N-3-aramid-5-cyclopropane spiro hydantoin derivative, preparation method and application thereof

A technology of spirocyclic hydantoin and cyclopropane, which is applied in the field of hydantoin derivatives and their preparation, can solve the problems of cognitive dysfunction, severe allergic reactions, adverse reactions and the like, and achieves simple preparation method and high yield. high rate effect

Inactive Publication Date: 2010-10-20
SYNCOM CHINA CO LTD WUHAN
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Problems solved by technology

Although the new antiepileptic drugs have partially improved the shortcomings of some antiepileptic drugs, most of the new drugs can...

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  • N-3-aramid-5-cyclopropane spiro hydantoin derivative, preparation method and application thereof
  • N-3-aramid-5-cyclopropane spiro hydantoin derivative, preparation method and application thereof
  • N-3-aramid-5-cyclopropane spiro hydantoin derivative, preparation method and application thereof

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Abstract

The invention relates to an N-3-aramid-5-cyclopropane spiro hydantoin derivative which has a structural formula described in the specification, wherein R1 is phenyl, substituted phenyl and heterocycle aryl. A preparation method comprises the steps of: reacting 1-carboxyl-2,2-dimethylcyclopropane carboxylic ethyl ester with ethyl chloroformate to generate 1-acid azide-2,2-dimethylcyclopropane carboxylic ethyl ester under the action of NaN3; carrying out Curtius rearrangement on the 1-acid azide-2,2-dimethylcyclopropane carboxylic ethyl ester to generate isocyanate, reacting the isocyanate with arylacethydrazide to obtain N'-aramid substituted carbamido cyclopropane; and then carrying out cyclization on the N'-aramid substituted carbamido cyclopropane under the alkaling condition to generate the N-3-aramid-5-cyclopropane spiro hydantoin derivative. The compound has relatively good convulsions resisting activity, simple preparation method and higher yield.

Description

technical field The invention relates to a hydantoin derivative, a preparation method and application thereof. Background technique Hydantoin, also known as hydantoin, has attracted widespread attention since its discovery in 1861. Some hydantoin derivatives have unique pharmacological activities and are widely used in medicine. Among them, a representative one is phenytoin sodium, chemical name 5-ethyl-5-phenylhydantoin, which is a common drug for treating epilepsy. However, it has been clinically found that long-term use of phenytoin sodium can cause gingival hyperplasia, with large side effects. Since the 1980s, with the in-depth study of the pathogenesis of epilepsy, the mechanism of action of antiepileptic drugs has been clarified, and some new antiepileptic drugs have been designed on this basis. At present, the new antiepileptic drugs that have been approved for clinical application abroad are: zonisamide, oxcarbazepine, lamotrigine, felbamate, vigabatrin, gabapen...

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Application Information

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IPC IPC(8): C07D235/02C07D405/12C07D409/12C07D401/12A61K31/4184A61K31/4439A61P25/08
Inventor 胡先明贺贤然
Owner SYNCOM CHINA CO LTD WUHAN
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