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Androgen receptor suppressors in treatment of hirsutism,acne and androgenetic alopecia

A technology of compounds and mixtures, applied in the field of androgen receptor inhibitors in the treatment and diagnosis of prostate cancer, alopecia and other androgen excess syndromes, can solve the problem of harmless long-term systemic treatment

Inactive Publication Date: 2003-05-07
BIOPHYSICA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No studies are available to demonstrate whether long-term systemic treatment of this hormone balance is harmless

Method used

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  • Androgen receptor suppressors in treatment of hirsutism,acne and androgenetic alopecia
  • Androgen receptor suppressors in treatment of hirsutism,acne and androgenetic alopecia
  • Androgen receptor suppressors in treatment of hirsutism,acne and androgenetic alopecia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: 4-nitro-3-trifluoromethyl-N-(2-hydroxy-2-methyl-3-amino-propionyl)aniline, (BP-34)

[0072] Add 4-nitro-3-trifluoromethyl-[2,3-epoxy-2-methylpropionyl]aniline, BP-33 (10.0g, 34.46mmol) (see image 3 ) And methanol (100ml). After cooling to 70°C, excess ammonia was condensed into the reactor, which was sealed and stirred for 14 hours. After evaporation, use cold CH for the crude solid 2 Cl 2 (50ml) Wash. It was filtered and dried to obtain 6.1 g of BP-34 (yield 58%).

[0073] Melting point: 142-145°C

Embodiment 2

[0074] Example 2: 4-Nitro-3-trifluoromethyl-N-(2′-hydroxy-2′-methyl-3′-N-(hexafluorobutyramide Yl)propionyl)aniline, (BP-521)

[0075] BP-34 (247mg, 0.80mmol) and CH under nitrogen 2 Cl 2 (5mL), THF (10mL) and NEt 3 (1.1 mL, 0.80 mmol) was cooled to 0°C and heptafluorobutyryl chloride (120 μl, 0.80 mmol) was added. After cooling to room temperature, remove the volatiles and add CH 2 Cl 2 (30mL) and H 2 O (50mL), separate the organic layer and use MgSO 4 dry. After silica gel chromatography (CHCl 3 / Acetone) The product was isolated after purification, which was a colorless oil (320 mg, yield 82%).

Embodiment 3

[0076] Example 3: 4-Nitro-3-trifluoromethyl-N-(2'-hydroxy-2'-methyl-3'-pentafluorooctanoylamino)- Propionamide, (BP-562)

[0077] To BP-34 (360mg, 1.17mmol) was added THF (10mL) and NEt 3 (485 μL, 3.5 mmol). The solution was cooled to 0°C and pentadecyl octanoyl chloride (295 μL, 1.17 mmol) was added. After reaching room temperature, the volatiles were removed. After silica gel chromatography (CHCl 3 After purification with acetone), the product was obtained as a pale yellow solid (689 mg, yield 84%).

[0078] Mass spectrum (m / z): 704 (MH + ); 726(M+Na + ). 19 F NMR(470MHz, CDCl 3 ): -56.8 ppm, -77.3, -116.3, -118.1, -118.6, -119.1, -119.4, -122.7.

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Abstract

The invention providing compound (2-hydroxy-2-methyl-N-(4-X-3-(trifluoromethyl)phenyl)-3-(2,2,2-perfluo roacylamino)propionamide) applied topically, specifically inhibits and / or eliminates cutaneous androgen receptors and thus finds cosmetic use in skin afflictions associated with excess androgens such as hair effluvium, hirsutism, acne and androgenic alopecia.

Description

Technical field [0001] The field of the invention is compounds and their use in the treatment of prostate cancer and hyperandrogen syndromes including alopecia, hirsutism and acne vulgaris. Background technique [0002] The existence of a variety of pathological syndromes depends on male hormones. Therefore, the growth of prostate cancer is driven by androgens at an early stage, and may, at least temporarily, stop due to androgen loss. Androgenetic alopecia is caused by an unexplained reason that androgens switch from promoting the growth of hair follicles to hair loss. In skin androgen-mediated diseases, such as hair loss, acne vulgaris and hirsutism, excessive androgen in the skin is found to be the main pathogenic factor. [0003] People still do not fully understand the pathophysiology of male and female hair loss and the treatment is unsatisfactory. People recognize that scalp blood flow, lack of nutrition and vitamins related to hair, and inflammatory lesions caused by micr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/10A61K31/165A61K31/167A61K31/277A61K31/40A61K31/417A61P5/00A61P5/28A61P17/10A61P17/14A61P35/00C07C231/02C07C237/04C07C237/22C07C255/56C07C255/60C07C275/30C07C317/46C07C323/60C07C335/08C07C335/16C07C335/22C07D207/40C07D207/408C07D233/02C07D233/72C07D233/86C07D233/88
CPCC07C335/08A61K31/165C07D233/86C07C275/30C07C237/04C07C323/60C07D233/88C07C317/46C07C237/22C07C335/22C07C255/60C07D207/408C07C335/16C07C255/56C07C2101/14C07C2601/14A61P17/10A61P17/14A61P35/00A61P5/00A61P5/28A61K31/167
Inventor 米洛斯·索瓦克艾伦·塞利格森詹姆斯·G·道格拉斯第三贾森·W·布朗布赖恩·坎皮恩
Owner BIOPHYSICA
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