HU226640B1 - Process for producing amorphous atorvastatin calcium salt - Google Patents
Process for producing amorphous atorvastatin calcium salt Download PDFInfo
- Publication number
- HU226640B1 HU226640B1 HU9903634A HUP9903634A HU226640B1 HU 226640 B1 HU226640 B1 HU 226640B1 HU 9903634 A HU9903634 A HU 9903634A HU P9903634 A HUP9903634 A HU P9903634A HU 226640 B1 HU226640 B1 HU 226640B1
- Authority
- HU
- Hungary
- Prior art keywords
- atorvastatin calcium
- amorphous
- atorvastatin
- polymorph
- amorphous atorvastatin
- Prior art date
Links
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical class CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 24
- 229960001770 atorvastatin calcium Drugs 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 19
- 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 description 11
- 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 description 11
- 229960005370 atorvastatin Drugs 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 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
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003339 best practice Methods 0.000 description 1
- 244000309464 bull Species 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
- 239000002178 crystalline material Substances 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
- 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
- 239000012467 final product Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (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)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9903634A HU226640B1 (en) | 1999-10-18 | 1999-10-18 | Process for producing amorphous atorvastatin calcium salt |
| DE60031882T DE60031882T2 (de) | 1999-10-18 | 2000-10-17 | Verfahren zur herstellung von amorphem atorvastatin-calcium |
| PL00354604A PL354604A1 (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| HK03102420.3A HK1050199B (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| YUP-283/02A RS50473B (sr) | 1999-10-18 | 2000-10-17 | Postupak za pripremanje amorfnog atorvastatin-kalcijuma |
| CA002388018A CA2388018C (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| SK519-2002A SK286861B6 (sk) | 1999-10-18 | 2000-10-17 | Spôsob prípravy amorfnej vápenatej soli atorvastatínu |
| AT00973115T ATE345327T1 (de) | 1999-10-18 | 2000-10-17 | Verfahren zur herstellung von amorphem atorvastatin kalzium |
| JP2001531799A JP2003512354A (ja) | 1999-10-18 | 2000-10-17 | 非晶質アトルバスタチンカルシウムの製法 |
| PCT/HU2000/000106 WO2001028999A1 (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| EP00973115A EP1235800B1 (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| UA2002054059A UA72777C2 (en) | 1999-10-18 | 2000-10-17 | A process for the preparation of amorphous atorvastatin calcium |
| RU2002113564/04A RU2255932C2 (ru) | 1999-10-18 | 2000-10-17 | Способ получения аморфного аторвастатина кальция |
| AU11663/01A AU1166301A (en) | 1999-10-18 | 2000-10-17 | Process for the preparation of amorphous atorvastatin calcium |
| CNB008144583A CN1157374C (zh) | 1999-10-18 | 2000-10-17 | 非晶形阿托伐他汀钙的制备方法 |
| CZ20021256A CZ300071B6 (cs) | 1999-10-18 | 2000-10-17 | Zpusob prípravy amorfní vápenaté soli atorvastatinu |
| KR1020027004906A KR100664353B1 (ko) | 1999-10-18 | 2000-10-17 | 비결정형 아토르바스타틴 칼슘의 제조 방법 |
| HR20020334A HRP20020334B1 (hr) | 1999-10-18 | 2000-10-17 | Proces za pripremu amorfnog kalcij-atorvastatina |
| US10/689,823 US20040063969A1 (en) | 1999-10-18 | 2003-10-20 | Process for the preparation of amorphous atorvastatin calcium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9903634A HU226640B1 (en) | 1999-10-18 | 1999-10-18 | Process for producing amorphous atorvastatin calcium salt |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HUP9903634D0 HUP9903634D0 (en) | 1999-12-28 |
| HUP9903634A2 HUP9903634A2 (hu) | 2001-12-28 |
| HUP9903634A3 HUP9903634A3 (en) | 2002-01-28 |
| HU226640B1 true HU226640B1 (en) | 2009-05-28 |
Family
ID=90014241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9903634A HU226640B1 (en) | 1999-10-18 | 1999-10-18 | Process for producing amorphous atorvastatin calcium salt |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1235800B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2003512354A (cg-RX-API-DMAC7.html) |
| KR (1) | KR100664353B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1157374C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE345327T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU1166301A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2388018C (cg-RX-API-DMAC7.html) |
| CZ (1) | CZ300071B6 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60031882T2 (cg-RX-API-DMAC7.html) |
| HR (1) | HRP20020334B1 (cg-RX-API-DMAC7.html) |
| HU (1) | HU226640B1 (cg-RX-API-DMAC7.html) |
| PL (1) | PL354604A1 (cg-RX-API-DMAC7.html) |
| RS (1) | RS50473B (cg-RX-API-DMAC7.html) |
| RU (1) | RU2255932C2 (cg-RX-API-DMAC7.html) |
| SK (1) | SK286861B6 (cg-RX-API-DMAC7.html) |
| UA (1) | UA72777C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2001028999A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (31)
| 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 |
| AU2002255479B2 (en) | 2001-07-30 | 2008-09-11 | Dr. Reddy's Laboratories Ltd. | Crystalline forms VI and VII of atorvastatin clacium |
| 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 |
| RU2309141C2 (ru) * | 2002-03-18 | 2007-10-27 | Байокон Лимитид | АМОРФНЫЕ ИНГИБИТОРЫ ГМГ-КоА-РЕДУКТАЗЫ И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| ITMI20020907A1 (it) * | 2002-04-29 | 2003-10-29 | Chemi Spa | Processo di preparazione della forma amorfa del sale di calcio della atorvastatina |
| WO2003099785A1 (en) * | 2002-05-28 | 2003-12-04 | 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 |
| US7655692B2 (en) * | 2003-06-12 | 2010-02-02 | Pfizer Inc. | Process for forming amorphous atorvastatin |
| US20050271717A1 (en) | 2003-06-12 | 2005-12-08 | Alfred Berchielli | Pharmaceutical compositions of atorvastatin |
| CZ298382B6 (cs) * | 2004-03-10 | 2007-09-12 | Zentiva, A. S. | Zpusob prípravy amorfní formy hemivápenaté soli atorvastatinu a její stabilizace |
| WO2005092852A1 (en) | 2004-03-17 | 2005-10-06 | Ranbaxy Laboratories Limited | Process for the production of atorvastatin calcium in amorphous form |
| CN1960972A (zh) * | 2004-04-16 | 2007-05-09 | 辉瑞产品公司 | 用于形成无定形阿托伐它汀钙的方法 |
| 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 |
| CA2649054A1 (en) | 2004-05-05 | 2005-11-10 | Pfizer Products Inc. | Salt forms of [r-(r*,r*)]-2-(4-fluorophenyl)-.beta., .delta.-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid |
| CA2573969C (en) * | 2004-07-16 | 2014-02-04 | 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 |
| WO2006037125A1 (en) | 2004-09-28 | 2006-04-06 | Teva Pharmaceutical Industries Ltd. | Process for preparing forms of atorvastatin calcium substantially free of impurities |
| CN101039906A (zh) * | 2004-10-18 | 2007-09-19 | 特瓦制药工业有限公司 | 通过将盐溶解于有机溶剂并除去该溶剂来制备无定形阿托伐他汀半钙的方法，所述有机溶剂为醇和酮和 /或酯的混合物 |
| WO2006046109A1 (en) | 2004-10-28 | 2006-05-04 | Warner-Lambert Company Llc | Process for forming amorphous atorvastatin |
| ATE466840T1 (de) | 2005-11-21 | 2010-05-15 | Warner Lambert Co | Neue formen von är-(r*,r*)ü-2-(4-fluorphenyl)-b,d-dihydroxy-5-( -methylethyl)-3-phenyl-4- ä(phenylamino)carbonylü-1h-pyrrol-1-heptansäure 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 |
| CN103274985B (zh) * | 2010-12-03 | 2016-03-09 | 上海科州药物研发有限公司 | 一种阿托伐他汀氨基酸盐 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| WO1998012200A1 (en) * | 1996-09-20 | 1998-03-26 | Meiji Seika Kaisha Ltd. | A crystalline substance of cefditoren pivoxyl and the production of the same |
-
1999
- 1999-10-18 HU HU9903634A patent/HU226640B1/hu not_active IP Right Cessation
-
2000
- 2000-10-17 KR KR1020027004906A patent/KR100664353B1/ko not_active Expired - Fee Related
- 2000-10-17 WO PCT/HU2000/000106 patent/WO2001028999A1/en not_active Ceased
- 2000-10-17 RU RU2002113564/04A patent/RU2255932C2/ru not_active IP Right Cessation
- 2000-10-17 CZ CZ20021256A patent/CZ300071B6/cs not_active IP Right Cessation
- 2000-10-17 PL PL00354604A patent/PL354604A1/xx not_active Application Discontinuation
- 2000-10-17 AU AU11663/01A patent/AU1166301A/en not_active Abandoned
- 2000-10-17 JP JP2001531799A patent/JP2003512354A/ja active Pending
- 2000-10-17 EP EP00973115A patent/EP1235800B1/en not_active Expired - Lifetime
- 2000-10-17 UA UA2002054059A patent/UA72777C2/uk unknown
- 2000-10-17 DE DE60031882T patent/DE60031882T2/de not_active Expired - Fee Related
- 2000-10-17 CN CNB008144583A patent/CN1157374C/zh not_active Expired - Fee Related
- 2000-10-17 HR HR20020334A patent/HRP20020334B1/xx not_active IP Right Cessation
- 2000-10-17 SK SK519-2002A patent/SK286861B6/sk not_active IP Right Cessation
- 2000-10-17 AT AT00973115T patent/ATE345327T1/de not_active IP Right Cessation
- 2000-10-17 CA CA002388018A patent/CA2388018C/en not_active Expired - Fee Related
- 2000-10-17 RS YUP-283/02A patent/RS50473B/sr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9903634A3 (en) | 2002-01-28 |
| RU2255932C2 (ru) | 2005-07-10 |
| RS50473B (sr) | 2010-03-02 |
| YU28302A (sh) | 2005-06-10 |
| CA2388018C (en) | 2008-04-08 |
| ATE345327T1 (de) | 2006-12-15 |
| EP1235800A1 (en) | 2002-09-04 |
| CA2388018A1 (en) | 2001-04-26 |
| CN1379760A (zh) | 2002-11-13 |
| HUP9903634D0 (en) | 1999-12-28 |
| DE60031882T2 (de) | 2007-07-05 |
| SK5192002A3 (en) | 2002-11-06 |
| WO2001028999A1 (en) | 2001-04-26 |
| CN1157374C (zh) | 2004-07-14 |
| KR20020063166A (ko) | 2002-08-01 |
| AU1166301A (en) | 2001-04-30 |
| HUP9903634A2 (hu) | 2001-12-28 |
| DE60031882D1 (de) | 2006-12-28 |
| HK1050199A1 (en) | 2003-06-13 |
| HRP20020334A2 (en) | 2004-02-29 |
| HRP20020334B1 (hr) | 2007-12-31 |
| JP2003512354A (ja) | 2003-04-02 |
| PL354604A1 (en) | 2004-01-26 |
| SK286861B6 (sk) | 2009-06-05 |
| UA72777C2 (en) | 2005-04-15 |
| KR100664353B1 (ko) | 2007-01-02 |
| EP1235800B1 (en) | 2006-11-15 |
| CZ20021256A3 (cs) | 2002-08-14 |
| CZ300071B6 (cs) | 2009-01-21 |
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| HC9A | Change of name, address |
Owner name: EGIS GYOGYSZERGYAR NYILVANOSAN MUEKOEDOE RESZV, HU Free format text: FORMER OWNER(S): EGIS GYOGYSZERGYAR RT., HU |
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| MM4A | Lapse of definitive patent protection due to non-payment of fees |