Thyroid receptor ligands and method II

US6989402B1 · kind B1 · utility

Assignee

• Karo Bio AB · SE

Inventors

• Jon J. Hangeland · Levittown, US
• Minsheng Zhang · Hackettstown, US
• Yolanda Caringal · Lawrenceville, US
• Denis E. Ryono · Princeton, US
• Yi Li · Hsinchu, TW
• Johan Malm · Älta, SE
• Ye Liu · Foster City, US
• Neeraj Garg · Tumba, SE
• Chris Litten · Tumba, SE
• Ana Maria Garcia Collazo · Stockholm, SE
• Konrad Koehler · Huddinge, SE

Key dates

• Filing date: Dec 23, 1999
• Grant date: Jan 24, 2006
• Expiry date: Dec 23, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D333/20
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

New thyroid receptor ligands are provided which have general formula (I) in which: n is an integer from 0 to 4; R1 is halogen, trifluoromethyl, or alkyl of 1 to 6 carbons or cycloalkyl of 3 to 7 carbons; R2 and R3 are the same or different and are hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 5 carbons, at least one of R2 and R3 being other than hydrogen; R4 is a carboxylic acid amide (CONR′R″) or an acylsulphonamide (CONHSO2R′) derivative, or a pharmaceutically acceptable salt thereof, and all stereoisomers thereof; or when n is equal to or greater than one, R4 may be a heteroaromatic moiety which may be substituted or unsubstituted, or an amine (NR′R″). R5 is hydrogen or an acyl (such as acetyl or benzoyl) or other group capable of bioconversion to generate the free phenol structure (wherein R5=H). In addition, a method is provided for preventing, inhibiting or treating a disease associated with metabolism dysfunction or which is dependent upon the expression of a T3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount. Examples of such diseases associated with metabolism dysfunction or are dependent upon t…