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Novel ester group-containing aromatic propionamide compound as well as preparation method and application thereof

A technology for aromatic propionamides and compounds, applied in the field of new ester-containing aromatic propionamide compounds and their preparation

Active Publication Date: 2014-05-07
CHANGCHUN GENESCIENCE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, selective non-steroidal androgen modulators have only recently been reported in the literature

Method used

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  • Novel ester group-containing aromatic propionamide compound as well as preparation method and application thereof
  • Novel ester group-containing aromatic propionamide compound as well as preparation method and application thereof
  • Novel ester group-containing aromatic propionamide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyanophenoxy)-2-methyl-1-oxypropyl-2-ethane Ester, (C 21 h 16 f 3 N 3 o 4 )

[0032]

[0033] Add 2.00 grams of raw materials, 1.05 grams of acetic anhydride, and 20 mL of anhydrous pyridine as a solvent in a 50 mL round bottom flask, reflux, stir, and the reaction time is 2.5 to 3.5 hours. Point the chromatography plate to determine the end point. Thin layer chromatography: ethyl acetate: Hexane=1:1, the product point is relatively single, and there is no raw material point.

[0034] After the reaction was completed, cool and drain to obtain an oil, which was separated and purified by silica gel column chromatography (dichloromethane: ethyl acetate = 98:2~95:5) to obtain a white powder, which was coaxed to dry and weighed. Yield 2.00 g, about 90.0%.

[0035] NMR spectrum: 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.48(s, 1H, NH), 8.29(s, 1H, ArH), 8.17(d, J=8.5Hz, 1H, ArH), 8.11(d, J=8.5Hz, 1H, ArH), 7.77( d, J=8.5Hz, ...

Embodiment 2

[0037] (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyanophenoxy)-2-methyl-1-oxypropyl-2-benzene Formate, (C 26 h 18 f 3 N 3 o 4 )

[0038]

[0039] Add 5.00 grams of raw materials, 14.53 grams of benzoic anhydride, and 35 mL of anhydrous pyridine as a solvent in a 100 mL round-bottomed flask, reflux, stir, and the reaction time is 9.5 to 10.5 hours. Point the chromatography plate to determine the end point, thin-layer chromatography: ethyl acetate : Hexane=1:1, the product point is relatively single, and there is no raw material point.

[0040] After the reaction was completed, cool and drain to obtain an oily substance, which was separated and purified by silica gel column chromatography (dichloromethane: ethyl acetate=95:5) to obtain a white powder substance, which was coaxed to dryness and weighed to obtain 6.00 grams. The yield is about 96.0%.

[0041] NMR spectrum: 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.59(s, 1H, NH), 8.30(s, 1H, ArH), 8.18(d, J=8.5Hz, 1H, ArH)...

Embodiment 3

[0043] (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyanophenoxy)-2-methyl-1-oxypropyl-2-methanol Sulfonate, (C 20 h 16 f 3 N 3 o 5 S)

[0044]

[0045] Add 1.00 g of raw materials and 20 mL of anhydrous tetrahydrofuran as a solvent in a 150 mL round-bottomed flask, and drop the temperature to 0°C, add 0.22 g of sodium hydride, stir for 2-3 hours, then add 0.60 g of methanesulfonyl chloride, raise the temperature to room temperature, and stir , the reaction time is 4-5 hours, point the chromatographic plate to determine the end point, thin-layer chromatography: dichloromethane: ethyl acetate = 19:1, the product point is relatively single, and there is no raw material point.

[0046] After the reaction was completed, it was drained to obtain an oil, which was separated and purified by silica gel column chromatography (dichloromethane:ethyl acetate=9 5:5~9:1) to obtain a white powder, which was coaxed to dry and weighed to obtain 1.05 g, the yield is about 85.1%.

...

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PUM

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Abstract

The invention discloses a novel ester group-containing aromatic propionamide compound as well as a preparation method and an application thereof, and provides a chemical structure formula of the novel ester group-containing aromatic propionamide compound. The compound is prepared by taking an acyl chloride compound and proline as starting raw materials. The compound has the effect of adjusting an androgen receptor and can be independently used or being used as a composition to be used for treating and / or preventing various diseases related to androgens, such as diseases of male androgen deficiency (ADAM), diseases of female androgen deficiency (ADIF), muscle consumption, muscle emaciation, amyotrophy, osteoporosis, sclerotin reduction, anemia, obesity, diabetes mellitus, cancers and the like; the compound can also be used for an exercise and / or body function enhancing agent or an animal feed additive.

Description

technical field [0001] The invention relates to the field of propionamide compounds, in particular to a new class of aromatic propionamide compounds containing ester groups, a preparation method and application thereof. Background technique [0002] The androgen receptor belongs to the class of steroid nuclear receptors and is a receptor for nuclear transcription factors induced by ligands. The androgen receptor is an important cellular regulatory protein that plays a vital role in numerous physiological processes through endogenous androgens, including the development and maintenance of male secondary sexual characteristics, including muscle and bone mass , prostate growth, male hair, and sperm development, etc. Endogenous steroidal androgens, generally known as male sex hormones, include testosterone and dihydrotestosterone (DHT). Testosterone is the major steroidal androgen found in male serum, secreted primarily by the testes. In many peripheral tissues, such as the p...

Claims

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Application Information

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IPC IPC(8): C07C255/60C07C253/30C07C303/28C07C309/73C07C309/66C07D213/803C07D213/80C07D263/44C07D263/40C07C275/50C07C273/18C07C271/64C07C269/00A61K31/277A61K31/4406A61K31/421A61P21/00A61P19/08A61P35/00A61P31/18A61P13/12A61P7/06A61P3/04A61P3/10A61P25/28A61P15/00A61P15/08A61P19/10A61P25/24A61P39/00A61P17/14A61P15/10A23K1/16
CPCA23K20/111A23L33/10A61P3/04A61P3/10A61P7/06A61P13/12A61P15/00A61P15/08A61P15/10A61P17/14A61P19/08A61P19/10A61P21/00A61P25/24A61P25/28A61P31/18A61P35/00A61P39/00C07C255/60C07C271/64C07C275/50C07C309/66C07C309/73C07D263/40C07D263/44
Inventor 朱新法孙继华梁发香
Owner CHANGCHUN GENESCIENCE PHARM CO LTD
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