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Phenyl pyrimidine derivative and preparation method and use thereof

A technology of methylpyrimidine and methylsulfonylbenzylphenyl, which is applied in the field of phenylpyrimidine derivatives and its preparation, can solve problems that have not yet been discovered, and achieve the effect of increasing glucose consumption, improving glucose tolerance, and obvious effects

Inactive Publication Date: 2017-01-04
陈晋莹 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the discovery of a new GPR119 agonist with good pharmacodynamic properties has become a hotspot in the field of diabetes, especially the discovery of a specific GPR119 agonist, but unfortunately, so far, no

Method used

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  • Phenyl pyrimidine derivative and preparation method and use thereof
  • Phenyl pyrimidine derivative and preparation method and use thereof
  • Phenyl pyrimidine derivative and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 Boc-4-(2-chloro-5-methylpyrimidine)-piperazine is synthesized

[0037] Put 100mg (0.61mmol) 2,4-dichloropentamethylpyrimidine and 171.39mg (0.92mmol) N-Boc-piperazine in a 100mL round bottom flask, add potassium carbonate 168.36mg (1.2mol) and stir at 50°C Overnight, the reaction solution was poured into ice water, immediately a large amount of white solid precipitated, filtered, washed 2-3 times with ether, and dried to obtain 180.5 mg of white solid, yield 94%.

[0038] The product parameters are as follows: 1 H NMR (400MHz, CDCl3) δ7.94(s,1H),3.82(s,4H),3.50(s,4H),2.25(s,3H),1.43(s,9H).MS(ES),m / z: 313.3 [M+H]+; HPLC purity: 98.0%.

Embodiment 2

[0039] Example 2 Synthesis of N-tert-butoxycarbonyl-4-(2-(4-methoxyphenyl)-5-methylpyrimidine)-4-piperazine

[0040] Put 200mg (0.64mol) of Boc-4-(2-chloro-5-methylpyrimidine)-piperazine and 106.4mg (0.7mol) of p-methoxyphenylboronic acid in a 100mL three-necked bottle, add tetratriphenyl Phosphine palladium 60 mg, seal the bottle mouth with a rubber stopper, vacuumize, and pass in nitrogen gas, ventilate back and forth 3 to 4 times, inject 4 mL of toluene: ethanol = 1:1 solution with a pinhole, 1 mL of 1N sodium carbonate solution, in Stir at 80 degrees Celsius for 6 hours, hang the reacted solution to dry and mix the sample, and purify by column chromatography, eluent conditions: petroleum ether: ethyl acetate = 3:1, dry and hang to give 110 mg of white solid, yield 44.8% .

[0041] The product parameters are as follows: 1 H NMR (400MHz, CDCl3) δ8.30(s,1H),7.93(d,2H,J=6.4Hz),7.39(s,1H),7.04(s,1H),3.82(s,3H),3.50 (s, 8H), 2.25 (s, 3H), 1.43 (s, 9H). MS (ES), m / z: 385.3 [M+...

Embodiment 3

[0042] Example 3 Synthesis of Boc-4-(2-(4-ethoxyphenyl)-5-methylpyrimidine-4-piperazine

[0043] Put 200mg (0.64mol) Boc-4-(2-chloro-5-methylpyrimidine)-piperazine and 116.2mg (0.7mol) p-ethoxyloxyphenylboronic acid in a 100mL three-necked bottle, add four three Phenylphosphine palladium 60 mg, seal the bottle mouth with a rubber stopper, vacuumize, and pass in nitrogen gas, ventilate back and forth 3 to 4 times, inject 4 mL of toluene: ethanol = 1:1 solution with a pinhole, 1 mL of 1N sodium carbonate solution , stirred at 80 degrees Celsius for 6 hours, suspended the reacted solution to dry and mixed samples, purified by column chromatography, eluent conditions: petroleum ether: ethyl acetate = 3:1, dried and suspended to obtain 100.6 mg of a white solid, the product rate 39.4%.

[0044] The product parameters are as follows: 1 H NMR (400MHz, CDCl3) δ8.23(d, 1H, J=8.8Hz), 7.19(s, 1H), 6.89(d, 1H, J=8.8Hz), 7.04(s, 1H), 3.91(m ,2H),3.52(d,8H,J=2.8Hz),2.17(s,3H),1.42(s,9H)....

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Abstract

The invention belongs to the field of chemistry and medicine, in particular to a phenyl pyrimidine derivative and a preparation method and use thereof. The phenyl pyrimidine derivative as a specific GPR119 inhibitor provides a new choice for preventing and treating the metabolic disorders associated with type 2 diabetes mellitus, adiposis, lipid metabolism disorder and the like. The structure of the phenyl pyrimidine derivative is shown as the formula I.

Description

technical field [0001] The invention relates to a phenylpyrimidine derivative and its preparation method and use. Background technique [0002] Diabetes is multifactorial and is characterized by elevated plasma glucose levels (hyperglycemia) in the fasted state or after administration of glucose during an oral glucose tolerance test. There are generally two recognized forms of diabetes, In type 1 diabetes, or insulin-dependent diabetes mellitus (IDDM), the patient produces little or no insulin, the hormone used to regulate glucose. In type 2 diabetes, or non-insulin-dependent diabetes (NIDDM), the body still produces insulin. Patients with type 2 diabetes are resistant to the action of insulin to stimulate insulin and lipid metabolism in the main insulin-sensitive tissues (muscle, liver and adipose tissue). These patients usually have normal levels of insulin and may have hyperinsulinemia (elevated plasma insulin levels) as they compensate for the lowering effects of insul...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D403/12C07D401/04C07D409/10C07D401/10C07D409/12C07D405/12C07D413/12A61K31/506A61P3/04A61P3/10
CPCC07D239/42C07D401/04C07D401/10C07D403/12C07D405/12C07D409/10C07D409/12C07D413/12
Inventor 邱能陈晋莹杨涛
Owner 陈晋莹