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A compound for inhibiting 11ss-hydroxy steroid dehydrogenase 1, and a pharmaceutical composition comprising the same

A compound and solvate technology, applied in the field of compounds for inhibiting 11β-hydroxysteroid dehydrogenase 1 and pharmaceutical compositions containing the compounds, can solve the problems of increased 11βHSD1 activity and other problems, and achieve excellent activity and solubility, formulation and Transfer effective effects

Inactive Publication Date: 2014-06-11
HYUNDAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For obese people, although their plasma cortisol levels are lower than or similar to those of lean controls, 11βHSD1 activity in subcutaneous fat is greatly increased (Rask E et al., 2001; J.Clin.Endocrinol.Metab.1418-1421 )

Method used

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  • A compound for inhibiting 11ss-hydroxy steroid dehydrogenase 1, and a pharmaceutical composition comprising the same
  • A compound for inhibiting 11ss-hydroxy steroid dehydrogenase 1, and a pharmaceutical composition comprising the same
  • A compound for inhibiting 11ss-hydroxy steroid dehydrogenase 1, and a pharmaceutical composition comprising the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0063] Preparation Example 1: Synthesis of N-(adamantan-2-yl)-2-methyl-2-(phenylsulfonamido)propionamide (compound 1)

[0064]

[0065] Put 2-amino-2-methylpropionic acid (3.0g, 29.1mmol) and methanol (45ml) into a 100-ml flask, set an ice bath, and slowly add thionyl chloride (4.25ml, 58.2mmol). After the addition is complete, remove the ice bath. The mixture was stirred for 3 hours at room temperature. The obtained product was vacuum distilled to remove the solvent, and then ether (30 ml) was added, stirred at room temperature for 30 minutes, and filtered. The solid obtained by filtration was dried in an oven at 60°C to obtain methyl 2-amino-2-methylpropionate hydrochloride (4.2 g, 94%).

[0066] 1 H NMR(400MHz, DMSO-d 6 )δ8.75(s, 3H), 3.75(s, 3H), 4.05(m, 1H), 1.45(s, 6H).

[0067]

[0068] Into a 50-mL flask, charge 2-amino-2-methylpropionic acid methyl ester hydrochloride (400 mg, 2.61 mmol) and dichloromethane (10 mL), and charge triethylamine (1.46 ml, 10.47 mmol) ), and ...

preparation Embodiment 2

[0076] Preparation Example 2: Synthesis of N-(adamantan-2-yl)-2-methyl-2-(4-fluorobenzenesulfonamido)propionamide (compound 2)

[0077] The target compound was obtained in the same manner as described in Preparation Example 1 of Example 1, except that 2-(4-fluorobenzenesulfonamido)-2-methylpropionic acid was used.

[0078]

[0079] 1 H NMR(400MHz, CDCl 3 )δ7.90-7.95(m, 2H), 7.18-7.23(m, 2H), 6.65(d, J=6.8Hz, -NH-CO-), 5.40(s, -NH-SO 2 ), 3.97 (d, J = 8.0 Hz, 1H), 1.67-1.90 (m, 14H), 1.46 (s, 6H).

preparation Embodiment 3

[0080] Preparation Example 3: Synthesis of N-(adamantan-2-yl)-2-methyl-2-(4-nitrobenzenesulfonamido)propionamide (compound 3)

[0081] The target compound was obtained in the same manner as described in Preparation Example 1 of Example 1 except that 2-(4-nitrobenzenesulfonamido)-2-methylpropionic acid was used.

[0082]

[0083] 1 HNMR(400MHz, CDCl 3 )δ8.37(dt, J=2.4, 8.8Hz, 2H), 8.10(dt, J=2.4, 9.2Hz, 2H), 6.36(d, J=7.6Hz, -NH-CO-), 5.85(s , -NH-SO 2 ), 3.96 (d, J=7.6Hz, 1H), 1.67-1.89 (m, 14H), 1.50 (s, 6H).

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Abstract

Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-ss-hydroxy steroid dehydrogenase type 1 (11ss-HSD1). The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-ss-hydroxy steroid dehydrogenase type 1 (11ss-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.

Description

Technical field [0001] The present invention relates to a novel compound for inhibiting human 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing the compound. Background technique [0002] 11-β-hydroxysteroid dehydrogenase type 1 (11β-hydroxysteroid dehydrogenase 1) glucocorticoid (cortisol in humans and corticosterone in rodents) is a counter-regulatory hormone that resists insulin (Dallman MF, Strack AM, Akana SF et al., 1993; Front Neuroendocrinol 14, 303-347). This controls the expression of glycogenase associated with gluconeogenesis and increases the substrate supply by releasing amino acids from muscle (decreasing protein synthesis and increasing proteolysis) and glycerol from adipose tissue (increasing lipolysis). Glucocorticoids are also important in the differentiation of preadipocytes into mature adipocytes capable of storing triglycerides (Bujalska IJ et al., 1999; Endocrinolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/05A61K31/18A61P9/12A61P3/10C07C233/00
CPCA61K31/18C07C2101/02C07C311/29C07C311/39C07C2101/14C07D215/36C07C2101/08C07D213/71C07C2101/04C07C311/19C07C311/20C07C311/13C07C2103/74A61P3/10A61P9/12C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07C2603/74C07C311/05
Inventor 李寅熙片斗赫申明弦黄政云朴昌珉金世焕蔡熙一文淳暎金素娟李在杰
Owner HYUNDAI PHARMA
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