JP2011518173A5 - - Google Patents
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- Publication number
- JP2011518173A5 JP2011518173A5 JP2011505181A JP2011505181A JP2011518173A5 JP 2011518173 A5 JP2011518173 A5 JP 2011518173A5 JP 2011505181 A JP2011505181 A JP 2011505181A JP 2011505181 A JP2011505181 A JP 2011505181A JP 2011518173 A5 JP2011518173 A5 JP 2011518173A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- indole
- alkylene
- ethyl
- pharmaceutically acceptable
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 alkyl Compound Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 208000000389 T-cell leukemia Diseases 0.000 claims 2
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 4
- 238000006751 Mitsunobu reaction Methods 0.000 description 4
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- HIZSJRADKKBIBA-VOTSOKGWSA-N (e)-3-[1-[2-(3-fluorophenoxy)ethyl]pyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound ONC(=O)\C=C\C1=CC=CN1CCOC1=CC=CC(F)=C1 HIZSJRADKKBIBA-VOTSOKGWSA-N 0.000 description 1
- KUIDHMIWFNGQKB-VOTSOKGWSA-N (e)-3-[1-[2-(3-fluorophenoxy)ethyl]pyrrol-2-yl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CN1CCOC1=CC=CC(F)=C1 KUIDHMIWFNGQKB-VOTSOKGWSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- LNWXALCHPJANMJ-UHFFFAOYSA-N 1-(bromomethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CBr)=C1 LNWXALCHPJANMJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 125000006016 2-bromoethoxy group Chemical group 0.000 description 1
- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FYSRAGLPXRVAPN-UHFFFAOYSA-N 3-(2-bromoethoxy)benzaldehyde Chemical compound BrCCOC1=CC=CC(C=O)=C1 FYSRAGLPXRVAPN-UHFFFAOYSA-N 0.000 description 1
- XFHTVCMRNSBQCF-UHFFFAOYSA-N 4-(2-bromoethoxy)benzaldehyde Chemical compound BrCCOC1=CC=C(C=O)C=C1 XFHTVCMRNSBQCF-UHFFFAOYSA-N 0.000 description 1
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- CAKODCTWHRNHKN-UHFFFAOYSA-N C1=CC(=CC(=C1)Cl)OCCC2=CC3=C(N2)C=C(C=C3)C(=O)NO Chemical compound C1=CC(=CC(=C1)Cl)OCCC2=CC3=C(N2)C=C(C=C3)C(=O)NO CAKODCTWHRNHKN-UHFFFAOYSA-N 0.000 description 1
- KHFLPCFHCFJBRY-UHFFFAOYSA-N C1=CC=C(C(=C1)OCCC2=CC3=C(N2)C=C(C=C3)C(=O)O)F Chemical compound C1=CC=C(C(=C1)OCCC2=CC3=C(N2)C=C(C=C3)C(=O)O)F KHFLPCFHCFJBRY-UHFFFAOYSA-N 0.000 description 1
- TXKGGQRJWMZGCZ-UHFFFAOYSA-N CC(C1=CN=C(C=C1)OC)S(=O)(=O)O Chemical compound CC(C1=CN=C(C=C1)OC)S(=O)(=O)O TXKGGQRJWMZGCZ-UHFFFAOYSA-N 0.000 description 1
- IVOXFNLQEQTKOM-UHFFFAOYSA-N CCC1=C(C=CC(=C1F)[N+](=O)[O-])C(=O)O Chemical compound CCC1=C(C=CC(=C1F)[N+](=O)[O-])C(=O)O IVOXFNLQEQTKOM-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
- BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 0.000 description 1
- ADXAVDLMQIGVDB-UHFFFAOYSA-N ethyl 3-(benzylamino)-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 ADXAVDLMQIGVDB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CTFHWBBSQCPUEW-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CN(CCO)C2=C1 CTFHWBBSQCPUEW-UHFFFAOYSA-N 0.000 description 1
- FGZCYRGXDOMXNB-UHFFFAOYSA-N methyl 1-[2-(3-chlorophenoxy)ethyl]indole-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2C=CN1CCOC1=CC=CC(Cl)=C1 FGZCYRGXDOMXNB-UHFFFAOYSA-N 0.000 description 1
- AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BXYXWBBROYOLIG-UHFFFAOYSA-N tert-butyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C(C)(C)C BXYXWBBROYOLIG-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4519808P | 2008-04-15 | 2008-04-15 | |
| US61/045,198 | 2008-04-15 | ||
| PCT/US2009/040709 WO2009129335A2 (en) | 2008-04-15 | 2009-04-15 | Selective inhibitors of histone deacetylase |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014224779A Division JP2015057414A (ja) | 2008-04-15 | 2014-11-04 | ヒストン脱アセチル化酵素の選択的インヒビター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011518173A JP2011518173A (ja) | 2011-06-23 |
| JP2011518173A5 true JP2011518173A5 (cg-RX-API-DMAC10.html) | 2014-12-25 |
| JP5670877B2 JP5670877B2 (ja) | 2015-02-18 |
Family
ID=41199715
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011505181A Active JP5670877B2 (ja) | 2008-04-15 | 2009-04-15 | ヒストン脱アセチル化酵素の選択的インヒビター |
| JP2014224779A Pending JP2015057414A (ja) | 2008-04-15 | 2014-11-04 | ヒストン脱アセチル化酵素の選択的インヒビター |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014224779A Pending JP2015057414A (ja) | 2008-04-15 | 2014-11-04 | ヒストン脱アセチル化酵素の選択的インヒビター |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US8466193B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2265590B8 (cg-RX-API-DMAC10.html) |
| JP (2) | JP5670877B2 (cg-RX-API-DMAC10.html) |
| CA (2) | CA2875549A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2575873T3 (cg-RX-API-DMAC10.html) |
| MX (1) | MX2010011168A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2009129335A2 (cg-RX-API-DMAC10.html) |
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| MX2010011168A (es) | 2008-04-15 | 2010-12-21 | Pharmacyclics Inc | Inhibidores selectivos de histona-desacetilasa. |
| CA2765678A1 (en) | 2009-06-22 | 2010-12-29 | Christopher Blackburn | Substituted hydroxamic acids and uses thereof |
| WO2010151317A1 (en) | 2009-06-22 | 2010-12-29 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2011106627A1 (en) | 2010-02-26 | 2011-09-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| TWI429628B (zh) | 2010-03-29 | 2014-03-11 | Univ Taipei Medical | 吲哚基或吲哚啉基羥肟酸化合物 |
| WO2011130163A1 (en) | 2010-04-12 | 2011-10-20 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| CA2795952A1 (en) * | 2010-04-16 | 2011-10-20 | Curis, Inc. | Treatment of cancers having k-ras mutations |
| WO2012027564A1 (en) * | 2010-08-26 | 2012-03-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012054332A1 (en) | 2010-10-18 | 2012-04-26 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2012088015A2 (en) | 2010-12-22 | 2012-06-28 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8404738B2 (en) * | 2011-01-21 | 2013-03-26 | Hoffmann-La Roche Inc. | 4-amino-N-hydroxy-benzamides for the treatment of cancer |
| JP5990106B2 (ja) | 2011-01-28 | 2016-09-07 | 佐藤製薬株式会社 | 縮環化合物 |
| JP2014515368A (ja) | 2011-05-26 | 2014-06-30 | 第一三共株式会社 | プロテインキナーゼ阻害剤としての複素環化合物 |
| CN102838625B (zh) * | 2011-06-22 | 2015-04-15 | 中国科学院上海药物研究所 | 四氢吡啶并噻唑类化合物、其制备方法、包含该化合物的药物组合物及其用途 |
| WO2012178208A2 (en) * | 2011-06-24 | 2012-12-27 | The Trustees Of The Stevens Institute Of Technology | Selective inhibitors of histone deacetylase isoform 6 and methods thereof |
| WO2013062344A1 (en) * | 2011-10-28 | 2013-05-02 | Chong Kun Dang Pharmaceutical Corp. | Hydroxamate derivatives for hdac inhibitor, and the pharmaceutical composition comprising thereof |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| TWI692469B (zh) | 2012-11-09 | 2020-05-01 | 南韓商Ｌｇ化學股份有限公司 | Ｇｐｒ４０受體促效劑，製造該促效劑的方法以及含有該促效劑作爲活性劑的醫藥組成物 |
| CN103086971B (zh) * | 2013-01-11 | 2015-08-26 | 中国科学院广州生物医药与健康研究院 | 含氮杂环衍生物,其制备方法及其在制备组蛋白去乙酰化酶ⅰ抑制剂中的应用 |
| JP6320506B2 (ja) * | 2013-03-12 | 2018-05-09 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| EP3052655B1 (en) * | 2013-09-30 | 2018-11-07 | Institute For Cancer Research D/b/a The Research Institute of Fox Chase Cancer Center | Closantel in combination with temozolomide for use in the treatment of a cancer in which is thymine dna glycosylase expressed |
| WO2017077008A1 (en) | 2015-11-03 | 2017-05-11 | Hochschule Darmstadt | Selective hdac8 inhibitors and their uses |
| CN108602812B (zh) * | 2015-12-22 | 2021-11-02 | 坎塞拉有限公司 | 可用作哺乳动物组蛋白去乙酰化酶活性的抑制剂的双环异羟肟酸类化合物 |
| WO2017143237A1 (en) * | 2016-02-17 | 2017-08-24 | Acetylon Pharmaceuticals, Inc. | Increasing expression of interferon regulated genes with combinatons of histone deacetylase inhibitors and immunomodulatory drugs |
| CN106478606B (zh) * | 2016-09-21 | 2019-05-10 | 沈阳药科大学 | N-取代吲哚类衍生物及其应用 |
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| CN109568302B (zh) * | 2018-11-01 | 2021-07-16 | 郑州大学第一附属医院 | 一种治疗晚期肝癌的药物复合物及其应用 |
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| KR102685068B1 (ko) * | 2020-03-16 | 2024-07-16 | 가부시키가이샤 만다무 | T 세포성 림프종의 지표의 검출 방법, 및 그 이용 |
| US11278602B2 (en) | 2020-03-25 | 2022-03-22 | Therapeutica Borealis Oy | Medicine for Covid-19 and treatment |
| US11007187B1 (en) * | 2020-03-25 | 2021-05-18 | Therapeutica Borealis Oy | Medicine for Covid-19 and treatment |
| US11638722B2 (en) | 2020-03-25 | 2023-05-02 | Therapeutica Borealis Oy C/O Avance Attorneys Ltd. | Medicine for Covid-19 and treatment |
| CN111518031B (zh) * | 2020-05-29 | 2023-01-17 | 中国药科大学 | 一种含有异羟肟酸的化合物及其制备方法、应用 |
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| SMT202500447T1 (it) | 2021-11-02 | 2026-01-12 | Flare Therapeutics Inc | Agonisti inversi di pparg e loro usi |
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| JP7823945B2 (ja) * | 2022-03-17 | 2026-03-04 | スンミョン ウィメンズ ユニヴァーシティ インダストリー アカデミック コーポレーション ファウンデーション | 新規なヘテロ環ヒストン脱アセチル化酵素阻害剤及びそれを含む薬学組成物 |
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| US6875598B1 (en) | 1999-12-08 | 2005-04-05 | Applera Corporation | Histone deacetylase-8 proteins, nuclei acids, and methods for use |
| JP2003083067A (ja) * | 2001-09-13 | 2003-03-19 | Toyota Motor Corp | 内燃機関のピストン温度制御装置 |
| WO2003083067A2 (en) * | 2002-03-28 | 2003-10-09 | Brigham And Women's Hospital, Inc. | Histone deacetylase inhibitors for the treatment of multiple sclerosis, amyotrophic lateral sclerosis and alzheimer's disease |
| KR101127201B1 (ko) | 2003-09-22 | 2012-04-12 | 에스*바이오 피티이 리미티드 | 벤즈이미다졸 유도체와 그의 제조방법 및 약학적 적용 |
| US20050137234A1 (en) | 2003-12-19 | 2005-06-23 | Syrrx, Inc. | Histone deacetylase inhibitors |
| US8338416B2 (en) * | 2006-03-16 | 2012-12-25 | Pharmacylics, Inc. | Indole derivatives as inhibitors of histone deacetylase |
| US20110150825A1 (en) * | 2006-11-14 | 2011-06-23 | Pharmacyclics, Inc. | Uses of selective inhibitors of hdac8 for treatment of inflammatory conditions |
| WO2008060721A1 (en) * | 2006-11-14 | 2008-05-22 | Pharmacyclics, Inc. | Uses of selective inhibitors of hdac8 for treatment of t-cell proliferative disorders |
| MX2010011168A (es) | 2008-04-15 | 2010-12-21 | Pharmacyclics Inc | Inhibidores selectivos de histona-desacetilasa. |
-
2009
- 2009-04-15 MX MX2010011168A patent/MX2010011168A/es active IP Right Grant
- 2009-04-15 US US12/988,271 patent/US8466193B2/en active Active
- 2009-04-15 ES ES09733489.0T patent/ES2575873T3/es active Active
- 2009-04-15 JP JP2011505181A patent/JP5670877B2/ja active Active
- 2009-04-15 WO PCT/US2009/040709 patent/WO2009129335A2/en not_active Ceased
- 2009-04-15 CA CA2875549A patent/CA2875549A1/en not_active Abandoned
- 2009-04-15 CA CA2721218A patent/CA2721218C/en active Active
- 2009-04-15 EP EP09733489.0A patent/EP2265590B8/en not_active Not-in-force
-
2013
- 2013-05-20 US US13/897,582 patent/US8906954B2/en active Active
-
2014
- 2014-10-22 US US14/521,377 patent/US20150320758A1/en not_active Abandoned
- 2014-11-04 JP JP2014224779A patent/JP2015057414A/ja active Pending
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