Roxatidine bismuth citrate, MX1
Chemical Name: 2-Hydroxy-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide 2-hydroxypropane-1,2,3-tricarboxylic acid bismuth (3+) complex (1:1:1)
CAS No. 178487-37-1, 164066-67-5 (error)
项目整合开发状态: Preclinical
项目研究机构: Chemical Pharmaceutical Res. Inst. (Originator)
合成路线:The alkylation of 3-hydroxybenzaldehyde (I) with N-(3-bromopropyl)phthalimide (II) in the presence of NaOMe leads to 3-(phthalimidopropoxy)benzaldehyde (III).The reductive alkylation of piperidine with aldehyde (III) in the presence of formic acid gives N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]phthalimide (IV),which is converted to N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amine (V) by treatment with 6N HCl.Condensation of (V) with glycolic acid in boiling xylene provides N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-2-hydroxyacetamide (VI),which is complexed with bismuth (+3) citrate (VII) in boiling water.
📌 参考资料/链接：
参考文献标题: N-(3-(3-(1-Piperidinylmethyl)phenoxy)propyl)propenetricarboxylate bismuth (3+) complex and the method for preparation
文献作者:Ivanov,C.B.; Lutakov,G.I.; Nikolov,G.N.; Atanassova,R.B.; Petkov,O.V.; Taskov,M.V.; Ninova,E.A.; Tomova,V.V.; Aneva,V.T.; Mondeschka,D.M.; Schopova,S.I.; Bachvarova,A.S.; Galabova,A.A.; et al.(Chemical Pharmaceutical Research Institute)
参考来源:WO 9509162
📄 详细内容
合成路线:The alkylation of 3-hydroxybenzaldehyde (I) with N-(3-bromopropyl)phthalimide (II) in the presence of NaOMe leads to 3-(phthalimidopropoxy)benzaldehyde (III).The reductive alkylation of piperidine with aldehyde (III) in the presence of formic acid gives N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]phthalimide (IV),which is converted to N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amine (V) by treatment with 6N HCl.Condensation of (V) with glycolic acid in boiling xylene provides N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-2-hydroxyacetamide (VI),which is complexed with bismuth (+3) citrate (VII) in boiling water.
参考文献标题:Synthesis,gastroprotective,antisecretory and anti-Helicobacter effect of +[3(3-(1-piperidinylmethyl)phenoxy)propyl]hydroxyacetamide-2-hydroxypropane-1,2,3-tricarboxylate-bismuth(3+) complex (MX1)
文献作者:Ivanov,C.; Petkov,O.; Petrov,P..; Taskov,M.; Atanassova,R.; Tsvetkova,E.; Kostev,V.; Lytakov,G.; Nikolov,G.; Savov,E.
参考来源:J Pharm Pharmacol 1996,3(3),297-301
合成路线:The alkylation of 3-hydroxybenzaldehyde (I) with N-(3-bromopropyl)phthalimide (II) in the presence of NaOMe leads to 3-(phthalimidopropoxy)benzaldehyde (III).The reductive alkylation of piperidine with aldehyde (III) in the presence of formic acid gives N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]phthalimide (IV),which is converted to N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amine (V) by treatment with 6N HCl.Condensation of (V) with glycolic acid in boiling xylene provides N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-2-hydroxyacetamide (VI),which is complexed with bismuth (+3) citrate (VII) in boiling water.
参考文献标题:Roxatidine Bismuth Citrate
文献作者:Mondeshka,D.; Spassov,G.; Krushkov,I.; Ivanov,C.; Marazova,K.
参考来源:Drugs Fut 2000,25(5),462