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Synthesis Studies on Duloxetine and Its Analogues

Author: GuoLei
Tutor: ZhangWenJun
School: Hebei University of Technology
Course: Applied Chemistry
Keywords: Antidepressant drugs Duloxetine Process optimization Synthesis
CLC: TQ463.53
Type: Master's thesis
Year: 2010
Downloads: 71
Quote: 0
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Abstract


In this paper, the synthesis of the antidepressant duloxetine and its analogues . Duloxetine chemically named (S)-N- methyl 3 - (1 - naphthyloxy ) 3 - ( 2 - thiophene- yl) -1 - propylamine, is a 5 - serotonin and norepinephrine reuptake has a dual inhibition of antidepressants . In addition it is also an effective treatment of female urinary incontinence , diabetic peripheral neuropathic pain . The clinical applications from the rapid onset , well tolerated and safe , with few side effects . Reported in the literature with different compounds as a starting material , or choose a different resolving agents and de- Preparation of methyl - step sequence duloxetine method , we have conducted a comprehensive study on the methods described in the literature to determine an economic viable synthetic route, and on the reaction process is optimized. 2 - acetyl thiophene and paraformaldehyde as a starting material , a total of seven-step reaction synthesis of duloxetine . Involving the Mannnich reactions , restore , split racemic subdivision , etherification , demethylation , salt and other reactions . The structure was confirmed by nuclear magnetic resonance (NMR), mass spectrometry (MS) and infrared (IR) confirmed. In this paper, two design concepts for the development of new antidepressants , design 5 duloxetine analogues , one based on duloxetine for the target compounds based the bioisosteric theory devised a degree Los vinpocetine like; other is a duloxetine as the parent to its terminal amino group with the aromatic acid chloride structure modification or connected to it with the 5-HT1A receptor blockers ( aromatic piperazine) via an amide chain , two effective groups put together in a molecule , four new target compounds . The structural characterization of these compounds by NMR, mass spectrometry and other analytical tools , with the expected results .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Production of organic compounds in drug > Heterocyclic compounds drugs > Five section heterocyclic
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