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Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds

A technology of amide compounds and mixtures, which is applied in the field of novel amide compounds and can solve problems such as the unmentioned compounds having MCH-antagonistic activity

Inactive Publication Date: 2005-12-14
BOEHRINGER INGELHEIM PHARM KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no mention of these compounds having MCH-antagonistic activity

Method used

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  • Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds
  • Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds
  • Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0541] Synthesis of Intermediates

[0542] Intermediate 1:

[0543]

[0544] Z1a) [2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine-hydrobromide

[0545] Add 40.00 g (1.00 mol) of potassium carbonate to 50.00 g (0.288 mol) of 2-chloro-4-nitro-phenol with 60.23 g (0.350 mol) of (2-chloro-ethyl)-diethyl-amine at 700 mL of DMF, and the mixture was stirred at 80°C for 16 hours. The reaction mixture was evaporated down i. vac, the residue was combined with water, and the aqueous phase was exhaustively extracted with EtOAc. The combined organic extracts were washed with water, dried over magnesium sulfate and evaporated down i. vac. The crude product was recrystallized from EtOAc, and the mother liquor was evaporated down in vacuo. The residue was purified by column chromatography (silica gel, gradient dichloromethane / MeOH 10:0→9:1) to give the desired product.

[0546] Yield: 29.00 g (37% of theory)

[0547] C 12 h 17 ClN 2 o 3 (M=272.734)

[0548] Calculated value...

Embodiment Z23f

[0938] Prepared similarly to Example Z23f from (4-piperidin-1-ylmethyl-phenyl)-acetonitrile. Yield: 1.4 g (85.9% of theory)

[0939] C 14 h 22 N 2 (M=218.34)

[0940] Calculated value: molecular peak (M+H) + :219

[0941] Measured value: Molecular peak (M+H) + :219

[0942] R f Value: 0.2 (silica gel, dichloromethane / ethanol / ammonia 20:1:0.1)

[0943] Intermediate 25:

[0944]

[0945] Z25a) Ethyl 5-hydroxy-2-nitrobenzoate

[0946] A solution of 5.00 g (27.304 mmol) of 5-hydroxy-2-nitrobenzoic acid in 200 mL of ethanol-containing HCl was refluxed for 5 hours and then stirred at room temperature for 48 hours. The reaction mixture was evaporated to dryness in vacuo and diluted with EtOAc. The organic phase is washed with water, dried over magnesium sulfate and evaporated down i. vac. The crude product was used in the next reaction step without any further purification.

[0947] Yield: 5.00 grams (87% of theory)

[0948] C 9 h 9 NO 5 (M=211.176)

[0949] Cal...

Embodiment 19

[1329]

[1330] 19) 2-(2-Chloro-4-trifluoromethyl-phenoxy)-N-[4-(2-diethylamino-ethoxy)-3-methoxy-phenyl]-B Amide

[1331] 171 mg (0.82 mmol) CDI was added to a solution of 185 mg (0.73 mmol) (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (see intermediate Z2b) in 5 mL THF , and the reaction mixture was stirred at 50 °C for 30 minutes. Then, 0.1 ml (0.73 mmol) of triethylamine and 200 mg (0.73 mmol) of 4-(2-diethylamino-ethoxy)-3-methoxy-aniline (see intermediate Z6b) were added, And the solution was stirred at room temperature for 16 hours. The reaction solution was added to water, and stirred at room temperature for 45 minutes. After filtration, the residue was dried in a circulating air drier.

[1332] Yield: 170 mg (49% of theory)

[1333] C 22 h 26 CIF 3 N 2 o 4 (M=474.912)

[1334] Calculated value: molecular peak (M+H) + : 475 / 477

[1335] Measured value: Molecular peak (M+H) + : 475 / 477(Cl)

[1336] R f Value: 0.30 (silica gel, dichloromethane / MeOH...

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Abstract

The invention relates to amides of the general formula (I), wherein the radicals and residues A, B, b, W, X, Y, Z, R1, R2 and R3 have the meanings given in claim 1. The invention also relates to medicaments comprising at least one of said amides. Due to the MCH receptor antagonism, the medicament is suitable for the treatment of metabolic and / or eating disorders, especially obesity, bulimia, anorexia, hyperphagia and diabetes.

Description

technical field [0001] The present invention relates to novel amide compounds, their physiologically acceptable salts, and their use as MCH antagonists, and their use in the preparation of pharmaceutical preparations, which are suitable for the prevention and / or treatment of A condition and / or disease that is causally related to MCH in some other way. The present invention also relates to the use of compounds according to the invention for influencing feeding behavior and reducing body weight and / or preventing any weight gain in mammals. It further relates to compositions and medicaments containing the compounds according to the invention, and methods for their preparation. Background technique [0002] The intake of food and its transformation in the body is an essential part of life for all living organisms. Thus, deviations in food intake and conversion generally lead to problems and illnesses. Changes in human lifestyle and nutrition, especially in industrialized coun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P3/00C07C233/29C07C235/24C07C237/04C07C255/60C07C275/32C07D207/09C07D207/20C07D209/08C07D211/46C07D211/62C07D213/30C07D213/56C07D295/02C07D295/03C07D295/092C07D295/13C07D307/42C07D333/16
CPCC07C233/29C07C235/24C07C237/04C07C255/60C07C275/32C07D207/09C07D207/20C07D209/08C07D211/46C07D211/62C07D213/30C07D213/56C07D295/03C07D295/088C07D295/13C07D307/42C07D333/16C07C2601/14A61P13/02A61P13/10A61P13/12A61P15/00A61P19/02A61P25/00A61P25/08A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P27/02A61P29/00A61P3/00A61P3/10A61P35/00A61P3/04A61P3/06A61P43/00A61P5/00A61P5/50A61P9/00A61P9/04A61P9/10A61P9/12
Inventor 德克·施滕坎普斯蒂芬·G·米勒杰拉尔德·J·罗思菲利普·勒斯滕伯格克劳斯·鲁道夫索尔斯滕·莱曼-林茨柯尔斯滕·阿恩特拉尔夫·R·H·洛茨马丁·伦特海克-安德烈亚·威兰
Owner BOEHRINGER INGELHEIM PHARM KG
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