CA2634766A1 - Pharmaceutical composition containing histone deacetylase inhibitor - Google Patents
Pharmaceutical composition containing histone deacetylase inhibitor Download PDFInfo
- Publication number
- CA2634766A1 CA2634766A1 CA002634766A CA2634766A CA2634766A1 CA 2634766 A1 CA2634766 A1 CA 2634766A1 CA 002634766 A CA002634766 A CA 002634766A CA 2634766 A CA2634766 A CA 2634766A CA 2634766 A1 CA2634766 A1 CA 2634766A1
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- combination according
- group
- ingredient
- carbons
- 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.)
- Abandoned
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 50
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title description 8
- 239000003276 histone deacetylase inhibitor Substances 0.000 title description 8
- 230000001093 anti-cancer Effects 0.000 claims abstract description 87
- 239000013543 active substance Substances 0.000 claims abstract description 85
- 239000004615 ingredient Substances 0.000 claims description 128
- 239000000126 substance Substances 0.000 claims description 120
- 206010028980 Neoplasm Diseases 0.000 claims description 82
- 201000011510 cancer Diseases 0.000 claims description 81
- 238000011282 treatment Methods 0.000 claims description 73
- 230000002401 inhibitory effect Effects 0.000 claims description 50
- 102000003964 Histone deacetylase Human genes 0.000 claims description 49
- 108090000353 Histone deacetylase Proteins 0.000 claims description 49
- 206010033128 Ovarian cancer Diseases 0.000 claims description 41
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 41
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 34
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 34
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 32
- 229930012538 Paclitaxel Natural products 0.000 claims description 27
- 150000003936 benzamides Chemical class 0.000 claims description 27
- 229960001592 paclitaxel Drugs 0.000 claims description 27
- 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 description 27
- 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 25
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 25
- 229960003668 docetaxel Drugs 0.000 claims description 25
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 25
- 201000002528 pancreatic cancer Diseases 0.000 claims description 25
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 25
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 claims description 25
- 229960003048 vinblastine Drugs 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 24
- 206010009944 Colon cancer Diseases 0.000 claims description 23
- 208000029742 colonic neoplasm Diseases 0.000 claims description 23
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 20
- 229960005277 gemcitabine Drugs 0.000 claims description 20
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 19
- 229960002949 fluorouracil Drugs 0.000 claims description 19
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 17
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 17
- 229940127093 camptothecin Drugs 0.000 claims description 17
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 17
- 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 16
- 229960004679 doxorubicin Drugs 0.000 claims description 16
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 16
- 229960001756 oxaliplatin Drugs 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 14
- 229960004316 cisplatin Drugs 0.000 claims description 14
- 229960004562 carboplatin Drugs 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 11
- 206010060862 Prostate cancer Diseases 0.000 claims description 10
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 10
- 229960005420 etoposide Drugs 0.000 claims description 10
- 206010006187 Breast cancer Diseases 0.000 claims description 9
- 208000026310 Breast neoplasm Diseases 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 abstract description 38
- 230000002195 synergetic effect Effects 0.000 abstract description 24
- 239000002246 antineoplastic agent Substances 0.000 abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 5
- 102000003893 Histone acetyltransferases Human genes 0.000 abstract 1
- 108090000246 Histone acetyltransferases Proteins 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 59
- 238000012360 testing method Methods 0.000 description 45
- 239000000203 mixture Substances 0.000 description 26
- -1 th.iazole Chemical compound 0.000 description 17
- 238000000034 method Methods 0.000 description 13
- 230000037396 body weight Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000002611 ovarian Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 9
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 108010010803 Gelatin Proteins 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| JP2003-148073 | 2003-05-26 | ||
| JP2003148073 | 2003-05-26 | ||
| CA002527191A CA2527191A1 (en) | 2003-05-26 | 2004-05-26 | Cancer treatment comprising a histone deacetylase inhibitor and another anticancer agent |
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| CA002527191A Division CA2527191A1 (en) | 2003-05-26 | 2004-05-26 | Cancer treatment comprising a histone deacetylase inhibitor and another anticancer agent |
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| CA2634766A1 true CA2634766A1 (en) | 2004-12-02 |
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| CA002634766A Abandoned CA2634766A1 (en) | 2003-05-26 | 2004-05-26 | Pharmaceutical composition containing histone deacetylase inhibitor |
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| CA002634765A Abandoned CA2634765A1 (en) | 2003-05-26 | 2004-05-26 | Pharmaceutical composition containing histone deacetylase inhibitor |
| CA002527191A Abandoned CA2527191A1 (en) | 2003-05-26 | 2004-05-26 | Cancer treatment comprising a histone deacetylase inhibitor and another anticancer agent |
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| CA002634709A Abandoned CA2634709A1 (en) | 2003-05-26 | 2004-05-26 | Pharmaceutical composition containing histone deacetylase inhibitor |
| CA002634765A Abandoned CA2634765A1 (en) | 2003-05-26 | 2004-05-26 | Pharmaceutical composition containing histone deacetylase inhibitor |
| CA002527191A Abandoned CA2527191A1 (en) | 2003-05-26 | 2004-05-26 | Cancer treatment comprising a histone deacetylase inhibitor and another anticancer agent |
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| ME (1) | MEP32308A (enExample) |
| MX (1) | MXPA05012345A (enExample) |
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| RS (1) | RS20050884A (enExample) |
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| TW (1) | TW200505424A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| KR20050122210A (ko) | 2003-03-17 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 히스톤 탈아세틸화 효소 억제제 |
| CA2540108A1 (en) * | 2003-09-25 | 2005-04-07 | Astellas Pharma Inc. | Antitumor agent_comprising a histone deacetylase inhibitor and a topoisomerase ii inhibitor |
| EP1712552A1 (en) * | 2005-04-11 | 2006-10-18 | INDENA S.p.A. | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
| US7446126B2 (en) * | 2004-10-08 | 2008-11-04 | Indena S.P.A. | Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel |
| JP2008524246A (ja) | 2004-12-16 | 2008-07-10 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| KR20080003334A (ko) * | 2005-03-11 | 2008-01-07 | 더 리젠트스 오브 더 유니버시티 오브 콜로라도 | 암 세포를 표피 성장 인자 억제제에 대해 감작화시키는히스톤 데아세틸라제 억제제 |
| US8999289B2 (en) | 2005-03-22 | 2015-04-07 | President And Fellows Of Harvard College | Treatment of protein degradation disorders |
| WO2006122319A2 (en) | 2005-05-11 | 2006-11-16 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| ZA200800901B (en) | 2005-07-14 | 2010-05-26 | Takeda San Diego Inc | Histone deacetylase inhibitors |
| US8222423B2 (en) | 2006-02-14 | 2012-07-17 | Dana-Farber Cancer Institute, Inc. | Bifunctional histone deacetylase inhibitors |
| JP5409015B2 (ja) | 2006-02-14 | 2014-02-05 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | ヒストンデアセチラーゼ阻害剤 |
| AU2007248656B2 (en) | 2006-05-03 | 2013-04-04 | Dana-Farber Cancer Institute, Inc. | Histone deacetylase and tubulin deacetylase inhibitors |
| GB0625283D0 (en) * | 2006-12-19 | 2007-01-24 | Cyclacel Ltd | Combination |
| PT2099442E (pt) | 2006-12-26 | 2015-02-10 | Pharmacyclics Inc | Métodos de utilização de inibidores de histona desacetilase e monitorização de biomarcadores em terapia de combinação |
| WO2009067453A1 (en) * | 2007-11-19 | 2009-05-28 | Syndax Pharmaceuticals, Inc. | Combinations of hdac inhibitors and proteasome inhibitors |
| US8293513B2 (en) * | 2007-12-14 | 2012-10-23 | Georgetown University | Histone deacetylase inhibitors |
| US8440716B2 (en) | 2008-07-23 | 2013-05-14 | President And Fellows Of Harvard College | Deacetylase inhibitors and uses thereof |
| SI2350005T1 (sl) * | 2008-08-29 | 2012-03-30 | Bayer Pharma AG | Polimorf B N aminofenil N piridin il metoksikarbonilaminometil benzamida MS |
| GB2462893B (en) * | 2008-08-29 | 2010-10-13 | Bayer Schering Pharma Ag | N-(2-aminophenyl)-4-[N-(pyridine-3-yl)-methoxycarbonyl-aminomethyl]-benzamide (MS-275) polymorph B |
| BRPI0924084B1 (pt) | 2008-12-19 | 2021-12-21 | Vertex Pharmaceuticals Incorporated | Derivados de pirazina e composição farmacêutica que os compreende |
| EP2395972A4 (en) * | 2009-02-11 | 2014-02-12 | Liangping Yu | PARTICULATE COMPOSITION AND METHOD FOR PRODUCING THE SAME |
| EP2424516A4 (en) * | 2009-05-01 | 2014-04-02 | Oncozyme Pharma Inc | PENTAMIDINE COMBINATIONS FOR THE TREATMENT OF CANCER |
| KR20120031170A (ko) * | 2009-06-08 | 2012-03-30 | 길리애드 사이언시즈, 인코포레이티드 | 알카노일아미노 벤즈아미드 아닐린 ｈｄａｃ 저해제 화합물 |
| US8716344B2 (en) | 2009-08-11 | 2014-05-06 | President And Fellows Of Harvard College | Class- and isoform-specific HDAC inhibitors and uses thereof |
| JP2013503174A (ja) * | 2009-08-25 | 2013-01-31 | アブラクシス バイオサイエンス， エルエルシー | タキサンおよびヘッジホッグ阻害剤のナノ粒子組成物を使用する併用療法 |
| AU2011253025A1 (en) | 2010-05-12 | 2012-11-29 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| NZ621221A (en) | 2011-09-13 | 2016-07-29 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor in combination with bendamustine and uses thereof |
| IN2014CN02501A (enExample) * | 2011-09-30 | 2015-06-26 | Vertex Pharma | |
| SG10201606774UA (en) | 2011-09-30 | 2016-10-28 | Vertex Pharma | Processes for making compounds useful as inhibitors of atr kinase |
| WO2013085902A1 (en) * | 2011-12-05 | 2013-06-13 | The University Of Texas M.D. | Combination therapy methods for treating an inflammatory breast cancer |
| US20140044802A1 (en) | 2012-04-05 | 2014-02-13 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase and combination therapies thereof |
| DK2904406T3 (en) | 2012-10-04 | 2018-06-18 | Vertex Pharma | METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE |
| US9738637B2 (en) | 2013-03-12 | 2017-08-22 | Celgene Quantical Research, Inc. | Histone demethylase inhibitors |
| WO2014141129A2 (en) * | 2013-03-14 | 2014-09-18 | Grueneberg Dorre A | Novel methods, compounds, and compositions for inhibition of ros |
| EA201592012A8 (ru) * | 2014-02-21 | 2018-10-31 | Общество С Ограниченной Ответственностью "Биолаб 612" | Применение флагеллина для улучшенной химиотерапии |
| EA201790604A1 (ru) | 2014-09-17 | 2017-09-29 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы гистондеметилазы |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| US11596612B1 (en) | 2022-03-08 | 2023-03-07 | PTC Innovations, LLC | Topical anesthetics |
| WO2025041160A1 (en) * | 2023-08-19 | 2025-02-27 | Birla Institute Of Technology And Science (Bits), Pilani | Bifunctional conjugate molecules for cancer treatment and process of making the same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2697752B1 (fr) * | 1992-11-10 | 1995-04-14 | Rhone Poulenc Rorer Sa | Compositions antitumorales contenant des dérivés du taxane. |
| US6174905B1 (en) * | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| JP3354090B2 (ja) * | 1996-09-30 | 2002-12-09 | シエーリング アクチエンゲゼルシャフト | 分化誘導剤 |
| US6794392B1 (en) * | 1996-09-30 | 2004-09-21 | Schering Aktiengesellschaft | Cell differentiation inducer |
| US5753637A (en) * | 1996-10-09 | 1998-05-19 | Ideal Ideas, Inc. | Method of treating acne conditions |
| YU22401A (sh) * | 1998-09-25 | 2004-03-12 | Warner-Lambert Company | Kombinacija acetildinalina sa gemcitabinom, capecitabinom i cisplatinom |
| EP1177796B1 (en) * | 1999-04-27 | 2011-04-27 | Mitsubishi Tanabe Pharma Corporation | Medicament for prevention or therapeutic treatment of liver disease |
| NZ518668A (en) * | 1999-11-10 | 2004-04-30 | Warner Lambert Co | Combination chemotherapy comprising acetyldinaline and paclitaxal and/or carboplatin |
| US6905669B2 (en) * | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| CZ20022216A3 (cs) * | 2001-07-02 | 2003-05-14 | Warner-Lambert Company | Kombinační chemoterapie |
| JP2003137866A (ja) * | 2001-11-01 | 2003-05-14 | Sankyo Co Ltd | フェニレンジアミン誘導体 |
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