有机化学人才网 | 最新人才 | 最新职位 | 技术交易 | 药物合成 |
   
全站搜索: |
  您当前位置:网站首页 >> 药物合成路线图解
 

药物详细合成路线

Name Aminoglutethimide;AG-1;Orimeten;Cytadren
Chemical Name 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
CAS 125-84-8
Related CAS
Formula C13H16N2O2
Structure
Formula Weight 232.28467
Stage 上市-1981
Company Novartis (Originator)
Activity/Mechanism Adrenocortical Dysfunction Therapy, Breast Cancer Therapy, Cushings Syndrome, Agents for, ENDOCRINE DRUGS, Oncolytic Drugs, Prostate Cancer Therapy, Antiglucocorticoids, Aromatase Inhibitors
Syn. Route 1
Route 1
an improved procedure for the large-scale preparation of (r)-aminoglutethimide has been reported. nucleophilic substitution of 1-chloro-4-nitrobenzene (i) with methyl cyanoacetate afforded the (nitrophenyl)cyanoacetate (ii), which was alkylated with diethyl sulfate in the presence of et3n, yielding (iii). hydrolysis and decarboxylation of the cyano ester (iii) by means of k2co3 in aqueous meoh provided the arylbutyronitrile (iv). subsequent michael addition with methyl acrylate gave adduct (v). this was hydrolyzed to the cyano acid (vi), which was further resolved with (-)-cinchonidine, yielding the desired (r)-enantiomer (vii). acid-catalyzed cyclization of (vii) in boiling toluene generated the glutarimide derivative (viii). the nitro group of (viii) was finally reduced to the title amino derivative by hydrogenation over pd/c.
List of intermediates No.
(4s,7r,8s,9s,16s)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecene-2,6-dione (i)
1-methyl-2-oxo-1,2-dihydro-4-pyridinecarbaldehyde
2-(2-phenyl-1h-indol-3-yl)-1-ethanamine; 2-(2-phenyl-1h-indol-3-yl)ethylamine
(1as,8r,9as)-3-(acetoxy)-7-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-8-(hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-1,1a,2,3,8,9a-hexahydro-9h-azireno[2,3-c][1]benzazocin-9-one (ii)
(1as,8r,9as)-7-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-3-hydroxy-8-(hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-1,1a,2,3,8,9a-hexahydro-9h-azireno[2,3-c][1]benzazocin-9-one (iii)
(8r,9s,10s,12s)-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-8-(hydroxymethyl)-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-ol (iv)
(1s,6r,15s,17s)-8-(benzyloxy)-10-[[(benzyloxy)methoxy]methyl]-16-[(4-methylphenyl)sulfonyl]-2,4,18-trioxa-13,16-diazapentacyclo[11.4.1.0(1,6).0(7,12).0(15,17)]octadeca-7,9,11-trien-3-one (v)
[(8r,9s,10s,12s)-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-9-hydroxy-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-8-yl]methyl carbamate (vi)
(8r,10s,12s)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate (vii)
(8r,10s,12s)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate (viii)
Reference 1:
    bunegar, m.j.; et al.; production of (r)-aminogluthimide: a new route from 1-chloro-4-nitrobenzene. org process res dev 1999, 3, 6, 442.

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氨鲁米特;英文名Aminoglutethimide;AG-1;Orimeten;Cytadren;CAS[125-84-8]

 
推荐VIP企业
无锡景耀生物科技有限公司
杭州卢普生物科技有限公司
宁波赛伦化工有限公司
苏州昊赛生物科技有限公司
北京嘉盛扬医药科技有限公司
上海泽涵生物医药科技有限公司
河北固安三利化工公司
郑州凯普瑞生物技术有限公司
上海药谷药业有限公司
兰州康寓信生物科技有限公司
湖北朗昕生化药业有限公司
武汉福鑫化工有限公司
嘉兴市英南化工有限公司
苏州迪飞医药科技有限公司
北京富安凯科技有限公司
上海盛中医药化工有限公司
连云港天和化学有限公司
南京晨瑞医药科技有限公司
南京苏如化工有限公司
常州瑞盛化工有限公司
热门文章
罗氏向 FDA 递交 Kadc
前列腺癌药物苯扎鲁胺达到 AR
欧盟批准武田霍奇金淋巴瘤药物
赛诺菲砍掉 38 个研发项目,
AZ 抗病毒药物 MEDI88
赛诺菲 Darzalex 竞争
默沙东向 FDA 提交两款抗菌
两降一涨!蓝丰/国发/新奥发布
华北地区醋酸价格
山东地区醋酸价格
河南地区醋酸价格暂稳
江苏地区醋酸价格下调
华北地区丁二烯市场观望为主
华北地区醋酸价格
华东地区BDO市场商谈整理
山东地区木薯酒精市场稳定
浙江地区醋酸价格
陕西地区醋酸价格下调
PTA止跌在眼前
华南地区BDO市场商谈出货
 友情链接
有机化学人才网  
首页 | 广告服务 | 建站服务 | 关于我们 | 联系我们 | 版权声明