KR101829940B1 - 프탈라지논 케톤 유도체, 이의 제조방법, 및 이의 약학적 용도 - Google Patents
프탈라지논 케톤 유도체, 이의 제조방법, 및 이의 약학적 용도 Download PDFInfo
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- KR101829940B1 KR101829940B1 KR1020137003185A KR20137003185A KR101829940B1 KR 101829940 B1 KR101829940 B1 KR 101829940B1 KR 1020137003185 A KR1020137003185 A KR 1020137003185A KR 20137003185 A KR20137003185 A KR 20137003185A KR 101829940 B1 KR101829940 B1 KR 101829940B1
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- pyrazine
- mmol
- methyl
- compound
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 113
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- 239000000243 solution Substances 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 125000000753 cycloalkyl group Chemical group 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 34
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
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- YEDUHTJDMOAIPF-UHFFFAOYSA-N 4-[[3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazine-7-carbonyl)-4-fluorophenyl]methyl]-2h-phthalazin-1-one Chemical compound C1CN2C=CN=C2CN1C(=O)C1=CC(CC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F YEDUHTJDMOAIPF-UHFFFAOYSA-N 0.000 description 21
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- YARSFSWHQVBNGV-UHFFFAOYSA-N methyl 3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate Chemical compound C1CNCC2=C(C(=O)OC)N=C(C(F)(F)F)N21 YARSFSWHQVBNGV-UHFFFAOYSA-N 0.000 description 13
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- OWUJPAWZSIXQKU-UHFFFAOYSA-N 4-[[4-fluoro-3-[1-(hydroxymethyl)-3-(trifluoromethyl)-6,8-dihydro-5h-imidazo[1,5-a]pyrazine-7-carbonyl]phenyl]methyl]-2h-phthalazin-1-one Chemical compound C1=CC=C2C(CC=3C=C(C(=CC=3)F)C(=O)N3CCN4C(=NC(=C4C3)CO)C(F)(F)F)=NNC(=O)C2=C1 OWUJPAWZSIXQKU-UHFFFAOYSA-N 0.000 description 9
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- ACFNKMMICIVVBI-UHFFFAOYSA-N imidazo[1,5-a]pyrazine-1-carboxylic acid Chemical compound C1=CN=CC2=C(C(=O)O)N=CN21 ACFNKMMICIVVBI-UHFFFAOYSA-N 0.000 description 7
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 7
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- RHYZIHOBSWRZDL-UHFFFAOYSA-N 2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Chemical compound C1CNCC2=NC(C(F)(F)F)=CN21 RHYZIHOBSWRZDL-UHFFFAOYSA-N 0.000 description 4
- SGMCGPUNBVSXKH-UHFFFAOYSA-N 3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1=NC=CN2C(C(F)F)=NN=C21 SGMCGPUNBVSXKH-UHFFFAOYSA-N 0.000 description 4
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- PUSQIDJRNISKAT-UHFFFAOYSA-N ethyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-3-carboxylate Chemical compound C1NCCN2C(C(=O)OCC)=CN=C21 PUSQIDJRNISKAT-UHFFFAOYSA-N 0.000 description 4
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
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Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010248307.5 | 2010-08-09 | ||
| CN2010102483075A CN102372716A (zh) | 2010-08-09 | 2010-08-09 | 酞嗪酮类衍生物、其制备方法及其在医药上的应用 |
| PCT/CN2011/001223 WO2012019427A1 (zh) | 2010-08-09 | 2011-07-26 | 酞嗪酮类衍生物、其制备方法及其在医药上的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20130110149A KR20130110149A (ko) | 2013-10-08 |
| KR101829940B1 true KR101829940B1 (ko) | 2018-02-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020137003185A Active KR101829940B1 (ko) | 2010-08-09 | 2011-07-26 | 프탈라지논 케톤 유도체, 이의 제조방법, 및 이의 약학적 용도 |
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|---|---|
| US (2) | US9273052B2 (enExample) |
| EP (1) | EP2604610B1 (enExample) |
| JP (1) | JP5808408B2 (enExample) |
| KR (1) | KR101829940B1 (enExample) |
| CN (2) | CN102372716A (enExample) |
| AU (1) | AU2011288876B2 (enExample) |
| BR (1) | BR112013002220B1 (enExample) |
| CA (1) | CA2806324C (enExample) |
| ES (1) | ES2582315T3 (enExample) |
| HU (1) | HUE029275T2 (enExample) |
| PL (1) | PL2604610T3 (enExample) |
| PT (1) | PT2604610T (enExample) |
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| CN102863393A (zh) * | 2012-09-26 | 2013-01-09 | 上海大学 | 1,2-二氢酞嗪类化合物及其合成方法 |
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| CA3095367A1 (en) * | 2018-03-29 | 2019-10-03 | Board Of Regents, The University Of Texas System | Imidazopiperazine inhibitors of transcription activating proteins |
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| CN111732594B (zh) * | 2020-08-18 | 2022-03-04 | 苏州富士莱医药股份有限公司 | 一种氟唑帕利的制备方法 |
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| MX2023013890A (es) * | 2021-05-24 | 2023-12-11 | Jiangsu Hengrui Pharmaceuticals Co Ltd | Compuesto heterociclico que contiene nitrogeno, metodo de preparacion del mismo y aplicacion del mismo en medicamentos. |
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| JP2024528021A (ja) * | 2021-07-29 | 2024-07-26 | 上海齊魯制藥研究中心有限公司 | 新規なｐａｒｐ７阻害剤及びその使用 |
| CN115650988B (zh) * | 2022-10-27 | 2024-09-13 | 江苏恒瑞医药股份有限公司 | 一种parp抑制剂的制备方法 |
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| KR100804564B1 (ko) | 2000-10-30 | 2008-02-20 | 쿠도스 파마슈티칼스 리미티드 | 프탈라지논 유도체 |
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| US20090023727A1 (en) * | 2007-07-05 | 2009-01-22 | Muhammad Hashim Javaid | Phthalazinone derivatives |
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| CN101468988A (zh) | 2007-12-26 | 2009-07-01 | 上海恒瑞医药有限公司 | 哌嗪类衍生物,其制备方法及其在医药上的应用 |
| JP2011509962A (ja) | 2008-01-17 | 2011-03-31 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換スルホンアミド誘導体 |
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| UA111161C2 (uk) | 2016-04-11 |
| US9566277B2 (en) | 2017-02-14 |
| CN102686591A (zh) | 2012-09-19 |
| EP2604610B1 (en) | 2016-05-11 |
| CN102372716A (zh) | 2012-03-14 |
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