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药物详细合成路线

Name Aceclofenac;YT-919;Beofenac;Preservex;Gerbin;Falcon;Airtal
Chemical Name Glycolic acid [2-(2,6-dichloroanilino)phenyl]acetate ester
      2-(2,6-Dichlorophenylamino)phenylacetic acid carboxymethyl ester
      2-[2-(2,6-Dichlorophenylamino)phenylacetoxy]acetic acid
CAS 89796-99-6
Related CAS
Formula C16H13Cl2NO4
Structure
Formula Weight 354.19231
Stage 上市-1992
Company Almirall Prodesfarma (Originator), Bristol-Myers Squibb (Licensee), Daewoong (Licensee), Gedeon Richter (Licensee), UCB (Licensee), Yakult Honsha (Licensee)
Activity/Mechanism ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Ankylosing Spondylitis, Treatment of, Antiarthritic Drugs, Osteoarthritis, Treatment of, Rheumatoid Arthritis, Treatment of, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Non-Steroidal Antiinflammatory Drugs
Syn. Route 3
Route 1
alkylation of the sodium salt of diclofenac (i) with benzyl bromoacetate (ii) in hot dmf yielded the (arylacetoxy)acetate (iii). subsequent hydrogenolysis of the benzyl ester of (iii) in the presence of pd/c gave the title carboxylic acid. alternatively, the benzyl ester group of (iii) was cleaved by means of the combination of chlorotrimethylsilane and sodium iodide. this method of selective ester hydrolysis with in situ generated iodotrimethylsilane was also applied to the corresponding methyl (iv) and tert-butyl (v) esters. in a related procedure, tert-butyl ester (v) was prepared by alkylation of diclofenac (vi) with tert-butyl bromoacetate (vii) in the presence of tertiary amines. selective cleavage of the tert-butyl ester group of (v) was then performed by treatment with either trifluoroacetic or formic acid.
List of intermediates No.
n-(2-[1-[(4-hydroxy-3,4-dihydro-2h-chromen-3-yl)methyl]-4-piperidinyl]ethyl)-n-phenylurea (ii)
(2s)-2-azido-2-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamide (vii)
(2s)-5-[(4r,5r)-5-[(2s,3e)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2-methylpentanal (vi)
Reference 1:
    casas, a.v. (almirall prodesfarma, sa); 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetyl derivs. and therapeutic compsns. containing same. ep 0119932; us 4548952 .
Reference 2:
    ginebreda martí, a.; agustí cruz, a. (almirall prodesfarma, sa); process for obtaining 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetic acid. es 2020146 .
Reference 3:
    schickaneder, h.; nikolopoulos, a.; murphy, t.; process for the preparation of aceclofenac. wo 9955660 .

Route 2
aceclofenac was prepared by selective hydrolysis of other labile ester precursors. alkylation of diclofenac sodium (i) with tetrahydropyranyl chloroacetate (ix), prepared by protection of chloroacetic acid (viii) with dihydropyran, furnished the tetrahydropyranyl ester of aceclofenac (x), which was then deprotected by treatment with hcl. similarly, the preparation of aceclofenac was reported by acidic hydrolysis of the analogous tetrahydrofuranyl ester (xi).
List of intermediates No.
5,6,9,10-tetrahydro-4h-pyrido[3,2,1-jk]carbazol-11(8h)-one (viii)
Reference 1:
    flores ramos, r. (almirall prodesfarma, sa); process for obtaining 2-[(2,6-dichlorophenyl)amino]phenylacetoxy acetic acid. es 2046141 .
Reference 2:
    zirngibl, l.; gnehm, r. (siegfried ag); process for the preparation of a phenylacetic acid deriv.. ch 682747 .

Route 3
alternatively, alkylation of diclofenac sodium (i) with either trichloroethyl bromoacetate (xii) of tribromoethyl bromoacetate (xiii) gave rise to the respective trichloroethyl (xiv) and tribromoethyl (xv) esters of aceclofenac. reductive cleavage of the trihaloethyl esters (xiv) and (xv) using zinc powder under acidic conditions furnished the title compound.
List of intermediates No.
Reference 1:
    frank, a.; karn, h.; spanig, h. (abbott gmbh & co. kg); production of 1-hydroxyalkyl-5-nitroimidazoles. de 2359625; fr 2253019; gb 1481349 .
Reference 2:
    frank, a.; dockner, t.; karn, h. (abbott gmbh & co. kg); process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. ep 0150407 .

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名醋氯芬酸;英文名Aceclofenac;YT-919;Beofenac;Preservex;Gerbin;Falcon;Airtal;CAS[89796-99-6]

 
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