4-(3-cyclohexyl-4-hydroxy or-methoxy phenylsulfonyl) 3,5 dibromo phenyl acetic thyromimetic cholesterol-lowering agents

• US 5,284,971 A
• Filed: 07/16/1992
• Issued: 02/08/1994
• Est. Priority Date: 07/16/1992
• Status: Expired due to Fees

• Current Assignee: Syntec Incorporated (Atos SE)
• Original Assignee: Syntec Incorporated (Atos SE)
• Inventors: Walker, Keith A., Labadie, Sharada S., Laughton, Craig W., Kertesz, Denis J.
• Primary Examiner(s): Daus, Donald G.
• Application Number:
  US07/914,837
• Time in Patent Office: 572 Days
• Field of Search: 562/429, 514/568, 514/570, 514/618, 514/513, 514/532
• US Class Current: 562/429
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 317/34 having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
• CPC Class Codes: C07D 237/14 Oxygen atoms

Abstract

Compounds of general formula (I) ##STR1## wherein R¹ is (CH₂)_n ((CHNR⁷ R⁸)_m C(O)R⁹ ; n=1-3; and m=0 or 1;

R³ and R⁵ are independently Cl, Br, I, or CH₃ ;

R⁷ and R⁸ are independently H or (C₁ -C₄)alkyl;

R⁹ is OH, (C₁ -C₄)alkoxy, or NR⁷ R⁸ ;

R³¹ is H, Cl, Br, I, (C₁ -C₄)alkyl, (C₄ -C₆)cycloalkyl, (C₁ -C₄)haloalkyl, (C₄ -C₆)halocycloalkyl, or --CH(R¹⁰)Ar where Ar is selected from 5-hydroxypyrid-2-yl, 6-hydroxypyrid-3-yl, 6-hydroxypyridazin-3-yl, 6-methoxypyridazin-3-yl, 6-hydroxypyridazin-3-yl N-oxide, and 6-methoxypyridazin-3-yl N-oxide and R¹⁰ is H or (C₁ -C₄)alkyl;

R⁴¹ is OH or a bioprecursor thereof; and the pharmaceutically acceptable salts thereof; are structural analogs of the thyroid hormones T₃ and T₄ and exhibit selective thyromimetic activity. Pharmaceutical compositions of the novel compounds and their use for the treatment of mammalian cholesteremia are provided.

Claims

1. 3,5-dibromo-4-(3-cyclohexyl-4-hydroxyphenylsulfonyl)phenylacetic acid.

2. 3,5-dibromo-4-(3-cyclohexyl-4-methoxyphenylsulfonyl)phenylacetic acid.