AU2005221834B2 - Sulphonylpyrroles as HDAC inhibitors - Google Patents
Sulphonylpyrroles as HDAC inhibitors Download PDFInfo
- Publication number
- AU2005221834B2 AU2005221834B2 AU2005221834A AU2005221834A AU2005221834B2 AU 2005221834 B2 AU2005221834 B2 AU 2005221834B2 AU 2005221834 A AU2005221834 A AU 2005221834A AU 2005221834 A AU2005221834 A AU 2005221834A AU 2005221834 B2 AU2005221834 B2 AU 2005221834B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- alkyl
- hydrogen
- methyl
- pyrrol
- 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.)
- Expired
Links
- 239000003276 histone deacetylase inhibitor Substances 0.000 title description 21
- JRZBWRPPYOMOJE-UHFFFAOYSA-N 2-sulfonylpyrrole Chemical class O=S(=O)=C1C=CC=N1 JRZBWRPPYOMOJE-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 454
- -1 1-4C-alkyl Inorganic materials 0.000 claims description 349
- 229910052739 hydrogen Inorganic materials 0.000 claims description 198
- 239000001257 hydrogen Substances 0.000 claims description 198
- 238000000034 method Methods 0.000 claims description 112
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 94
- 102000003964 Histone deacetylase Human genes 0.000 claims description 89
- 108090000353 Histone deacetylase Proteins 0.000 claims description 89
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 79
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- 150000003839 salts Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 67
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- 201000010099 disease Diseases 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 239000001301 oxygen Substances 0.000 claims description 41
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 39
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- 150000003254 radicals Chemical class 0.000 claims description 35
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
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- 230000000694 effects Effects 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
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- 125000002950 monocyclic group Chemical group 0.000 claims description 21
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- 125000001041 indolyl group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 15
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 14
- 230000003211 malignant effect Effects 0.000 claims description 14
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- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
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- 125000001624 naphthyl group Chemical group 0.000 claims description 11
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
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- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 8
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
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- BBXFDSLIDSRCBA-KPKJPENVSA-N (e)-n-(2-aminophenyl)-3-[1-[4-(dimethylamino)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1S(=O)(=O)N1C=C(\C=C\C(=O)NC=2C(=CC=CC=2)N)C=C1 BBXFDSLIDSRCBA-KPKJPENVSA-N 0.000 claims description 2
- NBWQNBFUZOCVOM-ZZXKWVIFSA-N (e)-n-hydroxy-3-[1-[4-(morpholin-4-ylmethyl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C(C=C1)=CC=C1CN1CCOCC1 NBWQNBFUZOCVOM-ZZXKWVIFSA-N 0.000 claims description 2
- OKZHXWOSKHLTNE-UHFFFAOYSA-N 3-(1-benzylsulfonylpyrrol-3-yl)-n-hydroxyprop-2-enamide Chemical compound C1=C(C=CC(=O)NO)C=CN1S(=O)(=O)CC1=CC=CC=C1 OKZHXWOSKHLTNE-UHFFFAOYSA-N 0.000 claims description 2
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| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
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| RU2416600C2 (ru) * | 2005-12-27 | 2011-04-20 | Универсидад Дель Паис Васко-Еускал Еррико Унибертситатеа (Упв-Ееу) | Новые производные пиррола с ингибирующей гистондеацетилазу активностью |
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| US8680113B2 (en) * | 2008-07-01 | 2014-03-25 | Ptc Therapeutics, Inc. | BMI-1 protein expression modulators |
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| CN101941948A (zh) * | 2009-07-10 | 2011-01-12 | 南开大学 | 点击化学合成具有分支结构的组蛋白去乙酰酶抑制剂 |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| WO2012118782A1 (en) | 2011-02-28 | 2012-09-07 | Repligen Corporation | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| BR112015023399A8 (pt) | 2013-03-15 | 2019-12-03 | Biomarin Pharm Inc | inibidores de hdac, seu uso e composição farmacêutica |
| AU2014337102B2 (en) * | 2013-10-18 | 2019-02-28 | The General Hospital Corporation | Imaging histone deacetylases with a radiotracer using positron emission tomography |
| KR102359214B1 (ko) | 2014-04-04 | 2022-02-07 | 델 마 파마슈티컬스 | 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체 |
| CN105801464B (zh) * | 2014-12-29 | 2019-05-28 | 成都先导药物开发有限公司 | 吡咯酰胺类化合物及其制备方法与用途 |
| WO2017178577A1 (en) | 2016-04-14 | 2017-10-19 | 4Sc Ag | Medical application of resminostat in asian patients |
| TW201912183A (zh) | 2017-08-31 | 2019-04-01 | 德商４Ｓｃ製藥公司 | Hdac抑制劑與抗代謝藥劑組合用於癌症治療 |
| WO2019200238A1 (en) | 2018-04-14 | 2019-10-17 | Dynavax Technologies Corporation | Combinations including a cpg-c type oligonucleotide and a histone deacetylase inhibitor for treating cancer |
| TW202002968A (zh) | 2018-04-17 | 2020-01-16 | 德商４Ｓｃ製藥公司 | 用於癌症治療的包含hdac 抑制劑、lag-3 抑制劑和pd-1 抑制劑或pd-l1抑制劑之組合 |
| TW202114659A (zh) | 2019-10-02 | 2021-04-16 | 德商４Ｓｃ製藥公司 | 用於癌症治療之含ｈｄａｃ抑制劑、ｃｔｌａ—４抑制劑及ｐｄ—１抑制劑或ｐｄ—ｌ１抑制劑之組合 |
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| JP2003514905A (ja) | 1999-11-23 | 2003-04-22 | メルク エンド カムパニー インコーポレーテッド | ピラジノン系トロンビン阻害薬 |
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| ES2327269T3 (es) * | 2005-03-15 | 2009-10-27 | 4Sc Ag | N-sulfonilpirroles y su utilizacion como inhibidores de la histona desacetilasa. |
| US20090117074A1 (en) * | 2005-04-07 | 2009-05-07 | Nycomed Gmbh | Sulfonylpyrroles as Histone Deacetylase Inhibitors |
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| EP2060565A1 (en) * | 2007-11-16 | 2009-05-20 | 4Sc Ag | Novel bifunctional compounds which inhibit protein kinases and histone deacetylases |
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| WO2001038322A1 (en) * | 1999-11-23 | 2001-05-31 | Methylgene, Inc. | Inhibitors of histone deacetylase |
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