UA72777C2 - A process for the preparation of amorphous atorvastatin calcium - Google Patents

A process for the preparation of amorphous atorvastatin calcium Download PDF

Info

Publication number: UA72777C2
Authority: UA; Ukraine
Prior art keywords: atorvastatin; amorphous; calcium; atorvastatin calcium; mixture
Prior art date: 1999-10-18

Application number

UA2002054059A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1999-10-18

Filing date

2000-10-17

Publication date

2005-04-15

2000-10-17 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

2005-04-15 Publication of UA72777C2 publication Critical patent/UA72777C2/uk

Links

OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 title claims abstract description 27
229960001770 atorvastatin calcium Drugs 0.000 title claims abstract description 27
238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title abstract description 3
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims abstract description 20
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims abstract description 20
229960005370 atorvastatin Drugs 0.000 claims abstract description 20
239000000203 mixture Substances 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
238000001953 recrystallisation Methods 0.000 claims abstract description 5
238000001816 cooling Methods 0.000 claims abstract description 4
239000003960 organic solvent Substances 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 10
238000009835 boiling Methods 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 4
238000001914 filtration Methods 0.000 claims description 4
BWFCZHDTTAYGNN-CNZCJKERSA-N calcium;(3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound [Ca].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 BWFCZHDTTAYGNN-CNZCJKERSA-N 0.000 claims description 3
238000005119 centrifugation Methods 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims 2
239000007858 starting material Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
208000035150 Hypercholesterolemia Diseases 0.000 abstract description 2
208000031226 Hyperlipidaemia Diseases 0.000 abstract description 2
238000010438 heat treatment Methods 0.000 abstract description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
229910052791 calcium Inorganic materials 0.000 abstract 1
239000011575 calcium Substances 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
159000000007 calcium salts Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000002994 raw material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000002050 international nonproprietary name Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OUCSEDFVYPBLLF-KAYWLYCHSA-N 5-(4-fluorophenyl)-1-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-n,4-diphenyl-2-propan-2-ylpyrrole-3-carboxamide Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@H]2OC(=O)C[C@H](O)C2)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 OUCSEDFVYPBLLF-KAYWLYCHSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
239000005516 coenzyme A Substances 0.000 description 1
229940093530 coenzyme a Drugs 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
230000003760 hair shine Effects 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA2002054059A 1999-10-18 2000-10-17 A process for the preparation of amorphous atorvastatin calcium UA72777C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU9903634A HU226640B1 (en)	1999-10-18	1999-10-18	Process for producing amorphous atorvastatin calcium salt
PCT/HU2000/000106 WO2001028999A1 (en)	1999-10-18	2000-10-17	Process for the preparation of amorphous atorvastatin calcium

Publications (1)

Publication Number	Publication Date
UA72777C2 true UA72777C2 (en)	2005-04-15

Family

ID=90014241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002054059A UA72777C2 (en)	1999-10-18	2000-10-17	A process for the preparation of amorphous atorvastatin calcium

Country Status (17)

Country	Link
EP (1)	EP1235800B1 (cs)
JP (1)	JP2003512354A (cs)
KR (1)	KR100664353B1 (cs)
CN (1)	CN1157374C (cs)
AT (1)	ATE345327T1 (cs)
AU (1)	AU1166301A (cs)
CA (1)	CA2388018C (cs)
CZ (1)	CZ300071B6 (cs)
DE (1)	DE60031882T2 (cs)
HR (1)	HRP20020334B1 (cs)
HU (1)	HU226640B1 (cs)
PL (1)	PL354604A1 (cs)
RS (1)	RS50473B (cs)
RU (1)	RU2255932C2 (cs)
SK (1)	SK286861B6 (cs)
UA (1)	UA72777C2 (cs)
WO (1)	WO2001028999A1 (cs)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7411075B1 (en)	2000-11-16	2008-08-12	Teva Pharmaceutical Industries Ltd.	Polymorphic form of atorvastatin calcium
SI20425A (sl) *	1999-12-10	2001-06-30	LEK tovarna farmacevtskih in kemi�nih izdelkov d.d.	Priprava amorfnega atorvastatina
US7501450B2 (en)	2000-11-30	2009-03-10	Teva Pharaceutical Industries Ltd.	Crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms
IL156055A0 (en)	2000-11-30	2003-12-23	Teva Pharma	Novel crystal forms of atorvastatin hemi calcium and processes for their preparation as well as novel processes for preparing other forms
WO2002057229A1 (en)	2001-01-19	2002-07-25	Biocon India Limited	FORM V CRYSTALLINE [R-(R,R)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1- HEPTANOIC ACID HEMI CALCIUM SALT. (ATORVASTATIN)
DE10135493A1 (de) *	2001-07-20	2003-01-30	Jobst Krauskopf	Pharmazeutische Zusammensetzung zur Behandlung von Hypercholesterinämie
RU2304139C2 (ru)	2001-07-30	2007-08-10	Д-р Редди'с Лабораторис Лтд	Кристаллические формы vi и vii кальциевой соли аторвастатина
RU2309141C2 (ru) *	2002-03-18	2007-10-27	Байокон Лимитид	АМОРФНЫЕ ИНГИБИТОРЫ ГМГ-КоА-РЕДУКТАЗЫ И СПОСОБ ИХ ПОЛУЧЕНИЯ
HUP0500074A3 (en) *	2002-03-18	2005-07-28	Biocon Ltd Bangalore	Amorphous hmg-coa reductase inhibitors of desired particle size and process for producing them
ITMI20020907A1 (it) *	2002-04-29	2003-10-29	Chemi Spa	Processo di preparazione della forma amorfa del sale di calcio della atorvastatina
AU2002356423A1 (en) *	2002-05-28	2003-12-12	Cadila Healthcare Limited	Process for the preparation of amorphous atorvastatin calcium
HU227041B1 (en) *	2003-03-24	2010-05-28	Richter Gedeon Nyrt	Process for the synthesis of amorphous atorvastatin calcium
US7790197B2 (en)	2003-06-09	2010-09-07	Warner-Lambert Company Llc	Pharmaceutical compositions of atorvastatin
US20050271717A1 (en)	2003-06-12	2005-12-08	Alfred Berchielli	Pharmaceutical compositions of atorvastatin
US7655692B2 (en) *	2003-06-12	2010-02-02	Pfizer Inc.	Process for forming amorphous atorvastatin
CZ298382B6 (cs) *	2004-03-10	2007-09-12	Zentiva, A. S.	Zpusob prípravy amorfní formy hemivápenaté soli atorvastatinu a její stabilizace
AU2004317570B2 (en)	2004-03-17	2011-01-06	Ranbaxy Laboratories Limited	Process for the production of atorvastatin calcium in amorphous form
CA2562844A1 (en) *	2004-04-16	2005-10-27	Pfizer Products Inc.	Process for forming amorphous atorvastatin calcium
CN1692906A (zh) *	2004-04-30	2005-11-09	鲁南制药集团股份有限公司	治疗高血脂症的组合物
US7875731B2 (en)	2004-05-05	2011-01-25	Pfizer Inc.	Salt forms of [R-(R,R)]-2-(4-fluorophenyl)-β, δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)Carbonyl]-1H-pyrrole-1-heptanoic acid
AU2005263550C1 (en) *	2004-07-16	2013-01-17	Lek Pharmaceuticals D.D.	Oxidative degradation products of atorvastatin calcium
JP2008506764A (ja)	2004-07-20	2008-03-06	ワーナー−ランバートカンパニーリミテッドライアビリティーカンパニー	［Ｒ−（Ｒ＊，Ｒ＊）］−２−（４−フルオロフェニル）−β、δ−ジヒドロキシ−５−（１−メチルエチル）−３−フェニル−４−［（フェニルアミノ）カルボニル］−１Ｈ−ピロール−１−ヘプタン酸カルシウム塩（２：１）の新規形態
US7674923B2 (en) *	2004-09-28	2010-03-09	Teva Pharmaceutical Industries Ltd	Process for preparing forms of atorvastatin calcium substantially free of impurities
KR20070054730A (ko) *	2004-10-18	2007-05-29	테바 파마슈티컬 인더스트리즈 리미티드	알콜 및 케톤 및/또는 에스테르의 혼합물인 유기 용매에아토르바스타틴 헤미-칼슘 염을 용해시키고 용매를제거하여 비결정형 아토르바스타틴 헤미-칼슘을 제조하는방법
CA2585836A1 (en)	2004-10-28	2006-05-04	Warner-Lambert Company Llc	Process for forming amorphous atorvastatin
WO2007057755A1 (en)	2005-11-21	2007-05-24	Warner-Lambert Company Llc	Novel forms of [r-(r,r)]-2-(4-fluorophenyl)-b,b-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-hept anoic acid magnesium
EP1810667A1 (en)	2006-01-20	2007-07-25	KRKA, tovarna zdravil, d.d., Novo mesto	Pharmaceutical composition comprising amorphous atorvastatin
KR100833439B1 (ko) *	2007-01-02	2008-05-29	씨제이제일제당 (주)	비결정형 아토르바스타틴 칼슘의 개선된 제조방법
CZ201039A3 (cs)	2010-01-19	2011-07-27	Zentiva, K. S	Zpusob prumyslové výroby amorfní formy hemivápenaté soli (3R,5R) 7-[3-fenyl-4-fenylkarbamoyl-2-(4-fluorfenyl)-5-isopropylpyrrol-1-yl]-3,5-dihydroxyheptanové kyseliny (atorvastatinu) s vysokým specifickým povrchem a jeho použití v lékové forme
HUP1000299A2 (hu)	2010-06-08	2012-02-28	Nanoform Cardiovascular Therapeutics Ltd	Nanostrukturált Atorvastatint, gyógyszerészetileg elfogadott sóit és kokristályait tartalmazó készítmény és eljárás elõállításukra
CN102424663B (zh) *	2010-12-03	2013-08-14	天津滨江药物研发有限公司	一种阿托伐他汀氨基酸盐及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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FI94339C (fi) *	1989-07-21	1995-08-25	Warner Lambert Co	Menetelmä farmaseuttisesti käyttökelpoisen /R-(R,R)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi
ATE123020T1 (de) *	1990-05-11	1995-06-15	American Cyanamid Co	N-acylierte arylpyrrole als insektizide, akarizide, nematizide und molluskizide wirkstoffe.
HRP960312B1 (en) *	1995-07-17	2001-10-31	Warner Lambert Co	NOVEL PROCESS FOR THE PRODUCTION OF AMORPHOUS /R-(R, R)/-2-(4-FLUOROPHENYL)-"beta", "delta"-DIHYDROXY-5-PHENYL-4-/(PHENYLAMINO)CARBONYL/-1H-PYRROLE -1-HEPTANOIC ACID CALCIUM SALT (2 : 1)
HU224196B1 (hu) *	1996-09-20	2005-06-28	Meiji Seika Kaisha Ltd.	Cefditoren-pivoxil kristályos formája, és eljárás annak előállítására

1999
- 1999-10-18 HU HU9903634A patent/HU226640B1/hu not_active IP Right Cessation
2000
- 2000-10-17 DE DE60031882T patent/DE60031882T2/de not_active Expired - Fee Related
- 2000-10-17 RS YUP-283/02A patent/RS50473B/sr unknown
- 2000-10-17 EP EP00973115A patent/EP1235800B1/en not_active Expired - Lifetime
- 2000-10-17 AU AU11663/01A patent/AU1166301A/en not_active Abandoned
- 2000-10-17 KR KR1020027004906A patent/KR100664353B1/ko not_active Expired - Fee Related
- 2000-10-17 HR HR20020334A patent/HRP20020334B1/xx not_active IP Right Cessation
- 2000-10-17 CZ CZ20021256A patent/CZ300071B6/cs not_active IP Right Cessation
- 2000-10-17 CN CNB008144583A patent/CN1157374C/zh not_active Expired - Fee Related
- 2000-10-17 AT AT00973115T patent/ATE345327T1/de not_active IP Right Cessation
- 2000-10-17 WO PCT/HU2000/000106 patent/WO2001028999A1/en not_active Ceased
- 2000-10-17 JP JP2001531799A patent/JP2003512354A/ja active Pending
- 2000-10-17 PL PL00354604A patent/PL354604A1/xx not_active Application Discontinuation
- 2000-10-17 SK SK519-2002A patent/SK286861B6/sk not_active IP Right Cessation
- 2000-10-17 CA CA002388018A patent/CA2388018C/en not_active Expired - Fee Related
- 2000-10-17 UA UA2002054059A patent/UA72777C2/uk unknown
- 2000-10-17 RU RU2002113564/04A patent/RU2255932C2/ru not_active IP Right Cessation

Also Published As

Publication number	Publication date
WO2001028999A1 (en)	2001-04-26
KR100664353B1 (ko)	2007-01-02
CN1379760A (zh)	2002-11-13
SK5192002A3 (en)	2002-11-06
CA2388018A1 (en)	2001-04-26
DE60031882D1 (de)	2006-12-28
HUP9903634A2 (hu)	2001-12-28
RU2255932C2 (ru)	2005-07-10
RS50473B (sr)	2010-03-02
JP2003512354A (ja)	2003-04-02
CZ20021256A3 (cs)	2002-08-14
AU1166301A (en)	2001-04-30
HK1050199A1 (en)	2003-06-13
PL354604A1 (en)	2004-01-26
HUP9903634A3 (en)	2002-01-28
KR20020063166A (ko)	2002-08-01
EP1235800A1 (en)	2002-09-04
CZ300071B6 (cs)	2009-01-21
DE60031882T2 (de)	2007-07-05
HRP20020334B1 (hr)	2007-12-31
YU28302A (sh)	2005-06-10
CA2388018C (en)	2008-04-08
CN1157374C (zh)	2004-07-14
HUP9903634D0 (en)	1999-12-28
HRP20020334A2 (en)	2004-02-29
ATE345327T1 (de)	2006-12-15
HU226640B1 (en)	2009-05-28
EP1235800B1 (en)	2006-11-15
SK286861B6 (sk)	2009-06-05

Publication	Publication Date	Title
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