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Tuesday, 5 January 2016

Fluorofenidone


2(1H)-Pyridinone, 1-(3-fluorophenyl)-5-methyl-.png
Fluorofenidone
1- (3-fluorophenyl) -5-methyl – 2 (1H) pyridone
2(1H)​-​Pyridinone, 1-​(3-​fluorophenyl)​-​5-​methyl-
1- (3_ fluorophenyl) -5_ methylpyridine _2 (IH) – one
C12 H10 F N O, 203.2123
PRECLINICAL, IND Filing
An anti-inflammatory agent potentially for the treatment of organ fibrosis.

CAS No. 848353-85-5
Synthesis
str1

PATENT

WO 2006108354

PATENT

(Compound 1)
A. (3_ fluorophenyl) methyl pyridine _2 (IH) 1- -5_ – -one
9. 6gDMF, 45 0g (0 2mol.) Inter-fluoro-iodobenzene, 21 8g (0. 2mol) 5_ methylpyridine _2_ (IH) -.. -one, 28g of anhydrous potassium carbonate and 1. Og copper powder, 160 ° -170 °, the reaction was stirred at reflux for 20 hours, the natural cooling to 110~120 ° C, was slowly added to about 330ml 80~90 ° C hot water, cooled to 20 ° C. Suction filtered, the filter cake was washed with about 20ml of water, remove the cake, with about 300ml of ethyl acetate ultrasound 30min, suction filtered, the filter residue was washed with 20ml of ethyl acetate. The combined ethyl acetate, washed with water three times (50ml * 3), and the filtrate layers were separated and allowed to stand for 15min, ethyl acetate fraction was concentrated to a non-steamed, hot added under stirring for about 85ml of petroleum ether, cooling to 15~20 ° C insulation ~ 1.5 hours. Filtration, the filter cake was washed twice with petroleum ether (about 20ml * 2) used to give 34. 9g crude. Recrystallized from 20% ethanol to give the product 1- (3_ fluorophenyl) -5_ methylpyridine _2 (IH) – one as a white solid # 30. Ig0 Μ P.: 132 · 1 ~133 7 °.. C.
PATENT
http://www.google.co.in/patents/WO2009149188A1?cl=zh-CN

PATENT
CN 102241625
http://www.google.com/patents/CN102241625A?cl=zh
PATENT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2009111947

PAPER

.
CN1386737A * Jun 11, 2002 Dec 25, 2002 中南大学湘雅医学院 Antifibrosis pyridinone medicine and its prepaing process
CN1846699A Apr 13, 2005 Oct 18, 2006 中南大学湘雅医院 Application of 1-(substituted phenyl)-5-methyl-2-(1H)-pyridone compound in preparing medicine for anti-other organifibrosis and tissue fibrosis except renal interstitial fibrosis
CN101235013A* Mar 10, 2008 Aug 6, 2008 广东东阳光药业有限公司;张中能 Crystallized 1-(3-fluorophenyl)-5-methyl-2-(1H)pyridine and its preparation method composition and application
US20070203203 May 1, 2007 Aug 30, 2007 Tao Li J Composition and Method for Treating Fibrotic Diseases

Patent Submitted Granted
COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY AND FIBROTIC DISORDERS [US2009318455] 2009-12-24
COMPOSITION AND METHOD FOR TREATING PROTEINURIA [US2010099719] 2010-04-22
COMPOSITION AND METHOD FOR TREATING FIBROTIC DISEASES [US2009258911] 2009-10-15
Composition and Method for Treating Fibrotic Diseases [US2008319027] 2008-12-25
METHODS FOR TREATING ACUTE MYOCARDIAL INFARCTIONS AND ASSOCIATED DISORDERS [US2010190731] 2010-07-29
Methods for Treating Acute Myocardial Infarctions and Associated Disorders [US2011218515] 2011-09-08
METHODS OF TREATING HIV PATIENTS WITH ANTI-FIBROTICS [US2012014917] 2012-01-19
Composition and Method for Treating Fibrotic Diseases Composition and Method for Treating Fibrotic Diseases [US2009005424] 2007-08-30
Crystalline 1-(3-fluorophenyl)-5-methyl-2-(1H)pyridone, the preparation methods, compositions and applications thereof [US8232408] 2009-03-10 2012-07-31
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CC1=CN(C(=O)C=C1)C2=CC(=CC=C2)F

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