/ATE380191T1/de not_active IP Right Cessation
- 2005-07-15 TW TW094124062A patent/TWI295993B/zh not_active IP Right Cessation
- 2005-07-26 AR ARP050103080A patent/AR050359A1/es unknown
Patent Citations (5)
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JP2001517685A (ja) * | 1997-09-30 | 2001-10-09 | イーライ・リリー・アンド・カンパニー | 2−メチル−チエノ−ベンゾジアゼピン製剤 |
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WO2003097650A1 (en) * | 2002-05-17 | 2003-11-27 | Institut Farmaceutyczny | Methods for preparation of olanzapine polymorphic form i |
WO2004006933A2 (en) * | 2002-07-15 | 2004-01-22 | Krka, D.D., Novo Mesto | Crystal forms of olanzapine and processes for their preparation |
WO2004058773A1 (en) * | 2002-12-24 | 2004-07-15 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of olanzapine, methods for their preparation and method for the preparation of known olanzapine crystal forms |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014065679A (ja) * | 2012-09-26 | 2014-04-17 | Tokuyama Corp | オランザピンの製造方法 |
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US7759484B2 (en) | 2010-07-20 |
KR20070063496A (ko) | 2007-06-19 |
ES2299049T3 (es) | 2008-05-16 |
ES2253091B1 (es) | 2007-02-01 |
PL1773841T3 (pl) | 2008-04-30 |
DE602005003678D1 (de) | 2008-01-17 |
EP1773841B1 (en) | 2007-12-05 |
US20080280884A1 (en) | 2008-11-13 |
WO2006013435A1 (en) | 2006-02-09 |
PT1773841E (pt) | 2008-02-20 |
DE602005003678T2 (de) | 2008-11-20 |
TWI295993B (en) | 2008-04-21 |
ATE380191T1 (de) | 2007-12-15 |
ZA200700670B (en) | 2008-08-27 |
ES2253091A1 (es) | 2006-05-16 |
TW200613284A (en) | 2006-05-01 |
AR050359A1 (es) | 2006-10-18 |
EP1773841A1 (en) | 2007-04-18 |
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