JP2008504264A5 - - Google Patents
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- Publication number
- JP2008504264A5 JP2008504264A5 JP2007518152A JP2007518152A JP2008504264A5 JP 2008504264 A5 JP2008504264 A5 JP 2008504264A5 JP 2007518152 A JP2007518152 A JP 2007518152A JP 2007518152 A JP2007518152 A JP 2007518152A JP 2008504264 A5 JP2008504264 A5 JP 2008504264A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thio
- bis
- compound
- methylcyclopropyl
- 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.)
- Granted
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 110
- -1 2,5-dimethoxyphenyl Chemical group 0.000 claims 28
- 150000001408 amides Chemical class 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 238000000034 method Methods 0.000 claims 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 11
- 230000007935 neutral effect Effects 0.000 claims 11
- 150000001768 cations Chemical class 0.000 claims 9
- 239000003960 organic solvent Substances 0.000 claims 7
- 239000002585 base Substances 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 239000012296 anti-solvent Substances 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 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 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 102000029749 Microtubule Human genes 0.000 claims 1
- 108091022875 Microtubule Proteins 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 210000004688 microtubule Anatomy 0.000 claims 1
- 229910052757 nitrogen Chemical group 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58259604P | 2004-06-23 | 2004-06-23 | |
| US60/582,596 | 2004-06-23 | ||
| US68136805P | 2005-05-16 | 2005-05-16 | |
| US60/681,368 | 2005-05-16 | ||
| PCT/US2005/021642 WO2006009940A1 (en) | 2004-06-23 | 2005-06-20 | Bis(thio-hydrazide amide) salts for treatment of cancers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008504264A JP2008504264A (ja) | 2008-02-14 |
| JP2008504264A5 true JP2008504264A5 (enExample) | 2008-08-07 |
| JP5362986B2 JP5362986B2 (ja) | 2013-12-11 |
Family
ID=34993190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007518152A Expired - Fee Related JP5362986B2 (ja) | 2004-06-23 | 2005-06-20 | 癌治療のためのビス（チオ‐ヒドラジドアミド）塩 |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US7385084B2 (enExample) |
| EP (2) | EP2305642A3 (enExample) |
| JP (1) | JP5362986B2 (enExample) |
| KR (1) | KR101313027B1 (enExample) |
| CN (1) | CN1993318B (enExample) |
| AU (1) | AU2005265202B2 (enExample) |
| BR (1) | BRPI0512526A (enExample) |
| CA (1) | CA2570698C (enExample) |
| DK (1) | DK1781604T3 (enExample) |
| ES (1) | ES2430373T3 (enExample) |
| HR (1) | HRP20131023T1 (enExample) |
| IL (1) | IL179632A (enExample) |
| ME (1) | ME01644B (enExample) |
| NO (1) | NO20070378L (enExample) |
| NZ (1) | NZ552159A (enExample) |
| PL (1) | PL1781604T3 (enExample) |
| PT (1) | PT1781604E (enExample) |
| RS (1) | RS52999B (enExample) |
| RU (2) | RU2406722C2 (enExample) |
| TW (1) | TWI389684B (enExample) |
| WO (1) | WO2006009940A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI252847B (en) | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| TWI332943B (en) | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI297335B (en) * | 2001-07-10 | 2008-06-01 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI330079B (en) | 2003-01-15 | 2010-09-11 | Synta Pharmaceuticals Corp | Treatment for cancers |
| AU2005265202B2 (en) | 2004-06-23 | 2009-07-23 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| AU2005306471B2 (en) | 2004-11-19 | 2009-12-17 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing Hsp70 expression |
| EP1877048A1 (en) * | 2005-04-15 | 2008-01-16 | Synta Pharmaceuticals Corporation | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| WO2006113572A1 (en) * | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Methods of increasing natural killer cell activity for therapy |
| US7709683B2 (en) * | 2005-05-16 | 2010-05-04 | Synta Pharmaceuticals Corp. | Synthesis of bis(thio-hydrazide amide) salts |
| WO2007021881A1 (en) | 2005-08-16 | 2007-02-22 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| US20100310587A1 (en) * | 2005-08-29 | 2010-12-09 | Academia Sinica | Immunomodulatory compositions |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP2059236A2 (en) * | 2006-08-21 | 2009-05-20 | Synta Pharmaceuticals Corporation | Combination with bis(thiohydrazide amides) for treating cancer |
| WO2008024304A2 (en) * | 2006-08-21 | 2008-02-28 | Synta Pharmaceuticals Corp. | Compounds for treatment of proliferative disorders |
| WO2008024305A2 (en) * | 2006-08-21 | 2008-02-28 | Synta Pharmaceuticals Corp. | Bis (thiohydrazide amides) for treating melanoma |
| KR20090045354A (ko) | 2006-08-21 | 2009-05-07 | 신타 파마슈티칼스 코프. | 증식성 장애를 치료하기 위한 화합물 |
| JP2010501559A (ja) * | 2006-08-21 | 2010-01-21 | シンタ ファーマシューティカルズ コーポレーション | 黒色腫の再発を予防するまたは遅らせるのに使用するためのビス（チオヒドラジドアミド） |
| US7939564B2 (en) | 2006-08-31 | 2011-05-10 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| US9498528B2 (en) * | 2006-09-13 | 2016-11-22 | Genzyme Corporation | Treatment of multiple sclerosis (MS) |
| WO2008033494A2 (en) * | 2006-09-15 | 2008-03-20 | Synta Pharmaceuticals Corp. | Purification of bis(thiohydrazide amides) |
| WO2009064374A2 (en) * | 2007-11-09 | 2009-05-22 | Synta Pharmaceuticals Corp. | Oral formulations of bis(thiohydrazide amides) |
| US8581004B2 (en) | 2008-02-21 | 2013-11-12 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| WO2009123704A2 (en) * | 2008-03-31 | 2009-10-08 | Synta Pharmaceuticals Corp. | Process for preparing bis(thiohydrazide amides) |
| CA2741189A1 (en) | 2008-10-22 | 2010-04-29 | Synta Pharmaceuticals Corp. | Transition metal complexes of bis[thiohydrazide amide] compounds |
| EP2373624A4 (en) | 2008-10-22 | 2014-06-11 | Synta Pharmaceuticals Corp | TRANSITION METAL COMPLEXES OF A TO [THIOHYDRAZIDAMID] COMPOUND |
| US8525776B2 (en) * | 2008-10-27 | 2013-09-03 | Lenovo (Singapore) Pte. Ltd | Techniques for controlling operation of a device with a virtual touchscreen |
| AU2009322603B2 (en) | 2008-12-01 | 2013-08-29 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| RU2400471C1 (ru) * | 2009-04-30 | 2010-09-27 | Учреждение Российской академии наук Институт органической химии им. Н.Д. Зелинского РАН (ИОХ РАН) | N-замещенные производные тиогидразидов оксаминовых кислот, способ их получения и их использование |
| WO2011069159A2 (en) * | 2009-12-04 | 2011-06-09 | Synta Pharmaceuticals Corp. | Bis[thiohydrazide amide] compounds for treating leukemia |
| US8815945B2 (en) * | 2010-04-20 | 2014-08-26 | Masazumi Nagai | Use of bis [thiohydrazide amide] compounds such as elesclomol for treating cancers |
| EP2640372A1 (en) | 2010-11-18 | 2013-09-25 | Synta Pharmaceuticals Corp. | Preselection of subjects for therapeutic treatment with elesclomol based on hypoxic status |
| CA2854186A1 (en) * | 2011-11-10 | 2013-05-16 | Jim SANG | Administration of a bis(thiohydrazide amide) compound for treating cancers |
| US20130149392A1 (en) | 2011-12-12 | 2013-06-13 | Synta Pharmaceuticals Corp. | Method of treating non-small cell lung cancer with bis-(thiohydrazide)amide compounds |
| WO2013103795A1 (en) | 2012-01-05 | 2013-07-11 | The Board Of Trustees Of The Leland Stanford Junior University | Bis (thiohydrazide amide) compounds for treating cancers |
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- 2005-06-20 EP EP10009536A patent/EP2305642A3/en not_active Withdrawn
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