EA023038B1 - Соединения - ингибиторы фермента - Google Patents
Соединения - ингибиторы фермента Download PDFInfo
- Publication number
- EA023038B1 EA023038B1 EA201290880A EA201290880A EA023038B1 EA 023038 B1 EA023038 B1 EA 023038B1 EA 201290880 A EA201290880 A EA 201290880A EA 201290880 A EA201290880 A EA 201290880A EA 023038 B1 EA023038 B1 EA 023038B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- pyrrolo
- pyridin
- chlorophenyl
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 239000002532 enzyme inhibitor Substances 0.000 title description 2
- 229940125532 enzyme inhibitor Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- -1 cyano, hydroxyl Chemical group 0.000 claims description 86
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000006413 ring segment Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 10
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- 229910052801 chlorine Inorganic materials 0.000 claims description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
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- PVKFTMXILNTSOY-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 PVKFTMXILNTSOY-UHFFFAOYSA-N 0.000 claims description 3
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- QKXXUOISKVZSIE-UHFFFAOYSA-N [1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methanol Chemical compound C12=CN=CC=C2C(CO)=CN1C1=CC=C(Cl)C=C1 QKXXUOISKVZSIE-UHFFFAOYSA-N 0.000 claims description 3
- ACDAWIRIJKZIBF-UHFFFAOYSA-N [1-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 ACDAWIRIJKZIBF-UHFFFAOYSA-N 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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- ICTHLQAYBCVJAA-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-[(1-methylpyrazol-4-yl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridine Chemical compound C1=NN(C)C=C1CN1CCC(C=2C3=CC=NC=C3N(C=3C=CC(Cl)=CC=3)C=2)CC1 ICTHLQAYBCVJAA-UHFFFAOYSA-N 0.000 claims description 2
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- KUKHQQQVBFTSPF-UHFFFAOYSA-N 1-(5-chloropyridin-2-yl)-3-(oxan-4-yl)pyrrolo[2,3-c]pyridine Chemical compound N1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCOCC2)=C1 KUKHQQQVBFTSPF-UHFFFAOYSA-N 0.000 claims description 2
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- WDTBPWKPLTZJPQ-UHFFFAOYSA-N 2-amino-1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 WDTBPWKPLTZJPQ-UHFFFAOYSA-N 0.000 claims description 2
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- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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| PCT/EP2011/053818 WO2011113798A2 (en) | 2010-03-15 | 2011-03-14 | New enzyme inhibitor compounds |
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| WO2011146313A1 (en) | 2010-05-19 | 2011-11-24 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| EP2755974A1 (en) * | 2011-09-14 | 2014-07-23 | Proximagen Limited | New enzyme inhibitor compounds |
| GB201115853D0 (en) * | 2011-09-14 | 2011-10-26 | Proximagen Ltd | New enzyme inhibitor compounds |
| BR112014007788A2 (pt) | 2011-10-03 | 2017-04-18 | Univ North Carolina Chapel Hill | compostos de pirrolopirimidina para tratamento do câncer |
| EP3438087A1 (en) | 2012-05-02 | 2019-02-06 | Boehringer Ingelheim International GmbH | Substituted 3-haloallylamine inhibitors of ssao and uses thereof |
| CN104302627A (zh) | 2012-05-22 | 2015-01-21 | 北卡罗来纳大学教堂山分校 | 用于治疗癌症的嘧啶化合物 |
| WO2014026330A1 (en) * | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| WO2014062774A1 (en) | 2012-10-17 | 2014-04-24 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| US9771330B2 (en) | 2012-11-27 | 2017-09-26 | The University Of North Carolina At Chapel Hill | Pyrimidine compounds for the treatment of cancer |
| GB201304527D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304526D0 (en) * | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| WO2014199171A1 (en) | 2013-06-12 | 2014-12-18 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| US20150291606A1 (en) | 2014-04-11 | 2015-10-15 | The University Of North Carolina At Chapel Hill | Mertk-specific pyrrolopyrimidine compounds |
| WO2015188368A1 (en) | 2014-06-13 | 2015-12-17 | Merck Sharp & Dohme Corp. | Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles |
| GB201416446D0 (en) | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| GB201416444D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| KR102412146B1 (ko) * | 2015-02-11 | 2022-06-22 | 주식회사 아이엔테라퓨틱스 | 소디움 채널 차단제 |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| HK1256174A1 (zh) | 2015-12-07 | 2019-09-13 | Benevolentai Cambridge Limited | 用於治疗疼痛的 vap-1 抑制剂 |
| US10709708B2 (en) | 2016-03-17 | 2020-07-14 | The University Of North Carolina At Chapel Hill | Method of treating cancer with a combination of MER tyrosine kinase inhibitor and an epidermal growth factor receptor (EGFR) inhibitor |
| CN106045876B (zh) * | 2016-06-07 | 2018-02-09 | 四川福思达生物技术开发有限责任公司 | 一种对氯苯肼盐酸盐的合成方法 |
| US10899758B2 (en) * | 2016-09-16 | 2021-01-26 | Vitae Pharmaceuticals, Llc | Inhibitors of the menin-MLL interaction |
| AU2019234574A1 (en) | 2018-03-12 | 2020-09-03 | Abbvie Inc. | Inhibitors of tyrosine kinase 2 mediated signaling |
| WO2022253167A1 (en) | 2021-06-01 | 2022-12-08 | Janssen Pharmaceutica Nv | SUBSTITUTED PHENYL-1H-PYRROLO [2, 3-c] PYRIDINE DERIVATIVES |
| AU2022357057A1 (en) * | 2021-10-01 | 2024-04-11 | Yuhan Corporation | Bicyclic fused ring derivative or salt thereof and pharmaceutical composition comprising same |
| EP4436957A1 (en) | 2021-11-24 | 2024-10-02 | Genentech, Inc. | Therapeutic indazole compounds and methods of use in the treatment of cancer |
| TW202340212A (zh) | 2021-11-24 | 2023-10-16 | 美商建南德克公司 | 治療性化合物及其使用方法 |
| WO2023193790A1 (en) * | 2022-04-08 | 2023-10-12 | Janssen Pharmaceutica Nv | Crystalline forms of an inhibitor of the menin/mll interaction |
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| WO2011019060A1 (ja) * | 2009-08-12 | 2011-02-17 | 協和発酵キリン株式会社 | ヘッジホッグシグナル阻害剤 |
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| DE19649460A1 (de) | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
| PT1216244E (pt) * | 1999-09-14 | 2003-12-31 | Aventis Pharma Inc | Derivados de benzisoxazolil- piridoisoxazolil- e benztienil-fenoxi uteis como antagonistas d4 |
| WO2002038153A1 (en) | 2000-11-09 | 2002-05-16 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-[4,5-c]pyridine derivatives |
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-
2010
- 2010-03-15 GB GBGB1004311.5A patent/GB201004311D0/en not_active Ceased
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2011
- 2011-03-14 WO PCT/EP2011/053818 patent/WO2011113798A2/en not_active Ceased
- 2011-03-14 JP JP2012557516A patent/JP5643347B2/ja not_active Expired - Fee Related
- 2011-03-14 SG SG2012066023A patent/SG183936A1/en unknown
- 2011-03-14 CN CN2011800140213A patent/CN103180319A/zh active Pending
- 2011-03-14 NZ NZ602141A patent/NZ602141A/en not_active IP Right Cessation
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- 2011-03-14 EP EP15158284.8A patent/EP2927233A1/en not_active Withdrawn
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- 2011-03-14 EP EP20110707689 patent/EP2547677B1/en not_active Not-in-force
- 2011-03-14 EA EA201290880A patent/EA023038B1/ru not_active IP Right Cessation
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2014
- 2014-10-30 JP JP2014221061A patent/JP2015017141A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006114180A1 (de) * | 2005-04-25 | 2006-11-02 | Merck Patent Gmbh | Neuartige aza-heterozyklen als kinase-inhibitoren |
| WO2009108551A2 (en) * | 2008-02-25 | 2009-09-03 | H. Lundbeck A/S | Heteroaryl amide analogues |
| WO2011019060A1 (ja) * | 2009-08-12 | 2011-02-17 | 協和発酵キリン株式会社 | ヘッジホッグシグナル阻害剤 |
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| ZA201206424B (en) | 2013-06-26 |
| EP2547677A2 (en) | 2013-01-23 |
| EP2927233A1 (en) | 2015-10-07 |
| GB201004311D0 (en) | 2010-04-28 |
| US20130102587A1 (en) | 2013-04-25 |
| DK2547677T3 (en) | 2015-06-01 |
| KR20130057971A (ko) | 2013-06-03 |
| JP2013529179A (ja) | 2013-07-18 |
| MX2012010292A (es) | 2013-03-12 |
| EP2547677B1 (en) | 2015-05-06 |
| WO2011113798A3 (en) | 2011-11-17 |
| US9227967B2 (en) | 2016-01-05 |
| BR112012023315A2 (pt) | 2016-05-24 |
| AU2011229267B2 (en) | 2013-07-18 |
| NZ602141A (en) | 2014-09-26 |
| JP5643347B2 (ja) | 2014-12-17 |
| CA2793125A1 (en) | 2011-09-22 |
| ES2538526T3 (es) | 2015-06-22 |
| JP2015017141A (ja) | 2015-01-29 |
| EA201290880A1 (ru) | 2013-03-29 |
| CN103180319A (zh) | 2013-06-26 |
| AU2011229267A1 (en) | 2012-09-20 |
| WO2011113798A2 (en) | 2011-09-22 |
| SG183936A1 (en) | 2012-10-30 |
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