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Compounds and methods of treating diabetes

a technology of compound and diabetes, applied in the field of compound and diabetes treatment, to achieve the effects of promoting insulin release in the blood stream, reducing blood glucose levels, and increasing insulin secretion

Inactive Publication Date: 2014-06-05
MEDIVATION TECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes methods for reducing blood glucose levels, increasing insulin secretion, and promoting insulin release in the blood stream. These methods may have potential therapeutic benefits for individuals with diabetes.

Problems solved by technology

In addition, more than a third of adults at least 20 years old have pre-diabetes, which is a significant risk factor for developing type 2 diabetes.

Method used

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  • Compounds and methods of treating diabetes
  • Compounds and methods of treating diabetes
  • Compounds and methods of treating diabetes

Examples

Experimental program
Comparison scheme
Effect test

example no.1

Example No. 1

Preparation of Compound No. 1

[0441]A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, 1 mmol), bromobenzene (0.314 g, 2 mmol), K3PO4 (0.424 g, 2 mmol), CuI (19 mg, 0.1 mmol) and L-Proline (23 mg, 0.2 mmol) in dry DMF (3 mL) was stirred at 150° C. for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as an off white solid (83 mg). 1H NMR(HCl salt, CD3OD) δ (ppm): 7.60 (t, 2H), 7.5 (t, 1H), 7.4 (d, 2H), 7.35 (s, 1H), 7.1 (d, 1H), 7.05 (d, 1H), 4.8 (d, 1H), 4.4 (d, 1H), 3.85-3.8 (m, 1H), 3.6-3.59 (m, 1H), 3.2-3.19 (m, 1H), 3.18 (s, 3H), 3-2.95 (m, 1H), 2.4 (s, 3H).

example no.2

Example No. 2

Preparation of Compound No. 2

[0442]A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, μmol), 4-bromopyridine (0.316 g, 2 mmol), K3PO4 (0.424 g, 2 mmol), CuI (19 mg, 0.1 mmol) and L-Proline (23 mg, 0.2 mmol) in dry DMF (3 mL) was stirred at 150° C. for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-pyridin-4-yl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as an off white solid (30 mg). 1H NMR(HCl salt, CD3OD) δ (ppm): 8.95 (d, 2H), 8.21 (d, 2H), 7.65 (d, 1H), 7.21 (s, 1H), 7.21 (d, 1H), 4.8 (d, 1H), 4.4 (d, 1H), 3.95-3.9 (m, 1H), 3.6-3.50 (m, 2H), 3.25 (m, 1H), 3.2 (s, 3H), 2.5 (s, 3H).

example no.3

Example No. 3

Preparation of Compound No. 3

[0443]A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, 1 mmol), 5-bromo-2-methyl-pyridine (0.348 g, 2 mmol), K3PO4 (0.424 g, 2 mmol), CuI (19 mg, 0.1 mmol) and L-Proline (23 mg, 0.2 mmol) in dry DMF (3 mL) was stirred at 150° C. for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-(6-methyl-pyridin-3-yl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as semisolid (8.6 mg). 1H NMR(HCl salt, CD3OD) δ (ppm): 8.6 (s, 1H), 8.05 (d, 1H), 7.7 (d, 1H), 7.19 (s, 1H), 7.19-7.05 (dd, 2H), 4.8 (m, 1H), 4.4 (m, 1H), 3.90-3.8 (m, 1H), 3.6-3.50 (m, 1H), 3.25-3.20 (m, 1H), 3.2 (s, 3H), 3.05-3.0 (m, 1H), 2.75 (s, 3H), 2.45 (s, 3H).

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Abstract

Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are antagonists of the adrenergic receptor a2A. The compounds may also bind to and are an antagonist of the adrenergic receptor α2B; or the compounds are not antagonists of the adrenergic receptor α2β and the compounds are administered in conjunction with a second agent that reduces, or is expected to reduce, blood pressure in an individual. The compounds may find use in therapy, e.g., to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. Use of the compounds to treat type 2 diabetes is particularly described.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority to U.S. Provisional Patent Application No. 61 / 444,626 filed Feb. 18, 2011, U.S. Provisional Patent Application No. 61 / 561,773 filed Nov. 18, 2011, U.S. Provisional Patent Application No. 61 / 444,622 filed Feb. 18, 2011, U.S. Provisional Patent Application No. 61 / 561,761 filed Nov. 18, 2011, and U.S. Provisional Patent Application No. 61 / 444,547 filed Feb. 18, 2011, the disclosures of each of which are incorporated herein by reference in their entireties.BACKGROUND OF THE INVENTION[0002]Type 2 diabetes is a serious and prevalent disease. This form of diabetes may involve insulin resistance and impaired insulin release. Approximately 25.8 million people in the United States alone suffer from diabetes, whereby type 2 diabetes accounts for about 90-95% of all diagnosed diabetes cases. From 1980 to 2008 the number of Americans with diabetes has more than tripled. Diabetes is also increasingly prevalent elsewhere...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D471/04A61K31/437A61K31/506A61K31/55A61K31/439C07D471/14A61K31/4985A61K31/519C07D487/14A61K45/06C07D471/18
CPCC07D487/04A61K31/437A61K31/439A61K31/4985A61K31/506C07D487/14A61K31/55A61K45/06C07D471/04C07D471/14C07D471/18A61K31/519C07D471/08C07D487/08C07D487/18
Inventor PROTTER, ANDREW ASHERCHAKRAVARTY, SARVAJIT
Owner MEDIVATION TECH INC
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