CN102149683B - 1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 - Google Patents
1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 Download PDFInfo
- Publication number
- CN102149683B CN102149683B CN2010800025776A CN201080002577A CN102149683B CN 102149683 B CN102149683 B CN 102149683B CN 2010800025776 A CN2010800025776 A CN 2010800025776A CN 201080002577 A CN201080002577 A CN 201080002577A CN 102149683 B CN102149683 B CN 102149683B
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- CN
- China
- Prior art keywords
- salt
- benzyl
- trifluoromethylpyridin
- flumethiazine
- ketone
- 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.)
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Links
- BKVAYZKWOPERDG-UHFFFAOYSA-N CC(C=C1)=C[I](Cc(cc2)ccc2F)C1=O Chemical compound CC(C=C1)=C[I](Cc(cc2)ccc2F)C1=O BKVAYZKWOPERDG-UHFFFAOYSA-N 0.000 description 1
- QFLFCHWGYSHABF-UHFFFAOYSA-N CC(Nc1ccc(CN(C=C(C(F)(F)F)C=C2)C2=O)cc1)=O Chemical compound CC(Nc1ccc(CN(C=C(C(F)(F)F)C=C2)C2=O)cc1)=O QFLFCHWGYSHABF-UHFFFAOYSA-N 0.000 description 1
- CKKRIGKYLQICRL-UHFFFAOYSA-N CC1(C=CC(N(C=C(C)C=C2)C2=O)=CC=C1)[RnH] Chemical compound CC1(C=CC(N(C=C(C)C=C2)C2=O)=CC=C1)[RnH] CKKRIGKYLQICRL-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*)c(CN(C=C(C(F)(F)F)C=C2)C2=O)c(*)c(*)c1* Chemical compound Cc1c(*)c(CN(C=C(C(F)(F)F)C=C2)C2=O)c(*)c(*)c1* 0.000 description 1
- UIAYXJPPPBABPM-UHFFFAOYSA-N O=C1N(Cc(cccc2)c2F)C=C(C(F)(F)F)C=C1 Chemical compound O=C1N(Cc(cccc2)c2F)C=C(C(F)(F)F)C=C1 UIAYXJPPPBABPM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010800025776A CN102149683B (zh) | 2009-05-25 | 2010-05-24 | 1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910043502.1 | 2009-05-25 | ||
| CN200910043502 | 2009-05-25 | ||
| PCT/CN2010/073131 WO2010135976A1 (zh) | 2009-05-25 | 2010-05-24 | 1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 |
| CN2010800025776A CN102149683B (zh) | 2009-05-25 | 2010-05-24 | 1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102149683A CN102149683A (zh) | 2011-08-10 |
| CN102149683B true CN102149683B (zh) | 2013-10-02 |
Family
ID=43222161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800025776A Active CN102149683B (zh) | 2009-05-25 | 2010-05-24 | 1-(取代苄基)-5-三氟甲基-2-(1h)吡啶酮化合物及其盐,其制备方法及其用途 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8377932B2 (https=) |
| EP (1) | EP2474533B1 (https=) |
| JP (1) | JP5722883B2 (https=) |
| KR (1) | KR101478133B1 (https=) |
| CN (1) | CN102149683B (https=) |
| AU (1) | AU2010252451B2 (https=) |
| DK (1) | DK2474533T3 (https=) |
| ES (1) | ES2536200T3 (https=) |
| WO (1) | WO2010135976A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102099036B (zh) | 2008-06-03 | 2015-05-27 | 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 |
| JP5924984B2 (ja) * | 2012-03-06 | 2016-05-25 | 国立大学法人東京農工大学 | トリフルオロメチルピリジノン化合物およびその製造方法 |
| BR112014030284B1 (pt) | 2012-07-18 | 2021-11-30 | Sunshine Lake Pharma Co., Ltd | Composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| KR20150018127A (ko) * | 2013-08-09 | 2015-02-23 | 삼성전자주식회사 | 디스플레이 장치 및 그 방법 |
| US9902712B2 (en) | 2013-12-19 | 2018-02-27 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| CN106466318B (zh) * | 2015-08-21 | 2019-01-01 | 中南大学 | 1-杂环取代苄基吡啶酮类化合物在制备治疗糖尿病肾病药物中的应用 |
| CN107663167A (zh) * | 2016-10-19 | 2018-02-06 | 广州南新制药有限公司 | 1‑(取代苄基)‑5‑三氟甲基‑2(1h)‑吡啶酮盐酸盐的晶型及制备方法 |
| CN107652228B (zh) * | 2016-10-28 | 2020-04-14 | 广州南新制药有限公司 | 抗肾纤维化药物1-(取代苄基)-5-三氟甲基-2(1h)-吡啶酮盐酸盐的合成方法 |
| CN113456642B (zh) * | 2021-07-09 | 2022-09-06 | 中南大学 | 一种美氟尼酮在制备治疗急性肾损伤药物中的应用 |
| WO2023168649A1 (zh) * | 2022-03-10 | 2023-09-14 | 广州南新制药有限公司 | 一种美氟尼酮盐酸盐的制备方法 |
| WO2023168650A1 (zh) * | 2022-03-10 | 2023-09-14 | 广州南新制药有限公司 | 一种美氟尼酮晶型的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN101235030A (zh) * | 2007-01-30 | 2008-08-06 | 中南大学 | 1-取代-5-三氟甲基-2-(1h)吡啶酮化合物、制备方法及其用途 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839346A (en) | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| US4052509A (en) | 1972-12-18 | 1977-10-04 | Affiliated Medical Research, Inc. | Method for reducing serum uric acid levels |
| US4042699A (en) | 1972-12-18 | 1977-08-16 | Affiliated Medical Research, Inc. | Method for reducing serum glucose levels |
| GB8523126D0 (en) * | 1985-09-19 | 1985-10-23 | Ici Plc | Aryl pyridones |
| GB8621217D0 (en) | 1986-09-03 | 1986-10-08 | Ici Plc | Chemical compounds |
| GB8825314D0 (en) | 1988-10-28 | 1988-11-30 | Ici Plc | Chemical compounds |
| GB9006479D0 (en) | 1989-04-17 | 1990-05-23 | Ici Plc | Novel compounds |
| US5310562A (en) | 1989-11-22 | 1994-05-10 | Margolin Solomon B | Composition and method for reparation and prevention of fibrotic lesions |
| US5518729A (en) | 1989-11-22 | 1996-05-21 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| US5716632A (en) | 1989-11-22 | 1998-02-10 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| US5238906A (en) | 1990-11-27 | 1993-08-24 | Sumitomo Chemical Company, Limited | Pyridone derivatives and use |
| 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 |
| ATE448784T1 (de) * | 2002-02-14 | 2009-12-15 | Pharmacia Corp | Substituierte pyridinone als modulatoren für p38 map kinase |
| US7166603B2 (en) * | 2003-07-23 | 2007-01-23 | Bristol-Myers Squibb Co. | Dihydropyrimidone inhibitors of calcium channel function |
| GB0324159D0 (en) * | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| CN100358872C (zh) | 2003-11-14 | 2008-01-02 | 上海睿星基因技术有限公司 | 吡啶酮衍生物及其应用 |
| DE102004027359A1 (de) | 2004-06-04 | 2005-12-29 | Abbott Gmbh & Co. Kg | Pyridin-2-onverbindungen und deren Verwendung |
| ES2600460T3 (es) | 2005-05-10 | 2017-02-09 | Intermune, Inc. | Derivados de piridona-2-ona como moduladores del sistema de proteína cinasa activada por estrés |
| CN101237869A (zh) * | 2005-05-10 | 2008-08-06 | 英特芒尼公司 | 用于调节应激-活化蛋白激酶系统的吡啶酮衍生物 |
| WO2007053610A2 (en) | 2005-11-01 | 2007-05-10 | The Regents Of The University Of California | Methods of treating atrial fibrillation wtih pirfenidone |
| KR20080076968A (ko) | 2005-11-23 | 2008-08-20 | 인터뮨, 인크. | 스트레스-활성화 단백질 키나제 시스템을 조절하는 방법 |
| US20090118135A1 (en) | 2007-06-08 | 2009-05-07 | The Burnham Institute | Methods and compounds for regulating apoptosis |
| CN101371833A (zh) | 2007-08-23 | 2009-02-25 | 中南大学 | 1-芳基-2(1h)-吡啶酮类化合物在制备治疗皮肤瘙痒药物中的应用 |
| CN102099036B (zh) | 2008-06-03 | 2015-05-27 | 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 |
| AP2011005824A0 (en) | 2009-01-26 | 2011-08-31 | Intermune Inc | Methods for treating acute myocardial infarctions and associated disorders. |
| WO2010135470A1 (en) | 2009-05-19 | 2010-11-25 | Intermune, Inc. | Pifenidone derivatives for treating bronchial asthma |
-
2010
- 2010-05-24 KR KR1020117030958A patent/KR101478133B1/ko not_active Expired - Fee Related
- 2010-05-24 EP EP10780057.5A patent/EP2474533B1/en not_active Not-in-force
- 2010-05-24 US US13/322,153 patent/US8377932B2/en not_active Expired - Fee Related
- 2010-05-24 ES ES10780057.5T patent/ES2536200T3/es active Active
- 2010-05-24 JP JP2012512189A patent/JP5722883B2/ja not_active Expired - Fee Related
- 2010-05-24 AU AU2010252451A patent/AU2010252451B2/en not_active Ceased
- 2010-05-24 DK DK10780057.5T patent/DK2474533T3/en active
- 2010-05-24 WO PCT/CN2010/073131 patent/WO2010135976A1/zh not_active Ceased
- 2010-05-24 CN CN2010800025776A patent/CN102149683B/zh active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN101235030A (zh) * | 2007-01-30 | 2008-08-06 | 中南大学 | 1-取代-5-三氟甲基-2-(1h)吡啶酮化合物、制备方法及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2010252451B2 (en) | 2014-04-03 |
| CN102149683A (zh) | 2011-08-10 |
| AU2010252451A1 (en) | 2011-12-15 |
| KR101478133B1 (ko) | 2014-12-31 |
| ES2536200T3 (es) | 2015-05-21 |
| KR20120060785A (ko) | 2012-06-12 |
| EP2474533B1 (en) | 2015-02-25 |
| EP2474533A1 (en) | 2012-07-11 |
| WO2010135976A1 (zh) | 2010-12-02 |
| JP5722883B2 (ja) | 2015-05-27 |
| US8377932B2 (en) | 2013-02-19 |
| HK1166791A1 (en) | 2012-11-09 |
| DK2474533T3 (en) | 2015-05-18 |
| JP2012527488A (ja) | 2012-11-08 |
| EP2474533A4 (en) | 2012-11-14 |
| US20120129859A1 (en) | 2012-05-24 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |