Sulphamoylphenyl-imidazolidinones

• US 3,963,706 A
• Filed: 11/19/1973
• Issued: 06/15/1976
• Est. Priority Date: 11/20/1972
• Status: Expired due to Term

• Current Assignee: ED. Geistlich Soehne AG Fuer Chemische Industrie
• Original Assignee: ED. Geistlich Soehne AG Fuer Chemische Industrie
• Inventors: Pfirrmann, Rolf Wilhelm
• Primary Examiner(s): Rosen, Sam
• Application Number:
  US05/416,854
• Time in Patent Office: 939 Days
• Field of Search: 260/239.9
• US Class Current: 548/321.1
• CPC Class Codes: A61P 25/08 Antiepileptics; Anticonvulsants
• CPC Class Codes: C07D 233/32 One oxygen atom
• CPC Class Codes: C07D 233/72 Two oxygen atoms, e.g. hydantoin

Abstract

N-Sulphamoylphenyl-substituted imidazolidin-4-ones having useful anti-epileptic activity are prepared by cyclising N-sulphamoylphenyl-substituted α-aminoacetamides with formaldehyde or a reactive derivative of carbonic acid, or by reacting N-halosulphonylphenyl-substituted imidazolidin-4-ones with ammonia.

Claims

1. A compound of the formula ##SPC8##

in which R¹ is phenyl;

phenyl substituted with alkoxy, lower alkyl or halogen;

or a cycloalkyl or cycloalkenyl group having 5-10 carbon atoms or a sulphamoylphenyl group, R⁴ represents a sulphamoylphenyl or phenyl group;

R² and R³ each represent hydrogen atoms or an oxo group; and

R⁵ and R⁶ are hydrogen atoms or lower alkyl or cycloalkyl groups;

with the proviso that one of R¹ and R⁴ , but not both is a sulphamoylphenyl group.

2. A compound according to claim 1 in which R⁴ represents a group of the formula ##SPC9##

in which R⁷ represents a hydrogen, fluorine, chlorine or bromine atom or a lower alkyl or trifluoromethyl group.

3. A compound according to claim 2 selected from the group consisting of

1-Phenyl-3-p-sulphamoylphenyl-imidazolidin-4-one;

1-phenyl-3-(2-fluoro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(3-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(2-bromo-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(2-methyl-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(3-trifluoromethyl-4-sulphamoylphenyl)-imidazolidin-4-one;

1-cyclohexyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-p-chlorophenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-p-methylphenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-p-methoxyphenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one; and

1-phenyl-3-(2-chloro-4-sulphamoylphenyl)-hydantoin.

4. A compound according to claim 2 selected from the group consisting of

1-cyclohexyl-3-p-sulphamoylphenyl-imidazolidin-4-one;

1-m-methoxyphenyl-3-(2-chloro-4-sulphamoylphenyl)-imidiazolidin-4-one;

1-m-methylphenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-m-chlorophenyl-3-(2-chloro-4-sulphamoylphenyl)-imidazolidin-4-one;

1-phenyl-3-(2-chloro-4-sulphamoylphenyl)-5-methylimidazolidin-4-one;

1-p-sulphamoylphenyl-3-phenylhydantoin; and

1-phenyl-3-p-sulphamoylphenylhydantoin.

5. A compound of the general formula ##SPC10##

in which R¹ is phenyl, phenyl substituted with alkoxy, lower alkyl or halogen;

or a cycloalkyl or cycloalkenyl group having 5-10 carbon atoms, R⁴ represents a sulphamoylphenyl group;

R² and R³ each represent hydrogen atoms or an oxo group; and

R⁵ and R⁶ are hydrogen atoms or lower alkyl or cycloalkyl groups.

6. A compound as claimed in claim 5, wherein R² and R³ each represent a hydrogen atom.

7. A compound according to claim 5 in which R⁴ represents a group of the formula ##SPC11##

in which R⁷ represents a hydrogen, fluorine, chlorine or bromine atom or a lower alkyl or trifluoromethyl group.

8. A compound according to claim 5 in which R¹ represents a phenyl group or a cyclohexyl group.

9. A compound according to claim 7 in which R⁷ is in the 2-position relative to the imidazolidine ring.

10. A compound according to claim 9 in which R⁷ represents a fluorine or chlorine atom or a methyl group.

11. 1-phenyl-3-(2-chloro-4-sulphamoylphenyl)imidazolidin-4-one.

12. 1-p-sulphamoylphenyl-3-cyclohexylhydantoin.