1313883-38-3

Upstream product

• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 1259224-00-4 [1-(4-amino-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester 
• 1259223-99-8 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoic acid 

Downstream Products

• 1313883-39-4 tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate 
• 1313881-59-2 tert-butyl (1-(4-(5-(3-acetamidophenyl)-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate 
• 1313883-53-2 tert-butyl (1-{4-[(6'-morpholin-4-yl-5-nitro-2,2'-bipyridin-6-yl)amino]phenyl}cyclobutyl)carbamate 
• 1416775-76-2 2-({3-[2-(2-aminopyridin-3-yl)-3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3H-imidazo[4,5-b]pyridin-5-yl]phenyl}amino)-1,1-dimethyl-2-oxoethyl acetate 
• 1416775-77-3 tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(2-hydroxy-2-methylpropanoyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate 
• 1416775-80-8 tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(1,4-dioxan-2-ylcarbonyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate 
• 1416775-82-0 tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(tetrahydro-2H-pyran-4-ylcarbonyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate 
• 1416775-89-7 tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[4-(dimethylcarbamoyl)piperidin-1-yl]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate 
• 1416477-58-1 tert-butyl (1-{4-[(6-morpholin-4-yl-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate 
• 1416477-56-9 tert-butyl {1-[4-(5-chloro-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]cyclobutyl}carbamate 
• 1429437-73-9 C₂₇H₃₁N₅O₄ 
• 1416477-57-0 tert-butyl (1-{4-[5-(3-morpholin-4-ylphenyl)-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate 
• 1416506-53-0 1-{4-[5-(3-morpholin-4-ylphenyl)-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutanamine 
• 1416477-38-7 1-[4-(5-morpholin-4-yl-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]cyclobutanamine 

Relevant academic research and scientific papers

Compositions and Methods for Treating Proliferation Disorders

The present invention relates to methods of treating cell proliferative disorders, such as cancer or Proteus syndrome, by utilizing 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine or 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-(3-morpholinophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine or N-(1-(3-(3-(4-(1-aminocyclobutyl)phenyl)-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)piperidin-4-yl)-N-methylacetamide. The methods of the present invention can also relate to methods of treating cell proliferative disorders, such as cancer or Proteus syndrome, by utilizing the above compounds in combination with ((R)-6-(2-fluorophenyl)-N-(3-(2-((2-methoxyethyl)amino)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine).

Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor

The work in this paper describes the optimization of the 3-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine chemical series as potent, selective allosteric inhibitors of AKT kinases, leading to the discovery of ARQ 092 (21a). The cocrystal structure of compound 21a bound to full-length AKT1 confirmed the allosteric mode of inhibition of this chemical class and the role of the cyclobutylamine moiety. Compound 21a demonstrated high enzymatic potency against AKT1, AKT2, and AKT3, as well as potent cellular inhibition of AKT activation and the phosphorylation of the downstream target PRAS40. Compound 21a also served as a potent inhibitor of the AKT1-E17K mutant protein and inhibited tumor growth in a human xenograft mouse model of endometrial adenocarcinoma.

BICYCLIC HETEROARYL DERIVATIVES AS KINASE INHIBITORS

The present invention provides compounds, including resolved enantiomers, resolved diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula 1: wherein Het, X, R1 and R2 are as defined herein.

Substituted Imidazopyridinyl Compounds

The present invention relates to substituted imidazopyridinyl compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazopyridinyl compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

Substituted Imidazopyridinyl-Aminopyridine Compounds

The present invention relates to substituted imidazopyridinyl-aminopyridine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted imidazopyridinyl-aminopyridine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.