RU2019126468A - Ингибитор lsd1, а также способ его получения и его применение - Google Patents
Ингибитор lsd1, а также способ его получения и его применение Download PDFInfo
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- RU2019126468A RU2019126468A RU2019126468A RU2019126468A RU2019126468A RU 2019126468 A RU2019126468 A RU 2019126468A RU 2019126468 A RU2019126468 A RU 2019126468A RU 2019126468 A RU2019126468 A RU 2019126468A RU 2019126468 A RU2019126468 A RU 2019126468A
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- alkyl
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- C07D207/04—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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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Claims (55)
1. Соединение формулы (I), его фармацевтически приемлемая соль или его таутомер,
где
f равняется 1 или 2;
r равняется 0, 1 или 2;
e равняется 0, 1 или 2;
p равняется 0 или 1;
m равняется 0, 1 или 2;
n равняется 1 или 2;
каждый из R1 и R2 независимо выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2 и -COOH, или представляет собой C1-3алкил, необязательно замещенный 1, 2 или 3 R;
или R1 и R2 соединены друг с другом с образованием 3-6-членного кольца;
R3 выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2, -COOH, -CONH2 и -L-R5, или выбран из группы, состоящей из C1-6алкила, фенила, 5-12-членного гетероарила, C3-7циклоалкила и 4-8-членного гетероциклоалкила, каждый из которых необязательно замещен 1, 2 или 3 R;
R4 представляет собой H или выбран из группы, состоящей из C1-6алкила и C1-6гетероалкила, каждый из которых необязательно замещен 1, 2 или 3 R;
R5 выбран из группы, состоящей из фенила, 5-10-членного гетероарила, C3-10циклоалкила, 4-10-членного гетероциклоалкила, 5-6-членного гетероциклоалкил-C(=O)- и 5-6-членного гетероциклоалкил-C1-3алкил-, каждый из которых необязательно замещен 1, 2 или 3 R;
R6 представляет собой H или выбран из группы, состоящей из C1-6алкила и C1-6гетероалкила, каждый из которых необязательно замещен 1, 2 или 3 R;
L представляет собой -C(=O)- или выбран из группы, состоящей из -C1-6алкил- и -5-9-членный-гетероарил-, -4-8-членный-гетероциклоалкил-, -фенил- и -C3-6циклоалкил-, каждый из которых необязательно замещен 1, 2 или 3 R;
R выбран из группы, состоящей из H, F, Cl, Br, I, OH, NH2, CN, -COOH и NH2-C(=O)-, или выбран из группы, состоящей из C1-6алкила, C1-6гетероалкила, фенил-C1-6алкил-, фенила, 5-6-членного гетероарила, фенил-C(=O)-, C3-6циклоалкил-C(=O)-, C3-6циклоалкил-C(=O)-NH, C3-6циклоалкил-NH-C(=O)- и C3-6циклоалкил-C1-3алкил-, каждый из которых необязательно замещен 1, 2 или 3 R’;
R’ выбран из группы, состоящей из F, Cl, Br, I, OH, NH2, COOH, C1-3алкила, C1-3алкила, замещенного 1-3 атомами галогена(галогенов), C1-3алкил-NH-, N,N-ди(C1-3алкил)-амино, C1-3алкил-O-C(=O)-, C3-6циклоалкила и C1-3алкоксила;
каждый из «гетерокомпонентов» в 5-12-членном гетероариле, 4-8-членном гетероциклоалкиле, C1-6гетероалкиле, 5-10-членном гетероариле, 5-6-членном гетероариле, 5-6-членном гетероциклоалкиле, 4-10-членном гетероциклоалкиле независимо выбран из группы, состоящей из -NH-, -S-, N, -O-, =O, -C(=O)-, -NH-C(=O)-, -O-C(=O)-, -S(=O)2-, -S(=O)-, -C(=O)-NH-;
в любом из вышеуказанных случаев количество гетероатомов или гетероатомных групп независимо составляет 1, 2, 3 или 4.
3. Соединение, его фармацевтически приемлемая соль или таутомер по п. 1, где R выбран из группы, состоящей из H, F, Cl, Br, I, OH, NH2, CN, COOH, NH2-C(=O)-, или выбран из группы, состоящей из метила, этила, пропила, изобутила, трет-бутила, C1-6алкоксила, фенил-C1-3алкил-, фенила, пиридила, 1,2,4-триазолила, фенил-C(=O)-, C1-3алкил-C(=O)-, C1-3алкил-NH-, циклопропил-C(=O)-, C1-3алкил-O-C(=O)-C1-3алкил-, C1-3алкил-O-C(=O)-, C1-3алкил-S(=O)2-, циклопропил-C(=O)-NH-, циклопропил-NH-C(=O)-, C1-3алкил-NH-C(=O)-, циклобутан-CH2- и C1-3алкил-C(=O)-NH-, каждый из которых необязательно замещен 1, 2 или 3 R’.
4. Соединение, его фармацевтически приемлемая соль или таутомер по п. 3, где R выбран из группы, состоящей из H, F, Cl, Br, I, OH, NH2, CN, COOH и NH2-C(=O)-, или выбран из группы, состоящей из Me, Et, , , , , , , , , , , , , , , , , , , , , , и , каждый из которых необязательно замещен 1, 2 или 3 R’.
6. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где каждый из R1 и R2 независимо выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2, -COOH, Me и Et.
7. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где L представляет собой -C(=O)- или выбран из группы, состоящей из -C1-3алкил-, -фенил-, -5-6-членный-гетероарил-, -5-6-членный-гетероциклоалкил- и -C3-6циклоалкил-, каждый из которых необязательно замещен 1, 2 или 3 R.
8. Соединение, его фармацевтически приемлемая соль или таутомер по п. 7, где L представляет собой -C(=O)- или выбран из группы, состоящей из -1,2,4-оксадиазолил-, -метилен-, -этил-, -1,3,4-оксадиазолил-, -изоксазолил-, -оксазолил-, -пиперидил-, -1,2,3-триазолил-, -циклопропанил- и -фенил-, каждый из которых необязательно замещен 1, 2 или 3 R.
11. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где R5 выбран из группы, состоящей из фенила, пиридила, пиперидинила, пирролидинила, азетидинила, циклогексила, циклобутила, бензо[d][1,3]-мета-диоксациклопентенила, пиперидил-2-кето, 7-азаспиро[3.5]нонила, циклогексил-CH2-, 3a,7a-дигидро-1H-индолила, пиразолила, пиридила, 3a,7a-дигидробензо[d]тиазолила, пиримидинила, циклопентила, спиро[3.3]гептанила, бицикло[2.2.2]октила, октагидроциклопента[c]пирролила, 2-азаспиро[3.5]нонила, пиперидинил-C(=O)-, 4,5,6,7-тетрагидро-1H-бензо[d]имидазолила, 5,6,7,8-тетрагидроимидазо[1,2-a]пиридила, пиперидинил-CH2-, бицикло[1.1.1]пентила и пиперазинила, каждый из которых необязательно замещен 1, 2 или 3 R.
13. Соединение, его фармацевтически приемлемая соль или таутомер по п. 12, где R5 выбран из группы, состоящей из , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , и .
15. Соединение, его фармацевтически приемлемая соль или таутомер по п. 14, где -L-R5 выбран из группы, состоящей из , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , и .
16. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где R3 выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2, -COOH, -CONH2 и -L-R5, или выбран из группы, состоящей из C1-3алкила, фенила, пирролидинила, 1H-имидазолила, 1H-1,2,4-триазолила, пиридила, тиазолила, тиенила, пирролила, 2H-тетразолила, 6,7-дигидро-5H-пирроло[1,2-a]имидазолила, имидазо[1,5-a]пиридила, оксазолила, бензо[d]изоксазолила, бензо[d]оксазолила, 1,2,3,4-4H-2,7-нафтиридинила, 1,2,3,4-тетрагидроизохинолинила, 2,3,4,5-тетрагидро-1H-бензо[d]азепинила, азетидинила, изоиндолила, пиперидинила, 2,3,4,5-тетрагидро-1H-бензо[b]азепинила, 2,3-дигидро-1H-пирроло[3,4-c]пиридила, бензоизоксазолила, 5,6,7,8-тетрагидропиридопиримидинила, 3a,7a-дигидробензо[d]тиазолила, 2,4,5,6-тетрагидропирроло[3,4-c]пиразолила, 1,4,5,6-тетрагидропирроло[3,4-c]пиразолила, пиперазинила, морфолинила, октагидропирроло[3,4-c]пирролила, 1,4-диазагептила, циклогексила и 1,2,4-оксадиазолила, каждый из которых необязательно замещен 1, 2 или 3 R.
17. Соединение, его фармацевтически приемлемая соль или таутомер по п. 16, где R3 выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2, -COOH, -CONH2 и -L-R5, или выбран из группы, состоящей из Me, Et, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , и , каждый из которых необязательно замещен 1, 2 или 3 R.
18. Соединение, его фармацевтически приемлемая соль или таутомер по п. 15 или п. 17, где R3 выбран из группы, состоящей из H, F, Cl, Br, I, OH, CN, NH2, -COOH, Me, Et,
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , и .
19. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где R4 представляет собой H или выбран из группы, состоящей из C1-3алкила и C1-4алкил-O-C(=O)-, каждый из которых необязательно замещен 1, 2 или 3 R.
21. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, где R6 представляет собой H или выбран из группы, состоящей из C1-3алкила и C1-4алкил-O-C(=O)-, каждый из которых необязательно замещен 1, 2 или 3 R.
25. Соединение, его фармацевтически приемлемая соль или таутомер по любому из пп. 1-5, 6, 11-13, которые выбраны из группы, состоящей из
где
e, f, m и n определены в п. 1;
R определен в любом из пп. 1, 3-5;
R определен в любом из пп. 1, 11-13;
каждый из q1 и q2 независимо равняется 1 или 2.
26. Соединение, его фармацевтически приемлемая соль или таутомер, выбранные из группы, состоящей из
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , и .
27. Фармацевтическая композиция, содержащая терапевтически эффективное количество соединения, его фармацевтически приемлемой соли или таутомера по любому из пп. 1-26 в качестве активного ингредиента и фармацевтически приемлемый носитель.
28. Применение соединения, его фармацевтически приемлемой соли или таутомера по любому из пп. 1-26 или композиции по п. 27 в изготовлении лекарственного препарата для лечения заболевания, связанного с LSD1.
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CN115551501B (zh) * | 2020-05-12 | 2024-03-22 | 石药集团中奇制药技术(石家庄)有限公司 | 一种lsd1抑制剂的用途 |
CN111454252B (zh) * | 2020-05-13 | 2021-06-11 | 郑州大学 | 含芳环/芳杂环-三氮唑-亚甲基-tcp衍生物及其制备方法和应用 |
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KR20230167102A (ko) | 2021-04-08 | 2023-12-07 | 오리존 지노믹스 에스.에이. | 골수성 암 치료를 위한 lsd1 억제제의 조합물 |
AR126996A1 (es) | 2021-09-08 | 2023-12-06 | Pi Industries Ltd | Compuestos de isoxazolina y su uso como agentes de control de plagas |
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WO2023217784A1 (en) | 2022-05-09 | 2023-11-16 | Oryzon Genomics, S.A. | Methods of treating nf1-mutant tumors using lsd1 inhibitors |
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US8993808B2 (en) * | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
EP3133059A1 (en) * | 2010-04-19 | 2017-02-22 | Oryzon Genomics, S.A. | Lysine specific demethylase-1 inhibitors and their use |
RU2611437C2 (ru) | 2010-07-29 | 2017-02-22 | Оризон Дженомикс С.А. | Ингибиторы деметилазы lsd1 на основе арилциклопропиламина и их применение в медицине |
JP5813855B2 (ja) | 2011-03-25 | 2015-11-17 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー2、リミテッドGlaxosmithkline Intellectual Property No.2 Limited | Lsd1阻害剤としてのシクロプロピルアミン |
CN105051005B (zh) * | 2012-10-12 | 2017-06-13 | 武田药品工业株式会社 | 环丙胺化合物及其用途 |
EP3626713B1 (en) | 2014-02-13 | 2021-09-29 | Incyte Corporation | Cyclopropylamines for use as lsd1 inhibitors |
EP3105219B9 (en) | 2014-02-13 | 2018-10-03 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
CN107200706A (zh) | 2016-03-16 | 2017-09-26 | 中国科学院上海药物研究所 | 一类氟取代的环丙胺类化合物及其制备方法、药物组合物和用途 |
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JP7217712B2 (ja) | 2023-02-03 |
KR20190112047A (ko) | 2019-10-02 |
EP3575285A1 (en) | 2019-12-04 |
RU2763898C9 (ru) | 2022-03-18 |
RU2019126468A3 (ru) | 2021-02-26 |
KR102576586B1 (ko) | 2023-09-11 |
AU2018213637A1 (en) | 2019-09-19 |
US20200345700A1 (en) | 2020-11-05 |
CN110248926B (zh) | 2022-12-06 |
AU2018213637B2 (en) | 2022-01-27 |
EP3575285A4 (en) | 2020-08-12 |
RU2763898C2 (ru) | 2022-01-11 |
JP2020506227A (ja) | 2020-02-27 |
US11433053B2 (en) | 2022-09-06 |
CA3056527A1 (en) | 2018-08-02 |
WO2018137644A1 (zh) | 2018-08-02 |
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