912454-75-2

Basic information

• Product Name: 6-benzyloxy-5-bromo-3-pyridinecarboxylic acid
• Synonyms: 6-benzyloxy-5-bromo-3-pyridinecarboxylic acid
• CAS NO: 912454-75-2
• Molecular Weight: 308.131
• Mol File: 912454-75-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-benzyloxy-5-bromo-3-pyridinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-benzyloxy-5-bromo-3-pyridinecarboxylic acid(912454-75-2)
• EPA Substance Registry System: 6-benzyloxy-5-bromo-3-pyridinecarboxylic acid(912454-75-2)

Safety Data

• Hazardous Substances Data: 912454-75-2(Hazardous Substances Data)

Upstream product

• 5006-66-6 6-hydroxy-3-pyridinecarboxylic acid 
• 41668-13-7 5-bromo-6-hydroxy-3-pyridinecarboxylic acid 
• 29241-62-1 5-bromo-6-chloronicotinic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 912454-36-5 5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide 

Relevant articles and documents

6-alkoxy-5-aryl-3-pyridinecarboxamides, a new series of bioavailable cannabinoid receptor type 1 (CB1) antagonists including peripherally selective compounds

We identified 6-alkoxy-5-aryl-3-pyridinecarboxamides as potent CB1 receptor antagonists with high selectivity over CB2 receptors. The series was optimized to reduce lipophilicity compared to rimonabant to achieve peripherally active molecules with minimal central effects. Several compounds that showed high plasma exposures in rats were evaluated in vivo to probe the contribution of central vs peripheral CB1 agonism to metabolic improvement. Both rimonabant and 14g, a potent brain penetrant CB1 receptor antagonist, significantly reduced the rate of body weight gain. However, 14h, a molecule with markedly reduced brain exposure, had no significant effect on body weight. PK studies confirmed similarly high exposure of both 14h and 14g in the periphery but 10-fold lower exposure in the brain for 14h. On the basis of these data, which are consistent with reported effects in tissue-specific CB1 receptor KO mice, we conclude that the metabolic benefits of CB1 receptor antagonists are primarily centrally mediated as originally believed.

Pyridine-3-carboxamide derivatives as CB1 inverse agonists

The present invention relates to compounds of the formula wherein X and R1 to R8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors, such as obesity.