710321-76-9

Upstream product

• 710322-80-8 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-vinyl-pyrazin-2-yl)propionamide 
• 1268252-63-6 N-[5-(2-Hydroxy-acetyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide 
• 1268252-62-5 2,2-Dimethyl-N-{5-[2-(tetrahydro-pyran-2-yloxy)-acetyl]-pyrazin-2-yl}-propionamide 
• 710322-83-1 N-[5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrazin-2-yl]-2,2-dimethyl-propionamide 
• 710322-82-0 N-[5-(1(S),2-dihydroxyethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide 
• 300356-14-3 (R)-2-(3-chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid 

Relevant academic research and scientific papers

Identification of RO4597014, a glucokinase activator studied in the clinic for the treatment of type 2 diabetes

To resolve the metabolite redox cycling associated with our earlier clinical compound 2, we carried out lead optimization of lead molecule 1. Compound 4 showed improved lipophilic ligand efficiency and demonstrated robust glucose lowering in diet-induced obese mice without a liability in predictive preclinical drug safety studies. Thus, it was selected as a clinical candidate and further studied in type 2 diabetic patients. Clinical data suggests no evidence of metabolite cycling, which is consistent with the preclinical profiling of metabolism.

PROCESS FOR THE PREPARATION OF A GLUCOKINASE ACTIVATOR COMPOUND

The present invention relates to a process for the preparation of a compound of formula I, wherein R1 is C1-6-alkyl and R2 is hydrogen or halogen. (R)-2-phenyl propionic acid derivatives of formula I are key intermediates in the synthesis of 5-substituted-pyrazine or pyridine glucokinase activators of the formula Xa, which have the potential to be useful for the treatment and/or prophylaxis of type II diabetes.

PROCESS FOR THE PREPARATION OF A GLUCOKINASE ACTIVATOR COMPOUND

The present invention related to a process for the preparation of formula (I), wherein R1 is C1-6-alkyl and R2 is hydrogen or halogen. (R)-2-phenyl propionic acid derivatives of the formula (I) are key intermediates in the synthesis of 5-substituted -pyra

CRYSTALLIZATION OF GLUCOKINASE ACTIVATORS

The present invention provides novel methods for crystallizing glucokinase activators from amorphous glucokinase activators. The amorphous glucokinase activator is dissolved in a non-chemically reactive lipid solvent to form a supersaturated solution and the supersaturated solution is maintained at a temperature range from 5 °C above to 5 °C below the glass transition temperature of the amorphous glucokinase activator for a period of time until a crystal of the glucokinase activator is formed. These novel methods for preparing crystallized glucokinase activators are useful in the treatment or control of a number of diseases. Furthermore the application discloses crystallization processes in which the compounds are dissolved in Capmul or Gelocire solvents, encapsulated and stored during prolonged time periods followed by dispersing the contents of the capsules and filtering the crystals.

5-SUBSTITUTED-PYRAZINE OR PYRIDINE GLUCOKINASE ACTIVATORS

The present invention provides a compound according to formula (I) where the substituent designations are provided in the specification. Pharmaceutical compositions comprising a compound according to formula (I) are also provided, said compounds being glucokinase activators which are useful in the treatment of type II diabetes.