RU2720678C2 - Ингибиторы гистондеацетилазы - Google Patents
Ингибиторы гистондеацетилазы Download PDFInfo
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- RU2720678C2 RU2720678C2 RU2018103753A RU2018103753A RU2720678C2 RU 2720678 C2 RU2720678 C2 RU 2720678C2 RU 2018103753 A RU2018103753 A RU 2018103753A RU 2018103753 A RU2018103753 A RU 2018103753A RU 2720678 C2 RU2720678 C2 RU 2720678C2
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- RU
- Russia
- Prior art keywords
- compound
- cycloalkyl
- alkyl
- alkylene
- compound according
- Prior art date
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- 239000003276 histone deacetylase inhibitor Substances 0.000 title abstract description 29
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 711
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- 238000000034 method Methods 0.000 claims abstract description 88
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- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 18
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims abstract description 12
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- 239000000203 mixture Substances 0.000 claims description 56
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 230000001575 pathological effect Effects 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
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Classifications
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562188139P | 2015-07-02 | 2015-07-02 | |
| US62/188,139 | 2015-07-02 | ||
| PCT/US2016/040705 WO2017004522A1 (en) | 2015-07-02 | 2016-07-01 | Histone deacetylase inhibtors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2018103753A RU2018103753A (ru) | 2019-08-02 |
| RU2018103753A3 RU2018103753A3 (enExample) | 2019-11-01 |
| RU2720678C2 true RU2720678C2 (ru) | 2020-05-12 |
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| RU2018103753A RU2720678C2 (ru) | 2015-07-02 | 2016-07-01 | Ингибиторы гистондеацетилазы |
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| US (3) | US10851058B2 (enExample) |
| EP (1) | EP3317253A1 (enExample) |
| JP (1) | JP2018525342A (enExample) |
| KR (1) | KR20180022840A (enExample) |
| CN (1) | CN107922342A (enExample) |
| AU (1) | AU2016288606A1 (enExample) |
| BR (1) | BR112017028139A2 (enExample) |
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| RU (1) | RU2720678C2 (enExample) |
| SG (1) | SG10201913192VA (enExample) |
| WO (1) | WO2017004522A1 (enExample) |
| ZA (1) | ZA201800058B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2911040T3 (es) * | 2017-07-10 | 2022-05-17 | Medibiofarma S L | Nuevos derivados de heteroaril amida como inhibidores selectivos de histona deacetilasa 1 y 2 (HDAC1/2) |
| CN108795867A (zh) * | 2018-06-05 | 2018-11-13 | 华东理工大学 | 用于构建结肠癌细胞腹膜转移体外三维模型的方法 |
| EP4074700A4 (en) | 2019-12-10 | 2024-02-07 | Shionogi & Co., Ltd | HISTONE DEACETYLASE INHIBITOR COMPRISING AROMATIC HETEROCYCLIC GROUP CONTAINING NITROGEN |
| GB202001023D0 (en) * | 2020-01-24 | 2020-03-11 | Univ Leicester | HDAC Degrader |
| CN112239422B (zh) * | 2020-10-16 | 2022-07-22 | 河北化工医药职业技术学院 | 一种布格替尼中间体、其盐、其制备方法以及布格替尼的制备方法 |
| WO2024245060A1 (zh) * | 2023-06-02 | 2024-12-05 | 苏州浦合医药科技有限公司 | HDAC1-CoREST高选择性抑制剂 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008109994A1 (en) * | 2007-03-13 | 2008-09-18 | Methylgene Inc. | Inhibitors of histone deacetylase |
| WO2009002534A1 (en) * | 2007-06-26 | 2008-12-31 | Gilead Colorado, Inc. | Imidazopyridinyl thiazolyl histone deacetylase inhibitors |
| RU2453536C2 (ru) * | 2007-10-22 | 2012-06-20 | Оркид Рисерч Лабораториз Лимитед | Ингибиторы гистондезацетилазы |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2465978C (en) * | 2001-09-14 | 2015-04-07 | Soon Hyung Woo | Inhibitors of histone deacetylase |
| TWI319387B (en) * | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| WO2005092899A1 (en) * | 2004-03-26 | 2005-10-06 | Methylgene Inc. | Inhibitors of histone deacetylase |
| AR057579A1 (es) * | 2005-11-23 | 2007-12-05 | Merck & Co Inc | Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac) |
| JP5554988B2 (ja) | 2006-04-07 | 2014-07-23 | メチルジーン インコーポレイテッド | ヒストンデアセチラーゼの阻害剤 |
| JP5469604B2 (ja) * | 2007-09-19 | 2014-04-16 | 4エスツェー アクチェンゲゼルシャフト | 新規テトラヒドロ融合ピリジン |
| CN102477001B (zh) | 2010-11-29 | 2015-07-15 | 江苏先声药物研究有限公司 | 一种苯甲酰胺类组蛋白去乙酰化酶抑制剂 |
| US8404738B2 (en) * | 2011-01-21 | 2013-03-26 | Hoffmann-La Roche Inc. | 4-amino-N-hydroxy-benzamides for the treatment of cancer |
| US8957066B2 (en) * | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| GB201111630D0 (en) * | 2011-07-07 | 2011-08-24 | Cancer Rec Tech Ltd | Novel compounds and their use |
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2016
- 2016-07-01 CA CA2990660A patent/CA2990660A1/en not_active Abandoned
- 2016-07-01 AU AU2016288606A patent/AU2016288606A1/en not_active Abandoned
- 2016-07-01 RU RU2018103753A patent/RU2720678C2/ru active
- 2016-07-01 HK HK18109798.5A patent/HK1250367A1/zh unknown
- 2016-07-01 US US15/740,437 patent/US10851058B2/en active Active
- 2016-07-01 SG SG10201913192VA patent/SG10201913192VA/en unknown
- 2016-07-01 MX MX2017017127A patent/MX2017017127A/es unknown
- 2016-07-01 WO PCT/US2016/040705 patent/WO2017004522A1/en not_active Ceased
- 2016-07-01 BR BR112017028139-2A patent/BR112017028139A2/pt not_active Application Discontinuation
- 2016-07-01 EP EP16739365.1A patent/EP3317253A1/en not_active Withdrawn
- 2016-07-01 JP JP2017567632A patent/JP2018525342A/ja active Pending
- 2016-07-01 KR KR1020187002149A patent/KR20180022840A/ko not_active Withdrawn
- 2016-07-01 CN CN201680037989.0A patent/CN107922342A/zh active Pending
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2017
- 2017-12-20 IL IL256438A patent/IL256438B/en active IP Right Grant
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2018
- 2018-01-04 ZA ZA2018/00058A patent/ZA201800058B/en unknown
- 2018-07-27 US US16/047,179 patent/US10308608B2/en active Active
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2020
- 2020-09-22 US US17/028,444 patent/US20210009519A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008109994A1 (en) * | 2007-03-13 | 2008-09-18 | Methylgene Inc. | Inhibitors of histone deacetylase |
| WO2009002534A1 (en) * | 2007-06-26 | 2008-12-31 | Gilead Colorado, Inc. | Imidazopyridinyl thiazolyl histone deacetylase inhibitors |
| RU2453536C2 (ru) * | 2007-10-22 | 2012-06-20 | Оркид Рисерч Лабораториз Лимитед | Ингибиторы гистондезацетилазы |
Non-Patent Citations (1)
| Title |
|---|
| Raeppel, S., Zhou, N., Gaudette, F., Leit, S., Paquin, I., Larouche, G. Vaisburg, A. (2009). SAR and biological evaluation of analogues of a small molecule histone deacetylase inhibitor N-(2-aminophenyl)-4-((4-(pyridin-3-yl)pyrimidin-2-ylamino)methyl)benzamide (MGCD0103). Bioorganic & Medicinal Chemistry Letters, 19(3), 644-649. doi:10.1016/j.bmcl.2008.12.048. * |
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| AU2016288606A1 (en) | 2018-01-18 |
| US10851058B2 (en) | 2020-12-01 |
| IL256438B (en) | 2020-06-30 |
| CA2990660A1 (en) | 2017-01-05 |
| US10308608B2 (en) | 2019-06-04 |
| RU2018103753A3 (enExample) | 2019-11-01 |
| US20210009519A1 (en) | 2021-01-14 |
| EP3317253A1 (en) | 2018-05-09 |
| ZA201800058B (en) | 2018-12-19 |
| MX2017017127A (es) | 2018-03-09 |
| US20190382342A1 (en) | 2019-12-19 |
| HK1250367A1 (zh) | 2018-12-14 |
| BR112017028139A2 (pt) | 2018-08-28 |
| US20180370915A1 (en) | 2018-12-27 |
| RU2018103753A (ru) | 2019-08-02 |
| CN107922342A (zh) | 2018-04-17 |
| JP2018525342A (ja) | 2018-09-06 |
| SG10201913192VA (en) | 2020-03-30 |
| IL256438A (en) | 2018-02-28 |
| KR20180022840A (ko) | 2018-03-06 |
| WO2017004522A1 (en) | 2017-01-05 |
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