851885-42-2

Upstream product

• 4984-22-9 (R)-1-methoxy-2-propanol 
• 54915-31-0 methyl 3-(benzyloxy)-5-hydroxybenzoate 
• 26550-55-0 (S)-1-Methoxy-propan-2-ol 
• 2446-83-5 di-isopropyl azodicarboxylate 
• 100-39-0 benzyl bromide 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 

Downstream Products

• 851885-41-1 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoic acid 
• 1325708-43-7 3-(6-cyclopropanesulfonylpyridin-3-yloxy)-5-((S)-2-methoxy-1-methylethoxy)benzoic acid methyl ester 
• 1325708-46-0 3-(6-cyclopropanesulfonylpyridin-3-yloxy)-5-((S)-2-methoxy-1-methylethoxy)benzoic acid 
• 919783-22-5 AZD₁₆₅₆ 
• 871656-70-1 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide 
• 871656-69-8 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide 
• 915949-14-3 N-(2-aminopyridin-3-yl)-3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzamide 
• 915948-91-3 (S)-3-{[2-(azetidin-1-ylcarbonyl)pyrimidin-5-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]benzoic acid 
• 915949-01-8 methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(2S)-1-methoxypropan-2-yl]oxy-benzoate 
• 915948-83-3 3-(3H-imidazo[4,5-b]pyridin-2-yl)-5-[(1S)-2-methoxy-1-methylethoxy]phenol 
• 1093121-03-9 C₂₈H₂₈FN₃O₅S 
• 915948-88-8 3-((S)-2-methoxy-1-methyl-ethoxy)-5-((S)-1-methyl-2-phenyl-ethoxy)-benzoic acid methyl ester 
• 915948-89-9 3-((S)-2-methoxy-1-methyl-ethoxy)-5-((S)-1-methyl-2-phenyl-ethoxy)-benzoic acid 
• 915771-82-3 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide 

Relevant academic research and scientific papers

Decoration of an α-Resorcylate Nucleus as Part of the Manufacture of a Glucokinase Activator

The need to define a set of processes for the manufacture of a glucokinase activator called for an evaluation of different strategies to differentiate the hydroxyls of an α-resorcylic acid derivative. While direct functionalization proved possible, it did not allow access to crystalline intermediates that offered control over the rejection of process impurities. The strategy taken forward involved the installation of a benzoyl protecting group using careful control of pH in order to achieve useful levels of selectivity. This allowed the remaining α-resorcylate hydroxyl to be functionalized using a Mitsunobu reaction, with liquid-liquid partitioning being used to separate downstream intermediates of interest away from the redox byproducts of this reaction. Downstream challenges that were overcome in order to deliver a commercially viable means of manufacturing the API included developing an amidation reaction with a poorly reactive aminopyrazine coupling partner.

Design of a potent, soluble glucokinase activator with increased pharmacokinetic half-life

The continued optimization of a series of glucokinase activators is described, including attempts to understand the interplay between molecular structure and the composite parameter of unbound clearance. These studies resulted in the discovery of a new sc

BENZAMIDE COMPOUNDS AS GLUCOKINASE ACTIVATORS AND THEIR PHARMACEUTICAL APPLICATION

Benzamide compounds of formula (I), their stereoisomers, tautomers, prodrugs, pharmaceutically acceptable salts, polymorphs, solvates and formulations thereof useful as Glucokinase activators or modulators are disclosed. The disclosure further relates to

N- ( PYRAZOLE- 3 -YL) -BENZAMIDE DERIVATIVES AS GLUCOKINASE ACTIVATORS

Novel heterocyclic compounds of the formula (I) in which R1, R2, R3, R4, R5, R6, R7, Alk and D have the meanings indicate in Claim 1, are activators of glucokinase and can be used for the prevention and/or treatment of Diabetes Typ 1 and 2, obesity, neuropathy and/or nephropathy.

NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME

Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R4 is —(CH2)n-Z-(CH2)m—PO(OR7)(OR8), —(CH2)nZ-(CH2)m—PO(OR7)Rg, —(CH2)n-Z-(CH2)m—OPO(OR7)Rg, —(CH2)nZ—(CH2)m—OPO(R9)(R10), or —(CH2)nZ—(CH2)m—PO(R9)(R10);R5 and R6 are independently selected from H, alkyl and halogen;Y is R7(CH2)s or is absent; andX, n, Z, m, R4, R5, R6, R7, and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

1, 3 - DIHYDROXY SUBSTITUTED PHENYLAMIDE GLUCOKINASE ACTIVATORS

Compounds are provided which are glucokinase activators and thus are useful in treating diabetes and related diseases and have the structure wherein in the ring represents one or two double bonds; R1 is alkyl, aryl, arylalkyl, heteroaryl, or he

HETEROARYL BENZAMIDE DERIVATIVES FOR USE AS GLK ACTIVATORS IN THE TREATMENT OF DIABETES

Compounds of formula (I) wherein R1, R2, R3, and HET-1 are as described in the specification, and their salts, are activators of glucokinase (GLK) and are thereby useful in the treatment of, for example, type 2 diabetes. P

2 -HETEROCYCLYLOXYBENZOYL AMINO HETEROCYCLYL COMPOUNDS AS MODULATORS OF GLUCOKINASE FOR THE TREATMENT OF TYPE 2 DIABETES

Compounds of formula (I) wherein R1, HET-1 and HET-2 are as described in the specification, and their salts, are activators of glucokinase (GLK) and are thereby useful in the treatment of, for example, type 2 diabetes. Processes for preparing compounds of formula (I) are also described.

HETEROARYL BENZAMIDE DERIVATIVES FOR USE AS GLK ACTIVATORS IN THE TREATMENT OF DIABETES

Compounds of formula (I), wherein R1, R4, HET-1 and HET-2 are as described in the specification, and their salts and pro-drugs, are activators of glucokinase (GLK) and are thereby useful in the treatment of, for example, type 2 diabetes. Processes for preparing compounds of formula (I) are also described.