Back to results
US 8,940,900 B2Granted
2,2,2-tri-substituted acetamide derivatives as glucokinase activators, their process and pharmaceutical application
AssigneeAdvinus Therapeutics Private Limited
InventorsKasim A. Mookhtiar, Debnath Bhuniya, Bhavesh Dave, Gobind S. Kapkoti, Sujay Basu, Anita Chugh, Siddhartha De, Venkata P. Palle
Life of this patent
Estimating the term…
Abstract
Compounds of the present disclosure are 2,2,2-tri-substituted acetamide derivatives of formula (I), its polymorphs, stereoisomers, prodrugs, solvates, pharmaceutically acceptable salts and formulations thereof, useful as Glucokinase activator. Processes of their preparation are also described in the disclosure. The disclosure also describes method to characterize partial glucokinase activators.
Claims16
A compound of formula (I)
- or its stereoisomer, or a pharmaceutically acceptable salt thereof, wherein,
- Ring-A is selected from a group consisting of phenyl, pyridinyl, naphthyl, indolyl, indanyl, and benzodioxolyl;
- wherein said ring A is further substituted with 0 to 4 numbers of substitutions independently selected from a group consisting of alkyl, alkenyl, alkynyl, halo, mono, di or per haloalkyl, nitrile, nitro, oxo, —NR6R7, —OR6, —SR6, —S(O)pR6, —S(O)pNR6R7, —NR6S(O)pR7, —NR6C(O)R7, —OS(O)pR7, —NR6C(O)OR7, —(CR8R9)n(CO)OR6, —(CR8R9)nC(O)R6, —S(O)p(NR6)R7, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl groups;
- which are further optionally substituted with common substituents;
- p=0-2;
- n=0-4;
- R6 and R7 are independently selected from a group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclylalkyl, and further substituted with common substituents;
- R8 and R9 are independently selected from a group consisting of hydrogen, fluorine, OR6, alkyl, and perfluoroalkyl;
- X is selected from a group consisting of O and NR6;
- wherein R6 is as described above;
- with a proviso that, X is not connected to another heteroatom from ring-A;
- R1 and R2 are independently selected from a group consisting of fluoro, alkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl, and cycloalkylalkyl, or are combined together to form a 3-7 membered ring;
- R3 is selected from a group consisting of hydrogen and alkyl;
- Ring-B is selected from a group consisting of thiazolyl and benzothiazolyl;
- with a proviso that the amide nitrogen of formula-(I) is not connected through any heteroatom of ring-B;
- R4 and R5 are independently selected from a group consisting of halogen, alkyl, —(CR8R9)n(CO)OR6, —(CR8R9)n(CO)NR6R7, —(CR8R9)nS(O)pNR6R7, —(CR8R9)nN(R6)C(O)R6, —(CR8R9)nOR6, —(CR8R9)nNR6R7, —(CR8R9)nCO(R6), cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, tetrazole, and tetrazolylalkyl, which are further optionally substituted with one or more substituents selected from a group consisting of halo, straight chain or branched chain alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, heterocycle, alkylsulphonyl, oxo, nitro, cyano, —COOR6, —C(O)NR6R7, —OR6, —SR6, and —NR6R7;
- wherein
- p=0-2;
- n=0-4;
- and
- R6, R7, R8, and R9 are as described above.
18 more elements
Dependencies are inferred from the claim text.