CN105008367B - 作为钾离子通道抑制剂的吡咯并三嗪类化合物 - Google Patents
作为钾离子通道抑制剂的吡咯并三嗪类化合物 Download PDFInfo
- Publication number
- CN105008367B CN105008367B CN201480013619.4A CN201480013619A CN105008367B CN 105008367 B CN105008367 B CN 105008367B CN 201480013619 A CN201480013619 A CN 201480013619A CN 105008367 B CN105008367 B CN 105008367B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- cycloalkyl
- membered
- phenyl
- substituted
- 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 CC1NC*CCN*1 Chemical compound CC1NC*CCN*1 0.000 description 25
- GTLZPFBXTPUGHQ-UHFFFAOYSA-N Brc1cncc(C2OC2)c1 Chemical compound Brc1cncc(C2OC2)c1 GTLZPFBXTPUGHQ-UHFFFAOYSA-N 0.000 description 1
- RNGPPSXPRNACLB-UHFFFAOYSA-N C(c1ccccc1)Nc1n[nH][n](cc2)c1c2-c1ccccc1 Chemical compound C(c1ccccc1)Nc1n[nH][n](cc2)c1c2-c1ccccc1 RNGPPSXPRNACLB-UHFFFAOYSA-N 0.000 description 1
- LOGVHBXNFUZUIO-UHFFFAOYSA-N CC(/N=C(\c([nH]cc1)c1C1=CC=CCC1)/NCc1ccccc1)=N Chemical compound CC(/N=C(\c([nH]cc1)c1C1=CC=CCC1)/NCc1ccccc1)=N LOGVHBXNFUZUIO-UHFFFAOYSA-N 0.000 description 1
- WXLBNANPLSOEPM-UHFFFAOYSA-N CC(C)(C)OC([n]1c(C(OC)=O)c(BC=C)cc1)=O Chemical compound CC(C)(C)OC([n]1c(C(OC)=O)c(BC=C)cc1)=O WXLBNANPLSOEPM-UHFFFAOYSA-N 0.000 description 1
- VBVQQAOWNGLZKG-UHFFFAOYSA-N CC(C)(OC1)OC1c1cc(-c(nc2NCC3C=CC=CC3)n[n](cc3)c2c3-c2ccccc2)cnc1 Chemical compound CC(C)(OC1)OC1c1cc(-c(nc2NCC3C=CC=CC3)n[n](cc3)c2c3-c2ccccc2)cnc1 VBVQQAOWNGLZKG-UHFFFAOYSA-N 0.000 description 1
- OUBARNFGCYHQBF-UHFFFAOYSA-N CC(C)(OC1)OC1c1cc([Br]=C)cnc1 Chemical compound CC(C)(OC1)OC1c1cc([Br]=C)cnc1 OUBARNFGCYHQBF-UHFFFAOYSA-N 0.000 description 1
- ARIDPRZCOYMNQD-UHFFFAOYSA-N CC1=NCCCN1 Chemical compound CC1=NCCCN1 ARIDPRZCOYMNQD-UHFFFAOYSA-N 0.000 description 1
- BUJFTKPQXSIZFX-UHFFFAOYSA-N CCC(C)(C)NC Chemical compound CCC(C)(C)NC BUJFTKPQXSIZFX-UHFFFAOYSA-N 0.000 description 1
- GPVVCMURZQLGEW-BCKIYVKGSA-N CCC(CNc1nc(-c2cncc(C(O)=O)c2)n[n](cc2)c1c2-c1ccccc1)/C=C\C=C/N Chemical compound CCC(CNc1nc(-c2cncc(C(O)=O)c2)n[n](cc2)c1c2-c1ccccc1)/C=C\C=C/N GPVVCMURZQLGEW-BCKIYVKGSA-N 0.000 description 1
- CRFIVNGQUXPWPY-UHFFFAOYSA-N COC(C(CCC1)N1C(c1cncc(-c(nc2NCc3ccccc3)n[n](cc3)c2c3-c2ccccc2)c1)=O)=O Chemical compound COC(C(CCC1)N1C(c1cncc(-c(nc2NCc3ccccc3)n[n](cc3)c2c3-c2ccccc2)c1)=O)=O CRFIVNGQUXPWPY-UHFFFAOYSA-N 0.000 description 1
- MHUQMBRORGZPQJ-UHFFFAOYSA-N Cc(nc1Cl)n[n](cc2)c1c2-c1ccccc1 Chemical compound Cc(nc1Cl)n[n](cc2)c1c2-c1ccccc1 MHUQMBRORGZPQJ-UHFFFAOYSA-N 0.000 description 1
- NTWSIHDXQCZTIB-UHFFFAOYSA-N NCCOc1nccnc1 Chemical compound NCCOc1nccnc1 NTWSIHDXQCZTIB-UHFFFAOYSA-N 0.000 description 1
- XMMNUXARWDMLLC-UHFFFAOYSA-N OC(CCc1cc(-c(nc2NCc3ccccc3)n[n](cc3)c2c3-c2ccccc2)cnc1)=O Chemical compound OC(CCc1cc(-c(nc2NCc3ccccc3)n[n](cc3)c2c3-c2ccccc2)cnc1)=O XMMNUXARWDMLLC-UHFFFAOYSA-N 0.000 description 1
- SXAXXCFYHZWNHH-UHFFFAOYSA-N OC(c1cncc(-c(nc2NCc3ccccn3)n[n](cc3)c2c3-c2ccccc2)c1)=O Chemical compound OC(c1cncc(-c(nc2NCc3ccccn3)n[n](cc3)c2c3-c2ccccc2)c1)=O SXAXXCFYHZWNHH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361775731P | 2013-03-11 | 2013-03-11 | |
| US61/775731 | 2013-03-11 | ||
| US14/200055 | 2014-03-07 | ||
| US14/200,055 US9050345B2 (en) | 2013-03-11 | 2014-03-07 | Pyrrolotriazines as potassium ion channel inhibitors |
| PCT/US2014/022265 WO2014143610A1 (en) | 2013-03-11 | 2014-03-10 | Pyrrolotriazines as potassium ion channel inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105008367A CN105008367A (zh) | 2015-10-28 |
| CN105008367B true CN105008367B (zh) | 2017-08-29 |
Family
ID=51488539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480013619.4A Expired - Fee Related CN105008367B (zh) | 2013-03-11 | 2014-03-10 | 作为钾离子通道抑制剂的吡咯并三嗪类化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9050345B2 (enExample) |
| EP (1) | EP2970296B1 (enExample) |
| JP (1) | JP6427551B2 (enExample) |
| CN (1) | CN105008367B (enExample) |
| AR (1) | AR095208A1 (enExample) |
| TW (1) | TW201444847A (enExample) |
| UY (1) | UY35381A (enExample) |
| WO (1) | WO2014143610A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2858987T3 (pl) * | 2012-06-11 | 2018-08-31 | Bristol-Myers Squibb Company | Proleki kwasu fosforoamidowego 5-[5-fenylo-4-(pirydyno-2-ylometylamino)chinazolino-2-ylo]pirydyno-3-sulfonamidu |
| US9458133B2 (en) | 2013-03-11 | 2016-10-04 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| ES2616025T3 (es) | 2013-03-11 | 2017-06-09 | Bristol-Myers Squibb Company | Pirrolotriazinas como inhibidores de canales de iones potasio |
| EP2970295B1 (en) | 2013-03-11 | 2016-12-28 | Bristol-Myers Squibb Company | Pyrrolopyridazines as potassium ion channel inhibitors |
| WO2017004134A1 (en) * | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| JP2018528951A (ja) * | 2015-08-31 | 2018-10-04 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | TGFβ受容体アンタゴニスト |
| CN105111154A (zh) * | 2015-09-15 | 2015-12-02 | 上海瑞博化学有限公司 | 一种5-氨基吡嗪-2-甲酸合成新工艺 |
| SG11201804901WA (en) | 2015-12-22 | 2018-07-30 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| PT3436461T (pt) | 2016-03-28 | 2024-01-23 | Incyte Corp | Compostos de pirrolotriazina como inibidores de tam |
| DK3450436T3 (da) * | 2016-04-28 | 2022-09-12 | Takeda Pharmaceuticals Co | Kondenseret heterocyklisk forbindelse |
| WO2018204721A1 (en) | 2017-05-05 | 2018-11-08 | Nino Sorgente | Methods and compositions for improving eye health |
| US11382881B2 (en) | 2017-05-05 | 2022-07-12 | Nino Sorgente | Methods and compositions for diagnosing and treating glaucoma |
| CA3066939A1 (en) | 2017-06-21 | 2018-12-27 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| WO2020132071A1 (en) | 2018-12-19 | 2020-06-25 | Shy Therapeutics. Llc | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and f1brotic disease |
| CN111825675B (zh) * | 2019-04-15 | 2023-08-01 | 武汉朗来科技发展有限公司 | Rock抑制剂及其制备方法和用途 |
| US20230416248A1 (en) * | 2020-11-10 | 2023-12-28 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| CA3246424A1 (en) | 2022-04-08 | 2023-10-12 | SHY Therapeutics LLC | Compounds interacting with proteins of the RAS superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| EP4522280A1 (en) | 2022-05-11 | 2025-03-19 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| CN116063183B (zh) * | 2023-01-28 | 2023-06-27 | 山东国邦药业有限公司 | 一种环丙胺的合成方法 |
| WO2025077671A1 (zh) * | 2023-10-09 | 2025-04-17 | 浙江海正药业股份有限公司 | 多取代芳基类衍生物及其制备方法和用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071129A1 (en) * | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| WO2002040486A2 (en) * | 2000-11-17 | 2002-05-23 | Bristol-Myers Squibb Company | METHODS OF TREATING p38 KINASE-ASSOCIATED CONDITIONS AND PYRROLOTRIAZINE COMPOUNDS USEFUL AS KINASE INHIBITORS |
| WO2009026254A1 (en) * | 2007-08-17 | 2009-02-26 | Icagen, Inc. | Heterocycles as potassium channel modulators |
| US20120232068A1 (en) * | 2009-09-03 | 2012-09-13 | Briston-Myers Squibb Company | Quinazolines as potassium ion channel inhibitors |
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| US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| KR20010083092A (ko) | 1998-07-06 | 2001-08-31 | 스티븐 비. 데이비스 | 이중 안지오텐신 엔도텔린 수용체 길항제로서의 비페닐술폰아미드 |
| US6867300B2 (en) | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| TWI329112B (en) | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| AU2003265349A1 (en) | 2002-08-02 | 2004-02-23 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| TW200420565A (en) * | 2002-12-13 | 2004-10-16 | Bristol Myers Squibb Co | C-6 modified indazolylpyrrolotriazines |
| KR20050099525A (ko) | 2003-02-05 | 2005-10-13 | 브리스톨-마이어스 스큅 컴퍼니 | 피롤로트리아진 키나제 억제제의 제조 방법 |
| US7504521B2 (en) | 2004-08-05 | 2009-03-17 | Bristol-Myers Squibb Co. | Methods for the preparation of pyrrolotriazine compounds |
| AU2005288858B2 (en) | 2004-09-30 | 2011-04-21 | Janssen R&D Ireland | HCV inhibiting bi-cyclic pyrimidines |
| ATE479687T1 (de) | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| MX2008011136A (es) | 2006-03-07 | 2008-09-08 | Squibb Bristol Myers Co | Compuestos de profamarco de pirrolotriazina anilina utiles como inhibidores de cinasa. |
| WO2007107005A1 (en) | 2006-03-22 | 2007-09-27 | Methylgene, Inc. | Inhibitors of protein tyrosine kinase activity |
| PT2041138E (pt) | 2006-07-07 | 2014-10-07 | Bristol Myers Squibb Co | Inibidores de pirrolotriazina quinase |
| US7531539B2 (en) | 2006-08-09 | 2009-05-12 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| WO2008057402A2 (en) | 2006-11-02 | 2008-05-15 | Cytovia, Inc. | N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| WO2008131050A1 (en) | 2007-04-18 | 2008-10-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| DE102007051762A1 (de) * | 2007-10-30 | 2009-05-07 | Bayer Healthcare Ag | Substituierte Pyrrolotriazine und ihre Verwendung |
| WO2009111531A1 (en) | 2008-03-06 | 2009-09-11 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| WO2010002472A1 (en) | 2008-07-02 | 2010-01-07 | Ambit Biosciences Corporation | Jak kinase modulating compounds and methods of use thereof |
| JP5592890B2 (ja) * | 2008-10-08 | 2014-09-17 | ブリストル−マイヤーズ スクイブ カンパニー | ピロロトリアジンキナーゼ阻害剤 |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| WO2011018894A1 (en) * | 2009-08-10 | 2011-02-17 | Raqualia Pharma Inc. | Pyrrolopyrimidine derivatives as potassium channel modulators |
| US20120077814A1 (en) | 2010-09-10 | 2012-03-29 | Zhong Wang | Sulfonamide, sulfamate, and sulfamothioate derivatives |
| JO3003B1 (ar) | 2011-01-14 | 2016-09-05 | Lilly Co Eli | مركب أيميدازو [4، 5 -c ] كينولين-2- واحد واستخدامه كمثبط كيناز PI3/mtor |
| CN103373996A (zh) | 2012-04-20 | 2013-10-30 | 山东亨利医药科技有限责任公司 | 作为crth2受体拮抗剂的二并环衍生物 |
| PL2858987T3 (pl) * | 2012-06-11 | 2018-08-31 | Bristol-Myers Squibb Company | Proleki kwasu fosforoamidowego 5-[5-fenylo-4-(pirydyno-2-ylometylamino)chinazolino-2-ylo]pirydyno-3-sulfonamidu |
-
2014
- 2014-03-07 US US14/200,055 patent/US9050345B2/en active Active
- 2014-03-10 CN CN201480013619.4A patent/CN105008367B/zh not_active Expired - Fee Related
- 2014-03-10 EP EP14713005.8A patent/EP2970296B1/en not_active Not-in-force
- 2014-03-10 WO PCT/US2014/022265 patent/WO2014143610A1/en not_active Ceased
- 2014-03-10 JP JP2016500933A patent/JP6427551B2/ja not_active Expired - Fee Related
- 2014-03-10 AR ARP140100817A patent/AR095208A1/es unknown
- 2014-03-10 TW TW103108204A patent/TW201444847A/zh unknown
- 2014-03-11 UY UY0001035381A patent/UY35381A/es unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071129A1 (en) * | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| CN1351498A (zh) * | 1999-05-21 | 2002-05-29 | 布里斯托尔-迈尔斯斯奎布公司 | 激酶的吡咯并三嗪抑制剂 |
| WO2002040486A2 (en) * | 2000-11-17 | 2002-05-23 | Bristol-Myers Squibb Company | METHODS OF TREATING p38 KINASE-ASSOCIATED CONDITIONS AND PYRROLOTRIAZINE COMPOUNDS USEFUL AS KINASE INHIBITORS |
| CN1622946A (zh) * | 2000-11-17 | 2005-06-01 | 布里斯托尔-迈尔斯斯奎布公司 | 治疗与p38激酶有关的症状的方法以及用作激酶抑制剂的吡咯并三嗪化合物 |
| WO2009026254A1 (en) * | 2007-08-17 | 2009-02-26 | Icagen, Inc. | Heterocycles as potassium channel modulators |
| CN101842011A (zh) * | 2007-08-17 | 2010-09-22 | 安克进药物公司 | 作为钾通道调节剂的杂环 |
| US20120232068A1 (en) * | 2009-09-03 | 2012-09-13 | Briston-Myers Squibb Company | Quinazolines as potassium ion channel inhibitors |
| CN102753535A (zh) * | 2009-09-03 | 2012-10-24 | 百时美施贵宝公司 | 作为钾离子通道抑制剂的喹唑啉 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2970296B1 (en) | 2016-12-21 |
| US9050345B2 (en) | 2015-06-09 |
| TW201444847A (zh) | 2014-12-01 |
| JP2016512505A (ja) | 2016-04-28 |
| WO2014143610A1 (en) | 2014-09-18 |
| UY35381A (es) | 2014-09-30 |
| EP2970296A1 (en) | 2016-01-20 |
| AR095208A1 (es) | 2015-09-30 |
| US20140256719A1 (en) | 2014-09-11 |
| JP6427551B2 (ja) | 2018-11-21 |
| CN105008367A (zh) | 2015-10-28 |
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