JPH05506434A - ヒドロキノンアミノ酸エステル類、その調製方法、及びそれを含む医薬品、化粧品用組成物 - Google Patents
ヒドロキノンアミノ酸エステル類、その調製方法、及びそれを含む医薬品、化粧品用組成物Info
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- JPH05506434A JPH05506434A JP91505499A JP50549991A JPH05506434A JP H05506434 A JPH05506434 A JP H05506434A JP 91505499 A JP91505499 A JP 91505499A JP 50549991 A JP50549991 A JP 50549991A JP H05506434 A JPH05506434 A JP H05506434A
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
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Abstract
Description
Claims (19)
- 1.ヒドロキノンの天然アミノ酸エステルに対応し、次式(I):▲数式、化学 式、表等があります▼(I)〔式中、 Aは天然のα−アミノ酸基またはその単純な誘導体、例えばジカルボキシアミノ 酸の場合、メチルまたはエチルエステル、或いは第一アミド等に相当する;R1 は水素原子、1〜6個の炭素原子を含むアルキル基、またはベンジル基を示す; R2は水素原子、アセチル基またはベンゾイル基、若しくは2〜20個の炭化水 素単位をもつアルキルカルボニル基、その他Aとともに窒素含有環を形成するも のを示す: 但し、AとR1がメチル基である場合、R2は水素原子以外のものであり、Aが 水素原子で、R1がメチル基である場合、R2はベンゾイル基以外のものであり 、Aがベンジル基で、R1がメチル基である場合、R2はアセチル基以外のもの である;そして、 R2は水素原子、或いは、AとR2が窒素含有環を形成する場合のみ、1〜20 個の線状炭化水素単位をもつアルキルカルボニル基または1〜18個の炭化水素 単位をもつ直鎖または分岐状のアルキル基を示す〕で表されることを特徴とする ヒドロキノン誘導体。
- 2.前記Aが、水素原子、前記R2と共に形成する窒素含有環、または1〜4個 の炭素原子を含むアルキル基のいずれかであり、前記炭素原子は、置換されてい ないか、若しくは、OH、SH、C6H4−OH、CO−NH2、COOH、N H2、NH−CH2−NH2、C6H5、インドール、S−CH3、イミダゾー ルからなる置換基のうちのいずれか一つに置換されており、前記置換基はそれ自 体エステル化されているか若しくはされていないことを特徴とする請求の範囲1 に記載の誘導体。
- 3.前記Aが、前記R2と共に、ピロリジン−2−オン環を含む生成物を与える ことによって、ピログルタミン酸基を形成し、前記生成物が、次式(II):▲ 数式、化学式、表等があります▼(II)〔式中R1、R2は、請求の範囲1ま たは2に規定するものである〕で表されることを特徴とする請求の範囲1または 2に記載の誘導体。
- 4.両親媒性を有することを特徴とする請求の範囲1〜3のいずれかに記載の誘 導体。
- 5.前記R2基が、アルキルカルボニル基であることを特徴とする請求の範囲1 、2、4のいずれかに記載の誘導体。
- 6.前記R2基が、アルキル基であることを特徴とする請求の範囲1〜4のいず れかに記載の誘導体。
- 7.前記R3基が、アルキルカルボニル基であることを特徴とする請求の範囲1 〜4のいずれかに記載の誘導体。
- 8.ヒドロキノンの天然アミノ酸エステルから成り、次式(I):▲数式、化学 式、表等があります▼(I)〔式中、 Aは天然のα−アミノ酸基またはその単純な誘導体、例えばジカルボキシアミノ 酸の場合、メチルまたはエチルエステル、或いは第一アミド等に相当する;R1 は水素原子、1〜6個の炭素原子を含むアルキル基、またはベンジル基を示す; R2は水素原子、アセチル基またはベンゾイル基、若しくは2〜20個の炭化水 素単位をもつアルキルカルボニル基、その他Aとともに窒素含有環を形成するも のを示し, R2が水素原子の場合、AとR1がメチル基であり、R2がベンゾイル基である 場合、Aは水素原子、R1はメチル基であり、R2がアセチル基の場合、Aはベ ンジル基、R1がメチル基であることを含む;そして、R3は水素原子、或いは 、AとR2が窒素含有環を形成する場合のみ、1〜20個の線状炭化水素単位を もつアルキルカルボニル基または1〜18個の炭化水素単位をもつ直鎖または分 岐状のアルキル基を示す〕で表されることを特徴とする脱色剤。
- 9.少なくとも請求の範囲8に記載の脱色剤を、適宜少なくとも一つの医薬的に 許容可能なビヒクルと組み合わせて含むことを特徴とする薬剤。
- 10.少なくとも請求の範囲8に記載の脱色剤を、適宜少なくとも一つの許容可 能なビヒクルと組み合わせて含むことを特徴とする化粧料。
- 11.請求の範囲8に記載の脱色剤を、0.01〜20重量%含有することを特 徴とする請求の範囲9または10に記載の組成物。
- 12.請求の範囲8に記載の脱色剤を、0.01〜10重量%含有することを特 徴とする請求の範囲11に記載の組成物。
- 13.人の皮膚の着色状態を変えるために、請求の範囲8に記載の脱色剤を適量 、局所に施用することを含む美容治療方法。
- 14.請求の範囲1に記載の式(I)の誘導体を調製する方法にして、R2とR 2が水素原子の場合、式p−OH−C6H4−OR1〔R1は上記に規定された もの〕で表される誘導体を、窒素を保護してそのカルボキシ酸基を適当な活性化 試薬を用いて活性化した適当なアミノ酸と反応させた後、保護基を、適当な不活 性溶媒中で加水分解を行うことによって除去することによって、次式(III) :▲数式、化学式、表等があります▼(III)で表される化合物が与えること を特徴とする方法。
- 15.カルボキシ酸基を活性化させる試薬が、1,1−カルボニルジイミダゾー ル、1,1カルボニルジ(1,2,4−トリアゾール)、N−ヒドロキシフタル イミド、N−ヒドロキシスクシンイミドの中から選択され、好適には1,1−カ ルボニルジイミダゾールであることを特徴とする請求の範囲14に記載の方法。
- 16.請求の範囲5に記載の誘導体を調製する方法にして、適当なアミノ酸を、 水/有機二相溶媒中で、酸R2OH(R2上述のアルキルカルボニル基)の反応 誘導体、好ましくはその塩化物を用いてアシル化することによって、次式(IV ): ▲数式、化学式、表等があります▼(IV)で表される化合物を与えることを特 徴とする方法。
- 17.式(II)で表される誘導体を調製する方法にして、R3が水素である場 合、溶媒を使わず不活性雰囲気中で、誘導体p−OH−C6H4−OR1〔R1 は上記に規定されたもの〕を用いて対応するアミノ酸の直接融解をおこなうこと を特徴とする方法。
- 18.請求の範囲1の式(I)の誘導体を調製する際の中間生成物にして、次式 (III): ▲数式、化学式、表等があります▼(III)〔式中、 Aは天然のα−アミノ酸基またはその単純な誘導体、例えばジカルボキシアミノ 酸の場合、メチルまたはエチルエステル、或いは第一アミド等に対応する;R1 は水素原子、1〜6個の炭素原子を含むアルキル基、またはベンジル基を示す〕 で表されることを特徴とする中間生成物。
- 19.請求の範囲5の誘導体を調製する際の中間生成物にして、次式(IV): ▲数式、化学式、表等があります▼(IV)〔式中、 Aは天然のα−アミノ酸基またはその単純な誘導体、例えばジカルボキシアミノ 酸の場合、メチルまたはエチルエステル、或いは第一アミド等に対応する;R1 は水素原子、1〜6個の炭素原子を含むアルキル基、またはベンジル基を示す; R2は請求の範囲5に規定されるものであるが、但し、Aがベンジル基でR1が メチル基である場合R2はアセチル基以外である〕で表されることを特徴とする 中間生成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR90/01822 | 1990-02-15 | ||
FR9001822A FR2658190B1 (fr) | 1990-02-15 | 1990-02-15 | Esters d'aminoacides de l'hydroquinone, leur procede de preparation et compositions pharmaceutiques ou cosmetiques les contenant. |
PCT/FR1991/000114 WO1991011996A1 (fr) | 1990-02-15 | 1991-02-13 | Esters d'aminoacides de l'hydroquinone, leur procede de preparation et compositions pharmaceutiques ou cosmetiques les contenant |
Publications (2)
Publication Number | Publication Date |
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JPH05506434A true JPH05506434A (ja) | 1993-09-22 |
JP2997313B2 JP2997313B2 (ja) | 2000-01-11 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP3505499A Expired - Lifetime JP2997313B2 (ja) | 1990-02-15 | 1991-02-13 | ヒドロキノンアミノ酸エステル類、その調製方法、及びそれを含む医薬品、化粧品用組成物 |
Country Status (11)
Country | Link |
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US (1) | US5527523A (ja) |
EP (1) | EP0515510B1 (ja) |
JP (1) | JP2997313B2 (ja) |
AT (1) | ATE121726T1 (ja) |
CA (1) | CA2075926C (ja) |
DE (1) | DE69109276T2 (ja) |
DK (1) | DK0515510T3 (ja) |
ES (1) | ES2074264T3 (ja) |
FR (1) | FR2658190B1 (ja) |
OA (1) | OA09665A (ja) |
WO (1) | WO1991011996A1 (ja) |
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JP2005119989A (ja) * | 2003-10-15 | 2005-05-12 | Kose Corp | 新規1,4−ベンゼンジオールカルボン酸エステル誘導体又はその塩、その製造方法及びそれを含有する皮膚外用剤 |
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ITMI20012139A1 (it) * | 2001-10-16 | 2003-04-16 | B & T S R L | Emulsionante naturale per cosmetici |
US7241808B2 (en) * | 2002-05-01 | 2007-07-10 | Marvin Klein | Composition for treatment of skin and method for stabilizing the composition |
EP2247277A2 (en) * | 2008-01-25 | 2010-11-10 | B & T S.r.l. | Use of transesterified olive oil in the cosmetic field |
CN110478294B (zh) * | 2019-09-17 | 2022-11-04 | 中国科学院昆明植物研究所 | 金边玫瑰活性提取物、护肤化合物及其制备和应用以及护肤品 |
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JPS57145803A (en) * | 1981-03-05 | 1982-09-09 | Sunstar Inc | External decoloring agent for skin |
US4466955A (en) * | 1982-06-09 | 1984-08-21 | Germaine Monteil Cosmetiques Corporation | Skin bleaching stick containing hydroquinone |
US4518789A (en) * | 1982-06-30 | 1985-05-21 | Yu Ruey J | Phenyl alpha-acyloxyacetamide derivatives and their therapeutic use |
JPH0832621B2 (ja) * | 1985-02-28 | 1996-03-29 | 株式会社資生堂 | 皮膚外用剤 |
US4762851A (en) * | 1985-11-29 | 1988-08-09 | Merck & Co., Inc. | Pyroglutamic acid esters used as dermal penetration enhancers for drugs |
US4876084A (en) * | 1986-08-04 | 1989-10-24 | Kao Corporation | P-hydroxycinnamamide derivatives and melanin inhibitor comprising the same |
FR2607498B1 (fr) * | 1986-12-01 | 1991-04-05 | Oreal | Nouveaux salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie |
JPH0314508A (ja) * | 1989-06-12 | 1991-01-23 | Sansho Seiyaku Co Ltd | メラニン生成抑制外用剤 |
-
1990
- 1990-02-15 FR FR9001822A patent/FR2658190B1/fr not_active Expired - Fee Related
-
1991
- 1991-02-13 DK DK91904756.3T patent/DK0515510T3/da active
- 1991-02-13 CA CA002075926A patent/CA2075926C/en not_active Expired - Lifetime
- 1991-02-13 DE DE69109276T patent/DE69109276T2/de not_active Expired - Lifetime
- 1991-02-13 WO PCT/FR1991/000114 patent/WO1991011996A1/fr active IP Right Grant
- 1991-02-13 JP JP3505499A patent/JP2997313B2/ja not_active Expired - Lifetime
- 1991-02-13 US US07/917,077 patent/US5527523A/en not_active Expired - Lifetime
- 1991-02-13 EP EP91904756A patent/EP0515510B1/fr not_active Expired - Lifetime
- 1991-02-13 AT AT91904756T patent/ATE121726T1/de not_active IP Right Cessation
- 1991-02-13 ES ES91904756T patent/ES2074264T3/es not_active Expired - Lifetime
-
1992
- 1992-08-14 OA OA60259A patent/OA09665A/fr unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005119989A (ja) * | 2003-10-15 | 2005-05-12 | Kose Corp | 新規1,4−ベンゼンジオールカルボン酸エステル誘導体又はその塩、その製造方法及びそれを含有する皮膚外用剤 |
JP4504656B2 (ja) * | 2003-10-15 | 2010-07-14 | 株式会社コーセー | 新規1,4−ベンゼンジオールカルボン酸エステル誘導体又はその塩、その製造方法及びそれを含有する皮膚外用剤 |
Also Published As
Publication number | Publication date |
---|---|
CA2075926A1 (en) | 1991-08-16 |
EP0515510B1 (fr) | 1995-04-26 |
CA2075926C (en) | 2004-04-06 |
ES2074264T3 (es) | 1995-09-01 |
EP0515510A1 (fr) | 1992-12-02 |
FR2658190B1 (fr) | 1992-06-05 |
FR2658190A1 (fr) | 1991-08-16 |
DK0515510T3 (da) | 1995-09-04 |
WO1991011996A1 (fr) | 1991-08-22 |
US5527523A (en) | 1996-06-18 |
JP2997313B2 (ja) | 2000-01-11 |
OA09665A (fr) | 1993-05-15 |
ATE121726T1 (de) | 1995-05-15 |
DE69109276D1 (de) | 1995-06-01 |
DE69109276T2 (de) | 1995-12-07 |
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