JP6267231B2 - カゼインキナーゼ1δ/ε阻害剤としての新規な置換イミダゾール - Google Patents
カゼインキナーゼ1δ/ε阻害剤としての新規な置換イミダゾール Download PDFInfo
- Publication number
- JP6267231B2 JP6267231B2 JP2015549756A JP2015549756A JP6267231B2 JP 6267231 B2 JP6267231 B2 JP 6267231B2 JP 2015549756 A JP2015549756 A JP 2015549756A JP 2015549756 A JP2015549756 A JP 2015549756A JP 6267231 B2 JP6267231 B2 JP 6267231B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- heterocyclyl
- carbocyclyl
- compound
- 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 - Fee Related
Links
- 0 *C(Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2I)nc2[n]1NCC=C2)=O Chemical compound *C(Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2I)nc2[n]1NCC=C2)=O 0.000 description 5
- GHFGSPPYGNSDIB-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(N)c3)c(-c(cc2)ccc2F)nc1C1CC1)=O Chemical compound CC(C)(C)OC(N(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(N)c3)c(-c(cc2)ccc2F)nc1C1CC1)=O GHFGSPPYGNSDIB-UHFFFAOYSA-N 0.000 description 1
- BWRBGJBNKVSWCN-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(C)=O)c3)c(-c(cc2)ccc2F)nc1)=O Chemical compound CC(C)(C)OC(N(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(C)=O)c3)c(-c(cc2)ccc2F)nc1)=O BWRBGJBNKVSWCN-UHFFFAOYSA-N 0.000 description 1
- ANANEWVZGRNJNN-UHFFFAOYSA-N CC(NC(c(cc1)ccc1F)S(c1ccc(C)cc1)(=O)=O)=O Chemical compound CC(NC(c(cc1)ccc1F)S(c1ccc(C)cc1)(=O)=O)=O ANANEWVZGRNJNN-UHFFFAOYSA-N 0.000 description 1
- QVOJTBNUMGJQSX-UHFFFAOYSA-N CC(Nc(nc1cc2)c[n]1nc2Cl)=O Chemical compound CC(Nc(nc1cc2)c[n]1nc2Cl)=O QVOJTBNUMGJQSX-UHFFFAOYSA-N 0.000 description 1
- WURYPQPUVUDCRZ-UHFFFAOYSA-N CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccncc2)=O)c3)c(-c(cc2)ccc2F)nc1 Chemical compound CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccncc2)=O)c3)c(-c(cc2)ccc2F)nc1 WURYPQPUVUDCRZ-UHFFFAOYSA-N 0.000 description 1
- JQDQVPVSACYZHG-UHFFFAOYSA-N COC(c(cc1)n[n]2c1nc(NC(c1c[s]c(-c3ccncc3)n1)=O)c2)=O Chemical compound COC(c(cc1)n[n]2c1nc(NC(c1c[s]c(-c3ccncc3)n1)=O)c2)=O JQDQVPVSACYZHG-UHFFFAOYSA-N 0.000 description 1
- MGSCZIZFTPZFOP-UHFFFAOYSA-N Cc1nc(-c(cc2)ccc2F)c(-c(cc2)n[n]3c2nc(N)c3)[n]1C Chemical compound Cc1nc(-c(cc2)ccc2F)c(-c(cc2)n[n]3c2nc(N)c3)[n]1C MGSCZIZFTPZFOP-UHFFFAOYSA-N 0.000 description 1
- ZSOOVSKWBMKKQH-UHFFFAOYSA-N Fc(cc1)ccc1-c1c[n](C2CCOCC2)cn1 Chemical compound Fc(cc1)ccc1-c1c[n](C2CCOCC2)cn1 ZSOOVSKWBMKKQH-UHFFFAOYSA-N 0.000 description 1
- OQPKHWUHNNRULF-UHFFFAOYSA-N Fc(cc1)ccc1-c1c[n](CCC2)c2n1 Chemical compound Fc(cc1)ccc1-c1c[n](CCC2)c2n1 OQPKHWUHNNRULF-UHFFFAOYSA-N 0.000 description 1
- NKIQEILZYPFNFA-UHFFFAOYSA-N Fc(cc1)ccc1-c1c[n](cc(cc2)Br)c2n1 Chemical compound Fc(cc1)ccc1-c1c[n](cc(cc2)Br)c2n1 NKIQEILZYPFNFA-UHFFFAOYSA-N 0.000 description 1
- NBLHICOAIJOVDF-UHFFFAOYSA-N NC(CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccnc4c2cccc4)=O)c3)c(-c(cc2)ccc2F)nc1)=O Chemical compound NC(CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccnc4c2cccc4)=O)c3)c(-c(cc2)ccc2F)nc1)=O NBLHICOAIJOVDF-UHFFFAOYSA-N 0.000 description 1
- AVDIQKQOLWAISB-UHFFFAOYSA-N Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc(cc2)[n]1cc2N1CCOCC1 Chemical compound Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc(cc2)[n]1cc2N1CCOCC1 AVDIQKQOLWAISB-UHFFFAOYSA-N 0.000 description 1
- GOSZBVDOIHYVQM-UHFFFAOYSA-N Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1CCNC2 Chemical compound Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1CCNC2 GOSZBVDOIHYVQM-UHFFFAOYSA-N 0.000 description 1
- RUBLXROTKDVNOG-UHFFFAOYSA-N Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1cccc2 Chemical compound Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1cccc2 RUBLXROTKDVNOG-UHFFFAOYSA-N 0.000 description 1
- UYBLFZBVBKCICC-UHFFFAOYSA-N Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCOCC1 Chemical compound Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCOCC1 UYBLFZBVBKCICC-UHFFFAOYSA-N 0.000 description 1
- KQUFIRRPLCJGGX-UHFFFAOYSA-N Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1CCN1CCOCC1 Chemical compound Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1CCN1CCOCC1 KQUFIRRPLCJGGX-UHFFFAOYSA-N 0.000 description 1
- DDHDBAOPZCGYMJ-UHFFFAOYSA-N O=C(c1cc(F)nc(F)c1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 Chemical compound O=C(c1cc(F)nc(F)c1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 DDHDBAOPZCGYMJ-UHFFFAOYSA-N 0.000 description 1
- DKCVJBNVFFJGJY-UHFFFAOYSA-N O=C(c1cc(F)nc(F)c1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCNCC1 Chemical compound O=C(c1cc(F)nc(F)c1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCNCC1 DKCVJBNVFFJGJY-UHFFFAOYSA-N 0.000 description 1
- VEJPKYUJLGXYMG-UHFFFAOYSA-N O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc(C2CC2)[n]1C1CCN(Cc2n[o]cc2)CC1 Chemical compound O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc(C2CC2)[n]1C1CCN(Cc2n[o]cc2)CC1 VEJPKYUJLGXYMG-UHFFFAOYSA-N 0.000 description 1
- KNSFETGCZAWZND-UHFFFAOYSA-N O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1CCCC2 Chemical compound O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc2[n]1CCCC2 KNSFETGCZAWZND-UHFFFAOYSA-N 0.000 description 1
- PFONAMGEFWUYAQ-UHFFFAOYSA-N O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 Chemical compound O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 PFONAMGEFWUYAQ-UHFFFAOYSA-N 0.000 description 1
- IPPLZBANPLRABR-UHFFFAOYSA-N O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCNCC1 Chemical compound O=C(c1cc(F)ncc1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCNCC1 IPPLZBANPLRABR-UHFFFAOYSA-N 0.000 description 1
- BQRSEOWMPIJJOD-UHFFFAOYSA-N O=C(c1cnc[s]1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 Chemical compound O=C(c1cnc[s]1)Nc(nc1cc2)c[n]1nc2-c1c(-c(cc2)ccc2F)nc[n]1C1CCN(CCC(F)(F)F)CC1 BQRSEOWMPIJJOD-UHFFFAOYSA-N 0.000 description 1
- ABFOSAMDGDQJQF-UHFFFAOYSA-N O=Cc(cc1)n[n]2c1nc(NC(c1ccnc(F)c1)=O)c2 Chemical compound O=Cc(cc1)n[n]2c1nc(NC(c1ccnc(F)c1)=O)c2 ABFOSAMDGDQJQF-UHFFFAOYSA-N 0.000 description 1
- SSHWVLCETWOFII-HSZRJFAPSA-N O[C@H](CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccncc2)=O)c3)c(-c(cc2)ccc2F)nc1)C(F)(F)F Chemical compound O[C@H](CN(CC1)CCC1[n]1c(-c(cc2)n[n]3c2nc(NC(c2ccncc2)=O)c3)c(-c(cc2)ccc2F)nc1)C(F)(F)F SSHWVLCETWOFII-HSZRJFAPSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261740564P | 2012-12-21 | 2012-12-21 | |
| US61/740,564 | 2012-12-21 | ||
| PCT/US2013/076795 WO2014100533A1 (en) | 2012-12-21 | 2013-12-20 | NOVEL SUBSTITUTED IMIDAZOLES AS CASEIN KINASE 1 δ/ε INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016507502A JP2016507502A (ja) | 2016-03-10 |
| JP2016507502A5 JP2016507502A5 (enExample) | 2017-01-12 |
| JP6267231B2 true JP6267231B2 (ja) | 2018-01-24 |
Family
ID=49943572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015549756A Expired - Fee Related JP6267231B2 (ja) | 2012-12-21 | 2013-12-20 | カゼインキナーゼ1δ/ε阻害剤としての新規な置換イミダゾール |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9556179B2 (enExample) |
| EP (1) | EP2935271B1 (enExample) |
| JP (1) | JP6267231B2 (enExample) |
| CN (1) | CN105073751B (enExample) |
| WO (1) | WO2014100533A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104837844B (zh) | 2012-12-21 | 2017-08-29 | 百时美施贵宝公司 | 作为酪蛋白激酶1 d/e抑制剂的吡唑取代的咪唑并哌嗪 |
| CN106661056B (zh) * | 2014-06-19 | 2019-07-05 | 百时美施贵宝公司 | 作为酪蛋白激酶1δ/ε抑制剂的咪唑并哒嗪衍生物 |
| WO2016081364A1 (en) | 2014-11-21 | 2016-05-26 | Rigel Pharmaceuticals, Inc. | Fused imidazole derivatives as tgf-beta inhibitors |
| KR20170122799A (ko) | 2015-03-02 | 2017-11-06 | 리겔 파마슈티칼스, 인크. | TGF-β 억제제 |
| US10722513B2 (en) | 2015-03-23 | 2020-07-28 | The University Of Melbourne | Treatment of respiratory diseases |
| US10526325B2 (en) | 2015-07-31 | 2020-01-07 | Merck Patent Gmbh | Bicyclic heterocyclic derivatives |
| US11053202B2 (en) | 2016-09-21 | 2021-07-06 | Vectus Biosystems Limited | Compositions for the treatment of hypertension and/or fibrosis |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| EP3774795B1 (en) * | 2018-03-29 | 2022-03-16 | Masarykova Univerzita | 4-(1h- imidazol- 5- yl) -1h-pyrrolo [2, 3-b] pyridines for use in the treatment of leukaemias, lymphomas and solid tumors |
| CN113301900B (zh) * | 2018-09-09 | 2024-11-29 | 夸纳特制药股份公司 | 酪蛋白激酶1抑制剂在治疗血管疾病中的应用 |
| AU2019374731B2 (en) | 2018-11-07 | 2025-08-21 | Tianli Biotech Pty Ltd | Compounds and compositions for the treatment of respiratory diseases |
| US11795160B2 (en) | 2019-02-22 | 2023-10-24 | Insilico Medicine Ip Limited | Kinase inhibitors |
| JP2024508818A (ja) | 2021-02-24 | 2024-02-28 | インシリコ メディシン アイピー リミテッド | 疾患の処置のための類似体 |
| WO2025231112A1 (en) * | 2024-05-01 | 2025-11-06 | Nimbus Salacia, Inc. | Sik2 modulators and uses thereof |
| WO2025231117A1 (en) * | 2024-05-01 | 2025-11-06 | Nimbus Salacia, Inc. | Sik2 modulators and uses thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1532118A2 (en) * | 2002-07-05 | 2005-05-25 | Axxima Pharmaceuticals Aktiengesellschaft | Imidazole compounds for the treatment of hepatitis c virus infections |
| US20070078136A1 (en) | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| EP2058309A4 (en) * | 2006-08-04 | 2010-12-22 | Takeda Pharmaceutical | CONDENSED HETEROCYCLIC COMPOUND |
| US8188083B2 (en) * | 2007-06-28 | 2012-05-29 | Abbott Laboratories | Triazolopyridazines |
| FR2918986B1 (fr) * | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| US7820665B2 (en) | 2007-12-19 | 2010-10-26 | Amgen Inc. | Imidazopyridazine inhibitors of PI3 kinase for cancer treatment |
| WO2009137081A2 (en) | 2008-05-07 | 2009-11-12 | Massachusetts Institute Of Technology | Small molecule inhibitors of plasmodium falciparum dihydroorotate dehydrogenase |
| TWI501965B (zh) | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為pde10a酵素抑制劑之新穎苯基咪唑衍生物 |
| FR2940284B1 (fr) | 2008-12-19 | 2011-02-18 | Sanofi Aventis | Derives de 6-cycloamino-2,3-di-pyridinyl-imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique |
| FR2940285A1 (fr) | 2008-12-19 | 2010-06-25 | Sanofi Aventis | Derives de 6-cycloamino-2-thienyl-3-(pyridin-4-yl)imidazo °1,2-b!-pyridazine et 6-cycloamino-2-furanyl-3- (pyridin-4-yl)imidazo°1,2-b!-pyridazine, leur preparation et leur application en therapeutique |
| US20100204265A1 (en) | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
| UA107791C2 (en) | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| JP5784620B2 (ja) | 2009-10-28 | 2015-09-24 | ファイザー・インク | カゼインキナーゼ阻害剤としてのイミダゾール誘導体 |
| CN104837844B (zh) | 2012-12-21 | 2017-08-29 | 百时美施贵宝公司 | 作为酪蛋白激酶1 d/e抑制剂的吡唑取代的咪唑并哌嗪 |
-
2013
- 2013-12-20 JP JP2015549756A patent/JP6267231B2/ja not_active Expired - Fee Related
- 2013-12-20 EP EP13818937.8A patent/EP2935271B1/en not_active Not-in-force
- 2013-12-20 CN CN201380073382.4A patent/CN105073751B/zh not_active Expired - Fee Related
- 2013-12-20 WO PCT/US2013/076795 patent/WO2014100533A1/en not_active Ceased
- 2013-12-20 US US14/653,895 patent/US9556179B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2935271B1 (en) | 2017-10-25 |
| US20150344481A1 (en) | 2015-12-03 |
| EP2935271A1 (en) | 2015-10-28 |
| WO2014100533A1 (en) | 2014-06-26 |
| CN105073751A (zh) | 2015-11-18 |
| JP2016507502A (ja) | 2016-03-10 |
| US9556179B2 (en) | 2017-01-31 |
| CN105073751B (zh) | 2018-11-30 |
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