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Details for Patent: 4,163,058

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Details for Patent: 4,163,058

Title: Derivatives of 5,5-diphenylhydantoin exhibiting enhanced solubility and the therapeutic use thereof
Abstract:Novel derivatives of 5,5-diphenylhydantoin, having the formula: ##STR1## wherein R is as defined in the specification and claims hereinafter, are disclosed. These compounds exhibit enhanced solubility over diphenylhydantoin per se and find therapeutic usefulness as anticonvulsants, antiepileptics and antiarrhythmics.
Inventor(s): Stella; Valentino J. (Lawrence, KS), Sloan; Kenneth B. (Eudora, KS)
Assignee: INTERX Research Corporation (Lawrence, KS)
Filing Date:Apr 22, 1977
Application Number:05/790,087
Claims:1. A 5,5-diphenylhydantoin compound having the formula: ##STR12## wherein R represents H or a member selected from the group consisting of ##STR13## wherein R.sub.1 represents a member selected from the group consisting of H and C.sub.1 -C.sub.7 straight or branched alkyl; wherein X is --O-- or --S--; and wherein R.sub.2 represents ##STR14## wherein R.sub.4 is an acyl residue of any naturally occurring protein amino acid; with the proviso that R in both occurrences cannot represent H simultaneously; or the pharmaceutically acceptable acid addition or basic salts, C.sub.1 -C.sub.4 alkylhalide quaternary salts or N-oxide thereof.

2. The compound of claim 1:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin.

3. The compound of claim 1:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin methanesulfonate.

4. The compound of claim 1:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin salicylate.

5. A pharmaceutical composition comprising an effective anticonvulsant, antiepileptic or antiarrythmic amount of a 5,5-diphenylhydantoin compound having the formula: ##STR15## wherein R represents H or a member selected from the group consisting of ##STR16## wherein R.sub.1 represents a member selected from the group consisting of H and C.sub.1 -C.sub.7 straight or branched alkyl; wherein X is --O-- or --S--; and wherein R.sub.2 represents ##STR17## wherein R.sub.4 is an acyl residue of any naturally occurring protein amino acid; with the proviso that R is both occurrences cannot represent H simultaneously; or the pharmaceutically acceptable acid addition or basic salts; C.sub.1 -C.sub.4 alkylhalide quaternary salts or N-oxide thereof in combination with a pharmaceutically acceptable inert carrier.

6. The combination of claim 5, wherein said compound is:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin.

7. The composition of claim 5, wherein said compound is:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin methanesulfonate.

8. The composition of claim 5, wherein sid compound is:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin salicylate.

9. A method for alleviating cardia arrythmias or convulsions in a warm-blooded animal which comprises administering thereto, an effective antiarrythmic or anticonvulsant amount of a 5,5-diphenylhydantoin compound having the formula: ##STR18## wherein R represents H or a member selected from the group consisting of ##STR19## wherein R.sub.1 represents a member selected from the group consisting of H or C.sub.1 -C.sub.7 straight or branched alkyl; wherein X is --O-- or --S--; and wherein R.sub.2 represents ##STR20## wherein R.sub.4 is an acyl residue of any naturally occurring protein amino acid; with the proviso that R in both occurrences cannot represent H simultaneously, or the pharmaceutically acceptable acid addition or basic salts, C.sub.1 -C.sub.4 alkylhalide quaternary salts or N-oxide thereof.

10. The method of claim 12, wherein said compound is administered in combination with a pharmaceutically acceptable inert carrier.

11. The method of claim 9, wherein said compound is:

3-(N,N-Dimethylglycycloxymethyl)diphenylhydantoin.

12. The method of claim 9, wherein said compound is:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin methanesulfonate.

13. The method of claim 9, wherein said compound is:

3-(N,N-Dimethylglycyloxymethyl)diphenylhydantoin salicylate.
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