RU2018142988A - Производные пиридиндикарбоксамида в качестве ингибиторов бромодомена - Google Patents
Производные пиридиндикарбоксамида в качестве ингибиторов бромодомена Download PDFInfo
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- RU2018142988A RU2018142988A RU2018142988A RU2018142988A RU2018142988A RU 2018142988 A RU2018142988 A RU 2018142988A RU 2018142988 A RU2018142988 A RU 2018142988A RU 2018142988 A RU2018142988 A RU 2018142988A RU 2018142988 A RU2018142988 A RU 2018142988A
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- 102000001805 Bromodomains Human genes 0.000 title 1
- 108050009021 Bromodomains Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- CJVCXRMYJNMDTP-UHFFFAOYSA-N pyridine-2,3-dicarboxamide Chemical class NC(=O)C1=CC=CN=C1C(N)=O CJVCXRMYJNMDTP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 17
- 201000010099 disease Diseases 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 229940125763 bromodomain inhibitor Drugs 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 241000894006 Bacteria Species 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000004968 inflammatory condition Effects 0.000 claims 2
- 230000028709 inflammatory response Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 244000045947 parasite Species 0.000 claims 2
- -1 pyrrolopyridinyl Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 239000003053 toxin Substances 0.000 claims 2
- 231100000765 toxin Toxicity 0.000 claims 2
- 108700012359 toxins Proteins 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Claims (43)
1. Соединение формулы (I)
или его соль, где:
R1 представляет собой -C1-3алкил или циклопропил;
R2 представляет собой -С0-3алкил-С3-7циклоалкил, где С3-7циклоалкильная группа возможно замещена одной, двумя или тремя группами R5, которые могут быть одинаковыми или разными;
R3 представляет собой -Н, -С1-4алкил, циклопропил, фтор, хлор, -CH2F, -С0-3алкилOR10 или С0-3алкилCN;
R4 представляет собой фенил или гетероарил, где каждый возможно замещен одной, двумя или тремя группами R6, которые могут быть одинаковыми или разными;
каждый R5 независимо выбран из фтора, групп -С1-6алкил-R13, -ОСН3, -О-С2-6алкил-R13, -CN, -ОН, -SO2C1-3алкил и -NR14R15;
каждый R6 независимо выбран из оксо, галогена, -OCF3, -OCHF2, групп -С1-4алкил, -С0-3алкил-OR8, -C0-3алкил-NRl4Rl5, -С0-3алкил-CONR11R12, -С0-3алкил-гетероциклил, -С0-3алкил-О-С1-2алкил-гетероциклил, -CN и -SO2R7, где гетероциклил возможно замещен одним или двумя заместителями, независимо выбранными из группы -C1-3алкил, -ОН и фтора;
R7 представляет собой -С1-3алкил или -NR11R12;
R8 представляет собой -Н, -C1-3алкил, -C2-3алкил-NR11R12, -С2-3алкил-ОН или -С2-3алкил-О-С1-3алкил;
R9 представляет собой -Н, -C1-3алкил, -C2-3алкил-NR11R12 или -С2-3алкил-ОН;
R10 представляет собой -Н или -C1-3алкил;
каждый R11 и каждый R12 независимо выбраны из -Н и группы -С1-3алкил; или R11 и R12 могут быть соединены с азотом, к которому они присоединены, с образованием гетероциклила, возможно содержащего дополнительный гетероатом, выбранный из азота, кислорода и серы, и возможно замещенного одним или двумя заместителями, независимо выбранными из группы -С1-3алкил, -ОН и фтора;
R13 представляет собой -Н, -OR9, -NR14R15 или -CN;
каждый R14 и каждый R15 независимо выбраны из -Н, -С(O)ОС(СН3)3, групп -С(O)С1-3алкил, -C1-6алкил, С3-7циклоалкил, гетероциклил, -С2-3алкил-ОН и -С2-3алкил-О-С1-3алкил, где -С1-6алкил и С3-7циклоалкил могут быть возможно замещены одним, двумя или тремя атомами фтора; или R14 и R15 могут быть соединены с азотом, к которому они присоединены, с образованием гетероциклила, возможно содержащего дополнительный гетероатом, выбранный из азота, кислорода и серы, и возможно замещенного одним или двумя заместителями, независимо выбранными из группы -С1-3алкил, -ОН и фтора.
2. Соединение или его соль по п. 1, где R1 представляет собой метил.
3. Соединение или его соль по п. 1 или 2, где R2 представляет собой циклопропил.
4. Соединение или его соль по п. 3, где R2 является незамещенным.
5. Соединение или его соль по п. 3, где R2 замещен одной группой R5, которая представляет собой метил.
6. Соединение или его соль по любому из пп. 1-5, где R3 представляет собой -Н, метил, этил, фтор, -ОСН3, -ОН, -CH2F, -СН2ОН, -СН(ОН)СН3, -СН2ОМе или -CH2CN.
7. Соединение или его соль по любому из пп. 1-6, где R4 представляет собой незамещенный фенил, или R4 представляет собой фенил, замещенный одной группой R6.
8. Соединение или его соль по любому из пп. 1-6, где R4 представляет собой незамещенный пирролопиридинил.
9. Соединение или его соль по п. 7, где R4 замещен одной группой R6, выбранной из оксо, фтора, -ОСН2СН2ОН, -ОСН2СН(СН3)ОН, метила, -ОСН3, -ОН и группы -ОСН2СН2-3-(4,4-дифторпиперидинил).
10. Соединение, выбранное из соединений по Примерам 1-124, или его соль.
11. Соединение по любому из пп. 1-10 или его фармацевтически приемлемая соль.
12. Фармацевтическая композиция, содержащая соединение или его фармацевтически приемлемую соль по п. 11 и один или более чем один фармацевтически приемлемый эксципиент.
13. Комбинация, содержащая соединение или его фармацевтически приемлемую соль по п. 11 вместе с одним или более чем одним другим терапевтически активным агентом.
14. Соединение или его фармацевтически приемлемая соль по п. 11 для применения в терапии.
15. Соединение или его фармацевтически приемлемая соль по п. 11 для применения в лечении заболевания или состояния, при котором показан ингибитор бромодомена.
16. Соединение для применения по п. 15, где заболевание или состояние представляет собой острое или хроническое аутоиммунное и/или воспалительное состояние.
17. Соединение для применения по п. 15, где заболевание или состояние включает воспалительную реакцию на инфекцию, вызываемую бактериями, вирусом, грибками, паразитом или их токсинами.
18. Соединение для применения по п. 15, где заболевание или состояние представляет собой вирусную инфекцию.
19. Соединение для применения по п. 15, где заболевание или состояние представляет собой рак.
20. Соединение для применения по п. 15, где заболевание или состояние представляет собой ревматоидный артрит.
21. Применение соединения или его фармацевтически приемлемой соли по п. 11 в изготовлении лекарственного средства для лечения заболевания или состояния, при котором показан ингибитор бромодомена.
22. Способ лечения заболевания или состояния, при котором показан ингибитор бромодомена, у субъекта, нуждающегося в этом, включающий введение терапевтически эффективного количества соединения или его фармацевтически приемлемой соли по п. 11.
23. Способ лечения по п. 22, где заболевание или состояние представляет собой острое или хроническое аутоиммунное и/или воспалительное состояние.
24. Способ лечения по п. 22, где заболевание или состояние включает воспалительную реакцию на инфекцию, вызываемую бактериями, вирусом, грибками, паразитом или их токсинами.
25. Способ лечения по п. 22, где заболевание или состояние представляет собой вирусную инфекцию.
26. Способ лечения по п. 22, где заболевание или состояние представляет собой рак.
27. Способ лечения по п. 22, где заболевание или состояние представляет собой ревматоидный артрит.
28. Способ лечения по любому из пп. 22-27, где субъект является человеком.
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| RU2018112312A (ru) | 2015-09-22 | 2019-10-23 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Пиридинондикарбоксамиды для применения в качестве ингибиторов бромодомена |
| KR20180059551A (ko) | 2015-10-05 | 2018-06-04 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 브로모도메인 억제제로서 2-옥소-1,2-디하이드로피리딘-3,5-디카복스아미드 화합물 |
| EP3440069B1 (en) | 2016-04-07 | 2020-10-28 | GlaxoSmithKline Intellectual Property (No. 2) Limited | Pyridyl derivatives as bromodomain inhibitors |
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| KR20180059551A (ko) | 2015-10-05 | 2018-06-04 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 브로모도메인 억제제로서 2-옥소-1,2-디하이드로피리딘-3,5-디카복스아미드 화합물 |
| EP3440069B1 (en) | 2016-04-07 | 2020-10-28 | GlaxoSmithKline Intellectual Property (No. 2) Limited | Pyridyl derivatives as bromodomain inhibitors |
| EP3464242A1 (en) | 2016-05-24 | 2019-04-10 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pyridine dicarboxamide derivatives as bromodomain inhibitors |
| GB201703282D0 (en) | 2017-03-01 | 2017-04-12 | Glaxosmithkline Intellectual Property (No 2) Ltd | Compounds |
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| EP3464242A1 (en) | 2019-04-10 |
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| US10844015B2 (en) | 2020-11-24 |
| WO2017202742A1 (en) | 2017-11-30 |
| CN109153646A (zh) | 2019-01-04 |
| CN109153646B (zh) | 2022-08-02 |
| CA3023765A1 (en) | 2017-11-30 |
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