DE69921855T2 - Kristallines bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoicacid]calcium salz - Google Patents
Kristallines bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoicacid]calcium salz Download PDFInfo
- Publication number
- DE69921855T2 DE69921855T2 DE69921855T DE69921855T DE69921855T2 DE 69921855 T2 DE69921855 T2 DE 69921855T2 DE 69921855 T DE69921855 T DE 69921855T DE 69921855 T DE69921855 T DE 69921855T DE 69921855 T2 DE69921855 T2 DE 69921855T2
- Authority
- DE
- Germany
- Prior art keywords
- crystalline form
- crystalline
- methyl
- form according
- methylsulfonyl
- Prior art date
- 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.)
- Expired - Lifetime
Links
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 3
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical class CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9900339.4A GB9900339D0 (en) | 1999-01-09 | 1999-01-09 | Chemical compounds |
| GB9900339 | 1999-01-09 | ||
| PCT/GB1999/004439 WO2000042024A1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3r,5s)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69921855D1 DE69921855D1 (en) | 2004-12-16 |
| DE69921855T2 true DE69921855T2 (de) | 2005-11-24 |
Family
ID=10845719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69921855T Expired - Lifetime DE69921855T2 (de) | 1999-01-09 | 1999-12-23 | Kristallines bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoicacid]calcium salz |
Country Status (32)
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9900339D0 (en) * | 1999-01-09 | 1999-02-24 | Zeneca Ltd | Chemical compounds |
| GB0001621D0 (en) * | 2000-01-26 | 2000-03-15 | Astrazeneca Ab | Pharmaceutical compositions |
| GB0003305D0 (en) * | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| DE10135493A1 (de) * | 2001-07-20 | 2003-01-30 | Jobst Krauskopf | Pharmazeutische Zusammensetzung zur Behandlung von Hypercholesterinämie |
| GB0218781D0 (en) * | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| US20060019269A1 (en) * | 2002-10-17 | 2006-01-26 | Decode Genetics, Inc. | Susceptibility gene for myocardial infarction, stroke, and PAOD, methods of treatment |
| US20080293750A1 (en) * | 2002-10-17 | 2008-11-27 | Anna Helgadottir | Susceptibility Gene for Myocardial Infarction, Stroke, Paod and Methods of Treatment |
| DE602004030780D1 (en) * | 2003-04-25 | 2011-02-10 | Nippon Chemiphar Co | Salze von (2s,3s)-3- ää(1s)-1-isobutoxymethyl-3-methylbutylücarbamoylü oxirane-2-carbonsäure |
| GB0312896D0 (en) * | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) * | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0322552D0 (en) | 2003-09-26 | 2003-10-29 | Astrazeneca Uk Ltd | Therapeutic treatment |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| CA2546701C (en) * | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| CZ200486A3 (cs) * | 2004-01-16 | 2005-08-17 | Zentiva, A.S. | Způsob výroby hemivápenaté soli (E)-7-[4-(4-fluorfenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxy-6-heptenové kyseliny |
| EP1709008A1 (en) * | 2004-01-19 | 2006-10-11 | Ranbaxy Laboratories Limited | Salts of hmg-coa reductase inhibitors and use thereof |
| EP1737828A1 (en) * | 2004-01-19 | 2007-01-03 | Ranbaxy Laboratories Limited | Amorphous magnesium salts of rosuvastatin |
| US8158362B2 (en) * | 2005-03-30 | 2012-04-17 | Decode Genetics Ehf. | Methods of diagnosing susceptibility to myocardial infarction and screening for an LTA4H haplotype |
| US20100216863A1 (en) * | 2004-01-30 | 2010-08-26 | Decode Genetics Ehf. | Susceptibility Gene for Myocardial Infarction, Stroke, and PAOD; Methods of Treatment |
| US7241800B2 (en) | 2004-03-17 | 2007-07-10 | Mai De Ltd. | Anhydrous amorphous form of fluvastatin sodium |
| EP1797046A2 (en) * | 2004-09-27 | 2007-06-20 | Ranbaxy Laboratories Limited | Novel processes for preparing amorphous rosuvastatin calcium and a novel polymorphic form of rosuvastatin sodium |
| EP1844021A1 (en) * | 2005-01-31 | 2007-10-17 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of rosuvastatin calcium salt |
| JP5146965B2 (ja) | 2005-06-24 | 2013-02-20 | レツク・フアーマシユーテイカルズ・デー・デー | 不純物を含まない非晶質ロスバスタチンカルシウムの調製方法 |
| CZ299215B6 (cs) * | 2005-06-29 | 2008-05-21 | Zentiva, A. S. | Zpusob výroby hemivápenaté soli (E)-7-[4-(4-fluorofenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl] (3R,5S)-3,5-dihydroxy-6-heptenovékyseliny |
| BRPI0605917A2 (pt) * | 2005-08-16 | 2009-05-26 | Teva Pharma | intermediário cristalino de rosuvastatina |
| HU227696B1 (en) * | 2006-04-13 | 2011-12-28 | Egyt Gyogyszervegyeszeti Gyar | Zinc salt of rosuvastatin, process for its preparation and pharmaceutical compositions containing it |
| EP2066644A2 (en) * | 2006-08-04 | 2009-06-10 | Glenmark Pharmaceuticals Limited | Salts of rosuvastatin and processes for their preparation |
| KR20080060284A (ko) * | 2006-09-18 | 2008-07-01 | 테바 파마슈티컬 인더스트리즈 리미티드 | 결정질 로수바스타틴 칼슘 |
| US20080249141A1 (en) * | 2007-04-06 | 2008-10-09 | Palepu Nageswara R | Co-therapy with and combinations of statins and 1,4-dihydropyridine-3,5-dicarboxydiesters |
| US20080248115A1 (en) * | 2007-04-09 | 2008-10-09 | Palepu Nageswara R | Combinations of statins and anti-obesity agent |
| WO2008124122A1 (en) * | 2007-04-09 | 2008-10-16 | Scidose, Llc | Combinations of statins and anti-obesity agent and glitazones |
| WO2009143776A1 (zh) | 2008-05-27 | 2009-12-03 | 常州制药厂有限公司 | 瑞舒伐他汀钙盐的制备方法及其中间体 |
| EP2336116A1 (en) * | 2009-12-16 | 2011-06-22 | LEK Pharmaceuticals d.d. | Process for the preparation of key intermediates for the synthesis of rosuvastatin or pharmaceutically acceptable salts thereof |
| WO2011074016A1 (en) | 2009-12-17 | 2011-06-23 | Matrix Laboratories Ltd | Novel polymorphic forms of rosuvastatin calcium and process for preparation of the same |
| US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| EP2643305A1 (en) | 2010-11-22 | 2013-10-02 | Basf Se | Multicomponent system of rosuvastatin calcium salt and sorbitol |
| US8716305B2 (en) | 2011-04-18 | 2014-05-06 | Basf Se | Multicomponent crystalline system of rosuvastatin calcium salt and vanillin |
| WO2014050874A1 (ja) * | 2012-09-27 | 2014-04-03 | 東和薬品株式会社 | ロスバスタチンカルシウムの新規結晶形態およびその製造方法 |
| RO129060B1 (ro) | 2013-04-25 | 2014-11-28 | Antibiotice S.A. | Compoziţie farmaceutică stabilă cu rosuvastatină calcică amorfă |
| CN103755643A (zh) * | 2013-12-31 | 2014-04-30 | 连云港金康医药科技有限公司 | 瑞苏伐他汀钙盐i晶型 |
| CN105153040B (zh) * | 2015-10-15 | 2018-04-13 | 江苏师范大学 | 瑞舒伐他汀钙新晶型及其制备方法 |
| EP3445751B9 (en) * | 2016-04-18 | 2023-07-26 | Morepen Laboratories Limited | New polymorphic form of crystalline rosuvastatin calcium&novel processes for crystalline as well as amorphous rosuvastatin calcium |
| CN105837516B (zh) * | 2016-05-16 | 2018-07-10 | 山东新时代药业有限公司 | 一种瑞舒伐他汀钙晶型及其制备方法 |
| CN114105885A (zh) * | 2020-08-28 | 2022-03-01 | 广东东阳光药业有限公司 | 一种瑞舒伐他汀钙晶型a的制备方法 |
| TW202302090A (zh) * | 2021-04-30 | 2023-01-16 | 大陸商江蘇恒瑞醫藥股份有限公司 | 血小板生成素受體激動劑的給藥方案 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027018D0 (en) * | 1990-12-12 | 1991-01-30 | Ici Plc | Heterocyclic compounds |
| JP2648897B2 (ja) * | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| GB9900339D0 (en) * | 1999-01-09 | 1999-02-24 | Zeneca Ltd | Chemical compounds |
-
1999
- 1999-01-09 GB GBGB9900339.4A patent/GB9900339D0/en not_active Ceased
- 1999-12-23 EP EP99962471A patent/EP1144389B1/en not_active Expired - Lifetime
- 1999-12-23 HU HU0104828A patent/HU228116B1/hu unknown
- 1999-12-23 TR TR2001/01894T patent/TR200101894T2/xx unknown
- 1999-12-23 CN CNB998155047A patent/CN1213033C/zh not_active Expired - Lifetime
- 1999-12-23 CZ CZ20012460A patent/CZ299843B6/cs not_active IP Right Cessation
- 1999-12-23 NZ NZ512560A patent/NZ512560A/en not_active IP Right Cessation
- 1999-12-23 EE EEP200100359A patent/EE05033B1/xx not_active IP Right Cessation
- 1999-12-23 AU AU18826/00A patent/AU762909B2/en not_active Ceased
- 1999-12-23 KR KR1020017008546A patent/KR100645858B1/ko not_active Expired - Fee Related
- 1999-12-23 BR BR9916786-7A patent/BR9916786A/pt not_active Application Discontinuation
- 1999-12-23 SI SI9930731T patent/SI1144389T1/xx unknown
- 1999-12-23 PT PT99962471T patent/PT1144389E/pt unknown
- 1999-12-23 PL PL348775A patent/PL201800B1/pl unknown
- 1999-12-23 DK DK99962471T patent/DK1144389T3/da active
- 1999-12-23 AT AT99962471T patent/ATE282027T1/de active
- 1999-12-23 WO PCT/GB1999/004439 patent/WO2000042024A1/en not_active Ceased
- 1999-12-23 ES ES99962471T patent/ES2232194T3/es not_active Expired - Lifetime
- 1999-12-23 CA CA002356212A patent/CA2356212C/en not_active Expired - Fee Related
- 1999-12-23 HK HK02102104.7A patent/HK1040989B/en not_active IP Right Cessation
- 1999-12-23 ID IDW00200101470A patent/ID29432A/id unknown
- 1999-12-23 SK SK963-2001A patent/SK285807B6/sk not_active IP Right Cessation
- 1999-12-23 IL IL14397799A patent/IL143977A0/xx not_active IP Right Cessation
- 1999-12-23 JP JP2000593592A patent/JP4996786B2/ja not_active Expired - Lifetime
- 1999-12-23 RU RU2001122164/04A patent/RU2236404C2/ru not_active IP Right Cessation
- 1999-12-23 DE DE69921855T patent/DE69921855T2/de not_active Expired - Lifetime
- 1999-12-23 US US09/869,462 patent/US6589959B1/en not_active Expired - Lifetime
-
2001
- 2001-06-08 IN IN758MU2001 patent/IN213326B/en unknown
- 2001-06-22 IS IS5977A patent/IS2410B/is unknown
- 2001-06-22 ZA ZA200105187A patent/ZA200105187B/en unknown
- 2001-07-06 NO NO20013368A patent/NO320189B1/no not_active IP Right Cessation
- 2001-07-06 MX MXPA01006953 patent/MX223771B/es active IP Right Grant
-
2003
- 2003-02-14 IN IN223MU2003 patent/IN2003MU00223A/en unknown
- 2003-04-10 US US10/410,650 patent/US20040009997A1/en not_active Abandoned
-
2009
- 2009-11-16 JP JP2009260812A patent/JP2010090128A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69921855T2 (de) | Kristallines bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoicacid]calcium salz | |
| DE60203260T2 (de) | Pharmazeutische kombination, die ein 4-chinazolinamin und paclitaxel, carboplatin oder vinorelbin enthält, zur behandlung von krebs | |
| DE69904600T2 (de) | Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy)propylcarbamat | |
| US8436167B2 (en) | Chemical compounds | |
| DE69613369T2 (de) | Chinazolin derivate | |
| CN101139345A (zh) | 1-[4-(5-氰基吲哚-3-基)丁基]-4-(2-氨甲酰-苯并呋喃-5-基)-哌嗪盐酸盐的多晶型物 | |
| EP2508521A2 (de) | Verfahren zur Herstellung von Aminocrotonylverbindungen | |
| DE69115526T2 (de) | 2,4-Pyrimidindionderivate und diese enthaltende Arzneimittel | |
| DE69319590T2 (de) | Melamine derivate zur verwendung in der behandlung von krebs | |
| DE60317675T2 (de) | KRYSTALLINE 2,5-DIONE-3-(1-METHYL-1H-INDOL-3-YL)-4-i1-(PYRIDIN-2-YLMETHYL)PIPERIDIN-4-YL -1H-INDOL-3-YL -1H-PYRROLE MONO-HYDROCHLORIDE | |
| DE60131416T2 (de) | Chirale fluochinolon-argininsalzformen | |
| DE202011110043U1 (de) | Mehrkomponentensystem von Rosuvastatin-Calciumsalz und Sorbit | |
| DE69208464T2 (de) | N-((4,5-dihydroxy- und 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracen-yl)carbonyl)aminosäure zur therapie osteoartikulärer leiden | |
| DE60000590T2 (de) | Nitroimidazolderivate als Empfindlichkeitsverstärker für Chemotherapie und Radiotherapie | |
| DE69510510T2 (de) | N-benzoylmethylsubstituierte paroxetinderivate | |
| DE69120221T2 (de) | Pyrimidin-verbindung und ihr pharmazeutisch annehmbares salz | |
| DE69706562T2 (de) | N-(4-acetyl-1-piperazinyl)-4-fluorobenzamidhydrat | |
| DE69006897T2 (de) | Benzothiazolinon-Derivate, ihre Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten. | |
| DE69520225T2 (de) | Verfahren zur Herstellung von 3-[2-[4-(3-Chlor-2-methylphenyl)-1- piperazinyl] ethyl]-5,6-dimethoxy-1-(4-imidazolylmethyl)-1H-indazol-dihydrochlorid-3.5-hydrat. | |
| DE10031971A1 (de) | Polymorphe Formen/Hydrate von N-[4-(3-Chlor-4-fluor-phenylamino)-7-(3-morpholin-4-yl-propoxy)-chinazolin-6-yl]-acrylamid Dihydrochlorid, Verfahren zu ihrer Herstellung sowie die Verwendung derselben zur Herstellung von Medikamenten mit irreversibler Tyrosinkinasehemmwirkung | |
| DE69809564T2 (de) | 2- 4-[4-(4,5-dichlor-2-methylimidazol-1-yl)butyl]piperazin-1-yl -5-fluorpyrimidin, seine herstellung und therapeutische verwendung | |
| AT355046B (de) | Verfahren zur herstellung von neuen 5-fluor- dihydrouracilen | |
| DE3320145C2 (de) | Verfahren zur Herstellung von Magnesiumdihydroorotatglycinaten und ihre Verwendung als Calcium-Antagonisten | |
| DE2748794A1 (de) | Malonylharnstoffderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE2214499A1 (de) | Verfahren zur Herstellung von Phenazinderivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |