TWI481401B - 藥劑 - Google Patents
藥劑 Download PDFInfo
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- TWI481401B TWI481401B TW100102774A TW100102774A TWI481401B TW I481401 B TWI481401 B TW I481401B TW 100102774 A TW100102774 A TW 100102774A TW 100102774 A TW100102774 A TW 100102774A TW I481401 B TWI481401 B TW I481401B
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- 239000002246 antineoplastic agent Substances 0.000 claims description 91
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- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 14
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- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 2
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
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- 201000003365 uterine corpus sarcoma Diseases 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
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Classifications
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/28—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
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- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| TWI636975B (zh) * | 2012-04-27 | 2018-10-01 | 日本臟器製藥股份有限公司 | 反式-2-癸烯酸衍生物及含該衍生物之藥劑 |
| KR102630750B1 (ko) * | 2013-12-17 | 2024-01-30 | 제넨테크, 인크. | Pd-1 축 결합 길항제 및 탁산을 이용한 암 치료 방법 |
| US9611244B2 (en) | 2015-05-08 | 2017-04-04 | Takeda Pharmaceutical Company Limited | Cyclic compounds |
| CA2986263A1 (en) | 2015-06-17 | 2016-12-22 | Genentech, Inc. | Methods of treating locally advanced or metastatic breast cancers using pd-1 axis binding antagonists and taxanes |
| EP3511320A4 (en) * | 2016-09-09 | 2020-04-15 | Takeda Pharmaceutical Company Limited | CYCLIC CONNECTION |
| JP7317804B2 (ja) * | 2017-09-07 | 2023-07-31 | シェンヅェン サルブリス ファーマシューティカルズ カンパニー リミテッド | ドセタキセル結合体の医薬組成物及び調製方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1495756A1 (en) * | 2002-04-08 | 2005-01-12 | Takeda Chemical Industries, Ltd. | Severe sepsis preventive therapeutic agent |
| EP2018872A1 (en) * | 2006-04-20 | 2009-01-28 | Takeda Pharmaceutical Company Limited | Pharmaceutical product |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5804374A (en) | 1980-12-05 | 1998-09-08 | Massachusetts Insti. Technology | Nuclear factors associates with transcriptional regulation |
| ATE106089T1 (de) | 1986-01-09 | 1994-06-15 | Massachusetts Inst Technology | Nukleare faktoren, die mit der regulierung der transkription assoziiert sind. |
| US6410516B1 (en) | 1986-01-09 | 2002-06-25 | President & Fellows Of Harvard College | Nuclear factors associated with transcriptional regulation |
| US4769372A (en) | 1986-06-18 | 1988-09-06 | The Rockefeller University | Method of treating patients suffering from chronic pain or chronic cough |
| US4785000A (en) | 1986-06-18 | 1988-11-15 | The Rockefeller University | Method of treating patients suffering from chronic pain or chronic cough |
| WO1988005083A1 (en) | 1986-12-24 | 1988-07-14 | Whitehead Institute For Biomedical Research | Method of inducible gene expression |
| WO1989007614A1 (en) | 1988-02-12 | 1989-08-24 | Massachusetts Institute Of Technology | Nuclear factors associated with transcriptional regulation |
| DE68910682T2 (de) | 1988-03-01 | 1994-06-01 | Whitehead Biomedical Inst | Aktivierung der nf-kappa b-vorstufe. |
| JP3479532B2 (ja) | 1989-03-31 | 2003-12-15 | ザ・チルドレンズ・メディカル・センター・コーポレーション | エイズの痴呆症、脊髄障害および失明の治療 |
| US5334618A (en) | 1991-04-04 | 1994-08-02 | The Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| US5506231A (en) | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
| US5059712A (en) | 1989-09-13 | 1991-10-22 | Cornell Research Foundation, Inc. | Isolating aminoarginine and use to block nitric oxide formation in body |
| US5158883A (en) | 1989-09-13 | 1992-10-27 | Cornell Research Foundation, Inc. | Method of using aminoarginine to block nitric oxide formation in vitro |
| EP0557290A1 (en) | 1990-08-23 | 1993-09-01 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy, peripheral neuropathy, and vision loss |
| US5614560A (en) | 1991-04-04 | 1997-03-25 | Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| WO1992017168A1 (en) | 1991-04-04 | 1992-10-15 | The Children's Medical Center Corporation | Method of preventing nmda receptor-mediated neuronal damage |
| US5455279A (en) | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
| US6071876A (en) | 1991-04-19 | 2000-06-06 | Children's Medical Center Corporation | Method of preventing NMDA receptor complex-mediated neuronal damage |
| ATE182076T1 (de) | 1991-04-19 | 1999-07-15 | Childrens Medical Center | Verfahren zur vorbeugung nmda-rezeptorkomplex- vermittelter neuronaler schäden |
| CA2224103A1 (en) * | 1995-06-07 | 1996-12-19 | Sugen, Inc. | Method and compositions for inhibition of adaptor protein/tyrosine kinase interactions |
| US20020052019A1 (en) | 1997-11-13 | 2002-05-02 | Genentech Inc | Human toll homologue |
| US20020086368A1 (en) | 1997-10-17 | 2002-07-04 | Genentech Inc | Human toll homologues |
| US20030032090A1 (en) | 1997-05-07 | 2003-02-13 | Schering Corporation, A New Jersey Corporation | Human receptor proteins; related reagents and methods |
| ATE463502T1 (de) | 1997-10-17 | 2010-04-15 | Genentech Inc | Menschliche toll-homologe |
| WO1999026657A1 (en) | 1997-11-25 | 1999-06-03 | Musc Foundation For Research Development | Inhibitors of nitric oxide synthase |
| US20080275104A1 (en) | 1997-11-25 | 2008-11-06 | Musc Foundation For Research Development | Methods of treating juvenile type 1 diabetes mellitus |
| US20040072138A1 (en) | 1997-11-25 | 2004-04-15 | Medical University Of South Carolina | Attenuation of ischemia/reperfusion injury |
| WO1999027101A1 (en) | 1997-11-25 | 1999-06-03 | Princeton University | Method for preparing adenovirus vectors, vectors so prepared, and uses thereof |
| RU2214398C2 (ru) | 1998-03-09 | 2003-10-20 | Такеда Кемикал Индастриз, Лтд. | Производное циклоалкена, способ его получения (варианты), фармацевтическая композиция, способ ингибирования, способ профилактики или лечения |
| CN1210257C (zh) | 1999-08-06 | 2005-07-13 | 武田药品工业株式会社 | 取代的芳香环化合物及其制备方法和用途 |
| SE9903930D0 (sv) * | 1999-10-29 | 1999-10-29 | Astra Pharma Inc | Novel compounds and a novel process for their preparation |
| KR100784752B1 (ko) | 2000-02-04 | 2007-12-13 | 다케다 야쿠힌 고교 가부시키가이샤 | 안정한 에멀젼 조성물 |
| CN1721443A (zh) | 2000-05-25 | 2006-01-18 | 先灵公司 | 人受体蛋白;相关的试剂和方法 |
| WO2002013816A1 (en) | 2000-08-10 | 2002-02-21 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition |
| KR100821546B1 (ko) | 2000-10-18 | 2008-04-11 | 다케다 야쿠힌 고교 가부시키가이샤 | 광학 활성 술폰아미드의 제조 방법 및 그의 합성용 중간체 |
| CA2398613C (en) | 2000-11-30 | 2006-09-12 | Tokuyama Corporation | Substrate and production method therefor |
| CA2431206C (en) | 2000-12-08 | 2009-09-01 | Takeda Chemical Industries, Ltd. | Combination drugs containing anti-sepsis cycloalkene compound |
| US7960416B2 (en) | 2001-08-03 | 2011-06-14 | Takeda Pharmaceutical Company Limited | Stable emulsion composition |
| US8710095B2 (en) | 2002-04-30 | 2014-04-29 | Bionumerik Pharmaceuticals, Inc. | Drugs for prophylaxis or mitigation of taxane-induced neurotoxicity |
| US20040259790A1 (en) | 2003-01-30 | 2004-12-23 | Bali Pulendran | Methods for identifying and administering agents that bias the immune response via dendritic cells |
| WO2004075865A2 (en) | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| EP1613956A2 (en) | 2003-03-25 | 2006-01-11 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| EP1664342A4 (en) | 2003-09-17 | 2007-12-26 | 3M Innovative Properties Co | SELECTIVE MODULATION OF TLR GENE EXPRESSION |
| US7927873B2 (en) | 2003-12-19 | 2011-04-19 | University Of Cincinnati | Polyamides for nucleic acid delivery |
| TWI462745B (zh) | 2005-04-28 | 2014-12-01 | Takeda Pharmaceutical | 安定的乳化組成物 |
| TWI404529B (zh) | 2005-06-03 | 2013-08-11 | Ono Pharmaceutical Co | 神經再生及/或保護劑 |
| US7618982B2 (en) | 2005-12-19 | 2009-11-17 | Nerviano Medical Sciences S.R.L. | Heteroarylpyrrolopyridinones active as kinase inhibitors |
| US20090175835A1 (en) | 2006-02-07 | 2009-07-09 | Korea Institute Of Radiological & Medical Sciences | Composition for treating damage of central or peripheral nerve system |
| US7985538B2 (en) | 2006-02-23 | 2011-07-26 | Yale University | Drug resistance and methods of reversing |
| US7943588B2 (en) | 2006-03-28 | 2011-05-17 | Trustees Of Dartmouth College | Method for preventing or treating neuropathic pain |
| WO2007114296A1 (ja) | 2006-03-30 | 2007-10-11 | Hiroshima University | スクリーニング方法 |
| JPWO2007132825A1 (ja) | 2006-05-15 | 2009-09-24 | 武田薬品工業株式会社 | 医薬 |
| US20090209585A1 (en) | 2006-07-07 | 2009-08-20 | Takashi Ichikawa | Cycloalkene derivatives, process for production of the derivatives, and use of the same |
| EP1882687A1 (en) * | 2006-07-27 | 2008-01-30 | Amorepacific Corporation | Heterocyclic compounds useful as vanilloid receptor antagonists and pharmaceutical compositions containing the same |
| US20080227846A1 (en) | 2007-03-13 | 2008-09-18 | Musc Foundation For Research Development | Methods of treating juvenile type 1 diabetes mellitus |
| US8399421B2 (en) | 2007-03-30 | 2013-03-19 | The Board Of Regents Of The University Of Texas System | Treatment for neuropathic pain due to spinal cord injury |
| WO2009059050A2 (en) | 2007-10-30 | 2009-05-07 | The Regents Of The University Of Colorado | Tlr modulators and methods for using the same |
| EP2262498A2 (en) | 2008-03-10 | 2010-12-22 | Vertex Pharmceuticals Incorporated | Pyrimidines and pyridines useful as inhibitors of protein kinases |
| JP5238381B2 (ja) | 2008-07-07 | 2013-07-17 | スタンレー電気株式会社 | 照明用車両用灯具 |
| EP2480536B1 (en) | 2009-09-23 | 2014-08-13 | The Regents of the University of Colorado, A Body Corporate | Toll-like receptor modulators and uses thereof |
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2011
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1495756A1 (en) * | 2002-04-08 | 2005-01-12 | Takeda Chemical Industries, Ltd. | Severe sepsis preventive therapeutic agent |
| EP2018872A1 (en) * | 2006-04-20 | 2009-01-28 | Takeda Pharmaceutical Company Limited | Pharmaceutical product |
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