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GPR119 agonist containing alkyl substituted benzenesulfonyl hydrazine as well as preparation method and application thereof

An alkyl and aspect technology, applied in the field of GPR119 agonists, can solve the problems of unclear exact cause, loss of sensitivity, decreased insulin secretion promoting effect, etc.

Active Publication Date: 2015-05-13
邳州市润宏实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in patients with type 2 diabetes it has been shown that the insulinotropic effect of GIP is decreased, although the insulinotropic effect of GLP-1 is maintained
What is puzzling is that patients with type 2 diabetes still have a good response to a large injection of GIP, but lose sensitivity to continuous small injections (Meier et al., Diabetes, 2004, 53, S220-S224), The exact reason for this decrease in GIP activity is therefore unclear

Method used

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  • GPR119 agonist containing alkyl substituted benzenesulfonyl hydrazine as well as preparation method and application thereof
  • GPR119 agonist containing alkyl substituted benzenesulfonyl hydrazine as well as preparation method and application thereof
  • GPR119 agonist containing alkyl substituted benzenesulfonyl hydrazine as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound I-1

[0029]

[0030] A. Synthesis of Compound IV-1

[0031] Compound II-11.81g (10mmol) and compound III 4.80g (30mmol) were dissolved in 20mL of dry THF, heated and refluxed for 3 hours, TLC found that the reaction was complete. The reaction mixture was poured into 100 mL ice water with 50 mL × 3 CH 2 Cl 2 After extraction, the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-1, a white solid, ESI-MS, m / z=342 ([M+H] + ).

[0032] B. Synthesis of Compound I-1

[0033] Compound IV-10.68g (2mmol) and Compound V-10.37g (2mmol) were dissolved in 10mL of dry THF, heated and refluxed for 3 hours, TLC found that the reaction was complete. The reaction mixture was poured into 100 mL ice water wi...

Embodiment 2-4

[0035] Referring to the method of Example 1, the compounds listed in the following table were synthesized.

[0036]

Embodiment 5

[0037] The preparation of embodiment 5 reference compound D-1

[0038] In order to further illustrate the beneficial effect of the compound of the present invention, the applicant has recorded the compound D-1 and pharmacological data that the applicant has studied but not yet published.

[0039]

[0040] A. Synthesis of Compound IV-5

[0041] Compound II-5 1.47g (10mmol) and compound III 4.80g (30mmol) were dissolved in 20mL of dry THF, heated and refluxed for 3 hours, TLC found that the reaction was complete. The reaction mixture was poured into 100 mL ice water with 50 mL × 3 CH 2 Cl 2 After extraction, the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-5, a white solid, ESI-MS, m / z=308 ([M+H] + ).

[0042] B. Synthesis of Compo...

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Abstract

The invention relates to the field of medicines related to type II diabetes mellitus and in particular relates to a GPR119 agonist containing an alkyl substituted benzenesulfonyl hydrazine structure, a preparation method of the GPR119 agonist and application of the GPR119 agonist to preparation of medicines related to type II diabetes mellitus. The GPR119 agonist has a structure shown in a general formula in the specification, wherein in the general formula, R is selected from C1-C3 alkyl.

Description

technical field [0001] The invention relates to the pharmaceutical field for the treatment of type 2 diabetes. More specifically, the present invention relates to a class of GPR119 agonists containing an alkyl-substituted benzenesulfonyl hydrazide structure that has a therapeutic effect on type 2 diabetes, its preparation method, and its use in pharmacy. Background technique [0002] Diabetes is increasingly threatening human health. In the United States today, approximately 16 million people are suffering from diabetes. Type 1 diabetes, also known as insulin-dependent diabetes, is an autoimmune disease. It is caused by the destruction of the pancreatic islet β cells that can produce insulin by the autoimmune system. There is currently no cure for this disease in the world, so patients must receive insulin injections. Without insulin injections, cells cannot absorb glucose for energy. Symptoms associated with type 1 diabetes usually appear in childhood and adolescence. ...

Claims

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Application Information

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IPC IPC(8): C07C311/49C07C303/40A61P3/10
Inventor 蔡子洋
Owner 邳州市润宏实业有限公司
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