CN1819992A - 纯化和分离rac－比卡鲁胺的方法 - Google Patents

纯化和分离rac－比卡鲁胺的方法 Download PDF

Info

Publication number: CN1819992A
Authority: CN; China
Prior art keywords: solvent; bicalutamide; enough; rough; solution
Prior art date: 2003-06-25
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.): Pending

Application number

CN03826678.4A

Other languages

English (en)

Chinese (zh)

Inventor

B·-Z·多利茨基

O·里尼

J·沙梅

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teva Pharmaceutical Works PLC

Original Assignee

Teva Pharmaceutical Works PLC

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.)

2003-06-25

Filing date

2003-06-25

Publication date

2006-08-16

2003-06-25 Application filed by Teva Pharmaceutical Works PLC filed Critical Teva Pharmaceutical Works PLC

2006-08-16 Publication of CN1819992A publication Critical patent/CN1819992A/zh

Status Pending legal-status Critical Current

Links

229960000997 bicalutamide Drugs 0.000 title claims abstract description 143
238000000034 method Methods 0.000 title claims abstract description 61
LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims abstract description 132
239000002904 solvent Substances 0.000 claims description 155
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 33
238000002425 crystallisation Methods 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 23
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 19
230000008025 crystallization Effects 0.000 claims description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
239000012296 anti-solvent Substances 0.000 claims description 17
239000013078 crystal Substances 0.000 claims description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 9
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 9
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
239000004698 Polyethylene Substances 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims 1
238000002955 isolation Methods 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 32
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 8
239000000126 substance Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000000051 antiandrogen Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
DPJHZJGAGIWXTD-UHFFFAOYSA-N 1-fluoro-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1 DPJHZJGAGIWXTD-UHFFFAOYSA-N 0.000 description 2
DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
KDPMIBMNNGCWTF-UHFFFAOYSA-N C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical class C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O KDPMIBMNNGCWTF-UHFFFAOYSA-N 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
208000002173 dizziness Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
231100000734 genotoxic potential Toxicity 0.000 description 1
239000011521 glass Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002267 hypothalamic effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
231100000683 possible toxicity Toxicity 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008844 regulatory mechanism Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CN03826678.4A 2003-06-25 2003-06-25 纯化和分离rac－比卡鲁胺的方法 Pending CN1819992A (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US2003/020307 WO2005009946A1 (en)	2003-06-25	2003-06-25	Process for purifying and isolating rac-bicalutamide

Publications (1)

Publication Number	Publication Date
CN1819992A true CN1819992A (zh)	2006-08-16

Family

ID=34102338

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN03826678.4A Pending CN1819992A (zh)	2003-06-25	2003-06-25	纯化和分离rac－比卡鲁胺的方法

Country Status (6)

Country	Link
EP (1)	EP1558570A1 (ja)
JP (1)	JP2007521224A (ja)
CN (1)	CN1819992A (ja)
AU (1)	AU2003247740A1 (ja)
CA (1)	CA2529232A1 (ja)
WO (1)	WO2005009946A1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105949095A (zh) *	2016-05-27	2016-09-21	山西振东制药股份有限公司	一种比卡鲁胺i晶型的制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20080177109A1 (en) *	2005-03-29	2008-07-24	Usv Limited	Novel Process for Preparation of Bicalutamide
CZ299577B6 (cs) *	2005-12-20	2008-09-03	Interpharma Praha, A. S.	Zpusob výroby vysoce cistého 4-kyano-3-trifluoromethyl-N-(3-p-fluorfenylsulfonyl-2-hydroxy-2-methylpropionyl) anilinu

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3372965D1 (en) *	1982-07-23	1987-09-17	Ici Plc	Amide derivatives
HU223950B1 (hu) *	1999-06-10	2005-03-29	Richter Gedeon Vegyészeti Gyár Rt.	Eljárás a racém, valamint az R-(-)- és S-(+)-N-[4-ciano-3-(trifluor-metil)-fenil]-3-[(4-fluor-fenil)-szulfonil]-2-hidroxi-2-metil-propánsavamid előállítására
CA2423158A1 (en) *	2000-09-21	2002-03-28	Bristol-Myers Squibb Company	Process for the preparation of n-(substituted phenyl)-3-alkyl-, aryl- and heteroarylsulfonyl-2-hydroxy-2-alkyl- and haloalkylpropanamide compounds
AU2002354475B2 (en) *	2001-12-13	2008-08-14	Sumitomo Chemical Company, Limited	Crystals of bicalutamide and process for their production
DE10222104A1 (de) *	2002-05-17	2003-12-04	Helm Ag	Verfahren zur Herstellung von N-(4'-Cyano-3'-trifluormethyl)-3-(4"-fluorphenylsulfonyl)-2-hydroxy-2-methylpropionamid

2003
- 2003-06-25 CA CA002529232A patent/CA2529232A1/en not_active Abandoned
- 2003-06-25 CN CN03826678.4A patent/CN1819992A/zh active Pending
- 2003-06-25 AU AU2003247740A patent/AU2003247740A1/en not_active Abandoned
- 2003-06-25 EP EP03816630A patent/EP1558570A1/en not_active Withdrawn
- 2003-06-25 WO PCT/US2003/020307 patent/WO2005009946A1/en active Application Filing
- 2003-06-25 JP JP2005504628A patent/JP2007521224A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105949095A (zh) *	2016-05-27	2016-09-21	山西振东制药股份有限公司	一种比卡鲁胺i晶型的制备方法

Also Published As

Publication number	Publication date
EP1558570A1 (en)	2005-08-03
CA2529232A1 (en)	2005-02-03
WO2005009946A1 (en)	2005-02-03
AU2003247740A1 (en)	2005-02-14
JP2007521224A (ja)	2007-08-02

Legal Events

Date	Code	Title
2006-08-16	C06	Publication
2006-08-16	PB01	Publication
2006-10-11	C10	Entry into substantive examination
2006-10-11	SE01	Entry into force of request for substantive examination
2008-09-17	C02	Deemed withdrawal of patent application after publication (patent law 2001)
2008-09-17	WD01	Invention patent application deemed withdrawn after publication

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CN1819992A - 纯化和分离rac－比卡鲁胺的方法 - Google Patents

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Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=34102338

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (2)

Family Cites Families (5)

Cited By (1)

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