Method and reagents for N-alkylating ureides

Details Method and reagents for N-alkylating ureides Method and reagents for N-alkylating ureides

2006-01-10

2006-01-10

Kifle, Bruck (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S328000, C514S391000, C514S425000, C544S302000, C546S216000, C546S272400, C546S243000, C548S317100, C548S545000, C548S547000

Reissue Patent

active

RE038934

ABSTRACT:
A method of N-alkoxyalkylating ureides according to the invention comprises reacting a ureide of structure Iwith an alkylating agent of structure IIIin the presence of a basic catalyst in an aprotic reaction medium. The ureide may be a 5,5-disubstituted barbituric acid, or it may be phenytoin, glutethimide, and ethosuximide. The alkylating agent is an ester of a sulfonic acid. The base may be a hydride or amine. A preferred process comprises N-alkoxyalkylating 5,5-diphenyl-barbituric acid with methoxymethyl methanesulfonate in the presence of di-isopropyl ethyl amine and isolating the resultant N,N′-bismethoxymethyl-5,5-diphenyl-barbituric acid. The invention also contemplates the novel compounds N-methoxymethyl-5,5-diphenylbarbituric acid, N-methoxymethyl ethosuximide, and N-methoxymethyl glutethimide, and a method comprising administering them to a patient.

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