Method and reagents for N-alkylating ureides

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

1997-10-02

2000-07-25

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

546216, 546242, 546243, 5483171, 548545, 548547, C07D23962, C07D23374, C07D26344, A61K 31515

Patent

active

06093820&

ABSTRACT:
A method of N-alkoxyalkylating ureides according to the invention comprises reacting a ureide of structure I ##STR1## with an alkylating agent of structure III ##STR2## in 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.

REFERENCES:
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JP Gesson, JC Jacquesy, D. Rambaud, A practical method for N-alkylation of succinimide and glutarimide, Bulletin De La Societe Chimique De France, vol. 129, No. 3, 1992, pp. 227-231.
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Foye, "Principles of Medicinal Chemistry", 3rd ed., 1990, pp. 164, 179.
Karger et al., "Methoxymethyl Methanesulfonate, A Novel Active Oxyalkylating Agent", Journal of the American Chemical Society, 91:5663 (1969).
Aldrich Chemical Catalog, 1990-1991, p. 303.
Groth et al., EP-726252, (1996) (Abstract only).
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