拉诺康唑 [CAS:101530-10-3]合成路线图解

药物详细合成路线

Name	Latoconazole;Lanoconazole;TJN-318;NND-318;Astat
Chemical Name	(±)-(E)-alpha-[4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene]-1H-imidazole-1-acetonitrile
CAS	101530-10-3
Related CAS
Formula	C₁₄H₁₀ClN₃S₂
Structure
Formula Weight	319.8369
Stage	撤市
Company	Nihon Nohyaku (Originator), Tsumura (Licensee)
Activity/Mechanism	Antifungal Agents, ANTIINFECTIVE THERAPY
Syn. Route	1

Route 1

the reaction of 2-(1-imidazolyl)acetonitrile (i) with cs2 and koh in dmf gives the dithiolate (ii), which is then cyclized with 1-(2-chlorophenyl)-1,2-di(methanesulfonyloxy)ethane (iii). a column chromatography over silicagel allows the separation of the (e)- and (z)-isomers.

List of intermediates	No.
2-[[(2-amino-5-methoxyphenyl)sulfanyl]methyl]-2-ethylhexanoic acid	(i)
3-butyl-3-ethyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5h)-one	(ii)
7-bromo-3-butyl-3-ethyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5h)-one	(iii)

Reference 1:

seo, a.; kanno, h.; hasegawa, n.; miyagi, y.; nishimura, a.; konaka, s.; ohmi, t.; munechika, y.; uchida, m.; ikeda, k. (nihon nohyaku co., ltd.); a novel ketene s,s-acetal deriv., a process for manufacturing thereof and a method for curing mycosis by administering it. ep 0218736 .

Reference 2:

seo, a.; sugano, h.; hasegawa, c.; ikeda, k.; munechica, y.; konoe, t.; konaka, m. (nihon nohyaku co., ltd.); antifungal agent. jp 1987093227 .

Reference 3:

seo, a.; sugano, h.; hasegawa, c.; ikeda, k.; nishimura, a.; miyashiro, y. (nihon nohyaku co., ltd.); non-medicinal bactericidal agents and method for their preparation. jp 1987093204 .

Reference 4:

seo, a.; kanno, h.; hasegawa, n.; miyagi, y.; nishimura, a.; konaka, s.; ohmi, t.; munechika, y.; uchida, m.; ikeda, k. (nihon nohyaku co., ltd.); antimycotic agent and fungicidal agent. us 4738976 .

Reference 5:

seo, a.; sugano, h.; hasegawa, c.; miyashiro, y.; nishimura, a.; ikeda, k. (nihon nohyaku co., ltd.); ketene s,s-acetals. jp 1985218387 .

Reference 6:

castaner, j.; prous, j.; lanoconazole. drugs fut 1993, 18, 3, 222.

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拉诺康唑；英文名Latoconazole;Lanoconazole;TJN-318;NND-318;Astat；CAS[101530-10-3]