JPWO2019231270A5 - - Google Patents
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- JPWO2019231270A5 JPWO2019231270A5 JP2020566706A JP2020566706A JPWO2019231270A5 JP WO2019231270 A5 JPWO2019231270 A5 JP WO2019231270A5 JP 2020566706 A JP2020566706 A JP 2020566706A JP 2020566706 A JP2020566706 A JP 2020566706A JP WO2019231270 A5 JPWO2019231270 A5 JP WO2019231270A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- pyrazine
- pyrido
- bromo
- alkyl
- 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.)
- Pending
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- NTYJJOPFIAHURM-UHFFFAOYSA-N histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 68
- 229960001340 histamine Drugs 0.000 claims description 34
- -1 -I) Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 21
- DCBOUXKSNFDXER-UHFFFAOYSA-N 1H-pyrido[2,3-b]pyrazin-2-one Chemical compound C1=CC=C2NC(=O)C=NC2=N1 DCBOUXKSNFDXER-UHFFFAOYSA-N 0.000 claims description 18
- 239000011780 sodium chloride Substances 0.000 claims description 16
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 12
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical group CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims description 10
- XGXKZNXCORZWLV-UHFFFAOYSA-N 1H-pyrido[3,4-b]pyrazin-2-one Chemical compound N1=CC=C2NC(=O)C=NC2=C1 XGXKZNXCORZWLV-UHFFFAOYSA-N 0.000 claims description 9
- 208000003251 Pruritus Diseases 0.000 claims description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
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- LZLSBXOVTMIABI-UHFFFAOYSA-N 1H-quinoxalin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=NC2=C1 LZLSBXOVTMIABI-UHFFFAOYSA-N 0.000 claims description 2
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- DVYWJRJQVBKHCC-UHFFFAOYSA-N BrC1=CC2=C(N=C(C=3N2NC(N=3)=O)N2CCN(CC2)C)N=C1 Chemical compound BrC1=CC2=C(N=C(C=3N2NC(N=3)=O)N2CCN(CC2)C)N=C1 DVYWJRJQVBKHCC-UHFFFAOYSA-N 0.000 claims description 2
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000005842 heteroatoms Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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| PCT/KR2019/006553 WO2019231270A1 (en) | 2018-05-31 | 2019-05-31 | Heterocyclic derivatives and use thereof |
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| WO2021174024A1 (en) | 2020-02-28 | 2021-09-02 | First Wave Bio, Inc. | Methods of treating iatrogenic autoimmune colitis |
| BR112022024729A2 (pt) | 2020-06-05 | 2023-02-28 | Kinnate Biopharma Inc | Inibidores de quinases do receptor do fator de crescimento de fibroblastos |
| EP4067357A1 (en) * | 2021-03-30 | 2022-10-05 | JW Pharmaceutical Corporation | Novel crystalline form of 1-(8-bromopyrido[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-n-methylazetidin-3-amine hydrogen sulfate monohydrate |
| CN113929634A (zh) * | 2021-11-22 | 2022-01-14 | 山西永津集团有限公司 | 一种2,3-二溴喹喔啉的合成方法 |
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| SE358395B (es) * | 1967-09-27 | 1973-07-30 | Siegfried Ag | |
| CA2520251A1 (en) * | 2003-03-27 | 2004-10-07 | Pfizer Products Inc. | Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines |
| WO2010030785A2 (en) * | 2008-09-10 | 2010-03-18 | Kalypsys Inc. | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| TW201204727A (en) * | 2010-03-10 | 2012-02-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| TW201206936A (en) * | 2010-07-19 | 2012-02-16 | Alcon Res Ltd | Methods and compositions for the treatment of allergy |
| US9586959B2 (en) * | 2011-09-30 | 2017-03-07 | C&C Research Laboratories | Substituted tricyclic heterocycles as histamine 4 receptor inhibitors |
| AU2014236606A1 (en) * | 2013-03-15 | 2015-09-24 | Epigenetix, Inc. | Oxazolo(5,4-c)quinolin-2-one compounds as bromodomain inhibitors |
| CN108431000A (zh) * | 2015-11-16 | 2018-08-21 | 基础应用医学研究基金会 | 作为dna甲基转移酶抑制剂的新型化合物 |
| JP7212612B2 (ja) * | 2016-07-28 | 2023-01-25 | プロメガ コーポレイション | セレンテラジン類縁体 |
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- 2019-05-31 EP EP19810281.6A patent/EP3807282A4/en not_active Withdrawn
- 2019-05-31 CN CN201980035540.4A patent/CN112204032A/zh active Pending
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- 2019-05-31 JP JP2020566706A patent/JP2021525738A/ja not_active Withdrawn
- 2019-05-31 AU AU2019279421A patent/AU2019279421A1/en not_active Abandoned
- 2019-05-31 WO PCT/KR2019/006553 patent/WO2019231270A1/en unknown
- 2019-05-31 MX MX2020011955A patent/MX2020011955A/es unknown
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