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Adamantane amide derivatives, their preparation method and use

A technology of alkyl compounds, applied in the field of drugs for the treatment of diabetes, can solve problems such as undiscovered weight gain

Inactive Publication Date: 2016-03-16
江苏天凤源食品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinical results show that this type of drug has a good hypoglycemic effect, and no adverse reactions such as weight gain and hypoglycemia, which are common in other diabetes drugs, have been found

Method used

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  • Adamantane amide derivatives, their preparation method and use
  • Adamantane amide derivatives, their preparation method and use
  • Adamantane amide derivatives, their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] In a 100mL round bottom flask, add 1.94g (10mmol) compound II-1, 3.21g (10mmol) compound III, 2.06g (10mmol) N, N'-dicyclohexylcarbodiimide (DCC) and 1.22g (10mmol) 4-dimethylaminopyridine (DMAP), dissolved in 20mL of dry THF, stirred at room temperature overnight, TLC showed that the reaction was almost complete. The reaction mixture was suction filtered to remove the solid, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by column chromatography to obtain compound IV-1, a white solid, ESI-MS, m / z=515 ([M+NH 4 ] + ).

[0029] 2.99g (6mmol) of compound IV-1 was dissolved in 30mL of THF, 0.10g of 10% Pd / C was added, catalytic hydrogenolysis was carried out at room temperature, and the reaction was completed within 12 hours. The reaction mixture was suction filtered to remove the catalyst, and the filtrate was concentrated on a rotary evaporator, poured into 200 mL of water, stirred, and extracted with 50 mL×3 dich...

Embodiment 2

[0033]

[0034] In a 100mL round bottom flask, add 2.08g (10mmol) compound II-2, 3.21g (10mmol) compound III, 2.06g (10mmol) N, N'-dicyclohexylcarbodiimide (DCC) and 1.22g (10mmol) 4-dimethylaminopyridine (DMAP), dissolved in 20mL of dry THF, stirred at room temperature overnight, TLC showed that the reaction was almost complete. The reaction mixture was suction filtered to remove the solid, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by column chromatography to obtain compound IV-2 as a white solid, ESI-MS, m / z=529 ([M+NH 4 ] + ).

[0035] 3.07g (6mmol) of compound IV-2 was dissolved in 30mL of THF, and 0.10g of 10% Pd / C was added to carry out catalytic hydrogenolysis at room temperature, and the reaction was completed within 12 hours. The reaction mixture was suction filtered to remove the catalyst, and the filtrate was concentrated on a rotary evaporator, poured into 200 mL of water, stirred, and extracted with 50 mL×3 di...

Embodiment 3-6

[0039] Using the same method as in Example 1, the following compounds could be prepared.

[0040]

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PUM

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Abstract

The invention relates to the field of medicine related to diabetes, in particular to a dipeptidyl peptidase-IV inhibitor which has a general formula I and includes an adamantane tetrazole structure, a preparation method of the dipeptidyl peptidase-IV inhibitor, and the application of the dipeptidyl peptidase-IV inhibitor and the preparation method in preparing diabetes medicine. Please see the formula in the specification, wherein R1 is selected from an alkyl group of H and C1-C5 and a naphthenic base of C3-C5.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a dipeptidyl peptidase-IV inhibitor containing an adamantane amide structure that has a therapeutic effect on diabetes, a preparation method thereof, a pharmaceutical composition containing them and a drug for treating diabetes. Background technique [0002] According to statistics, there were approximately 250 million diabetic patients in the world in 2007, most of whom were type II (ie, non-insulin-dependent) diabetic patients. The antidiabetic drugs currently in clinical use mainly include sulfonylureas, metformin and insulin drugs. In recent years, insulin sensitizers and α-glucosidase inhibitors have also been marketed. These drugs have good therapeutic effects, but severe side effects such as hypoglycemia are common, and there are safety problems in long-term treatment, such as liver toxicity and weight gain. [0003] Dipeptidyl pe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16A61P3/10
CPCC07D207/16
Inventor 蔡子洋
Owner 江苏天凤源食品有限公司