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 Metronidazole;IDR-90105(Ophthalmic);Rosased;Zidoval;Metrogel;Flagyl
Chemical Name 2-Methyl-5-nitro-1H-imidazole-1-ethanol
CAS 443-48-1
Related CAS 133884-00-1 (deleted CAS)
Formula C6H9N3O3
Structure
Formula Weight 171.15693
Stage 上市-1960
Company Pfizer (Originator), 3M Pharmaceuticals (Not Determined), Novartis (Not Determined), Pierre Fabre (Not Determined), Institute for Drug Research (Licensee)
Activity/Mechanism Acne Therapy, Antiamebics, Antibacterial Drugs, Antibacterial Ophthalmic Drugs, Antifungal Agents, ANTIINFECTIVE THERAPY, Antitrichomonals, DERMATOLOGIC DRUGS, Ocular Antiinflammatory and Antiinfective Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, Treatment of Protozoal Diseases
Syn. Route 6
Route 1
2-methylimidazole (i) is converted into the bisulfate salt, and then nitrated by means of a sulfonitric mixture in ac2o to produce 2-methyl-4-nitroimidazole (ii) . in a variant of this procedure, 2-methylimidazole (i) is nitrated by using a ferric nitrate-tonsyl adduct in several solvents. imidazole (ii) is then regioselectively alkylated with boiling 2-chloroethanol to produce the title compound. alternatively, the alkylation of (ii) has been reported by treatment with ethylene oxide (iii) under acidic conditions.
List of intermediates No.
3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-4-phenyl-1,4-dihydropyridine (iii)
(3ar,6as)-2-oxohexahydro-2h-cyclopenta[b]furan-4-carbaldehyde (i)
ethyl (1r,2s,4r)-2-isopropenyl-1-methyl-4-vinylcyclohexanecarboxylate (ii)
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 .

Route 2
in an alternative procedure, the title compound is obtained by hydrolysis of the bromoethyl imidazole (i) in the presence of formic acid in aqueous formamide
List of intermediates No.
Reference 1:
    sunjic, v.; fajdiga, t.; kajfez, f.; process for preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole. de 1695321; gb 1138805; us 3520900 .

Route 3
the title compound can be obtained by reaction of 1-(acetoxymethyl)-2-methyl-4-nitroimidazole (i) with ethylene oxide (ii) in the presence of sulfur trioxide, followed by hydrolysis in aqueous h2so4
List of intermediates No.
3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-4-phenyl-1,4-dihydropyridine (ii)
Reference 1:
    lavigne, m.; mandard-cazin, b. (aventis pharma sa); process for preparing hydroxyalkyl-1 nitro-5 imidazoles. wo 9113877 .

Route 4
in a related procedure, 1-(acetoxymethyl)-2-methyl-4-nitroimidazole (i) is condensed with ethyleneglycol diacetate (ii) in the presence of anhydrous h2so4, followed by hydrolysis or alcoholysis under acidic conditions to produce the title compound
List of intermediates No.
Reference 1:
    buforn, a.; massonneau, v.; mulhauser, m. (aventis sa); process for the preparation of 1-hydroxyalkyl-2-methyl-5-nitro-imidazoles. ep 0325513; fr 2625999 .

Route 5
alternatively, 2-methyl-4-nitroimidazole (i) is protected by acylation in hot acetic anhydride to give (ii). addition of ethylene oxide (iii) to the n-acetyl imidazole (ii) in the presence of so3, followed by acidic hydrolysis furnishes the title compound
List of intermediates No.
3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-4-phenyl-1,4-dihydropyridine (iii)
ethyl (1r,2s,4r)-2-isopropenyl-1-methyl-4-vinylcyclohexanecarboxylate (i)
Reference 1:
    lavigne, m.; mandard-cazin, b. (aventis pharma sa); process for preparing hydroxyalkyl-1 nitro-5 imidazoles. wo 9113877 .

Route 6
the title compound can also be obtained by alkylation, in different solvents, of 1-(acetoxymethyl)-2-methyl-4-nitroimidazole (i) with either ethylene sulfate (ii) or with bis-(2-acetoxyethyl) sulfate (iii) -generated from ethyleneglycol diacetate (iv) and either dimethyl sulfate or h2so4 - followed by hydrolysis or alcoholysis treatment
List of intermediates No.
Reference 1:
    massonneau, v.; mulhauser, m.; buforn, a. (aventis pharma sa); process for the preparation of hydroxyalkylating agents, the agents so prepared and their use. ep 0324692 .
Reference 2:
    massonneau, v.; mulhauser, m.; buforn, a.; madard-cazin, b. (aventis pharma sa); process for the preparation of 1-hydroxyalkyl-5-nitro-imidazoles. ep 0324691 .

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甲硝唑;英文名Metronidazole;IDR-90105(Ophthalmic);Rosased;Zidoval;Metrogel;Flagyl;CAS[443-48-1]

 
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
江苏地区粗苯价格暂稳
山东地区粗苯价格暂稳
华东地区丁二烯市场弱势盘整
浙江省化学农药使用量连续7年持
兴发集团实现草甘膦副产物高效高
华东地区丁二烯市场价格走低
2018年秋播小麦种子药剂处理
华南地区己二酸行情持稳
华北地区BDO市场弱势延续
红太阳/丰山集团等8家农药生产
刘学:浅析农药登记后再评价工作
中国农民礼赞!——写在第一个“
我国化工园区第一个国家标准已获
新安股份前三季度业绩预增,净利
农业农村部农药检定所征求《农药
丁香菌酯等农药产品入选《201
内蒙古元正精细化工高效氟吡甲禾
华北地区丁二烯市场行情弱势
丙炔氟草胺领军“其他PPO抑制
呋虫胺和烯啶虫胺继续扩作
 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