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2-substituted Retoamides

A technology of amides, esters and imides, applied in the field of new compounds and compositions for the treatment of hair loss in mammals, can solve problems such as inferior structure and complex FK506

Inactive Publication Date: 2002-01-23
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, the stimulation of hirsutism activity involving cyclosporine A and FK506 has been, in part, reported for hirsutism by various smaller, non-macrocyclic immunosuppressive and non-immunosuppressive compounds that are structurally less complex than FK506. appeased by the lack of

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] 1a.2-(1,7-diphenyl-4-heptyl)-4,4-dimethyl-2-oxazoline: 2,4,4-trimethyl-2-oxazoline ( 5.64 mL, 44.2 mmol) was dissolved in anhydrous THF (40 mL) at room temperature under an inert atmosphere. The solution was cooled to -78°C and n-butyllithium (31.3 mL / 1.6M in hexane, 50 mmol) was added dropwise. A solution of 1-bromo-3-phenylpropane (7.42 mL, 48.8 mmol) in THF (20 mL) was added over 10 minutes. The cooling bath was removed, and the reaction solution was allowed to come to room temperature. After 30 minutes, the solution was cooled to -78°C. n-BuLi (31.3 mL / 1.6M in hexane, 50 mmol) was added dropwise. After 30 minutes, a solution of 1-bromo-3-phenylpropane (7.42 mL, 48.8 mmol) in THF (20 mL) was added dropwise over 10 minutes. The reaction was slowly brought to room temperature with stirring over the next 12 hours. The reactant was poured into water (200 mL), acidified with 1N hydrochloric acid, extracted with ether (150 mL). The aqueous layer was cooled, neutraliz...

Embodiment 2

[0144] 2a. Cis-2-(N-tert-butoxycarbonylamino)-1-cyclopentanecarboxylic acid, 4-phenylbutylamide: the cis-2-(N-tert-butoxycarbonylamino)-1-cyclo Pentanecarboxylic acid (4.1 g, 17.7 mmol) was dissolved in 160 mL of DMF. Add 4-phenylbutylamine (2.4 g, 16.1 mmol) and i-Pr 2 NEt (5.6 mL, 32.2 mmol) followed by PyBOP (8.8 g, 16.9 mmol). The reaction was stirred at room temperature for 19 hours, then poured into ice-cold 0.1N hydrochloric acid (600 mL) and extracted with ethyl acetate (600 mL). The organic layer was washed sequentially with brine (100 mL), saturated sodium bicarbonate solution (300 mL) and brine (2 x 200 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography to afford the desired amide 2a.

[0145] 2b. cis-2-Amino-1-cyclopentanecarboxylic acid, 4-phenylbutylamide: Amide 2a (5.5 g, 15.3 mmol) was dissolved in 150 mL of anhydrous dichloromethane. TFA (120 mL) was added dropwise ...

Embodiment 3

[0148] 3a. Cis-1,2-diaminocyclohexane, (1,7-diphenyl-4-heptyl)carboxylic acid amide: Carboxylic acid 1b (2.0 g, 6.74 mmol) was dissolved at room temperature under an inert atmosphere Dissolved in DMF (100 mL). Add cis-1,2-diaminocyclohexane (1.43 g, 12.5 mmol), followed by i-Pr2 NEt (1.18 mL, 6.8 mmol) and PyBOP (3.9 g, 7.45 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, then poured into ethyl acetate (600 mL), washed with 0.1N hydrochloric acid (300 mL), brine (100 mL), saturated sodium bicarbonate solution (150 mL) and brine ( 100 ml) were washed sequentially. The organic solution was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by preparative chromatography on silica gel to afford the desired amide 3a.

[0149] 3b. Cis-1,2-diaminocyclohexane, 1-N-(1,7-diphenyl-4-heptyl) carboxylic acid amide, 2-N-(phenylglyoxyl) amide: the Amide 3a (1.46 g, 3.68 mmol) was dissolved in anhydrous DMF (50 mL)...

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Abstract

The present disclosure describes novel compounds and compositions which are particularly useful for treating hair loss in mammals, including arresting and / or reversing hair loss and promoting hair growth. The present compounds and compositions may also be useful against a variety of disorders including, for example, multi-drug resistance, human immunodeficiency virus (HIV), cardiac injury, and neurological disorders, and may be useful for controlling parasites and invoking immunosuppression.

Description

field of invention [0001] The present invention relates to novel compounds and compositions particularly useful for treating hair loss in mammals, including arresting and / or reversing hair loss and promoting hair growth. The compounds and compositions of the invention are also useful against a variety of diseases including, for example, multidrug resistance, human immunodeficiency virus (HIV), cardiac injury, and neurological disorders, and for controlling parasites and causing immunosuppression. [0002] cross reference [0003] Pursuant to § 35, USC 119(e), this application benefits from provisional application serial number 60 / 102,448, filed September 30, 1998. Background technique [0004] Hair loss is a common problem that occurs due to, for example, natural processes or is often chemically induced by the use of certain therapeutic drugs designed to alleviate diseases such as cancer. This type of hair loss is often accom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/40A61K8/00A61K8/44A61K31/137A61K31/165A61K31/341A61P17/14A61Q5/00A61Q5/02A61Q7/00C07C235/78C07C237/24C07C237/26C07D233/88
CPCC07C2102/10C07D233/88C07C237/26C07C235/78C07C2101/08C07C237/24A61Q7/00C07C2102/08C07C2101/14A61K8/44A61P17/14C07C2601/08C07C2601/14C07C2602/08C07C2602/10
Inventor 约翰·M·麦基弗查尔斯·R·德根哈特戴维·J·艾克霍夫
Owner THE PROCTER & GAMBLE COMPANY
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