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Aromatic amide compound as well as preparation method and application thereof

A technology of aromatic propionamides and compounds, applied in the field of drug synthesis, can solve the problems of limited effect, poor oral bioavailability of liver toxicity, etc.

Active Publication Date: 2014-11-19
NINGBO XIJIAN PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Testosterone injections, patches and gels are commonly used clinically. However, testosterone and its various derivatives belong to steroid hormones, so they all have the specific side effects of steroid hormones, especially the side effects of steroidal androgen, such as benign prostatic hyperplasia and Prostate cancer, gynecomastia, hepatotoxicity and poor oral bioavailability, etc.
Although various methods have been tried to overcome the limitations of hormonal drugs, the effect is limited

Method used

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  • Aromatic amide compound as well as preparation method and application thereof
  • Aromatic amide compound as well as preparation method and application thereof
  • Aromatic amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Compound (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyano-3-fluorophenoxy)-2-methyl- Synthesis of 1-oxypropyl-2-acetate (C 21 h 15 f 4 N 3 o 4 )

[0037]

[0038] In a 50mL round bottom flask, add 0.4 grams of raw materials, 2.1 grams of acetic anhydride, and 10 mL of anhydrous pyridine as a solvent, reflux, stir, and the reaction time is 2.5-3.5 hours. The point chromatography plate determines the end point, thin layer chromatography: ethyl acetate: Hexane=1:1, the product point is relatively single, and there is no raw material point.

[0039] After the reaction was completed, it was cooled and sucked dry to obtain an oil. Silica gel column chromatography (dichloromethane: ethyl acetate = 98:2-95:5) was separated and purified to obtain a white powder, which was coaxed to dryness and weighed to obtain 0.4 g with a purity of about 98%.

[0040] NMR spectrum: 1 H NMR(400 MHz,DMSO-d6)δ10.50(s,1H,NH),8.30(s,1H,ArH),8.19-8.12(m,2H,ArH),7.87-7.83(m...

Embodiment 2

[0041] Example 2: Compound (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyano-3-fluorophenoxy)-2-methyl- Synthesis of 1-oxypropyl-2-benzoate (C 26 h 17 f 4 N 3 o 4 )

[0042]

[0043] Add 0.20 grams of raw materials, 0.5 grams of benzoic anhydride, and 10 mL of anhydrous pyridine as a solvent in a 100 mL round bottom flask, reflux, stir, and the reaction time is 9-10 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.

[0044] After the reaction was completed, it was cooled and drained to obtain an oil, which was separated and purified by silica gel column chromatography (dichloromethane:ethyl acetate=95:5) to obtain a white powder, which was coaxed to dryness and weighed to obtain 0.21 grams. The purity is about 98%.

[0045] NMR spectrum: 1 H NMR(400 MHz,DMSO-d6)δ10.60(s,1H,NH),8.29(s,1H,ArH),8.19-8.12(m,2H,ArH),7.98-7....

Embodiment 3

[0046] Example 3: Compound (S)-1-(4-cyano-3-(trifluoromethyl)anilino)-3-(4-cyano-3-fluorophenoxy)-2-methyl- Synthesis of 1-oxypropyl-2-methylcarbamate (C 22 h 18 f 4 N 4 o 4 )

[0047]

[0048] Add 1.50 g of raw materials and 20 mL of anhydrous DMF as a solvent in a 100 mL round-bottomed flask, and drop the temperature to 0°C, add 0.40 g of sodium hydride, stir for 2-3 hours, then add 0.88 g of dimethylcarbamoyl chloride, and raise the temperature to room temperature. Stir, the reaction time is 5-6 hours, point the chromatographic plate to determine the end point, thin-layer chromatography: dichloromethane: ethyl acetate = 9:1, the product point is relatively single, and there is no raw material point.

[0049] After the reaction was stopped, it was drained to obtain an oil, and the main product was separated by silica gel column chromatography (ethyl acetate: hexane=1:1), purified to obtain a white toner substance, coaxed to dryness, and weighed to obtain 0.99 g. The...

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PUM

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Abstract

The invention provides an aromatic amide compound which is a new selective nonsteroidal androgen receptor modulator, has an effect on modulating an androgen receptor, can be used for treating or preventing various diseases related with androgen, such as male androgen deficiency (ADAM) symptom, female androgen deficiency (ADIF) symptom, muscle wasting, osteoporosis, osteopenia, anemia, obesity, fatty liver, diabetes, dry eyes, muscle wasting caused by diseases such as cancers, AIDS, kidney diseases, burn injury and the like, and also can be used for sports and / or physical enhancers, animal growth promoters, feed additives and the like.

Description

technical field [0001] The invention relates to an aromatic propionamide compound and its preparation method and application, belonging to the technical field of drug synthesis. Background technique [0002] The Androgen Receptor (AR) belongs to the steroid receptors in the nuclear receptor superfamily and is a receptor for nuclear transcription factors induced by ligands. It generally consists of four functional domains: the N-terminal transcription activation region ( NTD), a DNA-binding domain (DBD), a hinge region and a 261-residue ligand-binding domain (LBD) comprising the androgen-binding domain. The androgen receptor binds activated androgens with high affinity and low energy, and without the androgen receptor, the androgen would have no refractory response to tissues. Androgen receptors are mediators of androgen action. Androgen receptor is an important cell regulatory protein, its main function is to regulate gene expression as a DNA-binding transcription factor, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/60C07C253/30C07C271/12C07C269/00C07C303/28C07C309/66C07C309/73C07D213/80C07D213/803A61K31/277A61K31/4406A61P15/00A61P15/10A61P21/00A61P19/10A61P25/24A61P7/06A61P17/14A61P3/04A61P13/08A61P35/00A61P31/18A61P13/12A61P19/08A61P3/10A61P1/16A61P27/02A61P5/26A61P5/30A61P39/00A23K1/16A23K20/10
Inventor 朱新法孙继华梁发香
Owner NINGBO XIJIAN PHARM TECH CO LTD
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