【药物名称】DPP-NH[psi]
化学结构式(Chemical Structure):
参考文献No.24437
标题:New peptides
作者:Schiller, P. (AstraZeneca plc)
来源:EP 0678099; JP 1996505386; WO 9415959
合成路线图解说明:

The condensation of resin bounded L-phenylalanine (I) with N-(tert-butoxycarbonyl)-L-phenylalanine (II) by means of 1,3-diisopropylcarbodiimide (DIC) and HOBT gives the protected, resin bounded dipeptide (III), which is deprotected with TFA to yield the dipeptide (IV). The reductocondensation of (IV) with 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde (V) by means of NaBH3CN affords the protected pseudo tripeptide (VI), which is deprotected with TFA as before yielding the pseudo tripeptide (VII). The condensation of (VII) with the protected L-dimethyltyrosine (VIII) by means of DIC and HOBT affords the protected resin bounded seudotetrapeptide (IX), which is deprotected with TFA as before giving the resin bounded seudotetrapeptide (X). Finally, the target seudotetrapeptide is cleaved from the resin by means of HF and anisole.

合成路线图解说明:

The intermediate 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde (V) has been obtained as follows: The reaction of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (XI) with N,O-dimethylhydroxylamine (XII) by means of BOP gives the corresponding N-methoxy-N-methylamide (XIII), which the reduced to the target aldehyde (V) with LiAlH4.

参考文献No.548628
标题:The opioid mu agonist/delta antagonist DIPP-NH2[psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats
作者:Schiller, P.W.; Fundytus, M.E.; Merovitz, L.; Weltrowska, G.; Nguyen, T.M.; Lemieux, C.; Chung, N.N.; Coderre, T.J.
来源:J Med Chem 1999,42(18),3520
合成路线图解说明:

The condensation of resin bounded L-phenylalanine (I) with N-(tert-butoxycarbonyl)-L-phenylalanine (II) by means of 1,3-diisopropylcarbodiimide (DIC) and HOBT gives the protected, resin bounded dipeptide (III), which is deprotected with TFA to yield the dipeptide (IV). The reductocondensation of (IV) with 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde (V) by means of NaBH3CN affords the protected pseudo tripeptide (VI), which is deprotected with TFA as before yielding the pseudo tripeptide (VII). The condensation of (VII) with the protected L-dimethyltyrosine (VIII) by means of DIC and HOBT affords the protected resin bounded seudotetrapeptide (IX), which is deprotected with TFA as before giving the resin bounded seudotetrapeptide (X). Finally, the target seudotetrapeptide is cleaved from the resin by means of HF and anisole.

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