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1. WO2020110152 - NON-PEPTIDIC GLUCAGON-LIKE PEPTIDE-1 RECEPTOR AGONISTS AND METHOD OF PREPARATION THEREOF

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[ EN ]

The claims:

1. A compound of F ormula I :


Formula I

or a stereoisomer, salt, hydrate, solvate, or crystalline form thereof;

Wherein

Ri is independently selected from hydrogen, halogen, unsubstituted or substituted hydroxyl, unsubstituted or substituted sulphonate, unsubstituted or substituted nitro, unsubstituted or substituted isatin, unsubstituted or substituted alkyl;

R2 is independently selected from hydrogen, -COPh, unsubstituted or substituted sulphonate, unsubstituted or substituted alkyl, unsubstituted or substituted halide, unsubstituted or substituted dihabde; and

R3 is independently selected from hydrogen, halogen, unsubstituted or substituted hydroxyl, unsubstituted or substituted sulphonate, unsubstituted or substituted nitro, unsubstituted or substituted isatin, unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy.

2. The compound as claimed in claim 1, wherein Rl is Hydrogen, R2 is Hydrogen, - COPh and R3 is -N02, -CH3, -OCH3.

3. The compound as claimed in claim 1, wherein said compound is selected from:


4. A pharmaceutical composition comprising the compound as claimed in claims 1 to 3 along with one or more pharmaceutically acceptable carriers or excipients.

5. A process for preparing the compound of formula I, comprising the steps of:

(i) adding a mixture of isatin (1) and ortho-phenylenediamine (2) in acetic acid;


(ii) Filtering the precipitate, triturating the product obtained from step (i) with a solvent to get the purified compound of formula 3;

(iii) adding anhydrous metal carbonate in dry acetone to the mixture of compound of formula 3 of step (ii) and then adding propargyl bromide in the reaction mixture and refluxing the said mixture;


(IV) removing the solvent, extracting the residue and drying over anhydrous Na2SC>4, concentrating the same and triturating with hexane to get the purified product;

(v) dissolving aryl bromide in 1 : 1 : acetone: water mixture and sodium azide, reacting the same followed by removal of acetone under reduced pressure and extracting the product using a solvent; and


(vi) dehydrating and evaporating the solvent to obtain the azide; and adding freshly prepared solution of CUSO4.5H2O and sodium ascorbate in water to a mixture of 9- substituted-6-propargyl-indolo [2,3-b]quinoxalines and 1 -azido-arylbenzene, in Tetrahydrofuran (THF) to get the final product.


6. The method as claimed in claim 5, wherein the reaction mixture in step (i) is irradiated for around 10 min at about 120°C at 25W and the concentration of CUSO4.5H2O is around 5 mole% and that of sodium ascorbate is around 15 mole% in water and the ratio of 9- substituted-6-propargyl-indolo [2,3-b]quinoxalines and 1 -azido-arylbenzene is around 1 : 1.5, in dry Tetrahydrofuran (THF).

7. A method for treating diabetes and/or other metabolic diseases in a subject in need of such treatment, the method comprising the step of administering to a subject a therapeutically active amount of compound as claimed in claims 1 to 3.

8. A kit comprising the compound as claimed in claims 1 to 3.

9. Use of the compound as claimed in claims 1 to 3 in the treatment of diabetes and other metabolic diseases including but not limited to non-alcoholic fatty liver disease, cardiac dysfunction and obesity.

10. A compound of following formula: