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[关于一种新型福莫卡因的合成/第十次通讯:关于具有局部麻醉活性的新化合物的合成(作者译)]

[On a novel Fomocaine synthesis/10th communication: on syntheses of new compounds with local anaesthetic activity (author's transl)].

作者信息

Oelschläger H, Iglesias-Meier J, Götze G, Schatton W

出版信息

Arzneimittelforschung. 1977;27(9):1625-8.

PMID:579126
Abstract

4-[3-(4-phenoxymethyl-phenyl)-propyl]-morpholine (fomocaine, Erbocain) is a very active topical local anaesthetic with low toxicity. A new synthesis starting from 4-phenoxy-methyl-benzonitrile, via a modified Willgerodt-Kindler reaction, is reported. The yield is of the same order as with the known technical process starting from 3-phenylpropanol. The distinct advantage of the new procedure is the avoidance of the C-chloromethylation of 3-phenylpropylchloride during which process the o-chloromethyl derivative is also formed, and this cannot be separated by fractional distillation.

摘要

4-[3-(4-苯氧甲基苯基)丙基]吗啉(福莫卡因,厄波卡因)是一种活性很强的局部外用麻醉剂,毒性较低。本文报道了一种以4-苯氧甲基苯腈为起始原料,通过改进的威尔格罗德特-金德勒反应进行的新合成方法。其产率与从3-苯基丙醇开始的已知工业方法相当。新方法的显著优点是避免了3-苯基丙基氯的碳氯甲基化过程,在此过程中还会形成邻氯甲基衍生物,且无法通过分馏分离。

相似文献

1
[On a novel Fomocaine synthesis/10th communication: on syntheses of new compounds with local anaesthetic activity (author's transl)].[关于一种新型福莫卡因的合成/第十次通讯:关于具有局部麻醉活性的新化合物的合成(作者译)]
Arzneimittelforschung. 1977;27(9):1625-8.
2
[Synthesis and pharmacologic action of chiral fomocaine ((4-[2-methyl-3-(morpholin-4-yl)propyl)benzyl)-phenyl-ether and (4-(1-methyl-3-(morpholin-4-yl)propyl]benzyl)-phenyl-ether). 13. Synthesis of new compounds with local anesthetic action].
Pharmazie. 2001 Aug;56(8):620-5.
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Local anaesthetic effects and toxicity of seven new diethanolamine and morpholine derivatives of fomocaine. Testing in rats compared with procaine and tetracaine.
Arzneimittelforschung. 2003;53(3):221-8. doi: 10.1055/s-0031-1297098.
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[Metabolism of the local anaesthetic fomocaine by rat liver mitochondria (author's transl)].[大鼠肝线粒体对局部麻醉药福莫卡因的代谢(作者译)]
Arzneimittelforschung. 1981;31(10):1731-5.
5
[In vitro investigations of phase I metabolism of the fomocaine derivative Oe 9000 with pig liver homogenates].
Pharmazie. 2006 Nov;61(11):943-51.
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Antiarrhythmic activity of the local anaesthetic fomocaine and some of its analogues.
Arzneimittelforschung. 1989 Nov;39(11):1436-9.
7
[Synthesis of new compounds with local anesthetic activity. 11. Synthesis and action of 4-(3-bibenzyl-4-yl-propyl)-morpholine, a bioisosteric fomocaine].[具有局部麻醉活性的新化合物的合成。11. 生物电子等排体福莫卡因4-(3-联苄基-4-基丙基)-吗啉的合成与作用]
Arch Pharm (Weinheim). 1988 Feb;321(2):115-8. doi: 10.1002/ardp.19883210217.
8
Local anaesthetic effectivity and toxicity of fomocaine, five N-free fomocaine metabolites and two chiralic fomocaine derivatives in rats compared with procaine.
Arzneimittelforschung. 2001;51(6):451-8. doi: 10.1055/s-0031-1300062.
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[[Physical chemical, pharmacological and toxicologic properties of fomocaine metabolites] ].
Arzneimittelforschung. 2001 Jan;51(1):7-17. doi: 10.1055/s-0031-1299996.
10
[Studies on aromatic basic ethers with antispasmodic activity. V. Stereochemistry of 2-methyl-1-phenyl-3-piperidino-propyl phenyl ether derivatives (author's transl)].
Yakugaku Zasshi. 1973 Sep;93(9):1154-61.

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ACS Chem Neurosci. 2014 Jul 16;5(7):514-8. doi: 10.1021/cn500070w. Epub 2014 Jun 5.