N-3-arylamine-5-cyclopropane spirohydantoin and preparation method and application thereof

A spirohydantoin, N-3- technology, applied in pharmaceutical formulations, medical preparations containing active ingredients, organic active ingredients, etc., can solve cognitive dysfunction, severe allergic reactions, adverse reactions, etc. problem, to achieve the effect of a simple preparation method
CN103304483AInactive Publication Date: 2013-09-18JIANGHAN UNIVERSITY
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
JIANGHAN UNIVERSITY
Publication Date
2013-09-18
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses N-3-arylamine-5-cyclopropane spirohydantoin and a preparation method and application thereof. The structural general formula of the N-3-arylamine substituent-5-cyclopropane spirohydantoin is shown in the specification, wherein R1 is phenyl, substituted phenyl and heterocyclic arene. The preparation method comprises the following steps of: performing a reaction between 1-carboxyl-2,2-dimethylcyclopropane ethyl carboxylate and ethyl chloroformate to generate 1-acyl azide-2,2-dimethylcyclopropane ethyl carboxylate under the effect of NaN3; performing Curtius rearrangement on the 1-acyl azide-2,2-dimethylcyclopropane ethyl carboxylate to generate corresponding isocyanate; performing a reaction between the isocyanate and hydrazine to obtain N'-arylamine substituent ureidocyclopropane; and generating N-3-arylamine substituent-5-cyclopropane spirohydantoin from the N'-arylamine substituent ureidocyclopropane. The preparation method disclosed by the invention is simple, has higher yield, and can be used for easily preparing the N-3-arylamine substituent-5-cyclopropane spirohydantoin.
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Description

technical field

[0001] The invention relates to a 5-substituted hydantoin, specifically an N-3-arylamine-5-cyclopropane spirohydantoin and a preparation method and application thereof. Background technique

[0002] 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.

[0003] 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 app...

Claims

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