TW568910B - Epothilon derivatives, processes for their production and their use - Google Patents
Epothilon derivatives, processes for their production and their use Download PDFInfo
- Publication number
- TW568910B TW568910B TW088107412A TW88107412A TW568910B TW 568910 B TW568910 B TW 568910B TW 088107412 A TW088107412 A TW 088107412A TW 88107412 A TW88107412 A TW 88107412A TW 568910 B TW568910 B TW 568910B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- formula
- alkyl
- compound
- nr5r6
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000006239 protecting group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 monocyclic heteroaromatics Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000006619 Stille reaction Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- 239000011814 protection agent Substances 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000219495 Betulaceae Species 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000005382 boronyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19820599A DE19820599A1 (de) | 1998-05-08 | 1998-05-08 | Epothilonderivate, Verfahren zu deren Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW568910B true TW568910B (en) | 2004-01-01 |
Family
ID=7867085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088107412A TW568910B (en) | 1998-05-08 | 1999-05-14 | Epothilon derivatives, processes for their production and their use |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6982280B1 (https=) |
| EP (1) | EP1077980B1 (https=) |
| JP (1) | JP2002514649A (https=) |
| KR (1) | KR20010052325A (https=) |
| AR (1) | AR018344A1 (https=) |
| AT (1) | ATE234842T1 (https=) |
| AU (1) | AU754212B2 (https=) |
| CA (1) | CA2330812A1 (https=) |
| DE (2) | DE19820599A1 (https=) |
| ES (1) | ES2195577T3 (https=) |
| HU (1) | HUP0102283A3 (https=) |
| IL (1) | IL139480A0 (https=) |
| TW (1) | TW568910B (https=) |
| WO (1) | WO1999058534A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6204388B1 (en) | 1996-12-03 | 2001-03-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| CA2273083C (en) | 1996-12-03 | 2012-09-18 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| GB9810659D0 (en) | 1998-05-18 | 1998-07-15 | Ciba Geigy Ag | Organic compounds |
| US6518421B1 (en) | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| SI1483251T1 (sl) | 2002-03-12 | 2010-03-31 | Bristol Myers Squibb Co | C cian epotilonski derivati |
| DE10355223A1 (de) | 2003-11-26 | 2005-06-30 | Institut für Pflanzenbiochemie (IPB) | Neue Makrocyclen zur Behandlung von Krebserkrankungen |
| 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 |
| US7754850B2 (en) | 2005-02-11 | 2010-07-13 | University Of Southern California | Chimeric disintegrin domain |
| JP2009532035A (ja) | 2006-03-31 | 2009-09-10 | ブリストル−マイヤーズ スクイブ カンパニー | 微小管安定化剤に対する感受性を決定するためのバイオマーカーおよび方法 |
| EP2029156A4 (en) * | 2006-05-01 | 2010-07-21 | Univ Southern California | COMBINATION THERAPY FOR CANCER TREATMENT |
| 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 |
| US20110300150A1 (en) | 2010-05-18 | 2011-12-08 | Scott Eliasof | Compositions and methods for treatment of autoimmune and other disease |
| EP2793947B1 (en) | 2011-12-23 | 2021-02-03 | Innate Pharma | Enzymatic conjugation of polypeptides |
| US10132799B2 (en) | 2012-07-13 | 2018-11-20 | Innate Pharma | Screening of conjugated antibodies |
| EP3564259A3 (en) | 2012-11-09 | 2020-02-12 | Innate Pharma | Recognition tags for tgase-mediated conjugation |
| US10611824B2 (en) | 2013-03-15 | 2020-04-07 | 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 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4138042C2 (de) * | 1991-11-19 | 1993-10-14 | Biotechnolog Forschung Gmbh | Epothilone, deren Herstellungsverfahren sowie diese Verbindungen enthaltende Mittel |
| US5351146A (en) * | 1993-03-01 | 1994-09-27 | At&T Bell Laboratories | All-optical network architecture |
| US5781537A (en) * | 1995-07-07 | 1998-07-14 | International Business Machines Corporation | Setting up, taking down and maintaining connections in a communications network |
| DE19542986A1 (de) * | 1995-11-17 | 1997-05-22 | Biotechnolog Forschung Gmbh | Epothilon-Derivate und deren Verwendung |
| JP4183099B2 (ja) | 1995-11-17 | 2008-11-19 | ゲゼルシャフト・フュア・ビオテヒノロジッシェ・フォルシュング・ミット・ベシュレンクテル・ハフツング（ゲー・ベー・エフ） | エポチロンｃおよびｄ、製造法ならびに組成物 |
| ES2312695T3 (es) | 1996-11-18 | 2009-03-01 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Epotilones e y f. |
| US6380394B1 (en) | 1996-12-13 | 2002-04-30 | The Scripps Research Institute | Epothilone analogs |
| US6304349B1 (en) * | 1998-06-30 | 2001-10-16 | Lucent Technologies Inc. | WDM optical communications networks and methods for provisioning |
| US6445844B1 (en) * | 1999-09-15 | 2002-09-03 | Xros, Inc. | Flexible, modular, compact fiber optic switch |
| US7092633B2 (en) * | 2000-11-14 | 2006-08-15 | University Of Texas System Board Of Regents | System and method for configuring optical circuits |
| US6982951B2 (en) * | 2000-12-21 | 2006-01-03 | At&T Corp. | Method for selecting a restoration path in a mesh network |
| US7212495B2 (en) * | 2001-02-21 | 2007-05-01 | Polytechnic University | Signaling for reserving a communications path |
| WO2002080428A2 (en) * | 2001-03-29 | 2002-10-10 | Atoga Systems, Inc. | Open ring architectures for optical wdm networks |
| US20020194339A1 (en) * | 2001-05-16 | 2002-12-19 | Lin Philip J. | Method and apparatus for allocating working and protection bandwidth in a telecommunications mesh network |
| WO2003003156A2 (en) * | 2001-06-27 | 2003-01-09 | Brilliant Optical Networks | Distributed information management schemes for dynamic allocation and de-allocation of bandwidth |
-
1998
- 1998-05-08 DE DE19820599A patent/DE19820599A1/de not_active Withdrawn
-
1999
- 1999-05-07 ES ES99926300T patent/ES2195577T3/es not_active Expired - Lifetime
- 1999-05-07 HU HU0102283A patent/HUP0102283A3/hu unknown
- 1999-05-07 AU AU43611/99A patent/AU754212B2/en not_active Ceased
- 1999-05-07 IL IL13948099A patent/IL139480A0/xx unknown
- 1999-05-07 WO PCT/EP1999/003159 patent/WO1999058534A2/de not_active Ceased
- 1999-05-07 KR KR1020007012437A patent/KR20010052325A/ko not_active Ceased
- 1999-05-07 US US09/674,877 patent/US6982280B1/en not_active Expired - Fee Related
- 1999-05-07 JP JP2000548338A patent/JP2002514649A/ja not_active Withdrawn
- 1999-05-07 CA CA002330812A patent/CA2330812A1/en not_active Abandoned
- 1999-05-07 DE DE59904632T patent/DE59904632D1/de not_active Expired - Lifetime
- 1999-05-07 AT AT99926300T patent/ATE234842T1/de not_active IP Right Cessation
- 1999-05-07 EP EP99926300A patent/EP1077980B1/de not_active Expired - Lifetime
- 1999-05-10 AR ARP990102186A patent/AR018344A1/es not_active Application Discontinuation
- 1999-05-14 TW TW088107412A patent/TW568910B/zh not_active IP Right Cessation
-
2004
- 2004-02-17 US US10/780,181 patent/US20040259922A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6982280B1 (en) | 2006-01-03 |
| US20040259922A1 (en) | 2004-12-23 |
| DE59904632D1 (de) | 2003-04-24 |
| ES2195577T3 (es) | 2003-12-01 |
| AU754212B2 (en) | 2002-11-07 |
| HUP0102283A3 (en) | 2002-03-28 |
| WO1999058534A2 (de) | 1999-11-18 |
| JP2002514649A (ja) | 2002-05-21 |
| HUP0102283A2 (hu) | 2001-10-28 |
| ATE234842T1 (de) | 2003-04-15 |
| CA2330812A1 (en) | 1999-11-18 |
| KR20010052325A (ko) | 2001-06-25 |
| AU4361199A (en) | 1999-11-29 |
| EP1077980B1 (de) | 2003-03-19 |
| IL139480A0 (en) | 2001-11-25 |
| AR018344A1 (es) | 2001-11-14 |
| DE19820599A1 (de) | 1999-11-11 |
| EP1077980A2 (de) | 2001-02-28 |
| WO1999058534A3 (de) | 2000-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |