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Compounds useful as sglt2 inhibitors and their preparation and use

A technology of compounds and ketone compounds, applied to compounds that can be used as SGLT2 inhibitors and the fields of their preparation and use, can solve weight gain, hypoglycemia and gastrointestinal discomfort, involve many targets, and complex pathogenesis of type 2 diabetes And other issues

Active Publication Date: 2018-12-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional hypoglycemic drugs mainly include insulin sensitizers, insulin secretagogues, and α-glucosidase inhibitors. However, the pathogenesis of type 2 diabetes is complex and involves many targets. Traditional therapeutic drugs, such as sulfonylureas (Insulin secretagogues), thiazolidinediones (insulin sensitizers) and α-glucosidase inhibitors are mostly dependent on insulin secretion, and side effects such as weight gain, hypoglycemia and gastrointestinal discomfort are more obvious , so its development and application are greatly restricted

Method used

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  • Compounds useful as sglt2 inhibitors and their preparation and use
  • Compounds useful as sglt2 inhibitors and their preparation and use
  • Compounds useful as sglt2 inhibitors and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Nitric acid ((1-(2-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethyl)-1H-1,2, Preparation of 3-triazol-4-yl)methylcarbonic anhydride.

[0079] Step 1: Preparation of intermediate 2H-benzo[b][1,4]oxazin-3(4H)-one

[0080]

[0081] 2-Aminophenol (5.7g, 52.0mmol) was dissolved in 100mL acetonitrile and pre-cooled for 10min, TEBA (1.2g, 5.2mmol) and NaHCO were added at 0°C 3 (8.7 g, 103.6 mmol) and kept stirring. Then a solution of 2-chloroacetyl chloride (4.9 mL, 62.4 mmol) in 20 mL of acetonitrile was slowly added dropwise. After the dropwise addition was completed, keep stirring at 0°C for 40 minutes, then transfer to a 55°C oil bath for stirring and reacting for 8 hours, concentrate the reaction solution with a rotary evaporator, then recrystallize with ethanol:water (1:1) mixture, suction filter, vacuum After drying, 5.3 g of light brown solid 2H-benzo[b][1,4]oxazin-3(4H)-one was obtained, with a yield of 68.4%. m.p.: 171-173°C; 1 H NMR (400MHz, CDCl 3 )δ(p...

Embodiment 1-15

[0095] According to the general preparation method, 2H-benzo[b][1,4]oxazin-3(4H)-one SGLT2 inhibitors listed in Table 1 were synthesized using different substituted forms of 2-aminophenol as raw materials .

[0096] Table 1 2H-Benzo[b][1,4]oxazin-3(4H)-one compounds

[0097]

Embodiment 1～15

[0098] Embodiment 1~15 1 H NMR and MALDI-TOF-MS data

[0099] Nitric acid ((1-(2-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethyl)-1H-1,2, 3-triazol-4-yl)methylcarbonic acid)anhydride (Example 1): white solid, yield 35.3%, m.p.: 67.5-68.4°C. 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 8.34 (s, 1H), 7.06 (ddd, J = 7.5, 6.2, 2.9Hz, 1H), 7.06-6.92 (m, 3H), 5.42 (s, 2H), 4.79 (s, 2H ), 4.50(t, J=5.7Hz, 2H), 3.86(t, J=5.7Hz, 2H).MALDI-TOF: m / z 363([M+H] + ).

[0100] Nitric acid ((1-(3-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)propyl)-1H-1,2, 3-triazol-4-yl)methylcarbonic acid) anhydride (Example 2): white solid, yield 39.3%, m.p.: 80.3-81.7°C. 1 H NMR (400MHz, DMSO-d 6)δ(ppm):7.64(s,1H),7.11-6.95(m,2H),6.99-6.91(m,2H),5.42(s,2H),4.79(s,2H),4.42(t,J =7.4Hz, 2H), 4.30(t, J=7.7Hz, 2H), 2.13(p, J=7.6Hz, 2H).MALDI-TOF: m / z 377([M+H] + ).

[0101] Nitric acid ((1-(4-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)butyl)-1H-1,2, 3-triazol-4-yl)methylcarbonic anhydride (Example...

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Abstract

The invention discloses a 2H-benzo [b][1,4] oxazine-3(4H)-ketone compound as shown in a formula (I) or salts, hydrates, solvents, and stereoisomerides, which are pharmaceutically acceptable, a preparation method of the 2H-benzo [b][1,4] oxazine-3(4H)-ketone compound, a preparation containing the compound, and an application of the 2H-benzo [b][1,4] oxazine-3(4H)- ketone compound in the aspects of treating diabetes and complications thereof.

Description

technical field [0001] The present invention relates to a class of compounds that can be used as sodium-glucose co-transporter 2 (SGLT2) inhibitors, a preparation method thereof, and an application thereof in the preparation of anti-diabetes and its complications. Background technique [0002] Diabetes is a comprehensive high-morbidity metabolic disease caused by insulin deficiency or relative deficiency (insulin resistance, etc.) in the body, with hyperglycemia as the main feature. In recent years, its incidence has become more widespread and younger. According to the report of the International Diabetes Federation (IDF) in 2015, there are 415 million diabetic patients worldwide, and it is expected to reach 642 million by 2040, of which type 2 patients account for the total number of diabetic patients. 90% to 95% of that. Diabetes itself is not terrible, but it often causes a variety of complications, such as diabetic neuropathy, diabetic retinopathy and diabetic nephropat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/06A61K31/538A61P3/08A61P3/10A61P3/04A61P35/00A61P25/00A61P37/00A61P3/06
CPCC07D413/06
Inventor 彭圣明黄秀东丁永兰李怡欢
Owner XIANGTAN UNIV
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