RU2406722C2 - Соли бис-(тиогидразидамида) для лечения рака - Google Patents
Соли бис-(тиогидразидамида) для лечения рака Download PDFInfo
- Publication number
- RU2406722C2 RU2406722C2 RU2007101898/04A RU2007101898A RU2406722C2 RU 2406722 C2 RU2406722 C2 RU 2406722C2 RU 2007101898/04 A RU2007101898/04 A RU 2007101898/04A RU 2007101898 A RU2007101898 A RU 2007101898A RU 2406722 C2 RU2406722 C2 RU 2406722C2
- Authority
- RU
- Russia
- Prior art keywords
- thiohydrazidamide
- bis
- organic solvent
- base
- solvent
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract 5
- 201000011510 cancer Diseases 0.000 title claims abstract 5
- 150000001408 amides Chemical class 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 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 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 11
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 229930012538 Paclitaxel Natural products 0.000 claims abstract 4
- 229960001592 paclitaxel Drugs 0.000 claims abstract 4
- 230000001093 anti-cancer Effects 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 230000002708 enhancing effect Effects 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 14
- 239000003960 organic solvent Substances 0.000 claims 11
- 239000002585 base Substances 0.000 claims 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 239000000243 solution Substances 0.000 claims 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 7
- 230000007935 neutral effect Effects 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000012296 anti-solvent Substances 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 239000000203 mixture Substances 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- -1 alkyl glycol ether Chemical compound 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 claims 1
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 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
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical group [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
- 208000025113 myeloid leukemia Diseases 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 1
- NHITUGACHSROGE-MDMDSUOFSA-N CC(C)(C)OC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H](C[C@H]2OC3)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)O)C(C)(C)[C@@]14O)=O)OC(COC(C[C@@H](C(N)=O)N)=O)=O)C1CC1)=O Chemical compound CC(C)(C)OC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H](C[C@H]2OC3)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)O)C(C)(C)[C@@]14O)=O)OC(COC(C[C@@H](C(N)=O)N)=O)=O)C1CC1)=O NHITUGACHSROGE-MDMDSUOFSA-N 0.000 description 1
- UBCKDQWEECHQJC-MPSZKIJFSA-N CC(C)(C)OC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H]([C@@H]([C@H]2OC3)F)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)c1ccccc1)=O Chemical compound CC(C)(C)OC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H]([C@@H]([C@H]2OC3)F)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)c1ccccc1)=O UBCKDQWEECHQJC-MPSZKIJFSA-N 0.000 description 1
- 0 CC(C)(C)SC(N[C@]([C@](C(O[C@@](C1)C(C)=C([C@](C([C@](C)([C@](C[C@]2OC3)O)[C@]([C@@]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)*1ccc[o]1)=O Chemical compound CC(C)(C)SC(N[C@]([C@](C(O[C@@](C1)C(C)=C([C@](C([C@](C)([C@](C[C@]2OC3)O)[C@]([C@@]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)*1ccc[o]1)=O 0.000 description 1
- UBJAHGAUPNGZFF-XOVTVWCYSA-N CC(C)([C@@](C1)([C@H]([C@H]([C@]2([C@@H](C[C@@H]3OCSC)OC2)OC(C)=O)[C@]3(C)C([C@@H]2OC(C)=O)=O)OC(c3ccccc3)=O)O)C2=C(C)[C@H]1OC([C@@H]([C@H](c1ccccc1)NC(c1ccccc1)=O)O)=O Chemical compound CC(C)([C@@](C1)([C@H]([C@H]([C@]2([C@@H](C[C@@H]3OCSC)OC2)OC(C)=O)[C@]3(C)C([C@@H]2OC(C)=O)=O)OC(c3ccccc3)=O)O)C2=C(C)[C@H]1OC([C@@H]([C@H](c1ccccc1)NC(c1ccccc1)=O)O)=O UBJAHGAUPNGZFF-XOVTVWCYSA-N 0.000 description 1
- RRZWOVDBXXQXBW-WCFPGISDSA-N CC(C)CSC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H](C[C@H]2OC3)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)/C(/C)=C/C=C\O)=O Chemical compound CC(C)CSC(N[C@H]([C@H](C(O[C@@H](C1)C(C)=C([C@H](C([C@](C)([C@H](C[C@H]2OC3)O)[C@H]([C@@H]4OC(c5ccccc5)=O)[C@@]23OC(C)=O)=O)OC(C)=O)C(C)(C)[C@@]14O)=O)O)/C(/C)=C/C=C\O)=O RRZWOVDBXXQXBW-WCFPGISDSA-N 0.000 description 1
- MGJBERWKPZUCJM-UHFFFAOYSA-L CN(C(C1CC1)=S)/N=C(/C/C(/[O-])=N/N(C)C(C1CC1)=S)\[O-] Chemical compound CN(C(C1CC1)=S)/N=C(/C/C(/[O-])=N/N(C)C(C1CC1)=S)\[O-] MGJBERWKPZUCJM-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/56—Amides of thiocarboxylic acids having nitrogen atoms of thiocarboxamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010145056/04A Division RU2010145056A (ru) | 2004-06-23 | 2010-11-08 | Соли бис (тиогидразидамида) для лечения рака |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007101898A RU2007101898A (ru) | 2008-07-27 |
| RU2406722C2 true RU2406722C2 (ru) | 2010-12-20 |
Family
ID=34993190
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007101898/04A RU2406722C2 (ru) | 2004-06-23 | 2005-06-20 | Соли бис-(тиогидразидамида) для лечения рака |
| RU2010145056/04A RU2010145056A (ru) | 2004-06-23 | 2010-11-08 | Соли бис (тиогидразидамида) для лечения рака |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010145056/04A RU2010145056A (ru) | 2004-06-23 | 2010-11-08 | Соли бис (тиогидразидамида) для лечения рака |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US7385084B2 (enExample) |
| EP (2) | EP1781604B1 (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 |
|---|---|---|---|---|
| TWI332943B (en) | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI252847B (en) * | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| 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 |
| ES2430373T3 (es) | 2004-06-23 | 2013-11-20 | Synta Pharmaceuticals Corp. | Sales de bis(tio-hidrazida amida) para tratamiento de cánceres |
| AU2005306471B2 (en) | 2004-11-19 | 2009-12-17 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing Hsp70 expression |
| WO2006113572A1 (en) * | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Methods of increasing natural killer cell activity for therapy |
| NZ562572A (en) | 2005-04-15 | 2011-01-28 | Synta Pharmaceuticals Corp | Combination cancer therapy with BIS (thiohydrazide) amide compounds |
| NZ563124A (en) * | 2005-05-16 | 2010-12-24 | Synta Pharmaceuticals Corp | Synthesis of bis(thio-hydrazide amide) salts |
| CA2618723C (en) * | 2005-08-16 | 2014-05-27 | 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 |
| WO2008024305A2 (en) * | 2006-08-21 | 2008-02-28 | Synta Pharmaceuticals Corp. | Bis (thiohydrazide amides) for treating melanoma |
| EP2059236A2 (en) * | 2006-08-21 | 2009-05-20 | Synta Pharmaceuticals Corporation | Combination with bis(thiohydrazide amides) for treating cancer |
| WO2008024303A2 (en) * | 2006-08-21 | 2008-02-28 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| US20080176828A1 (en) * | 2006-08-21 | 2008-07-24 | Martin Williams | Treating melanoma with BIS(THIOHYDRAZIDE AMIDES) |
| JP2010501563A (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 | 増殖性障害を治療するための化合物 |
| JP2010502616A (ja) | 2006-08-31 | 2010-01-28 | シンタ ファーマシューティカルズ コーポレーション | 癌を治療するためのビス（チオヒドラジドアミド）の組み合わせ |
| US9498528B2 (en) * | 2006-09-13 | 2016-11-22 | Genzyme Corporation | Treatment of multiple sclerosis (MS) |
| TW200829543A (en) * | 2006-09-15 | 2008-07-16 | Synta Pharmaceuticals Corp | Purification of bis(thiohydrazide amides) |
| US8618170B2 (en) * | 2007-11-09 | 2013-12-31 | 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) |
| US8461199B2 (en) | 2008-10-22 | 2013-06-11 | Synta Pharmaceuticals Corp. | Transition metal complexes of a bis[thio-hydrazide amide] compound |
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