OA13042A - Process for preparing a polymorph of rosiglitazonemaleate. - Google Patents

Process for preparing a polymorph of rosiglitazonemaleate. Download PDF

Info

Publication number: OA13042A
Authority: OA; OAPI
Prior art keywords: compound; solvent; maleate; mixture; preparing
Prior art date: 2003-03-28

Application number

OA1200500267A

Other languages

English (en)

Inventor

Andrew Simon Craig

Robert Gordon Giles

Tim Chien Ting Ho

Michael John Sasse

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

2003-03-28

Filing date

2004-03-25

Publication date

2006-11-10

2004-03-25 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2006-11-10 Publication of OA13042A publication Critical patent/OA13042A/en

Links

229960003271 rosiglitazone maleate Drugs 0.000 title claims abstract description 58
SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 title claims abstract description 58
238000004519 manufacturing process Methods 0.000 title claims abstract description 20
229940125904 compound 1 Drugs 0.000 claims abstract description 52
238000002425 crystallisation Methods 0.000 claims abstract description 10
239000000463 material Substances 0.000 claims abstract description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
239000002904 solvent Substances 0.000 claims description 50
238000000034 method Methods 0.000 claims description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 32
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 24
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 8
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 7
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
229940043265 methyl isobutyl ketone Drugs 0.000 claims description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
238000010899 nucleation Methods 0.000 claims description 6
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 5
229940011051 isopropyl acetate Drugs 0.000 claims description 5
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
-1 isopropyl acétate Chemical compound 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims 2
229940075894 denatured ethanol Drugs 0.000 claims 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 abstract description 6
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 52
239000007787 solid Substances 0.000 description 39
229960004586 rosiglitazone Drugs 0.000 description 26
239000000706 filtrate Substances 0.000 description 17
238000001914 filtration Methods 0.000 description 17
239000000047 product Substances 0.000 description 17
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
229940093499 ethyl acetate Drugs 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 13
239000011976 maleic acid Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000010992 reflux Methods 0.000 description 10
238000010438 heat treatment Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
239000012065 filter cake Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000004566 IR spectroscopy Methods 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000000634 powder X-ray diffraction Methods 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 3
239000011928 denatured alcohol Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
238000002050 diffraction method Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000011282 treatment Methods 0.000 description 2
BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 1
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
238000001069 Raman spectroscopy Methods 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000010030 glucose lowering effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200500267A 2003-03-28 2004-03-25 Process for preparing a polymorph of rosiglitazonemaleate. OA13042A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0307259.2A GB0307259D0 (en)	2003-03-28	2003-03-28	Process

Publications (1)

Publication Number	Publication Date
OA13042A true OA13042A (en)	2006-11-10

Family

ID=9955778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500267A OA13042A (en)	2003-03-28	2004-03-25	Process for preparing a polymorph of rosiglitazonemaleate.

Country Status (18)

Country	Link
US (1)	US20070167494A1 (fr)
EP (1)	EP1615918A1 (fr)
JP (1)	JP2006521340A (fr)
KR (1)	KR20050120670A (fr)
CN (1)	CN1768057A (fr)
AU (2)	AU2004224068A1 (fr)
BR (1)	BRPI0408752A (fr)
CA (1)	CA2520249A1 (fr)
EA (1)	EA009331B1 (fr)
EC (1)	ECSP056038A (fr)
GB (1)	GB0307259D0 (fr)
IS (1)	IS8087A (fr)
MA (1)	MA27727A1 (fr)
MX (1)	MXPA05010413A (fr)
NO (1)	NO20054911L (fr)
OA (1)	OA13042A (fr)
WO (1)	WO2004085435A1 (fr)
ZA (1)	ZA200507100B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20020137940A1 (en)	1997-12-16	2002-09-26	Smithkline Beecham P.L.C.	5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical
US20040248945A1 (en)	1999-04-23	2004-12-09	Smithkline Beecham P.L.C.	Thiazolidinedione derivative and its use as antidiabetic
GB2405403A (en) *	2003-08-29	2005-03-02	Cipla Ltd	Rosiglitazone maleate of particular polymorphic forms and methods of preparing rosiglitazone free base
ITMI20041537A1 (it) *	2004-07-28	2004-10-28	Chemi Spa	Nuova forma polimorfa del rosiglitazone maleato
CZ298424B6 (cs) *	2005-05-24	2007-09-26	Zentiva, A. S.	Zpusob krystalizace rosiglitazonu a jeho derivátuze smesných rozpouštedel
MY199695A (en)	2017-01-27	2023-11-18	Neurocrine Biosciences Inc	Methods for the administration of certain vmat2 inhibitors
DK3684333T3 (da)	2017-09-21	2025-05-12	Neurocrine Biosciences Inc	Valbenazin-formulering med høj dosis og sammensætninger, fremgangsmåder og kits relateret hertil
US20200230127A1 (en)	2017-10-10	2020-07-23	Neurocrine Biosciences, Inc.	Methods for the Administration of Certain VMAT2 Inhibitors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9218830D0 (en) *	1992-09-05	1992-10-21	Smithkline Beecham Plc	Novel compounds
GB9723295D0 (en) *	1997-11-04	1998-01-07	Smithkline Beecham Plc	Novel process
RS50114B (sr) *	1999-04-23	2009-03-25	Smithkline Beecham P.L.C.,	Novi polimorfni oblik 5-/4-/2-(n-metil- n-(2-piridil)amino/ etoksi/benzil/ tiazolidin-2,4-dion, soli maleinske kiseline
EA003031B1 (ru) *	1999-04-23	2002-12-26	Смитклайн Бичам Плс	Новый фармацевтический препарат
CN1167702C (zh) *	1999-04-23	2004-09-22	史密丝克莱恩比彻姆有限公司	5-[4-[2-n-甲基-n-(2-吡啶基)氨基]乙氧基]苄基]噻唑烷-2,4-二酮马来酸盐的多晶型物
AU9123201A (en) *	2000-09-26	2002-04-08	Reddy S Res Foundation	Novel polymorphic forms of 5-(4-(2-(N-methyl-N-(2-pyridyl)amino)ethoxy)benzyl) thiazolidine-2,4-dione maleate and process for their preparation

2003
- 2003-03-28 GB GBGB0307259.2A patent/GB0307259D0/en not_active Ceased
2004
- 2004-03-25 JP JP2006506028A patent/JP2006521340A/ja not_active Withdrawn
- 2004-03-25 EP EP04723254A patent/EP1615918A1/fr not_active Withdrawn
- 2004-03-25 EA EA200501527A patent/EA009331B1/ru unknown
- 2004-03-25 OA OA1200500267A patent/OA13042A/en unknown
- 2004-03-25 CN CNA2004800083916A patent/CN1768057A/zh active Pending
- 2004-03-25 AU AU2004224068A patent/AU2004224068A1/en not_active Abandoned
- 2004-03-25 WO PCT/GB2004/001306 patent/WO2004085435A1/fr not_active Ceased
- 2004-03-25 BR BRPI0408752-6A patent/BRPI0408752A/pt not_active IP Right Cessation
- 2004-03-25 CA CA002520249A patent/CA2520249A1/fr not_active Abandoned
- 2004-03-25 US US10/551,021 patent/US20070167494A1/en not_active Abandoned
- 2004-03-25 KR KR1020057018143A patent/KR20050120670A/ko not_active Withdrawn
- 2004-03-25 MX MXPA05010413A patent/MXPA05010413A/es unknown
2005
- 2005-09-05 ZA ZA200507100A patent/ZA200507100B/en unknown
- 2005-09-26 EC EC2005006038A patent/ECSP056038A/es unknown
- 2005-10-11 MA MA28549A patent/MA27727A1/fr unknown
- 2005-10-24 IS IS8087A patent/IS8087A/is unknown
- 2005-10-24 NO NO20054911A patent/NO20054911L/no not_active Application Discontinuation
2008
- 2008-10-30 AU AU2008237610A patent/AU2008237610A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU2008237610A1 (en)	2008-11-27
EP1615918A1 (fr)	2006-01-18
GB0307259D0 (en)	2003-05-07
US20070167494A1 (en)	2007-07-19
NO20054911L (no)	2005-10-24
EA200501527A1 (ru)	2006-02-24
CN1768057A (zh)	2006-05-03
AU2004224068A1 (en)	2004-10-07
KR20050120670A (ko)	2005-12-22
MXPA05010413A (es)	2005-11-04
ECSP056038A (es)	2006-01-27
JP2006521340A (ja)	2006-09-21
BRPI0408752A (pt)	2006-03-28
MA27727A1 (fr)	2006-01-02
EA009331B1 (ru)	2007-12-28
ZA200507100B (en)	2006-07-26
WO2004085435A1 (fr)	2004-10-07
CA2520249A1 (fr)	2004-10-07
IS8087A (is)	2005-10-24

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