JP6232380B2 - アミノ酸のn−アシル誘導体とジオールとの新規のエステル、それを調製する方法、並びに化粧品における及び薬物としてのその使用 - Google Patents
アミノ酸のn−アシル誘導体とジオールとの新規のエステル、それを調製する方法、並びに化粧品における及び薬物としてのその使用 Download PDFInfo
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- 210000000264 venule Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
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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
- A61K8/42—Amides
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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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- A61K8/00—Cosmetics or similar toiletry preparations
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
-
- 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
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07—ORGANIC CHEMISTRY
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- 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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- C07C233/00—Carboxylic acid amides
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- 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
- C07C233/49—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 carbon atom of an acyclic unsaturated carbon skeleton
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- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Pyrrole Compounds (AREA)
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Description
の領域において低酸素状態を生じ、非炎症型の浮腫の出現、特に目の下のくま及び/又はたるみの出現、又は下肢では脚重感の出現をもたらし、特にふくらはぎ及び/又は足及び/又は足首の腫れを生じる可能性がある。
及び/又は回復する必要があるという欠点がある。
R’−O−A−O−R’’ (I)
(式(I)中、R’及びR’’は同一であるか又は異なり、
水素原子、又は、
式(IIa):
R1は、7個〜30個の炭素原子を含む飽和又は不飽和の、線状又は分岐状の脂肪族ラジカルを表し、
R2は水素原子、又は以下のラジカル:メチル、イソプロピル、イソブチル、1−メチルプロピル、ヒドロキシメチル、1−ヒドロキシエチル、チオメチル、2−メチルチオエチル、4−アミノブチル、3−グアニジノプロピル、3−ウレイドプロピル、(1−アミノカルボニル)メチル、2−(アミノカルボニル)エチル、ベンジル、4−ヒドロキシベンジル、3,4−ジヒドロキシベンジル、[1H−インドール−3−イル]メチル、(1H−イミダゾール−4−イル)メチル、3−アミノプロピルから選ばれるラジカルを表し、R3は水素原子又はメチルラジカルを表す)の一価のラジカル、又は、
式(IIb):
R1は式(IIa)に規定されるとおりであり、
R4は水素原子又はヒドロキシラジカルを表す)の一価のラジカルを表すが、
ただし、ラジカルR’又はR’’の少なくとも一方が水素原子ではなく、ラジカルR’及びR’’がいずれも水素原子ではない場合にR’及びR’’は同一であり、
式(I)中、Aは式(III):
−CH(X1)−[C(X2)(X3)]p−CH(X4)− (III)
(式中、X1、X2、X3及びX4は同一であるか又は異なり、水素原子又はメチルラジ
カル若しくはエチルラジカルであり、
pは1以上6以下の整数である)の二価のラジカルを表す)。
水素原子、又は、
式(IIa)(式中、R1及びR3は先に規定されるとおりであり、R2はメチルラジカル、イソプロピルラジカル、イソブチルラジカル、1−メチルプロピルラジカル又はベンジルラジカルから選ばれるラジカルである)の一価のラジカル、又は、
式(IIb)(式中、R1は先に規定されるとおりであり、R4は水素原子である)の一価のラジカルである、先に規定されるような式(I)の化合物である。
−(CH2)q− (IIIa)
(式中、qは3、4又は6に等しい)の二価のラジカルを表し、X1、X2、X3及びX4が同一であり、各々が水素原子を表す式(III)に相当し、pが1、2又は4に等しい整数を表す、先に規定されるような式(I)の化合物である。
R’−O−A−O−H (Ia)
の化合物、より具体的には、
式(Ia11):
式(Ia12):
式(Ia13):
式(Ia14):
式(Ia15):
式(Ia21):
式(Ia22):
式(Ia23):
式(Ia24):
式(Ia25):
式(Ia31):
式(Ia32):
式(Ia33):
1,3−プロパンジオールモノN−ヘキサデカノイルバリネート、
1,3−プロパンジオールモノN−オクタノイルバリネート、
1,3−プロパンジオールモノN−(ω−ウンデシレノイル)バリネート、
1,3−プロパンジオールモノN−(ω−ウンデシレノイル)プロリネート、
1,3−プロパンジオールモノN−オクタノイルロイシネート。
1,3−ブタンジオールモノN−ヘキサデカノイルバリネート、
1,3−ブタンジオールモノN−オクタノイルバリネート、
1,3−ブタンジオールモノN−(ω−ウンデシレノイル)バリネート、
1,3−ブタンジオールモノN−(ω−ウンデシレノイル)プロリネート、
1,3−ブタンジオールモノN−オクタノイルロイシネート。
1,6−ヘキサンジオールモノN−オクタノイルバリネート、
1,6−ヘキサンジオールモノN−(ω−ウンデシレノイル)バリネート、
1,6−ヘキサンジオールモノN−ヘキサデカノイルプロリネート。
R−O−A−O−R (Ib)
の化合物、より具体的には、以下の化合物の1つ:
式(Ib11):
式(Ib12):
式(Ib13):
式(Ib14):
式(Ib15):
式(Ib21):
式(Ib22):
式(Ib23):
式(Ib24):
式(Ib25):
式(Ib31):
式(Ia32):
式(Ib33):
、式(Ib14)及び式(Ib15)の化合物はそれぞれ、より具体的には以下の化合物から選ばれる:
1,3−プロパンジオールジN−ヘキサデカノイルバリネート、
1,3−プロパンジオールジN−オクタノイルバリネート、
1,3−プロパンジオールジN−(ω−ウンデシレノイル)バリネート、
1,3−プロパンジオールジN−(ω−ウンデシレノイル)プロリネート、
1,3−プロパンジオールジN−オクタノイルロイシネート。
1,3−プロパンジオールジN−ヘキサデカノイルバリネート、
1,3−プロパンジオールジN−オクタノイルバリネート、
1,3−プロパンジオールジN−(ω−ウンデシレノイル)バリネート、
1,3−プロパンジオールジN−(ω−ウンデシレノイル)プロリネート、
1,3−プロパンジオールジN−オクタノイルロイシネート。
1,6−ヘキサンジオールジN−オクタノイルバリネート、
1,6−ヘキサンジオールジN−(ω−ウンデシレノイル)バリネート、
1,6−ヘキサンジオールジN−ヘキサデカノイルプロリネート。
式(IVa):
式(IVb):
式(V):
H−O−A−O−H (V)
(式中、Aは先に規定されるような式(III)の二価のラジカルである)でエステル化する工程であって、それにより式(Ia)の化合物若しくは式(Ib)の化合物、又は式(Ia)の化合物と式(Ib)の化合物との混合物(M)を得る、工程a)と、
必要又は所望に応じて、
工程(a)で得られる混合物(M)から、式(Ia)の化合物及び前記式(Ib)の化合物を分離する工程b)と、
を含む、方法である。
R5−OH (VI)
(式中、R5は1個〜4個の炭素原子を含む線状脂肪族ラジカルである)のアルコールでエステル化する工程であって、それにより、
式(VIIa):
式(VIIb):
工程a1)で得られる式(VIIa)の化合物又は式(VIIb)の化合物を、式(V)の化合物との反応によってエステル交換する工程であって、それにより式(Ia)の化合物若しくは式(Ib)の化合物、又は該式(Ia)の化合物と該式(Ib)の化合物との混合物(M)を得る、工程a2)と、
必要又は所望に応じて、
工程b)と、
を含む、上に規定されるような調製方法の変法である。
99質量%〜20質量%の先に規定されるような式(Ia)の少なくとも1つの化合物と、
1質量%〜80質量%の先に規定されるような式(Ib)の少なくとも1つの化合物と、
を含む、組成物(C1)である。
O/W)エマルション若しくは水中油中水型(W/O/W)エマルション等の多相エマルション(油は植物油又は鉱油であり得る)の形態、又は粉末の形態である。局所使用化粧品配合物を、繊維製品、又はワイプ、ペーパータオル若しくは布地を問わず不織布材料に分散又は含浸させてもよい。
ルホアセテート、アルキルサルコシネート、アシル化チオネート、N−アシルタウレート、アシルラクテートが挙げられる。
場合によってアルコキシル化されたアルキルポリグリコシド、とりわけエトキシ化メチルポリグルコシドの脂肪エステル、例えばそれぞれGLUCAMATE(商標)LT及びGLUMATE(商標)DOE120という名で市販されている、PEG 120トリオレイン酸メチルグルコース及びPEG 120ジオレイン酸メチルグルコース;
アルコキシル化脂肪酸エステル、例えばCROTHIX(商標)DS53という名で市販されているPEG 150テトラステアリン酸ペンタエリスリチル(pentaerythrityl)
、ANTIL(商標)141という名で市販されているPEG 55オレイン酸プロピレングリコール;
脂肪鎖を有するカルバミン酸ポリアルキレングリコール、例えばELFACOS(商標)T211という名で市販されているPPG 14ジカルバミン酸ラウレスイソホリル、ELFACOS(商標)GT2125という名で市販されているPPG 14ジカルバミン酸パルメス60ヘキシル。
又は脚のだるさを治療処置する方法に使用される先に規定されるような式(I)の化合物又は組成物(C1)である。
実施例1:式(Ia21)及び式(Ib21)の化合物を含む組成物A1の調製
239g、すなわち1モル当量のバリンを、効果的な撹拌装置及び窒素バブリング装置を備える、熱伝導流体を循環させた二重ジャケットガラス反応器内の1512gの水と649gのイソプロパノールとからなる2161gの混合物中に、20℃の温度で反応器の底部から導入する。このようにして調製される媒体のpHを、30%ソーダ溶液(soda solution)を添加することによってpH値10に調整する。次いで、450g、すなわち0.8モル当量のヘキサデカノイルクロリドを20℃〜30℃の温度で媒体に徐々に添加して発熱反応を制御する。同時に30%ソーダ溶液を媒体に添加して、媒体のpHを10〜10.5に維持する。
酸価(NFT 60−204に従う)=36.5
水中5%の組成物A1のpH(NFT 73−206の方法に従う)=7.1
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=135.5
エステル価(鹸化価(NFT 60−110に従う)−酸価)=100.8
実施例1に記載の方法の作業手順を1モル当量のバリン、0.8モル当量のヘキサデカノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物A2を得る:
酸価(NFT 60−204に従う)=28.3
水中5%の組成物A2のpH(NFT 73−206の方法に従う)=6.7
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=80.5
エステル価(鹸化価(NFT 60−110に従う)−酸価)=121.7
実施例1に記載の方法の作業手順を1モル当量のバリン、0.8モル当量のオクタノイルクロリド及び1モル当量の1,3−ブタンジオールに対して行い、以下の分析特性を有する組成物B1を得る:
酸価(NFT 60−204に従う)=55.7
水中5%の組成物B1のpH(NFT 73−206の方法に従う)=4.2
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=194.6
エステル価(鹸化価(NFT 60−110に従う)−酸価)=128.2
実施例1に記載の方法の作業手順を1モル当量のバリン、0.8モル当量のオクタノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物B2を得る:
酸価(NFT 60−204に従う)=54.2
水中5%の組成物B2のpH(NFT 73−206の方法に従う)=4.5
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=21.2
エステル価(鹸化価(NFT 60−110に従う)−酸価)=159.0
実施例1に記載の方法の作業手順を1モル当量のバリン、0.8モル当量のウンデシレノイルクロリド及び1モル当量の1,3−ブタンジオールに対して行い、以下の分析特性を有する組成物D1を得る:
酸価(NFT 60−204に従う)=50.0
水中5%の組成物D1のpH(NFT 73−206の方法に従う)=5.3
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=149.9
エステル価(鹸化価(NFT 60−110に従う)−酸価)=114.0
実施例1に記載の方法の作業手順を1モル当量のバリン、0.8モル当量のウンデシレノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物D2を得る:
酸価(NFT 60−204に従う)=38.6
水中5%の組成物D2のpH(NFT 73−206の方法に従う)=5.7
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=189.7
エステル価(鹸化価(NFT 60−110に従う)−酸価)=135.1
実施例1に記載の方法の作業手順を1モル当量のプロリン、0.8モル当量のウンデシレノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物E1を得る:
酸価(NFT 60−204に従う)=41.9
水中5%の組成物E1のpH(NFT 73−206の方法に従う)=5.0
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=142.6
エステル価(鹸化価(NFT 60−110に従う)−酸価)=116.0
実施例1に記載の方法の作業手順を1モル当量のプロリン、0.8モル当量のウンデシレノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物E2を得る:
酸価(NFT 60−204に従う)=25.6
水中5%の組成物E2のpH(NFT 73−206の方法に従う)=5.3
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=149.7
エステル価(鹸化価(NFT 60−110に従う)−酸価)=152.2
実施例1に記載の方法の作業手順を1モル当量のロイシン、0.8モル当量のオクタノイルクロリド及び1モル当量の1,3−プロパンジオールに対して行い、以下の分析特性を有する組成物F1を得る:
酸価(NFT 60−204に従う)=27.1
水中5%の組成物F1のpH(NFT 73−206の方法に従う)=5.3
ヒドロキシル価(米国薬局方XXI NF XVI 01/011985に従う)=99.9
エステル価(鹸化価(NFT 60−110に従う)−酸価)=169.4
プロトコル
R3期のHUVEC(ヒト臍帯静脈内皮細胞(Human Umbilical Vein Endothelial Cells en langue anglaise))を、96ウェルプレート内に2000細胞/ウェルで播種する。
の分子カーペット(molecular carpets)の溶解後に評価する。
(1)Chang et al: "Aging and survival of cutaneous microvasculature", J. Invest
Dermatol. 2002 May; 118(5):752-8.
(2)Chung et al: "Differential effects of photoaging vs intrinsic aging on the
vascularisation of human skin" Arch. Dermatol. 2002 Nov; 138(11):1437-42.
(3)Toyoda et al "Ultrastructural characterisation of microvasculature in photoaging" J. Dematol Sci. 2001 Aug; 27 Supp 1:S32-41.
(4)Janssens, "Effect of venotropic drugs on the respiratory activity of isolated mitochondria and in endothelial cells", in British Journal of Pharmacology (2000) 130, 1513-1524.
Claims (16)
- 下記式(I)の化合物:
R’−O−A−O−R’’ (I)
(式(I)中、R’及びR’’は同一であるか又は異なり、
水素原子、又は、
式(IIa):
R1は、7個〜30個の炭素原子を含む飽和又は不飽和の、線状又は分岐状の脂肪族基を表し、
R2は水素原子、又は以下の基:メチル、イソプロピル、イソブチル、1−メチルプロピル、ヒドロキシメチル、1−ヒドロキシエチル、チオメチル、2−メチルチオエチル、4−アミノブチル、3−グアニジノプロピル、3−ウレイドプロピル、(1−アミノカルボニル)メチル、2−(アミノカルボニル)エチル、ベンジル、4−ヒドロキシベンジル、3,4−ジヒドロキシベンジル、[1H−インドール−3−イル]メチル、(1H−イミダゾール−4−イル)メチル、3−アミノプロピルから選ばれる基を表し、R3は水素原子を表す)の一価の基、又は、
式(IIb):
R1は式(IIa)に規定されるとおりであり、
R4は水素原子又はヒドロキシ基を表す)の一価の基を表すが、
ただし、基R’又はR’’の少なくとも一方が水素原子ではなく、基R’及びR’’がいずれも水素原子ではない場合にR’及びR’’は同一であり、
式(I)中、Aは式(III):
−CH(X1)−[C(X2)(X3)]p−CH(X4)− (III)
(式中、X1、X2、X3及びX4は同一であるか又は異なり、水素原子又はメチル基若しくはエチル基であり、
pは1以上6以下の整数である)の二価の基を表す)。 - 式(IIa)及び(IIb)において、基R1−C(=O)−が以下の基:オクタノイル、デカノイル、ω−ウンデシレノイル、ドデカノイル、テトラデカノイル、ヘキサデカノイル、オクタデカノイル、エイコサノイル、ドコサノイル、9−オクタデセノイル、エイコセノイル、13−ドコセノイル、9,12−オクタデカジエノイル又は9,12,15−オクタデカトリエノイルから選ばれる基を表す、請求項1に記載の式(I)の化合物。
- 基R’及びR’’が同一であるか又は異なり、
水素原子、又は、
式(IIa)(式中、R1及びR3は先に規定されるとおりであり、R2はメチル基、イソプロピル基、イソブチル基、1−メチルプロピル基又はベンジル基から選ばれる基である)の一価の基、又は、
式(IIb)(式中、R1は先に規定されるとおりであり、R4は水素原子である)の一価の基である、請求項1又は2に記載の式(I)の化合物。 - Aが式(IIIa):
−(CH2)q− (IIIa)
(式中、qは3、4又は6に等しい)の二価の基を表し、X1、X2、X3及びX4が同一であり、各々が水素原子を表す式(III)に相当し、pが1、2又は4に等しい整数を表す、請求項1〜3のいずれか一項に記載の式(I)の化合物。 - Aが二価の基:
−(CH2)3−
を表す、請求項4に記載の式(I)の化合物。 - Aが二価の基:
−(CH2)2−CH(CH3)−
を表す、請求項1〜3のいずれか一項に記載の式(I)の化合物。 - 請求項1〜6のいずれか一項に記載の式(I)においてR’’が水素原子であるものに
相当する、式(Ia):
R’−O−A−O−H (Ia)
の化合物。 - 請求項1〜6のいずれか一項に記載の式(I)において基R’及びR’’が同一である化合物。
- 請求項1〜8のいずれか一項に記載の式(I)の化合物を調製する方法であって、
式(IVa):
式(IVb):
式(V):
H−O−A−O−H (V)
(式中、Aは先に規定されるような式(III)の二価の基である)でエステル化する工程であって、それにより請求項7に記載の式(Ia)の化合物若しくは請求項8に記載の化合物、又は該式(Ia)の化合物と該請求項8に記載の化合物との混合物(M)を得る、工程a)と、
必要又は所望に応じて、
工程(a)で得られる前記混合物(M)から、前記式(Ia)の化合物及び前記請求項8に記載の化合物を分離する工程b)と、
を含む、方法。 - 請求項1〜8のいずれか一項に記載の式(I)の化合物を調製する方法であって、
工程a1)
式(IVa):
式(IVb):
式(VI):
R5−OH (VI)
(式中、R5は1個〜4個の炭素原子を含む線状脂肪族基である)のアルコールでエステル化する工程であって、それにより、
式(VIIa):
式(VIIb):
工程a2)工程a1で得られる前記式(VIIa)の化合物又は前記式(VIIb)の化合物を、
式(V):
H−O−A−O−H (V)
(式中、Aは先に規定される式(III)の二価の基である)の化合物との反応によってエステル交換する工程であって、それにより請求項7に記載の式(Ia)の化合物若しくは請求項8に記載の化合物、又は該式(Ia)の化合物と該請求項8に記載の化合物との混合物(M)を得る、工程a2)と、
必要又は所望に応じて、
工程b)工程(a2)で得られる前記混合物(M)から、前記式(Ia)の化合物及び前記請求項8に記載の化合物を分離する工程b)と、
を含む、方法。 - 組成物(C1)であって、その質量を100%として、
99質量%〜20質量%の請求項7に記載の式(Ia)の少なくとも1つの化合物と、
1質量%〜80質量%の請求項8に記載の少なくとも1つの化合物と、
を含む、組成物(C1)。 - ヒトの身体の内皮細胞の低酸素状態によって生じる非審美的影響の、防止用及び/又は制限用の、化粧品活性物質としての請求項1〜8のいずれか一項に記載の式(I)の化合物又は請求項11に記載の組成物(C1)。
- 少なくとも1つの化粧品に許容可能な賦形剤と、有効量の請求項1〜8のいずれか一項に記載の式(I)の化合物又は請求項11に記載の組成物(C1)とを含むことを特徴とする、局所使用化粧品配合物。
- 眼周囲のくま若しくはたるみ、及び/又は、脚のだるさの現象の出現を防止すること、及び/又は、それらの現象を低減することを意図した、ヒトの皮膚を処置する非治療的方法であって、有効量の請求項13に記載の局所使用化粧品配合物を前記ヒトの皮膚に適用する少なくとも1つの工程を含む、非治療的方法。
- ヒト又は動物の身体の治療処置方法の実施用の、請求項1〜8のいずれか一項に記載の式(I)の化合物又は請求項11に記載の組成物(C1)。
- ヒト又は動物の身体の内皮細胞の低酸素状態を治療処置する方法に使用される、請求項1〜8のいずれか一項に記載の式(I)の化合物又は請求項11に記載の組成物(C1)。
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FR1159762 | 2011-10-27 | ||
PCT/FR2012/052324 WO2013060964A1 (fr) | 2011-10-27 | 2012-10-12 | Nouveaux esters de derives n-acyles d'acides amines et de diols, procede pour leur preparation, et utilisation en cosmetique et comme medicament |
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FR3029104B1 (fr) * | 2014-11-27 | 2016-12-02 | Soc D'exploitation De Produits Pour Les Ind Chimiques Seppic | Utilisation d'esters de alpha,omega-diols et de derives n-acyles d'acides amines comme agent de brunissage et/ou de bronzage de la peau humaine |
FR3029108B1 (fr) * | 2014-11-27 | 2016-12-02 | Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic | Utilisation d'esters de alpha, omega-alcanediols et de derives n-acyles d'acide amines, comme agent eclaircissant de la peau humaine |
FR3029105B1 (fr) * | 2014-11-27 | 2018-01-26 | Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic | Utilisation d'esters de alpha, omega-alcanediols et de derives n-acyles d'acide amines, comme agent antivieillissement de la peau humaine |
FR3029411B1 (fr) * | 2014-12-04 | 2018-03-02 | Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic | Utilisation d'esters avec le 1,3-butanediol de derives n-acyles d'acide amines, comme agent eclaircissant de la peau humaine |
FR3029410B1 (fr) * | 2014-12-04 | 2016-12-30 | Soc D'exploitation De Produits Pour Les Ind Chimiques Seppic | Utilisation d'esters de 1,3-butanediol et de derives n-acyles d'acides amines comme agent de brunissage et/ou de bronzage de la peau humaine |
FR3029412B1 (fr) * | 2014-12-04 | 2018-01-26 | Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic | Utilisation de derives n-acyles d'acide amines esterifies avec le 1,3-butanediol, comme agent antivieillissement de la peau humaine |
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JP2000229921A (ja) | 1999-02-08 | 2000-08-22 | Ajinomoto Co Inc | N−アシルアミノ酸ポリオールエステルの製造法 |
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