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 (enExample) | 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 (enExample) |
| EP (1) | EP2265590B8 (enExample) |
| JP (2) | JP5670877B2 (enExample) |
| CA (2) | CA2875549A1 (enExample) |
| ES (1) | ES2575873T3 (enExample) |
| MX (1) | MX2010011168A (enExample) |
| WO (1) | WO2009129335A2 (enExample) |
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| EP2265590B8 (en) | 2008-04-15 | 2016-07-27 | Pharmacyclics LLC | Selective inhibitors of histone deacetylase |
| US8624040B2 (en) | 2009-06-22 | 2014-01-07 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| EP2445340B1 (en) | 2009-06-22 | 2016-05-18 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8546588B2 (en) | 2010-02-26 | 2013-10-01 | 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 |
| JP2013525308A (ja) * | 2010-04-16 | 2013-06-20 | キュリス，インコーポレイテッド | Ｋ−ｒａｓ変異を有する癌の治療 |
| WO2012027564A1 (en) * | 2010-08-26 | 2012-03-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8765773B2 (en) | 2010-10-18 | 2014-07-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8778931B2 (en) | 2010-12-22 | 2014-07-15 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
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| 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 |
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| US11007187B1 (en) * | 2020-03-25 | 2021-05-18 | Therapeutica Borealis Oy | 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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| 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 |
| US7820711B2 (en) * | 2006-11-14 | 2010-10-26 | Pharmacyclics Inc. | Uses of selective inhibitors of HDAC8 for treatment of T-cell proliferative disorders |
| EP2265590B8 (en) | 2008-04-15 | 2016-07-27 | Pharmacyclics LLC | Selective inhibitors of histone deacetylase |
-
2009
- 2009-04-15 EP EP09733489.0A patent/EP2265590B8/en active Active
- 2009-04-15 JP JP2011505181A patent/JP5670877B2/ja active Active
- 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 WO PCT/US2009/040709 patent/WO2009129335A2/en not_active Ceased
- 2009-04-15 ES ES09733489.0T patent/ES2575873T3/es active Active
- 2009-04-15 CA CA2875549A patent/CA2875549A1/en not_active Abandoned
- 2009-04-15 CA CA2721218A patent/CA2721218C/en active Active
-
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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