Anti-atherosclerotic diaryl compounds

• US 5,290,814 A
• Filed: 11/05/1992
• Issued: 03/01/1994
• Est. Priority Date: 11/21/1988
• Status: Expired due to Fees

• Current Assignee: Burroughs Wellcome Co. (GlaxoSmithKline PLC)
• Original Assignee: Burroughs Wellcome and Co.
• Inventors: O'Connor, Kevin J., Dann, John G., Booth, Robert F. G., Harris, Clifford J., Arrowsmith, Richard J., Jackson, William P.
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): O'Sullivan, P.
• Application Number:
  US07/971,252
• Time in Patent Office: 481 Days
• Field of Search: 564/48, 564/50, 564/52, 564/53, 564/54, 514/824, 514/596, 514/597, 514/598, 71/120
• US Class Current: 514/596
• CPC Class Codes: C07C 233/07 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 233/11 with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 271/44 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 275/24 containing six-membered aromatic rings
• CPC Class Codes: C07C 275/28 having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
• CPC Class Codes: C07C 275/30 being further substituted by halogen atoms, or by nitro or nitroso groups
• CPC Class Codes: C07C 279/28 having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
• CPC Class Codes: C07C 327/44 to carbon atoms of an unsaturated carbon skeleton

Abstract

The present invention is concerned with compounds of formula (I) ##STR1## wherein m is 0 or 1;

W is hydrogen, a C_1-16 straight, branched, or cyclic alkyl group, or a C_2-16 straight, branched, or cyclic alkenyl or alkynyl group, or Ph(CH₂)_n -- where Ph is phenyl and n is an integer of from 0 to 2, the phenyl group being optionally substituted by one or more atoms or groups independently selected from halogen, hydroxy, nitro, C_1-4 alkoxy and C_1-4 alkyl wherein one or more of the hydrogen atoms in said alkyl group is optionally replaced by halogen, or R¹ NHCO-- where R¹ is hydrogen or a C_1-6 alkyl group, or R² CONH-- where R² is hydrogen or a C_1-6 alkyl group; X is ##STR2## where A is halogen; Y is --(CH₂)_q, where q is an integer of from 1 to 3, or --CH═CH-- (E or Z);

Z is a C_1-6 alkyl group optionally substituted by one or more independently selected polar groups; and

ring A is optionally substituted by one or more atoms or groups independently selected from halogen, hydroxy, nitro, C_1-4 alkoxy and C_1-4 alkyl wherein one or more of the hydrogen atoms in said alkyl group is optionally replaced by halogen.

Claims

1. The compound N-heptyl-N'"'"'-(2,4-difluoro-6-{2-[4-(2,2-dimethylpropyl)phenyl]ethyl}phenylurea.

2. A physiologically acceptable salt of N-heptyl-N'"'"'-(2,4-difluoro-6-{2-[4-(2,2-dimethylpropyl)phenyl]ethyl}phenylurea.

3. A pharmaceutical composition comprising a compound N-heptyl-N'"'"'-(2,4-difluoro-6-{2-[4-(2,2-dimethylpropyl)phenyl]ethyl}phenylurea or a physiologically acceptable thereof together with a pharmaceutical acceptable carrier or excipient therefor.

4. The composition of claim 3 in the form of a tablet or capsule.