Imoproxifan, -Drug Synthesis Database

【结构式】

【药物名称】Imoproxifan

【化学名称】1-[4-[3-(1H-Imidazol-4-yl)propoxy]phenyl]ethan-1-one oxime

【CA登记号】184025-69-2, 184025-70-5 (maleate salt (1:1))

【分子式】C₁₄H₁₇N₃O₂

【分子量】259.31049

【开发单位】Bioprojet (Originator), INSERM (Originator)

【药理作用】Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, Histamine H3 Receptor Antagonists

合成路线1

Urocanic acid (I) was hydrogenated to imidazolepropionic acid (II) and then esterified with EtOH and H2SO4. The resulting imidazole ester (III) was protected as the N-trityl derivative (IV) and then reduced to alcohol (V) by means of LiAlH4 (1). Coupling of (V) with 4'-hydroxyacetophenone (VI) under Mitsunobu conditions furnished ether (VII). The trityl protecting group of (VII) was then cleaved by acidic treatment to give (VIII). Finally, condensation of (VIII) with hydroxylamine provided the target E-oxime.

参考文献中间体

【1】 Derrick, I.; et al.; 3-Deoxyclocinnamox: The first high-affinity, nonpeptide mu-opioid antagonist lacking a phenolic hydroxyl group. J Med Chem 2000, 43, 17, 3348.
【2】 Imidazole derivs. as histamine receptor H3 (ant)agonists. EP 0760811; FR 2732017; JP 1998501001; WO 9629315 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	27420	Urocanic acid; (E)-3-(1H-imidazol-4-yl)-2-propenoic acid	104-98-3	C₆H₆N₂O₂	详情	详情
(II)	27421	3-(1H-imidazol-4-yl)propionic acid		C₆H₈N₂O₂	详情	详情
(III)	27422	ethyl 3-(1H-imidazol-4-yl)propanoate		C₈H₁₂N₂O₂	详情	详情
(IV)	27423	ethyl 3-(1-trityl-1H-imidazol-4-yl)propanoate		C₂₇H₂₆N₂O₂	详情	详情
(V)	27424	3-(1-trityl-1H-imidazol-4-yl)-1-propanol		C₂₅H₂₄N₂O	详情	详情
(VI)	18123	1-(4-hydroxyphenyl)-1-ethanone; 4'-Hydroxyacetophenone	99-93-4	C₈H₈O₂	详情	详情
(VII)	44104	1-[4-[3-(1-trityl-1H-imidazol-4-yl)propoxy]phenyl]-1-ethanone		C₃₃H₃₀N₂O₂	详情	详情
(VIII)	44105	1-[4-[3-(1H-imidazol-4-yl)propoxy]phenyl]-1-ethanone		C₁₄H₁₆N₂O₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)