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Tauroursodeoxycholic acid, Ursodeoxycholyltaurine, UR-906

牛磺熊去氧胆酸Chemical Name: N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)taurine
CAS No. 14605-22-2
项目整合开发状态: Phase II
项目研究机构: Mitsubishi Pharma (Originator), Children's Hosp. Med. Center, Cincinnati (Codevelopment)
合成路线:The reaction of 5-carboxy-2-acetylthiophene (I) first with SOCl2 in refluxing toluene,and then with aqueous ammonia gives 5-carbamoyl-2-acetylthiophene (II),which is brominated with Br2 in hot acetic acid yielding 5-carbamoyl-2-bromoacetylthiophene (III).The cyclization of (III) with ammonium dithiocarbamate (A) in refluxing methanol-DMF affords 2-mercapto-4-(5'-carbamoyl-2'-thienyl)thiazole (IV),which is finally condensed with 1-chloro-3-tert-butylaminoisopropanol (V) by means of NaOH in water methanol.

合成路线:Ursodeoxycholic acid (I) was activated as the mixed anhydride (II) with ethyl chloroformate and triethylamine,and subsequently coupled with the triethylamine salt of taurine (III) to produce the title conjugated bile acid.Optionally,the mixed anhydride (II) was previously converted to the active phenol ester (V) by treatment with p-hydroxypropiophenone (IV),and subsequently condensed with taurine (III).Alternatively,ursodeoxycholic acid (I) was directly coupled to taurine (III) employing as the coupling reagents 2-isobutyl-N-isobutyloxycarbonyl-1,2-dihydroquinoline (IIDQ),diethylphosphorocyanidate (DEPC),or 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) under microwave irradiation.
📌 参考资料/链接:
参考文献标题:Process for preparing ursodeoxycholic acid derivates and their inorganic and organic salts having therapeutic activity
文献作者:Reiner,A.(SkyePharma AG)
参考来源:EP 0272462

📄 详细内容


合成路线:Ursodeoxycholic acid (I) was activated as the mixed anhydride (II) with ethyl chloroformate and triethylamine,and subsequently coupled with the triethylamine salt of taurine (III) to produce the title conjugated bile acid.Optionally,the mixed anhydride (II) was previously converted to the active phenol ester (V) by treatment with p-hydroxypropiophenone (IV),and subsequently condensed with taurine (III).Alternatively,ursodeoxycholic acid (I) was directly coupled to taurine (III) employing as the coupling reagents 2-isobutyl-N-isobutyloxycarbonyl-1,2-dihydroquinoline (IIDQ),diethylphosphorocyanidate (DEPC),or 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) under microwave irradiation.

参考文献标题:Process for the preparation of taurine-conjugated bile acids
文献作者:Bonadi,A.; Molinari,E.
参考来源:EP 0582891


合成路线:A further method was based on the microbial hydroxylation of taurolithocholic acid (VIII) by the action of a microorganism belonging to the Mortierella genus.

参考文献标题:Procuding conjugated ursodeoxycholic acids
文献作者:Sawada,H.; Watanuki,M.(Yakult Honsha Co.,Ltd.)
参考来源:EP 0119040


合成路线:In a related method,ursodeoxycholic acid (I) was activated as either the mixed anhydrides (VI) or (VII) with pivaloyl chloride or benzoyl chloride,respectively.Subsequent coupling with taurine (III) produced the title conjugated bile acid.

参考文献标题:Process for the preparation of taurocholic acids
文献作者:Rossetti,V.; Arosio,R.(Sanofi-Synthabo)
参考来源:EP 0629634


合成路线:Ursodeoxycholic acid (I) was activated as the mixed anhydride (II) with ethyl chloroformate and triethylamine,and subsequently coupled with the triethylamine salt of taurine (III) to produce the title conjugated bile acid.Optionally,the mixed anhydride (II) was previously converted to the active phenol ester (V) by treatment with p-hydroxypropiophenone (IV),and subsequently condensed with taurine (III).Alternatively,ursodeoxycholic acid (I) was directly coupled to taurine (III) employing as the coupling reagents 2-isobutyl-N-isobutyloxycarbonyl-1,2-dihydroquinoline (IIDQ),diethylphosphorocyanidate (DEPC),or 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) under microwave irradiation.

参考文献标题:An improved synthesis of taurine- and glycine-conjugated bile acids
文献作者:Momose,T.; Tsubaki,T.; Iida,T.; Nambara,T.
参考来源:Lipids 1997,32(7),775


合成路线:Ursodeoxycholic acid (I) was activated as the mixed anhydride (II) with ethyl chloroformate and triethylamine,and subsequently coupled with the triethylamine salt of taurine (III) to produce the title conjugated bile acid.Optionally,the mixed anhydride (II) was previously converted to the active phenol ester (V) by treatment with p-hydroxypropiophenone (IV),and subsequently condensed with taurine (III).Alternatively,ursodeoxycholic acid (I) was directly coupled to taurine (III) employing as the coupling reagents 2-isobutyl-N-isobutyloxycarbonyl-1,2-dihydroquinoline (IIDQ),diethylphosphorocyanidate (DEPC),or 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) under microwave irradiation.
参考文献标题:Microwave-induced rapid synthesis of bile acid conjugates
文献作者:Dayal,B.; et al.
参考来源:Synlett 1997,(8),861


产品链接: CAS No. 14605-22-2››