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Tiquizium bromide, HSR-902, Thiaton,71731-58-3,C19-H24-N-S2.

发布时间:2011-12-12 来源:安徽省医疗机构协会信息中心



【药物名称】Tiquizium bromide, HSR-902, Thiaton
【化学名】3-(Di-2-thienylmethylene)-5-methyl-trans-quinolizidinium bromide
【CAS登记号】71731-58-3
【结构式】
【分子式】C19-H24-N-S2.Br
【分子量】410.442
【原研厂家】Abbott (Originator)
【作用类别】Antispasmodics, GASTROINTESTINAL DRUGS
【研发状态】Launched-1984

【合成情况】 
〖来源〗Drugs Fut
〖合成路线〗
〖标题〗Tiquizium bromide
〖合成方法〗The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX). Finally, this compound is quaternirzed with methyl bromide in acetone.
〖作者〗Blancafort, P.; Serradell, M.N.; Casta馿r, J.; Thorpe, P.J.
〖参考〗Blancafort, P.; Serradell, M.N.; Casta馿r, J.; Thorpe, P.J.; Tiquizium bromide. Drugs Fut 1982, 7, 9, 655
〖出处〗Drugs Fut1982,7,(9):655
〖备注〗Synthesis of 115074: The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX) (1). Finally this compound is quaternirzed with methyl bromide in acetone (1,2). (Scheme 11507401a) Description
Colorless prisms, m.p. 263-5?(1); m.p. 261-3?(decomp.) (2). Manufacturer
Hokuriku Seiyaku Co., Ltd. (Japan). References 1. Koshinaka, E., Ogawa, N., Kurata, S., Yamagishi, K., Kubo, S., Matsubara, I. and Kato, H.; Studies on antispasmodics. I. Synthesis and anticholinergic activity of 1-, 2- and 3-diarylmethylenequinolizidine quaternary ammonium salts; Chem Pharm Bull 1979, 27(6), 1454-1463. 2. Kato, H., Koshinaka, E., Ogawa, N., Kurata, S., Yamagishi, K. and Ishikuza, M. (Hokuriku Pharm. Co., Ltd.); BE 866988, JP 8034148.

〖来源〗Chem Pharm Bull
〖合成路线〗
〖标题〗Studies on antispasmodics. I. Synthesis and anticholinergic activity of 1-, 2- and 3-diarylmethylenequinolizidine quaternary ammonium salts
〖合成方法〗The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX). Finally, this compound is quaternirzed with methyl bromide in acetone.
〖作者〗Ogawa, N.; Matsubara, I.; Kato, H.; Kurata, S.; Koshinaka, E.; Yamagishi, K.; Kubo, S.
〖参考〗Ogawa, N.; Matsubara, I.; Kato, H.; Kurata, S.; Koshinaka, E.; Yamagishi, K.; Kubo, S.; Studies on antispasmodics. I. Synthesis and anticholinergic activity of 1-, 2- and 3-diarylmethylenequinolizidine quaternary ammonium salts. Chem Pharm Bull 1979, 27, phen-2-ylp
〖出处〗Chem Pharm Bull1979,27,(6):1454-63
〖备注〗

〖来源〗BE 0866988; DE 2820687; FR 2390956; GB 1602927; JP 8034148
〖合成路线〗
〖标题〗Substituted quinolizidine and indolizidine derivatives and the preparation thereof
〖合成方法〗The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX). Finally, this compound is quaternirzed with methyl bromide in acetone.
〖作者〗Kato, H.; Koshinaka, E.; Ogawa, N.; Kurata, S.; Yamagishi, K.; Ishikuza, M. (Hokuriku Seiyaku Co., Ltd.)
〖参考〗Kato, H.; Koshinaka, E.; Ogawa, N.; Kurata, S.; Yamagishi, K.; Ishikuza, M. (Hokuriku Seiyaku Co., Ltd.); Substituted quinolizidine and indolizidine derivatives and the preparation thereof

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