SK2982003A3 - Preparation of risperidone - Google Patents

Preparation of risperidone Download PDF

Info

Publication number: SK2982003A3
Authority: SK; Slovakia
Prior art keywords: risperidone; isopropanol; ray powder; powder diffraction; risperidone form
Prior art date: 2000-08-14

Application number

SK2982003A

Other languages

English (en)

Slovak (sk)

Inventor

Barnaba Krochmal

Dov Diller

Ben-Zion Dolitzky

Judith Aronhime

Original Assignee

Teva Pharma

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.)

2000-08-14

Filing date

2001-08-14

Publication date

2004-10-05

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26919535&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK2982003(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-08-14 Application filed by Teva Pharma filed Critical Teva Pharma

2004-10-05 Publication of SK2982003A3 publication Critical patent/SK2982003A3/sk

Links

RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 title claims abstract description 234
229960001534 risperidone Drugs 0.000 title claims abstract description 233
238000002360 preparation method Methods 0.000 title claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 73
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 78
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 41
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 34
238000000634 powder X-ray diffraction Methods 0.000 claims description 30
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
238000001556 precipitation Methods 0.000 claims description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 20
239000000243 solution Substances 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 7
MRMGJMGHPJZSAE-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C1CCNCC1 MRMGJMGHPJZSAE-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
-1 tetrtahydrofuran Chemical compound 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
CMWCQQUYLPYOMY-UHFFFAOYSA-N 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1CCCN2C(=O)C(CCCl)=C(C)N=C21 CMWCQQUYLPYOMY-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 2
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
239000006185 dispersion Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 10
239000000706 filtrate Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
239000012065 filter cake Substances 0.000 description 8
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
238000009835 boiling Methods 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000001309 chloro group Chemical class Cl* 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000008298 dragée Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002547 new drug Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000001144 powder X-ray diffraction data Methods 0.000 description 1
229940106887 risperdal Drugs 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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)
Psychiatry (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK2982003A 2000-08-14 2001-08-14 Preparation of risperidone SK2982003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US22536100P	2000-08-14	2000-08-14
US24326300P	2000-10-25	2000-10-25
PCT/US2001/025387 WO2002014286A1 (fr)	2000-08-14	2001-08-14	Preparation de risperidone

Publications (1)

Publication Number	Publication Date
SK2982003A3 true SK2982003A3 (en)	2004-10-05

Family

ID=26919535

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK2982003A SK2982003A3 (en)	2000-08-14	2001-08-14	Preparation of risperidone

Country Status (20)

Country	Link
US (2)	US6750341B2 (fr)
EP (2)	EP1982980A1 (fr)
JP (3)	JP3751942B2 (fr)
KR (2)	KR100818875B1 (fr)
AT (1)	ATE401313T1 (fr)
AU (1)	AU2001284880A1 (fr)
CA (1)	CA2419314C (fr)
CZ (1)	CZ2003668A3 (fr)
DE (1)	DE60134899D1 (fr)
ES (1)	ES2310410T3 (fr)
HR (1)	HRP20030154B1 (fr)
HU (1)	HUP0302874A2 (fr)
IL (2)	IL154417A0 (fr)
IS (1)	IS6713A (fr)
MX (1)	MXPA03001337A (fr)
NZ (1)	NZ524554A (fr)
PL (1)	PL365608A1 (fr)
PT (1)	PT1783118E (fr)
SK (1)	SK2982003A3 (fr)
WO (1)	WO2002014286A1 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7666445B2 (en) *	2000-10-20	2010-02-23	The Trustees Of The University Of Pennsylvania	Polymer-based surgically implantable haloperidol delivery systems and methods for their production and use
AU2003256006A1 (en) *	2002-08-30	2004-03-19	Sunil Sadanand Nadkarni	Improved process for preparation of risperidone
KR20040034996A (ko) *	2002-10-18	2004-04-29	한미약품 주식회사	리스페리돈의 개선된 제조방법
CN100390146C (zh)	2002-11-13	2008-05-28	斯索恩有限公司	制备利培酮的方法和用于该方法的中间体
US20040180935A1 (en) *	2003-02-28	2004-09-16	Dr. Reddy's Laboratories Limited Dr. Reddy's Laboratories Inc.	Crystalline form Z of rabeprazole sodium and process for preparation thereof
AU2003245028A1 (en) *	2003-04-16	2004-11-04	Hetero Drugs Limited	A novel crystalline form of risperidone
ES2803516T3 (es)	2003-10-16	2021-01-27	Symed Labs Ltd	Una forma cristalina de linezolid
US8221778B2 (en)	2005-01-12	2012-07-17	The Trustees Of The University Of Pennsylvania	Drug-containing implants and methods of use thereof
AU2005206143B2 (en) *	2004-01-12	2010-12-16	The Trustees Of The University Of Pennsylvania	Long-term delivery formulations and methods of use thereof
US8329203B2 (en) *	2004-01-12	2012-12-11	The Trustees Of The University Of Pennsylvania	Drug-containing implants and methods of use thereof
US7307163B2 (en) *	2004-04-19	2007-12-11	Symed Labs Limited	Process for the preparation of linezolid and related compounds
HUP0401379A3 (en)	2004-07-08	2006-04-28	Richter Gedeon Vegyeszet	Process for the preparation of risperidon
CA2579642A1 (fr) *	2004-09-08	2006-03-16	Dermatrends, Inc.	Administration transdermique d'agents bioactifs hydrophobes
HUP0402163A2 (en) *	2004-10-25	2006-05-29	Richter Gedeon Vegyeszet	Process for the preparation of risperidone
KR20080012896A (ko) *	2005-04-27	2008-02-12	유엠엔 파마 아이엔씨	췌장염 예방 및 치료제
US8852638B2 (en)	2005-09-30	2014-10-07	Durect Corporation	Sustained release small molecule drug formulation
WO2007093870A2 (fr) *	2006-02-15	2007-08-23	Orchid Chemicals & Pharmaceuticals Limited	Procédé de synthèse de la rispéridone
US7820816B2 (en) *	2006-08-23	2010-10-26	Teva Pharmaceutical Industries Ltd.	Process for the synthesis of CMHTP and intermediates thereof
CN101801415B (zh)	2007-05-25	2015-09-23	Rb医药品有限公司	利培酮化合物的持续递送制剂
MX353752B (es)	2009-01-20	2018-01-26	Los Angeles Biomedical Res Inst Harbor Ucla Medical Ct	Los ácidos sórbico y benzoico y sus derivados aumentan la actividad de un neurofármaco.
CN102786521B (zh) *	2011-05-18	2016-01-13	中国医学科学院药物研究所	利培酮晶iii型物质及制备方法与在药品和保健品中应用
CN105367570B (zh) *	2015-12-08	2017-10-10	天津市亨必达化学合成物有限公司	一种利培酮晶i型物质的制备方法
ES2936094T3 (es)	2016-06-13	2023-03-14	Syneurx Int Taiwan Corp	Cocristales de benzoato de sodio y usos de los mismos
RU2765625C2 (ru)	2016-06-13	2022-02-01	Сайньюрекс Интернэшнл (Тайвань) Корп.	Сокристаллы бензоата лития и их применения

Family Cites Families (10)

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Publication number	Priority date	Publication date	Assignee	Title
US4804663A (en) *	1985-03-27	1989-02-14	Janssen Pharmaceutica N.V.	3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles
US5158952A (en) *	1988-11-07	1992-10-27	Janssen Pharmaceutica N.V.	3-[2-[4-(6-fluoro-1,2-benzisoxozol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9 tetrahydro-9-hydroxy-2-methyl-4H-pyrido [1,2-a]pyrimidin-4-one, compositions and method of use
ES2050069B1 (es)	1992-07-10	1994-12-16	Vita Invest Sa	Procedimiento para la obtencion de 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-il)piperidino)etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido(1,2-a) pirimidin-4-ona.
ES2074966B1 (es)	1994-02-11	1996-06-16	Vita Invest Sa	Procedimiento para la obtencion de 3-(2-(4-(6-fluoro-benzo(d)isoxazol-3-il)piperidin-1-il)-etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido-(1,2-a)pirimidin-4-ona.
JP2000503986A (ja) *	1996-01-26	2000-04-04	ファルマシア・アンド・アップジョン・カンパニー	Ｈｉｖ―１陽性であるヒトにおけるデラビルジンおよびプロテアーゼ・インヒビターの使用
TW487572B (en) *	1996-05-20	2002-05-21	Janssen Pharmaceutica Nv	Aqueous suspensions of 9-hydroxyrisperidone fatty acid esters
IT1294931B1 (it) *	1997-09-22	1999-04-23	Sigma Tau Ind Farmaceuti	Derivati della 2-amminotetralina procedimento per la loro preparazione e composizioni farmaceutiche che li contengono, attive nella
EP1280804B1 (fr)	2000-05-05	2004-04-14	RPG Life Sciences Limited	Procede de preparation de 3- 2- 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4h-pyrido 1,2,-a]pyrimidin-4-one antipsychotique
AU2001284763A1 (en) *	2000-08-08	2002-02-18	Teva Pharmaceutical Industries Ltd.	Preparation of risperidone
US20020193386A1 (en)	2002-03-28	2002-12-19	Inigo Pfeiffer	Polymorphic form of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-alpha]pyrimidin-4-one and formulations thereof

2001
- 2001-08-14 WO PCT/US2001/025387 patent/WO2002014286A1/fr not_active Ceased
- 2001-08-14 EP EP08011131A patent/EP1982980A1/fr not_active Withdrawn
- 2001-08-14 KR KR1020037002036A patent/KR100818875B1/ko not_active Expired - Fee Related
- 2001-08-14 IL IL15441701A patent/IL154417A0/xx unknown
- 2001-08-14 US US09/929,808 patent/US6750341B2/en not_active Expired - Fee Related
- 2001-08-14 HR HR20030154A patent/HRP20030154B1/xx not_active IP Right Cessation
- 2001-08-14 HU HU0302874A patent/HUP0302874A2/hu unknown
- 2001-08-14 NZ NZ524554A patent/NZ524554A/en unknown
- 2001-08-14 AU AU2001284880A patent/AU2001284880A1/en not_active Abandoned
- 2001-08-14 DE DE60134899T patent/DE60134899D1/de not_active Revoked
- 2001-08-14 PT PT07001138T patent/PT1783118E/pt unknown
- 2001-08-14 AT AT07001138T patent/ATE401313T1/de not_active IP Right Cessation
- 2001-08-14 PL PL01365608A patent/PL365608A1/xx not_active Application Discontinuation
- 2001-08-14 KR KR1020087005461A patent/KR20080028513A/ko not_active Withdrawn
- 2001-08-14 JP JP2002519429A patent/JP3751942B2/ja not_active Expired - Fee Related
- 2001-08-14 SK SK2982003A patent/SK2982003A3/sk not_active Application Discontinuation
- 2001-08-14 EP EP01963971A patent/EP1317434A4/fr not_active Withdrawn
- 2001-08-14 ES ES07001138T patent/ES2310410T3/es not_active Expired - Lifetime
- 2001-08-14 CZ CZ2003668A patent/CZ2003668A3/cs unknown
- 2001-08-14 MX MXPA03001337A patent/MXPA03001337A/es active IP Right Grant
- 2001-08-14 CA CA002419314A patent/CA2419314C/fr not_active Expired - Fee Related
2003
- 2003-02-11 IS IS6713A patent/IS6713A/is unknown
- 2003-02-12 IL IL154417A patent/IL154417A/en not_active IP Right Cessation
- 2003-09-23 US US10/669,272 patent/US7256195B2/en not_active Expired - Fee Related
2005
- 2005-08-25 JP JP2005244095A patent/JP2006028192A/ja not_active Withdrawn
2007
- 2007-11-14 JP JP2007296023A patent/JP2008056699A/ja active Pending

Also Published As

Publication number	Publication date
EP1317434A4 (fr)	2005-06-22
US20040229905A1 (en)	2004-11-18
CA2419314C (fr)	2006-07-11
PT1783118E (pt)	2008-08-19
IL154417A (en)	2008-11-03
EP1982980A1 (fr)	2008-10-22
AU2001284880A1 (en)	2002-02-25
US6750341B2 (en)	2004-06-15
IL154417A0 (en)	2003-09-17
KR100818875B1 (ko)	2008-04-01
JP2006028192A (ja)	2006-02-02
EP1317434A1 (fr)	2003-06-11
JP3751942B2 (ja)	2006-03-08
IS6713A (is)	2003-02-11
ATE401313T1 (de)	2008-08-15
JP2008056699A (ja)	2008-03-13
HUP0302874A2 (hu)	2003-12-29
WO2002014286A1 (fr)	2002-02-21
CZ2003668A3 (en)	2004-04-14
JP2004506622A (ja)	2004-03-04
ES2310410T3 (es)	2009-01-01
WO2002014286A9 (fr)	2003-03-27
DE60134899D1 (de)	2008-08-28
KR20030022389A (ko)	2003-03-15
HRP20030154B1 (en)	2009-03-31
NZ524554A (en)	2005-07-29
KR20080028513A (ko)	2008-03-31
US7256195B2 (en)	2007-08-14
MXPA03001337A (es)	2005-06-30
US20020115673A1 (en)	2002-08-22
HRP20030154A2 (en)	2005-04-30
CA2419314A1 (fr)	2002-02-21
PL365608A1 (en)	2005-01-10

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