Melanocortin-4 receptor agonists

A melanocortin receptor and agonist technology, applied in the direction of anti-inflammatory agents, non-central analgesics, metabolic diseases, etc., can solve the problems of side effects, lack of selectivity of regulators, etc., to prevent or treat obesity, excellent stimulant The effect of agent activity

Pending Publication Date: 2022-01-14
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, modulators lack selectivity for each subtype and have a major disadvantage that long-term administration is accompanied by various side effects

Method used

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  • Melanocortin-4 receptor agonists
  • Melanocortin-4 receptor agonists
  • Melanocortin-4 receptor agonists

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0073] Preparation Example 1: Preparation of (2S,4S)-4-(N-((1s,4R)-4-methylcyclohexyl)isobutyrylamide)pyrrolidine-2-methanol Acid methyl ester hydrochloride

[0074]

[0075] The title compound was obtained by the following steps A, B, C, D and E.

[0076] Step A: Preparation of (2S,4S)-4-azidopyrrolidine-1,2-dicarboxylic acid 1-(tert-butyl)2-methyl ester

[0077] Dissolve (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 1-(tert-butyl)2-methyl ester (48.5 g, 150 mmol) in N,N'-dimethylformamide (250ml), and sodium azide (19.5g, 300ml) was added thereto. After stirring at 80° C. for 16 hours, the reaction solvent was concentrated under reduced pressure, water was added, and extraction was performed twice using ethyl acetate. The organic layer was washed with aqueous sodium chloride and water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude product (39.59 g, 98%) which was used i...

preparation example 2

[0095] Preparation Example 2: Preparation of (3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid

[0096]

[0097] The title compound was obtained by the method described in International Publication No. WO 2004 / 092126.

[0098] MS[M+H]=282(M+1)

[0099] 1 H NMR (400MHz, CD 3 OD)δ7.43-7.33(m,4H),3.90-3.69(m,3H),3.59(dd,J=11.2,10.0Hz,1H),3.29(dd,J=11.2,11.2Hz,1H), 3.18-3.09(m,1H),1.44(s,9H)

preparation example 3

[0100] Preparation Example 3: Preparation of (2S,4S)-4-(N-((1s,4R)-4-methylcyclohexyl)propionamido)pyrrolidine-2-carboxylic acid Methyl ester hydrochloride

[0101]

[0102] The title compound was obtained by steps A and B.

[0103] Step A: Preparation of (2S,4S)-4-(N-((1s,4R)-4-methylcyclohexyl)propionamido)pyrrolidine-1,2-dicarboxylic acid Preparation of 1-(tert-butyl)2-methyl ester

[0104]

[0105] By using (2S,4S)-4-((1s,4R)-4-methylcyclohexyl)amino)pyrrolidine-1,2-dicarboxylic acid 1-(tert-butyl) obtained in Step C of Preparation Example 1 base) 2-methyl ester (1.0 g, 2.9 mmol) and propionyl chloride (0.33 g, 3.5 mmol), the title compound (0.98 g, 84%) was obtained in the same manner as in Step D of Preparation 1.

[0106] MS[M+Na]=419.5(M+23)

[0107] 1 H NMR (400MHz, CD 3 OD)δ4.33(m,1H),4.00-3.80(m,2H),3.75(m,3H),3.58(m,1H),3.47(m,1H),2.85-2.68(m,1H), 2.38(q,2H),2.31(m,1H),1.93(m,1H),1.80(m,2H),1.72-1.55(m,4H),1.45(m,2H),1.45-1.41(m, 9H),1.07(m,6H) ...

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PUM

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Abstract

The present invention relates to a compound exhibiting excellent agonist activity against melanocortin receptors. More specifically, the present invention relates to a compound of Formula 1, a pharmaceutical composition comprising the compound as an active ingredient, and a use thereof, and the compound of the present invention exhibits excellent agonist activity against melacortin-4 receptors and can be particularly useful in preventing or treating obesity, diabetes, inflammation and erectile dysfunction.

Description

technical field [0001] The present invention relates to a compound exhibiting excellent agonist activity on melanocortin receptors. More specifically, the present invention relates to a compound of the following formula 1, a pharmaceutical composition comprising the compound as an active ingredient, and uses thereof, and the compound of the present invention exhibits excellent agonist activity against the melanocortin-4 receptor, and in May be especially useful in preventing or treating obesity, diabetes, inflammation and erectile dysfunction: [0002] [Formula 1] [0003] [0004] where R1 is C 2 -C 5 alkyl. Background technique [0005] Leptin is a hormone secreted by body fat cells (adipocytes), and its secretion increases with body fat content. The protein leptin regulates the function of various neuropeptides produced in the hypothalamus, thereby regulating appetite, body fat content, and various in vivo functions including energy metabolism, (Schwartz et al., N...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16A61P3/04A61P3/10A61P29/00A61P15/10A61K31/5377
CPCC07D207/16A61P3/04A61P3/10A61P29/00A61P15/10A61K31/5377C07D413/14
Inventor 姜承完朴熙东朴喜东余秀真朴贤绪洪智豪安慧沅崔恩实
Owner LG CHEM LTD
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