UA75365C2 - Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon - Google Patents
Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon Download PDFInfo
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- UA75365C2 UA75365C2 UA2003032259A UA2003032259A UA75365C2 UA 75365 C2 UA75365 C2 UA 75365C2 UA 2003032259 A UA2003032259 A UA 2003032259A UA 2003032259 A UA2003032259 A UA 2003032259A UA 75365 C2 UA75365 C2 UA 75365C2
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- 229930013356 epothilone Natural products 0.000 title claims abstract description 34
- 150000003883 epothilone derivatives Chemical class 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000012986 modification Methods 0.000 title claims description 28
- 230000004048 modification Effects 0.000 title claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims abstract description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 75
- 239000000725 suspension Substances 0.000 claims description 39
- 239000013078 crystal Substances 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 26
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- -1 1-methyl-2-(2- methyl-4-thiazolyl)ethenyl Chemical group 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 229910003986 SicO Inorganic materials 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- LZWPOLSJFGLQCE-UHFFFAOYSA-N heptadecane-5,9-dione Chemical compound CCCCCCCCC(=O)CCCC(=O)CCCC LZWPOLSJFGLQCE-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22559000P | 2000-08-16 | 2000-08-16 | |
| PCT/US2001/024540 WO2002014323A2 (en) | 2000-08-16 | 2001-08-01 | Polymorphs of an epothilone analog |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75365C2 true UA75365C2 (en) | 2006-04-17 |
Family
ID=22845469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003032259A UA75365C2 (en) | 2000-08-16 | 2001-01-08 | Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon |
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| AU (2) | AU2001281082B2 (no) |
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| UA (1) | UA75365C2 (no) |
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| YU (1) | YU12103A (no) |
| ZA (1) | ZA200300522B (no) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050043376A1 (en) * | 1996-12-03 | 2005-02-24 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| DE69734362T2 (de) | 1996-12-03 | 2006-07-20 | Sloan-Kettering Institute For Cancer Research | Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| US6194181B1 (en) * | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US20020058286A1 (en) * | 1999-02-24 | 2002-05-16 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6518421B1 (en) * | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| MXPA03006412A (es) * | 2001-01-25 | 2003-10-15 | Bristol Myers Squibb Co | Metodos para administrar analogos de epotilona para tratamiento de cancer. |
| SK8552003A3 (en) * | 2001-01-25 | 2004-06-08 | Bristol Myers Squibb Co | Parenteral formulation containing epothilone analogs |
| HUP0303175A2 (hu) | 2001-02-20 | 2003-12-29 | Bristol-Myers Squibb Co. | Epotilonszármazékok alkalmazása makacs tumorok kezelésére alkalmas gyógyszerkészítmény előállítására |
| CA2440555A1 (en) * | 2001-03-14 | 2002-09-19 | Bristol-Myers Squibb Company | Combination of epothilone analogs and chemotherapeutic agents for the treatment of proliferative diseases |
| MXPA04008707A (es) * | 2002-03-08 | 2006-03-08 | Novartis Ag | Combinaciones que comprenden derivados de epotilona y agentes de alquilacion. |
| ES2281692T3 (es) * | 2002-08-23 | 2007-10-01 | Sloan-Kettering Institute For Cancer Research | Sintesis de epotilones, sus intermediarios, sus analogos y sus usos. |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US20050171167A1 (en) * | 2003-11-04 | 2005-08-04 | Haby Thomas A. | Process and formulation containing epothilones and analogs thereof |
| ITMI20032144A1 (it) * | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
| US20090004277A1 (en) * | 2004-05-18 | 2009-01-01 | Franchini Miriam K | Nanoparticle dispersion containing lactam compound |
| EP1640004A1 (en) * | 2004-09-24 | 2006-03-29 | Schering Aktiengesellschaft | Use of epothilones in the treatment of bone metastases and bone tumors or cancers |
| KR20070084325A (ko) * | 2004-11-18 | 2007-08-24 | 브리스톨-마이어스 스큅 컴퍼니 | 익사베필론을 포함하는 장용성 코팅된 비드 및 그의 제조방법 |
| EP1824458A1 (en) * | 2004-11-18 | 2007-08-29 | Bristol-Myers Squibb Company | Enteric coated bead comprising epothilone or an epothilone analog, and preparation and administration thereof |
| US20060121511A1 (en) | 2004-11-30 | 2006-06-08 | Hyerim Lee | Biomarkers and methods for determining sensitivity to microtubule-stabilizing agents |
| EP1674098A1 (en) | 2004-12-23 | 2006-06-28 | Schering Aktiengesellschaft | Stable and tolerable parental formulations of highly reactive organic drug substances with low or no solubility in water |
| JP2008536479A (ja) | 2005-02-11 | 2008-09-11 | ユニバーシティ オブ サザン カリフォルニア | ジスルフィド架橋を有するタンパク質の発現法 |
| SI1698630T1 (sl) * | 2005-03-03 | 2015-01-30 | Alfa Wassermann S.P.A. | Nove polimorfne oblike rifaksimina, postopki za njihovo pripravo in njihova uporaba v medicinskih pripravkih |
| EP1883627B1 (en) | 2005-05-18 | 2018-04-18 | Pharmascience Inc. | Bir domain binding compounds |
| US7693596B2 (en) | 2005-12-14 | 2010-04-06 | Dell Products L.P. | System and method for configuring information handling system integrated circuits |
| US20080286325A1 (en) * | 2006-01-05 | 2008-11-20 | Med Institute, Inc. | Cyclodextrin elution media for medical device coatings comprising a taxane therapeutic agent |
| US7919108B2 (en) * | 2006-03-10 | 2011-04-05 | Cook Incorporated | Taxane coatings for implantable medical devices |
| US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
| EP1994412A2 (en) | 2006-03-31 | 2008-11-26 | Brystol-Myers Squibb Company | Biomarkers and methods for determining sensitivity to microtubule-stabilizing agents |
| US8008256B2 (en) | 2006-05-01 | 2011-08-30 | University Of Southern California | Combination therapy for treatment of cancer |
| NZ572836A (en) | 2006-05-16 | 2011-12-22 | Pharmascience Inc | Iap bir domain binding compounds |
| KR20090038902A (ko) * | 2006-08-16 | 2009-04-21 | 노파르티스 아게 | 에포틸론 ｂ의 결정 형태 및 제약 조성물에서의 용도 |
| US8463852B2 (en) * | 2006-10-06 | 2013-06-11 | Oracle International Corporation | Groupware portlets for integrating a portal with groupware systems |
| US20110124690A1 (en) * | 2007-02-23 | 2011-05-26 | Danishefsky Samuel J | Compositions and methods for treating cancer or a neurotrophic disorder |
| EP2065054A1 (en) | 2007-11-29 | 2009-06-03 | Bayer Schering Pharma Aktiengesellschaft | Combinations comprising a prostaglandin and uses thereof |
| DE102007059752A1 (de) | 2007-12-10 | 2009-06-18 | Bayer Schering Pharma Aktiengesellschaft | Funktionalisierte, feste Polymernanopartikel enthaltend Epothilone |
| EP2070521A1 (en) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Surface-modified nanoparticles |
| US8802394B2 (en) | 2008-11-13 | 2014-08-12 | Radu O. Minea | Method of expressing proteins with disulfide bridges with enhanced yields and activity |
| EP2210584A1 (en) | 2009-01-27 | 2010-07-28 | Bayer Schering Pharma Aktiengesellschaft | Stable polymeric composition comprising an epothilone and an amphiphilic block copolymer |
| SG10201501095WA (en) | 2010-02-12 | 2015-04-29 | Pharmascience Inc | Iap bir domain binding compounds |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| WO2011153221A1 (en) * | 2010-06-01 | 2011-12-08 | Plus Chemicals Sa | Solid state forms of ixabepilone |
| EP2793949B1 (en) | 2011-12-23 | 2018-08-22 | Innate Pharma | Enzymatic conjugation of antibodies |
| ITBO20120368A1 (it) | 2012-07-06 | 2014-01-07 | Alfa Wassermann Spa | Composizioni comprendenti rifaximina e amminoacidi, cristalli di rifaximina derivanti da tali composizioni e loro uso. |
| EP2872894B1 (en) | 2012-07-13 | 2019-04-17 | Innate Pharma | Screening of conjugated antibodies |
| EP2916872B1 (en) | 2012-11-09 | 2019-02-27 | Innate Pharma | Recognition tags for tgase-mediated conjugation |
| CN103183681B (zh) * | 2013-03-06 | 2016-01-13 | 浙江海正药业股份有限公司 | 伊沙匹隆的新晶型及其制备方法 |
| EP2968582B1 (en) | 2013-03-15 | 2020-07-01 | Innate Pharma | Solid phase tgase-mediated conjugation of antibodies |
| EP3010547B1 (en) | 2013-06-20 | 2021-04-21 | Innate Pharma | Enzymatic conjugation of polypeptides |
| CN105517577A (zh) | 2013-06-21 | 2016-04-20 | 先天制药公司 | 多肽的酶促偶联 |
| WO2019092148A1 (en) | 2017-11-10 | 2019-05-16 | Innate Pharma | Antibodies with functionalized glutamine residues |
| EP4097245A1 (en) | 2020-01-31 | 2022-12-07 | Allarity Therapeutics Europe ApS | Methods for predicting ixabepilone responsiveness in cancer patients |
| CN112409366A (zh) * | 2020-11-30 | 2021-02-26 | 湖北宏中药业股份有限公司 | 一种伊沙匹隆二聚体的高收率制备方法 |
| CN112457320A (zh) * | 2020-11-30 | 2021-03-09 | 湖北宏中药业股份有限公司 | 一种提高伊沙匹隆合成反应速率的方法 |
| CN112375085A (zh) * | 2020-11-30 | 2021-02-19 | 湖北宏中药业股份有限公司 | 一种伊沙匹隆反应液的高收率高纯度处理方法 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1000809A (en) * | 1960-11-02 | 1965-08-11 | James Oakes & Company Riddings | Pipe manufacture |
| DE2308418B2 (de) * | 1972-06-21 | 1976-04-08 | Petzetakis, Aristovoulos George, Moschaton, Piräus (Griechenland) | Verfahren und vorrichtung zum herstellen eines insbesondere grosskalibrigen rohres aus thermoplastischem kunststoff |
| JPS5240337B2 (no) * | 1973-01-29 | 1977-10-12 | ||
| SE386365B (sv) * | 1973-07-25 | 1976-08-09 | L Brendling | Behallare av plast, gummi eller annat bojligt material, spec. avsedd for uppsamling av urin och/eller fekalier |
| JPS6398413A (ja) * | 1986-10-15 | 1988-04-28 | Smc Corp | 二重管およびその連続製造法 |
| DE3927569A1 (de) * | 1989-08-21 | 1991-02-28 | Fritz Egger Gmbh | Elektroabscheider zum abscheiden von schwebstoffen aus gasen |
| DE3939714A1 (de) * | 1989-12-01 | 1991-06-06 | Baedje K H Meteor Gummiwerke | Schlauch |
| AU6431790A (en) * | 1990-01-05 | 1991-08-05 | Orscheln Co. | Flexible synthetic plastic conduit |
| DE4138042C2 (de) | 1991-11-19 | 1993-10-14 | Biotechnolog Forschung Gmbh | Epothilone, deren Herstellungsverfahren sowie diese Verbindungen enthaltende Mittel |
| DE4206096A1 (de) * | 1992-02-27 | 1993-09-02 | Wolf Woco & Co Franz J | Koaxialrohr |
| EP1440973A3 (de) | 1995-11-17 | 2004-10-20 | Gesellschaft für biotechnologische Forschung mbH (GBF) | Epothilonderivate, Herstellung und Mittel |
| DE19542986A1 (de) | 1995-11-17 | 1997-05-22 | Biotechnolog Forschung Gmbh | Epothilon-Derivate und deren Verwendung |
| DE19639456A1 (de) | 1996-09-25 | 1998-03-26 | Biotechnolog Forschung Gmbh | Epothilon-Derivate, Herstellung und Mittel |
| DE19645361A1 (de) | 1996-08-30 | 1998-04-30 | Ciba Geigy Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B, Teil II |
| DE19636343C1 (de) | 1996-08-30 | 1997-10-23 | Schering Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B |
| JP2001500851A (ja) | 1996-08-30 | 2001-01-23 | ノバルティス アクチエンゲゼルシャフト | エポシロンの製造法および製造過程中に得られる中間生産物 |
| DE19645362A1 (de) | 1996-10-28 | 1998-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von Epothilon A und B und Derivaten |
| HU229833B1 (en) | 1996-11-18 | 2014-09-29 | Biotechnolog Forschung Gmbh | Epothilone d production process, and its use as cytostatic as well as phytosanitary agents |
| US6515016B2 (en) | 1996-12-02 | 2003-02-04 | Angiotech Pharmaceuticals, Inc. | Composition and methods of paclitaxel for treating psoriasis |
| DE69734362T2 (de) | 1996-12-03 | 2006-07-20 | Sloan-Kettering Institute For Cancer Research | Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon |
| US6204388B1 (en) | 1996-12-03 | 2001-03-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| DE19701758A1 (de) | 1997-01-20 | 1998-07-23 | Wessjohann Ludgar A Dr | Epothilone-Synthesebausteine |
| CA2281105A1 (en) | 1997-02-25 | 1998-09-03 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Epothilones with a modified side chain |
| DE19713970B4 (de) | 1997-04-04 | 2006-08-31 | R&D-Biopharmaceuticals Gmbh | Epothilone-Synthesebausteine II - Prenylderivate |
| US6348551B1 (en) | 1997-04-18 | 2002-02-19 | Studiengesellschaft Kohle Mbh | Selective olefin metathesis of bifunctional or polyfunctional substrates in compressed carbon dioxide as reaction medium |
| DE19821954A1 (de) | 1997-05-15 | 1998-11-19 | Biotechnolog Forschung Gmbh | Verfahren zur Herstellung eines Epothilon-Derivats |
| DE19720312A1 (de) | 1997-05-15 | 1998-11-19 | Hoechst Ag | Zubereitung mit erhöhter in vivo Verträglichkeit |
| DE19726627A1 (de) | 1997-06-17 | 1998-12-24 | Schering Ag | Zwischenprodukte, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Epothilon |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| JP2001510189A (ja) | 1997-07-16 | 2001-07-31 | シエーリング アクチエンゲゼルシヤフト | チアゾール誘導体、その製造法および使用 |
| DE59814067D1 (de) | 1997-08-09 | 2007-09-06 | Bayer Schering Pharma Ag | Neue epothilon-derivate, verfahren zu deren herstellung und ihre pharmazeutische verwendung |
| DE19747580A1 (de) | 1997-10-28 | 1999-04-29 | Siemens Ag | Rangierfeld mit Anschlußleiste |
| US6365749B1 (en) | 1997-12-04 | 2002-04-02 | Bristol-Myers Squibb Company | Process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs |
| BR9907647B1 (pt) | 1998-02-05 | 2014-04-01 | Novartis Ag Novartis S A Novartis Inc | Formulação farmacêutica na forma de um concentrado para infusão, o qual deve ser diluído antes da administração, e solução para infusão |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| DE19807505A1 (de) | 1998-02-21 | 1999-08-26 | Roland Man Druckmasch | Bogenrotationsdruckmaschine mit Druckeinheiten für den Mehrfarbendruck und wenigstens einer Beschichtungseinheit |
| FR2775187B1 (fr) | 1998-02-25 | 2003-02-21 | Novartis Ag | Utilisation de l'epothilone b pour la fabrication d'une preparation pharmaceutique antiproliferative et d'une composition comprenant l'epothilone b comme agent antiproliferatif in vivo |
| NZ506742A (en) | 1998-02-25 | 2003-09-26 | Sloan Kettering Inst Cancer | Synthesis of desoxyepothilones and hydroxy acid derivative intermediates |
| WO2000000485A1 (de) | 1998-06-30 | 2000-01-06 | Schering Aktiengesellschaft | Epothilon-derivate, verfahren zu deren herstellung, zwischenprodukte und ihre pharmazeutische verwendung |
| AU5325699A (en) * | 1998-08-12 | 2000-03-06 | Proteus Inc. | Ribbed core dual wall structure |
| AU2795000A (en) | 1998-12-22 | 2000-07-12 | Novartis Ag | Epothilone derivatives and their use as antitumor agents |
| PE20010116A1 (es) | 1999-04-30 | 2001-02-15 | Schering Ag | Derivados de 6-alquenil-, 6-alquinil- y 6-epoxi-epotilona, procedimientos para su preparacion |
| US6605559B1 (en) * | 1999-09-29 | 2003-08-12 | Daihatsu Motor Co., Ltd. | Dimethyl ether reforming catalyst |
| US6518421B1 (en) | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| SK8552003A3 (en) * | 2001-01-25 | 2004-06-08 | Bristol Myers Squibb Co | Parenteral formulation containing epothilone analogs |
| NZ526870A (en) | 2001-01-25 | 2005-11-25 | Bristol Myers Squibb Co | Methods of administering epothilone analogs for the treatment of cancer |
| US9317043B2 (en) | 2013-12-19 | 2016-04-19 | Google Inc. | Path based power generation control for an aerial vehicle |
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