【药物名称】Nalfurafine hydrochloride, TRK-820
化学结构式(Chemical Structure):
参考文献No.21563
标题:Morphinan deriv. and medicinal use
作者:Nagase, H.; Kawai, K.; Kawamura, K.; Hayakawa, J.; Endo, T. (Toray Industries, Inc.)
来源:EP 0577847; EP 0846694; JP 1994509616; US 6277859; US 6323212; WO 9315081
合成路线图解说明:

The reductocondensation of naltrexone (I) with N-methylbenzylamine (II) by means of sodium cyanoborohydride in THF gives the N-benzyl-N-methylaminomorphinan derivative (III), which is debenzylated by hydrogenation with H2 over Pd/C in methanol yielding the methylaminomorphinan (IV). Finally, this compound is acylated with 3(E)-(3-furyl)acryloyl chloride and NaOH, Na2CO3 or triethylamine in methanol, THF or chloroform. Alternatively, methylaminomorphinan (IV) can also be obtained by direct reductocondensation of naltrexone (I) with methylamine by means of H2 over PtO2 in methanol.

参考文献No.25872
标题:Antitussive
作者:Nagase, H.; Kawai, K.; Endo, T.; Ueno, S.; Negishi, Y. (Toray Industries, Inc.)
来源:EP 0657163; JP 1995503397; US 5739145; WO 9501178
合成路线图解说明:

The reductocondensation of naltrexone (I) with N-methylbenzylamine (II) by means of sodium cyanoborohydride in THF gives the N-benzyl-N-methylaminomorphinan derivative (III), which is debenzylated by hydrogenation with H2 over Pd/C in methanol yielding the methylaminomorphinan (IV). Finally, this compound is acylated with 3(E)-(3-furyl)acryloyl chloride and NaOH, Na2CO3 or triethylamine in methanol, THF or chloroform. Alternatively, methylaminomorphinan (IV) can also be obtained by direct reductocondensation of naltrexone (I) with methylamine by means of H2 over PtO2 in methanol.

参考文献No.26069
标题:Morphinan derivative and medicinal use
作者:Nagase, H.; Hayakawa, J.; Kawamura, H.; Kawai, K.; Endoh, T. (Toray Industries, Inc.)
来源:AU 686203; AU 7237394; EP 0663401
合成路线图解说明:

The reductocondensation of naltrexone (I) with N-methylbenzylamine (II) by means of sodium cyanoborohydride in THF gives the N-benzyl-N-methylaminomorphinan derivative (III), which is debenzylated by hydrogenation with H2 over Pd/C in methanol yielding the methylaminomorphinan (IV). Finally, this compound is acylated with 3(E)-(3-furyl)acryloyl chloride and NaOH, Na2CO3 or triethylamine in methanol, THF or chloroform. Alternatively, methylaminomorphinan (IV) can also be obtained by direct reductocondensation of naltrexone (I) with methylamine by means of H2 over PtO2 in methanol.

参考文献No.524678
标题:Discovery of a structurally novel opioid kappa-agonist derived from 4,5-epoxymorphinan
作者:Nagase, H.; Hayakawa, J.; Kawamura, K.; Kawai, K.; Takezawa, Y.; Matsuura, H.; Tajima, C.; Endo, T.
来源:Chem Pharm Bull 1998,46(2),366
合成路线图解说明:

The reductocondensation of naltrexone (I) with N-methylbenzylamine (II) by means of sodium cyanoborohydride in THF gives the N-benzyl-N-methylaminomorphinan derivative (III), which is debenzylated by hydrogenation with H2 over Pd/C in methanol yielding the methylaminomorphinan (IV). Finally, this compound is acylated with 3(E)-(3-furyl)acryloyl chloride and NaOH, Na2CO3 or triethylamine in methanol, THF or chloroform. Alternatively, methylaminomorphinan (IV) can also be obtained by direct reductocondensation of naltrexone (I) with methylamine by means of H2 over PtO2 in methanol.

参考文献No.723584
标题:Nalfurafine Hydrochloride
作者:Leeson, P.A.; Sorbera, L.A.; Casta馿r, J.
来源:Drugs Fut 2003,28(3),237
合成路线图解说明:

The reductocondensation of naltrexone (I) with N-methylbenzylamine (II) by means of sodium cyanoborohydride in THF gives the N-benzyl-N-methylaminomorphinan derivative (III), which is debenzylated by hydrogenation with H2 over Pd/C in methanol yielding the methylaminomorphinan (IV). Finally, this compound is acylated with 3(E)-(3-furyl)acryloyl chloride and NaOH, Na2CO3 or triethylamine in methanol, THF or chloroform. Alternatively, methylaminomorphinan (IV) can also be obtained by direct reductocondensation of naltrexone (I) with methylamine by means of H2 over PtO2 in methanol.

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