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药物详细合成路线

Name Rimonabant hydrochloride;SR-141716A;Acomplia
Chemical Name 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide hydrochloride
CAS 158681-13-1
Related CAS 168273-06-1 (free base)
Formula C22H22Cl4N4O
Structure
Formula Weight 500.25884
Stage 上市-2006
Company Sanofi-synthélabo (Originator)
Activity/Mechanism Alzheimers Dementia, Treatment of , Antiobesity Drugs, Antiparkinsonian Drugs, Cognition Disorders, Treatment of, Extrapyramidal Disorders, Treatment of, METABOLIC DRUGS, NEUROLOGIC DRUGS, Smoking Cessation, Aid to, Treatment of Nutritional Disorders, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Cannabinoid CB1 Antagonists
Syn. Route 2
Route 1
claisen condensation of 4-chloropropiophenone (i) with diethyl oxalate in the presence of lithium hexamethyldisilazide afforded the corresponding diketo ester lithium salt (ii). this was condensed with 2,4-dichlorophenylhydrazine (iii) to afford hydrazone (iv), which was further cyclized to pyrazole (v) in refluxing hoac. in an improved procedure, 4-chloropropiophenone (i) was initially converted to the silyl enol ether (vi) using chlorotrimethylsilane and triethylamine. acylation of (vi) with ethyl chloroglyoxylate in the presence of zncl2 produced diketo ester (vii). condensation of (vii) with hydrazine (iii), followed by acid cyclization of the intermediate hydrazone (iv), also produced pyrazole (v). hydrolysis of ethyl ester (v) gave carboxylic acid (viii), which was then activated as the acid chloride (ix). finally, coupling of acid chloride (ix) with n-aminopiperidine (x) furnished the title hydrazide.
List of intermediates No.
1-benzyl-3-piperidinone (i)
3-ethyl 5-methyl 4-(2-chlorophenyl)-2-[(2-iodoethoxy)methyl]-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate (iii)
3-ethyl 5-methyl 2-[(2-chloroethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate (x)
Reference 1:
    rinaldi, m.; anne-archard, g.; barth, f.; casellas, p.; congy, c.; martinez, s. (sanofi-synthélabo); substd. n-piperidino 3-pyrazolecarboxamide. ca 2136893; ep 0576357; ep 0656354; fr 2692575; fr 2713224; fr 2713225; jp 1994073014; jp 1995309841; jp 2001026541; us 5624941 .

Route 2
the reaction of rimonabant (i) with buli and 1-chloro-2-iodoethane gives a mixture of the iodo derivatives (ii) and (iii), which are separated by chromatography. the desired isomer (ii) is then hydrogenated with tritium over pd/c in ethanol.
List of intermediates No.
Reference 1:
    seltzman, h.h.; et al.; tritiation of sr141716 by metallation-iodination-reduction: tritium-proton noe study. j label compd radiopharm 2002, 45, 1, 59.

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盐酸利莫那班;英文名Rimonabant hydrochloride;SR-141716A;Acomplia;CAS[158681-13-1]

 
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