CN103570630A - 氮杂环衍生物及其在药物中的应用 - Google Patents
氮杂环衍生物及其在药物中的应用 Download PDFInfo
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- CN103570630A CN103570630A CN201310303212.2A CN201310303212A CN103570630A CN 103570630 A CN103570630 A CN 103570630A CN 201310303212 A CN201310303212 A CN 201310303212A CN 103570630 A CN103570630 A CN 103570630A
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- bicyclic
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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Classifications
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- 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
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
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Abstract
Description
Claims (26)
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Publication number | Priority date | Publication date | Assignee | Title |
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Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3185689A (en) * | 1965-05-25 | Tolyl-x-(jh)-pyrimidones | ||
CN1386737A (zh) * | 2002-06-11 | 2002-12-25 | 中南大学湘雅医学院 | 抗纤维化吡啶酮药物及其生产工艺方法 |
WO2006041968A1 (en) * | 2004-10-06 | 2006-04-20 | Nps Pharmaceuticals, Inc. | Reversed pyrimidinone compounds as calcilytics |
CN1930126A (zh) * | 2004-03-05 | 2007-03-14 | 万有制药株式会社 | 吡啶酮衍生物 |
CN1968937A (zh) * | 2003-04-03 | 2007-05-23 | 法马西亚公司 | 嘧啶-4-酮衍生物和它们作为p38激酶调节剂的用途 |
CN101039921A (zh) * | 2004-10-13 | 2007-09-19 | 法玛西雅厄普约翰有限责任公司 | 3-[5-氯-4-[(2,4-二氟苄基)氧基]-6-氧代嘧啶-1(6h)-基]-n-(2-羟乙基)-4-甲基苯甲酰胺的晶形 |
WO2010135972A1 (zh) * | 2009-05-25 | 2010-12-02 | 中南大学 | 1-(取代芳基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐的制备方法及其用途 |
CN102099036A (zh) * | 2008-06-03 | 2011-06-15 | 英特芒尼公司 | 用于治疗炎性疾患和纤维化疾患的化合物和方法 |
CN102292124A (zh) * | 2009-01-26 | 2011-12-21 | 英特芒尼公司 | 用于治疗急性心肌梗死和相关疾患的方法 |
Family Cites Families (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2808193A1 (de) | 1978-02-25 | 1979-09-06 | Basf Ag | Pyridazon-verbindungen |
DE3202678A1 (de) | 1982-01-28 | 1983-08-04 | Basf Ag, 6700 Ludwigshafen | Substituierte 4,5-dimethoxy-pyridazone, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
US5149810A (en) | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
GB8818560D0 (en) | 1988-08-04 | 1988-09-07 | Ici Plc | Novel compounds |
JPH02215719A (ja) | 1989-02-15 | 1990-08-28 | Yamauchi Akitomo | 線維化病変組織の修復並びに線維化病変の阻止剤 |
GB8908638D0 (en) | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
GB8915962D0 (en) | 1989-07-12 | 1989-08-31 | Ici Plc | Novel compounds |
AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
IE912114A1 (en) | 1990-07-02 | 1992-01-15 | Union Pharma Scient Appl | Novel pyrimidine derivatives which are angiotensin ii¹receptor antagonists, their methods of preparation and¹pharmaceutical compositions in which they are present |
US5470975A (en) | 1990-10-16 | 1995-11-28 | E.R. Squibb & Sons, Inc. | Dihydropyrimidine derivatives |
GB9022445D0 (en) | 1990-10-16 | 1990-11-28 | Ici Plc | Heterocyclic compounds |
TW229142B (zh) | 1992-04-15 | 1994-09-01 | Nissan Detrochem Corp | |
BR9301666A (pt) | 1992-04-28 | 1993-11-03 | Sumitomo Chemical Co | Composto,composto intermediario,composicao herbicida,processo para exterminar ervas daninhas indesejadas,uso do dito composto e processo para produzi-lo |
WO1995011235A1 (en) | 1993-10-20 | 1995-04-27 | The Upjohn Company | Pyrimidinones as antiarthritic and anti-inflammatories |
DE4343528A1 (de) * | 1993-12-16 | 1995-06-22 | Schering Ag | Zweifach heterocyclisch substituierte Benzole und Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
DE4431218A1 (de) | 1994-09-02 | 1996-03-07 | Bayer Ag | Substituierte Pyrimidin(thi)one |
DE4432888A1 (de) | 1994-09-15 | 1996-03-21 | Bayer Ag | Verwendung von Aryluracilen im semi- und nicht-selektiven Bereich der Unkrautbekämpfung |
KR100300566B1 (ko) | 1994-09-17 | 2001-11-22 | 조생현 | 피리미디논유도체와그의제조방법및용도 |
DE19520613A1 (de) | 1995-06-06 | 1996-12-12 | Bayer Ag | Phenylpyridazinone |
US6369067B1 (en) | 1997-10-27 | 2002-04-09 | Dr. Reddy's Research Foundation | Monocyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
EP1070055A1 (de) | 1998-04-09 | 2001-01-24 | Bayer Aktiengesellschaft | Substituierte phenylpyridazinone |
DE60137426D1 (de) * | 2000-06-12 | 2009-03-05 | Eisai R&D Man Co Ltd | 1,2-dihydropyridinverbindungen, verfahren zu deren herstellung und deren verwendung |
WO2002053156A1 (en) | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating glaucoma ii b |
EP1441732A2 (en) | 2001-11-08 | 2004-08-04 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivative and pharmaceutical use thereof |
US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
CA2474239A1 (en) | 2002-01-18 | 2003-07-24 | Pharmacia Corporation | Substituted pyridazinones as inhibitors of p38 |
CA2476012C (en) | 2002-02-14 | 2011-04-19 | Pharmacia Corporation | Substituted pyridinones as modulators of p38 map kinase |
TW200307667A (en) * | 2002-05-06 | 2003-12-16 | Bristol Myers Squibb Co | Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors |
EP1642898B1 (en) * | 2003-06-27 | 2013-03-27 | Msd K.K. | Heteroaryloxy nitrogenous saturated heterocyclic derivative |
CL2004002050A1 (es) | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
CN1867560A (zh) | 2003-08-13 | 2006-11-22 | 武田药品工株式会社 | 4-嘧啶酮衍生物及其作为肽基肽酶抑制剂的用途 |
EP1699777B1 (en) | 2003-09-08 | 2012-12-12 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
WO2005047256A1 (fr) | 2003-11-14 | 2005-05-26 | Shanghai Genomics, Inc. | Derives de pyridone, et utilisation correspondante |
CA2565437A1 (en) * | 2004-06-18 | 2006-01-05 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
CN1308028C (zh) | 2004-09-10 | 2007-04-04 | 石药集团中奇制药技术(石家庄)有限公司 | 一种治疗肝纤维化的药物及其制备方法 |
JP4912314B2 (ja) * | 2004-10-26 | 2012-04-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 因子Xa化合物 |
CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1-(取代苯基)-5-甲基-2-(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
KR20080080136A (ko) | 2005-11-22 | 2008-09-02 | 스미스클라인 비참 코포레이션 | 칼실리틱 화합물 |
US20070129379A1 (en) | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
BRPI0711296A2 (pt) * | 2006-05-05 | 2011-08-23 | Millennium Phamaceutical Inc | inibidores de fator xa |
UY30378A1 (es) | 2006-06-02 | 2008-01-02 | Janssen Pharmaceutica Nv | Nuevos derivados de piridinona n-aril y n-heteroaril sustituidos para usar en enfermedades mediadas por mch-1 |
WO2007142217A1 (ja) | 2006-06-07 | 2007-12-13 | Banyu Pharmaceutical Co., Ltd. | 1-フェニルピリドン誘導体 |
AU2007275682B2 (en) * | 2006-07-20 | 2012-05-17 | Amgen Inc. | Substituted pyridone compounds and methods of use |
WO2008022979A1 (en) | 2006-08-25 | 2008-02-28 | Boehringer Ingelheim International Gmbh | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
WO2008041090A1 (en) | 2006-10-06 | 2008-04-10 | Pfizer Limited | Malanin concentrating hormone receptor-1 antagonist pyridinones |
CA2664112C (en) | 2006-12-05 | 2015-02-17 | Janssen Pharmaceutica N.V. | Novel substituted diaza-spiro-pyridinone derivatives for use in mch-1 mediated diseases |
JP2010515691A (ja) * | 2007-01-05 | 2010-05-13 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 第Xa因子阻害剤 |
US8198276B2 (en) | 2007-06-06 | 2012-06-12 | Xcovery Holding Company Llc | Kinase inhibitor compounds |
WO2008156607A1 (en) | 2007-06-12 | 2008-12-24 | Neurogen Corporation | Substituted pyrimidinones |
DE102007028320A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
CA2691215C (en) | 2007-06-27 | 2016-03-29 | Astrazeneca Ab | Pyrazinone derivatives and their use in the treatment of lung diseases |
WO2009036132A1 (en) * | 2007-09-11 | 2009-03-19 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole n-oxides |
US8329711B2 (en) | 2007-10-23 | 2012-12-11 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
GB0724342D0 (en) | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
US8153813B2 (en) * | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
KR20100117123A (ko) | 2008-02-21 | 2010-11-02 | 쉐링 코포레이션 | Erk 억제제인 화합물 |
CN101235013A (zh) | 2008-03-10 | 2008-08-06 | 广东东阳光药业有限公司 | 结晶型1-(3-氟苯基)-5-甲基-2-(1h)吡啶酮、其制备方法、及其组合物和应用 |
SG10201401169QA (en) * | 2009-04-02 | 2014-05-29 | Merck Serono Sa | Dihydroorotate dehydrogenase inhibitors |
US8377932B2 (en) | 2009-05-25 | 2013-02-19 | Central South University | Preparation of 1-(substituted benzyl)-5-trifluoromethyl-2(1H)pyridone compounds and salts thereof and their applications |
CN101921225B (zh) | 2009-06-11 | 2013-04-03 | 北京凯得尔森生物技术有限公司 | 吡啡尼酮类化合物、其制备方法和应用 |
NO2542084T3 (zh) | 2010-03-04 | 2018-05-19 | ||
WO2012011592A1 (ja) | 2010-07-23 | 2012-01-26 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
US20130303551A1 (en) * | 2011-01-10 | 2013-11-14 | Nicholas D. Adams | Pyrimidinone derivatives as fatty acid synthase inhibitors |
US9056110B2 (en) | 2011-12-06 | 2015-06-16 | Confluence Life Sciences, Inc. | Substituted pyrimidinone-phenyl-pyrimidinyl compounds |
US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
-
2013
- 2013-07-18 EP EP13819193.7A patent/EP2875001B1/en active Active
- 2013-07-18 MX MX2015000830A patent/MX2015000830A/es unknown
- 2013-07-18 JP JP2015521942A patent/JP6186434B2/ja active Active
- 2013-07-18 CN CN201310303212.2A patent/CN103570630B/zh active Active
- 2013-07-18 WO PCT/CN2013/000860 patent/WO2014012360A1/en active Application Filing
- 2013-07-18 BR BR112014030284-7A patent/BR112014030284B1/pt active IP Right Grant
- 2013-07-18 KR KR1020157002193A patent/KR102057877B1/ko active IP Right Grant
- 2013-07-18 RU RU2015105262A patent/RU2701156C9/ru active
- 2013-07-18 AU AU2013292950A patent/AU2013292950C1/en active Active
- 2013-07-18 CA CA2872110A patent/CA2872110C/en active Active
- 2013-07-18 US US14/396,754 patent/US9434695B2/en active Active
- 2013-07-18 ES ES13819193T patent/ES2716008T3/es active Active
-
2015
- 2015-08-06 HK HK15107599.3A patent/HK1207065A1/zh unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3185689A (en) * | 1965-05-25 | Tolyl-x-(jh)-pyrimidones | ||
CN1386737A (zh) * | 2002-06-11 | 2002-12-25 | 中南大学湘雅医学院 | 抗纤维化吡啶酮药物及其生产工艺方法 |
CN1968937A (zh) * | 2003-04-03 | 2007-05-23 | 法马西亚公司 | 嘧啶-4-酮衍生物和它们作为p38激酶调节剂的用途 |
CN1930126A (zh) * | 2004-03-05 | 2007-03-14 | 万有制药株式会社 | 吡啶酮衍生物 |
WO2006041968A1 (en) * | 2004-10-06 | 2006-04-20 | Nps Pharmaceuticals, Inc. | Reversed pyrimidinone compounds as calcilytics |
CN101039921A (zh) * | 2004-10-13 | 2007-09-19 | 法玛西雅厄普约翰有限责任公司 | 3-[5-氯-4-[(2,4-二氟苄基)氧基]-6-氧代嘧啶-1(6h)-基]-n-(2-羟乙基)-4-甲基苯甲酰胺的晶形 |
CN102099036A (zh) * | 2008-06-03 | 2011-06-15 | 英特芒尼公司 | 用于治疗炎性疾患和纤维化疾患的化合物和方法 |
CN102292124A (zh) * | 2009-01-26 | 2011-12-21 | 英特芒尼公司 | 用于治疗急性心肌梗死和相关疾患的方法 |
WO2010135972A1 (zh) * | 2009-05-25 | 2010-12-02 | 中南大学 | 1-(取代芳基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐的制备方法及其用途 |
Non-Patent Citations (1)
Title |
---|
陈军 等: "抗纤维化活性5-三氟甲基吡啶酮衍生物的涉及合成及构效关系研究", 《2011年全国药物化学学术会议》 * |
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CN104725356A (zh) * | 2013-12-19 | 2015-06-24 | 广东东阳光药业有限公司 | 氮杂环衍生物及其在药物中的应用 |
CN106397408A (zh) * | 2015-07-30 | 2017-02-15 | 四川大学 | 5-甲基-2(1h)吡啶酮衍生物及其制备方法和用途 |
CN106397408B (zh) * | 2015-07-30 | 2019-04-02 | 四川大学 | 5-甲基-2(1h)吡啶酮衍生物及其制备方法和用途 |
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WO2018019166A1 (en) | 2016-07-27 | 2018-02-01 | Sunshine Lake Pharma Co., Ltd. | Salts of 2, 6-dimethylpyrimidone derivatives and uses thereof |
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RU2701156C2 (ru) | 2019-09-25 |
CN103570630B (zh) | 2016-04-20 |
RU2015105262A (ru) | 2016-09-10 |
HK1207065A1 (zh) | 2016-01-22 |
EP2875001A1 (en) | 2015-05-27 |
EP2875001A4 (en) | 2016-06-01 |
JP2015526411A (ja) | 2015-09-10 |
US20150087639A1 (en) | 2015-03-26 |
KR102057877B1 (ko) | 2019-12-20 |
US9434695B2 (en) | 2016-09-06 |
CA2872110C (en) | 2019-08-06 |
BR112014030284A2 (pt) | 2017-06-27 |
BR112014030284B1 (pt) | 2021-11-30 |
KR20150036223A (ko) | 2015-04-07 |
CA2872110A1 (en) | 2014-01-23 |
AU2013292950A1 (en) | 2014-11-13 |
EP2875001B1 (en) | 2019-01-09 |
MX2015000830A (es) | 2015-10-26 |
ES2716008T3 (es) | 2019-06-07 |
AU2013292950C1 (en) | 2016-01-21 |
JP6186434B2 (ja) | 2017-08-23 |
RU2701156C9 (ru) | 2019-12-18 |
AU2013292950B2 (en) | 2015-09-10 |
WO2014012360A1 (en) | 2014-01-23 |
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