公开(公告)号：KR1020080029342A

公开(公告)日：2008-04-03

申请号：KR1020060095279

申请日：2006-09-29

Applicant: (주)아모레퍼시픽

Inventor： 유재원 ,  노호식 ,  이진영 ,  심종원 ,  최동원 ,  김덕희

IPC: C07C233/11 ,  C07C233/21

Abstract: A retinoic acid derivative is provided to exhibit a collagen production effect and a collagenase expression inhibition effect and cause less skin irritation. A method for preparing a retinoic acid derivative includes the steps of: (i) reacting retinoic acid with alkylchloroformate to prepare an anhydride compound represented by the following formula 2; and (ii) reacting the prepared anhydride compound with an amine hydrochloride represented by the following formula 3 to prepare the retinoic acid derivative represented by the following formula 1. In the formulae, R1 is hydrogen, linear or branched C1-7 alkyl or C3-7 cycloalkyl, R2 is hydroxyl, linear or branched C1-7 alkyl substituted by 1-4 hydroxyl groups, or linear branched C1-5 alkyl substituted by hydroxy pyranone, and R3 is C1-7 alkyl.

Abstract translation: 提供视黄酸衍生物以表现出胶原产生效果和胶原酶表达抑制作用，并且引起较少的皮肤刺激。 视黄酸衍生物的制备方法包括以下步骤：（i）使视黄酸与氯甲酸烷基酯反应，制备下式2表示的酸酐化合物; 和（ii）使所制备的酸酐化合物与由下式3表示的胺盐酸盐反应以制备由下式1表示的视黄酸衍生物。在式中，R 1是氢，直链或支链C 1-7烷基或C 3- 7环烷基，R2是羟基，被1-4个羟基取代的直链或支链C 1-7烷基，或被羟基吡喃酮取代的直链支链C 1-5烷基，R 3是C 1-7烷基。

公开(公告)号：KR1020080014279A

公开(公告)日：2008-02-14

申请号：KR1020060075755

申请日：2006-08-10

Applicant: (주)아모레퍼시픽

Inventor： 백흥수 ,  유재원 ,  노호식 ,  김덕희

IPC: C07C233/10 ,  C07C233/11 ,  C07C235/36

CPC classification number: C07C235/36 ,  C07C231/02

Abstract: A hydroxycinnamic acid derivative compound is provided to realize improved anti-oxidation property and skin permeability, effects of inhibiting active oxygen and melanin generation and stimulating procollagen generation, thereby providing a cosmetic composition for improving wrinkles and whitening. A hydroxycinnamic acid derivative compound has an adamantyl amide linking group and is represented by the following formula I. In formula I, R1 is H or a C1-C7 alkyl group; and A is -CH=CH- or -CH2-CH2-. The hydroxycinnamic acid derivative compound is obtained by the method comprising the steps of: (1) substituting the hydroxyl group of hydroxycinnamic acid with an acetyl group to provide an acetylated compound; (2) reacting the acetylated compound with ethyl chloroformate and oleophilic group-containing adamantanamine to provide an amide compound; and (3) hydrolyzing the acetyl group of the amide compound.

Abstract translation: 提供羟基肉桂酸衍生物以提高抗氧化性和皮肤渗透性，抑制活性氧和黑色素产生的作用，刺激前胶原生成，从而提供改善皱纹和美白的化妆品组合物。 羟基肉桂酸衍生物具有金刚烷基酰胺连接基团，由下式I表示。在式I中，R 1为H或C 1 -C 7烷基; A是-CH = CH-或-CH 2 -CH 2 - 。 通过包括以下步骤的方法获得羟基肉桂酸衍生物化合物：（1）用乙酰基取代羟基肉桂酸的羟基以提供乙酰化合物; （2）使乙酰化化合物与氯甲酸乙酯和含亲油基团的金刚烷胺反应，得到酰胺化合物; 和（3）水解酰胺化合物的乙酰基。

公开(公告)号：KR100786300B1

公开(公告)日：2007-12-18

申请号：KR1020060090560

申请日：2006-09-19

Applicant: (주)아모레퍼시픽

Inventor： 유재원 ,  노호식 ,  김수정 ,  윤준원 ,  안성연 ,  김덕희

IPC: A61K8/49 ,  A61Q19/08

CPC classification number: A61Q19/08 ,  A61K8/498

Abstract: A 4-substituted benzoic acid derivative compound having 3,4-methylenedioxybenzene or 3,4-ethylenedioxybenzene moiety is provided to promote the biosynthesis of main constituents of skin dermis such as collagen, elastin, fibrillin, glycosaminoglycan(GAG) closely related to skin wrinkles, thereby being usefully used as medicines and skin external applying agents for preventing aging and improving the wrinkles. An anti-aging cosmetic composition comprises 0.01-20.0 wt.% of a 4-substituted benzoic acid derivative compound having 3,4-methylenedioxybenzene or 3,4-ethylenedioxybenzene moiety and represented by the formula(I), wherein R1 is -CH2- or -CH2=CH2-, R2 is the structural formula(Ia), and R3 is H, methyl or ethyl. A method for preparing the 4-substituted benzoic acid derivative compound comprises the steps of: (a) preparing a compound(1) represented by the formula(1) from 3,4-methylenedioxybenzoic acid or 3,4-ethylenedioxybenzoic acid; and (b) hydrolyzing the compound of the formula(1) with a base to prepare a compound(2) represented by the formula(2).

Abstract translation: 提供具有3,4-亚甲二氧基苯或3,4-亚乙二氧基苯部分的4-取代苯甲酸衍生物化合物，以促进皮肤真皮主要成分的生物合成，如与皮肤皱纹密切相关的胶原蛋白，弹性蛋白，纤维蛋白，糖胺聚糖（GAG） 从而有效地用作用于防止老化和改善皱纹的药物和皮肤外用施用剂。 抗衰老化妆品组合物包含0.01-20.0重量％的具有3,4-亚甲二氧基苯或3,4-亚乙二氧基苯部分并由式（I）表示的4-取代苯甲酸衍生物化合物，其中R 1是-CH 2 - 或-CH 2 = CH 2 - ，R 2是结构式（Ia），R 3是H，甲基或乙基。 制备4-取代苯甲酸衍生物化合物的方法包括以下步骤：（a）由3,4-亚甲二氧基苯甲酸或3,4-亚乙二氧基苯甲酸制备由式（1）表示的化合物（1） 和（b）用碱水解式（1）的化合物以制备由式（2）表示的化合物（2）。

公开(公告)号：KR100740575B1

公开(公告)日：2007-07-18

申请号：KR1020060029631

申请日：2006-03-31

Applicant: (주)아모레퍼시픽

Inventor： 유재원 ,  백흥수 ,  노호식 ,  김덕희 ,  장이섭

IPC: C07D319/18 ,  C07D317/60

Abstract: 2,3-Dihydroxybenzoic acid derivatives, a preparation method thereof, and a skin-whitening cosmetic composition containing the same compounds are provided to inhibit activity of tyrosinase and melanin formation while cytotoxicity of the compounds is very low, so that the compounds are useful for improvement of pigmentation in the skin. The method for preparing the 2,3-dihydroxybenzoic acid derivatives represented by the formula(1) comprises the steps of: (A) reacting 2,3-dihydroxybenzoic acid with acetic acid anhydride in the presence of base to prepare a 2,3-diacetyloxybenzoic acid compound represented by the formula(2); (B) preparing an amide compound represented by the formula(3) from the 2,3-diacetyloxybenzoic acid compound by using ethylchloroformate and amine having a lipophilic group; and (C) hydrolyzing an acetyl group of the amide compound represented by formula (3) to prepare 2,3-dihydroxybenzoic acid represented by the formula (1), wherein R is 4-ethoxyphenyl, 2-cyclohexenylethyl, cycloheptyl, cyclohexyl, tert-octyl, 4-isopropylphenyl, 2,3-dihydrobenzo[1,4]dioxin-7-yl, benzo[1,3]-dioxol-6-yl or adamantyl-1-yl; and the amine having the lipophilic group is an amine selected from 4-ethoxyphenylamine, 2-cyclohexenylethylamine, cycloheptylamine, cyclohexylamine, tert-octylamine, 4-isopropylphenylamine, 2,3-dihydrobenzo[1,4]dioxin-7-amine, benzo[1,3]-dioxol-6-amine or adamantyl-1-amine. The skin-whitening cosmetic composition contains 0.01-20 wt.% of the 2,3-dihydroxybenzoic acid derivatives represented by the formula(1).

Abstract translation: 提供了2,3-二羟基苯甲酸衍生物，其制备方法和含有相同化合物的美白化妆品组合物，以抑制酪氨酸酶的活性和黑色素形成，同时化合物的细胞毒性非常低，使得该化合物可用于 改善皮肤色素沉着。 制备式（1）代表的2,3-二羟基苯甲酸衍生物的方法包括以下步骤：（A）使2,3-二羟基苯甲酸与乙酸酐在碱存在下反应，制得2,3-二羟基苯甲酸衍生物， 由式（2）表示的二乙酰氧基苯甲酸化合物; （B）使用氯甲酸乙酯和具有亲油性基团的胺，由2,3-二乙酰氧基苯甲酸化合物制备式（3）所示的酰胺化合物; （C）水解式（3）所示的酰胺化合物的乙酰基，制备式（1）所示的2,3-二羟基苯甲酸，其中R为4-乙氧基苯基，2-环己烯基乙基，环庚基，环己基，叔丁基 - 辛基，4-异丙基苯基，2,3-二氢苯并[1,4]二氧杂环己烯-7-基，苯并[1,3] - 二氧杂环戊烯-6-基或金刚烷基-1-基; 具有亲脂性基团的胺是选自4-乙氧基苯胺，2-环己烯基乙胺，环庚胺，环己胺，叔辛胺，4-异丙基苯胺，2,3-二氢苯并[1,4]二氧杂环己烯-7-胺，苯并[ 1,3] - 二氧六环-6-胺或金刚烷基-1-胺。 该美白化妆品组合物含有0.01-20重量％的由式（1）表示的2,3-二羟基苯甲酸衍生物。

公开(公告)号：KR1020060130835A

公开(公告)日：2006-12-20

申请号：KR1020050048717

申请日：2005-06-08

Applicant: (주)아모레퍼시픽

Inventor： 노호식 ,  유재원 ,  김덕희 ,  장이섭

IPC: C07F9/54

CPC classification number: A61K8/55 ,  A61K2800/522 ,  A61Q19/08 ,  C07F9/65517

Abstract: Sesamol derivatives or their salts, a process for preparing the same compounds, and a skin external composition containing the same compounds are provided to prevent aging of the biological membrane by slowly releasing sesamol and 3-aminopropan phosphate, and reduce the skin irritation. The sesamol derivatives represented by the formula(I) or their salts are provided, wherein the salt is alkali metal salt or alkali earth metal salt. The process for preparing the sesamol derivatives represented by the formula(I) or their salts comprises the steps of: (A) reacting sesamol with phosphorus oxychloride in the presence of organic base at 12-18 deg. C for 1-2 hours to prepare dichloro[3,4-methylene dioxy penoxy]-phosphino-1-one; (B) reacting the dichloro[3,4-methylene dioxy penoxy]-phosphino-1-one with organic solvent in the presence of base to prepare [3,4-methylene dioxy penoxy]-1,3,2-oxazaphosphorin P-oxide; (C) after filtering the reaction solution and concentrating the filtered solution under reduced pressure, adding the acid solution into the concentrate and reacting them at 5-100 deg. C for 3-12 hours to prepare sesamol(3-aminopropane phosphate diester); and (D) crystallizing the sesamol(3-aminopropane phosphate diester) by slowly dropping polar organic solvent into the sesamol.

Abstract translation: 提供芝麻酚衍生物或其盐，制备相同化合物的方法和含有相同化合物的皮肤外用组合物，以通过缓慢释放芝麻酚和3-氨基丙酸磷酸盐来防止生物膜的老化，并减少皮肤刺激。 提供由式（I）表示的芝麻酚衍生物或其盐，其中盐为碱金属盐或碱土金属盐。 制备由式（I）表示的芝麻酚衍生物或其盐的方法包括以下步骤：（A）在有机碱的存在下在12-18℃使芝麻酚与磷酰氯反应。 C 1-2小时制备二氯[3,4-亚甲二氧二氧基] - 膦酰基-1-酮; （B）在碱存在下使二氯[3,4-亚甲二氧基二氧基]膦基-1-酮与有机溶剂反应，制备[3,4-亚甲基二氧基壬氧基] -1,3,2-氧杂磷杂环磷酸P- 氧化物; （C）过滤反应溶液后，减压浓缩滤液，加入酸溶液至浓缩物，并在5〜100℃反应。 3〜12小时制备芝麻酚（3-氨基丙烷磷酸二酯）; 和（D）通过将极性有机溶剂缓慢滴入芝麻酚中来结晶芝麻酚（3-氨基丙烷磷酸二酯）。

公开(公告)号：KR1020050099406A

公开(公告)日：2005-10-13

申请号：KR1020040024704

申请日：2004-04-10

Applicant: (주)아모레퍼시픽

Inventor： 유재원 ,  이찬우 ,  김덕희 ,  김길중 ,  남개원 ,  이병석 ,  장이섭

IPC: C07C31/24

CPC classification number: C09K19/06 ,  A61K8/39 ,  A61Q19/00 ,  C07C67/08 ,  C07C69/708 ,  C11D3/2093 ,  C11D17/0026

Abstract: 본 발명은 피부에 적용되었을 때 각질층의 수분 유지 능력을 향상시키며, 특히 건조환경에서도 높은 보습력을 보이는, 하기 화학식 1로 표시되는 펜타에리스리톨 유도체 및 이의 제조방법, 그리고 이를 포함하는 액정베이스에 관한 것이다.

(상기 식에서, R은 서로 동일하거나 다른 수소 또는 히드록시기를 포함하거나 포함하지 않는 탄소수 1 내지 24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이고; m은 0 내지 10, n은 1 내지 10의 서로 동일하거나 다른 정수이다.)