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A series of compounds for treatment of skin diseases and other conditions

A compound, pyridyl technology, applied in skin diseases, effective ingredients of hydroxyl compounds, drug combinations, etc., can solve problems such as adverse side effects, less skin whitening agents, and toxicity

Pending Publication Date: 2021-09-28
UNIGEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] Although remarkable progress has been made in the field of skin care and many compounds from natural as well as synthetic sources have been reported as potent tyrosinase inhibitors with anti-melanogenesis activity, very few of them have been shown to be effective skin brightener
Most of these agents were found to be toxic or shown to have adverse side effects in humans
Additionally, many compounds have been reported as strong anti-melanogen or anti-microbial or anti-inflammatory agents to inhibit PIH, none of them have quadruple action

Method used

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  • A series of compounds for treatment of skin diseases and other conditions
  • A series of compounds for treatment of skin diseases and other conditions
  • A series of compounds for treatment of skin diseases and other conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Example 1: General and Specific Methods for the Synthesis of Compounds of Formula I

[0147] Compounds of formula I were prepared generally as described in Scheme 1, using a substituted benzyl phosphonate as R for purposes of illustration. Phosphonate reagents were prepared following the Arbuzov reaction with the corresponding benzyl bromide treated with triethyl phosphite. Briefly, 1,5-diene compounds of formula I are prepared from the corresponding phosphonates with the appropriate ketones by the Wittig reaction. The coupled diene product is then treated with methylmagnesium iodide for demethylation to yield the desired phenolic diene.

[0148]

[0149] Representative procedure for Scenario 1:

[0150] synthesis( E / Z )-4-(2,6-dimethylhept-1,5-dienyl)phenol (1):

[0151] General / typical procedure for the synthesis of phosphonates via the Albuzov reaction: 4-Methoxybenzyl bromide (20 g, 100 mmol) in P(OEt) 3 (23 mL, 140 mmol) was refluxed for 5 hours, then b...

Embodiment 2

[0159] Example 2 : General and specific methods of synthetic formula II compounds

[0160] Compounds of formula II are prepared generally as described in Scheme 2, using substituted bromobenzenes as R for illustrative purposes. Briefly, 1,6-diene compounds of formula II are prepared from the corresponding Grignard reagents with appropriate aldehydes by Grignard addition reactions. Grignard reagents were prepared from the corresponding aryl bromides using activated Mg chips. Then use POCl 3 Treatment of the coupled product for dehydration followed by demethylation with MeMgI affords the desired phenolic diene.

[0161] Scenario 2

[0162]

[0163] Representative procedure for Scheme 2: Synthesis ( E )-4-(3,7-dimethyloct-1,6-dienyl)phenol (5):

[0164] General / Typical Procedure for Grignard Addition Reaction: 4-Bromoanisole (11.2 g, 60 mmol) in THF (60 mL) was added dropwise to THF ( 10 mL) of magnesium turnings (1.9 g, 80 mmol) and iodine (a little). After the addit...

Embodiment 3

[0195] Example 3 : General and specific methods of synthetic formula III compounds

[0196] Compounds of formula III are prepared generally as described in Scheme 4, using a substituted benzyl phosphonate as R for illustrative purposes. Phosphonate reagents were prepared following the Albuzov reaction with the corresponding benzyl bromide treated with triethyl phosphite. Briefly, 1,7-diene compounds of formula III are prepared from the corresponding phosphonates with appropriate ketones by Wittig reactions. The coupled olefinic product is then treated with methylmagnesium iodide for demethylation to yield the desired phenolic diene.

[0197] Option 4

[0198]

[0199] General / typical procedure for the synthesis of phosphonates via the Albuzov reaction: p-methoxybenzyl bromide (10.5 g, 52.2 mmol) in P(OEt) 3 (25 mL) was refluxed for 5 hours, then bromoethane and excess triethyl phosphite were removed by distillation under reduced pressure. The residue afforded 12.8 g ...

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PUM

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Abstract

Compounds and methods related to the prevention and treatment of diseases and conditions, some of which are facilitated by melanogenesis are disclosed. Specifically, the present subject matter includes a series of compounds and compositions and their use for anti-melanogenic and antioxidant activity. This subject matter also includes the treatment of skin disorder due to acne vulgaris and related inflammatory and post inflammatory hyperpigmentation. Methods for synthesizing contemplated compounds are also disclosed.

Description

[0001] This Patent Cooperation Treaty (PCT) application claims priority to U.S. Provisional Application Serial No.: 62 / 745380, filed October 14, 2018, entitled "A Series of Novel Compounds for Treatment of Acne Vulgaris, Inflammation, and Skin Disorders," It is commonly owned and is hereby incorporated by reference in its entirety. [0002] field of invention [0003] This topic is primarily concerned with the prevention and treatment of diseases and conditions, some of which are promoted by melanogenesis. In particular, the subject matter includes a series of compounds and compositions and their use for anti-melanogenesis and antioxidant activity. This topic also includes the treatment of skin conditions caused by acne vulgaris and related inflammatory and postinflammatory hyperpigmentation. The subject matter also includes methods of synthesizing these compounds. Background technique [0004] Materials capable of inhibiting or preventing hyperpigmentation of the skin are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/19C07C39/225C07C59/68C07D213/06C07C235/06C07D213/64
CPCA23B7/154A23L2/44A23L5/41C07C39/19C07C39/225C07C59/68C07D213/06C07C235/06C07D213/64A61P17/00A61P17/10A61P39/06A23V2002/00A23V2200/048C07C235/20A61K31/045A61K31/047A61K31/05A61K31/4406A61K31/194A61P29/00A61P31/04A61P35/00A23L3/349C07B2200/09C07C39/20C07C59/54C07C233/91C07D213/16C07D213/30
Inventor S·K·南迪T·霍尔姆K·R·道金斯
Owner UNIGEN
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