3 -AMINO- PYRIDINE DERIVATIVES FOR THE TREATMENT OF METABOLIC DISORDERS

• Main Authors: KULKARNI, RHUSHIKESH ARUN, PADIYA, KAMLESH JYOTINDRA, MARITA, ROSALIND ADAIKALASAMY, BAJARE, SWAPNIL RAMESH, HARIHARAN, SIVARAMAKRISHNAN, DEKA, NABAJYOTI, KHAN, TAJ USMAN
• Format: Patent
• Language: English
• Published: 22.12.2011
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

Disclosed is a compound of general formula (I) e.g. 2,4-Dichloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-5 3-yl)benzenesulfonamide wherein Ar is a quinoline or isoquinoline moiety; B is -O-, -S-, or -NH-; R1 to R9 are defined in the specification; n is an integer from 1-3; and a pharmaceutically acceptable salt or solvate thereof for treating insulin resistance or hyperglycemia, type 2 diabetes, obesity, glucose intolerance, dyslipidemia, hyperinsulinemia, atherosclerotic disease, polycystic ovary syndrome, coronary artery disease, hypertension, non-alcoholic fatty liver disease or stroke. Also disclosed is a process for the preparation of a compound of general formula (I) which comprises a) reacting a nitrated halopyridine with an aryl amine, alcohol or thiol in presence of a base such as cesium carbonate, to obtain a nitro pyridine compound, subjecting the nitro compound to reduction to obtain a corresponding amino compound; c) reacting the amino compound with one equivalent of sulfonic in the presence of a base to obtain the compound of formula (I),; or reacting the amino compound with two equivalents of sulfonyl at 20 degrees C, in the presence of triethyl amine as a base, to obtain the compound of formula (I); or refluxing the amino compound with an anhydride [(CH2)n(CO)2O] wherein n is as defined above, to obtain an acid of formula (I); or refluxing the amino compound of with a carbonochloridate, in the presence of pyridine or triethyl amine as a base to obtain the compound of formula (I).