ES2554776T3 - Combinación consistente en ácido pirrolidono-5-carboxílico y al menos un compuesto de citrulina, arginina y asparraguina y su uso en el tratamiento de la dermatitis atópica - Google Patents
Combinación consistente en ácido pirrolidono-5-carboxílico y al menos un compuesto de citrulina, arginina y asparraguina y su uso en el tratamiento de la dermatitis atópica Download PDFInfo
- Publication number
- ES2554776T3 ES2554776T3 ES08759934.6T ES08759934T ES2554776T3 ES 2554776 T3 ES2554776 T3 ES 2554776T3 ES 08759934 T ES08759934 T ES 08759934T ES 2554776 T3 ES2554776 T3 ES 2554776T3
- Authority
- ES
- Spain
- Prior art keywords
- citrulline
- arginine
- pyrrolidono
- treatment
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 title abstract description 7
- 229960001230 asparagine Drugs 0.000 title abstract description 7
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 title abstract description 6
- 235000009582 asparagine Nutrition 0.000 title abstract description 6
- 229960002173 citrulline Drugs 0.000 title abstract description 6
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 title abstract description 5
- 235000013477 citrulline Nutrition 0.000 title abstract description 5
- 239000004475 Arginine Substances 0.000 title abstract description 4
- 235000009697 arginine Nutrition 0.000 title abstract description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 title abstract description 4
- 206010012438 Dermatitis atopic Diseases 0.000 title abstract 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 title abstract 2
- 229960003121 arginine Drugs 0.000 title abstract 2
- 201000008937 atopic dermatitis Diseases 0.000 title abstract 2
- -1 asparagine compound Chemical class 0.000 title 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CRPCXAMJWCDHFM-DFWYDOINSA-M sodium;(2s)-5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@@H]1CCC(=O)N1 CRPCXAMJWCDHFM-DFWYDOINSA-M 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229940069078 citric acid / sodium citrate Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000037067 skin hydration Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/4015—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 having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Combinación de ácido pirrolidono-5-carboxílico con al menos uno de los compuestos seleccionados entre citrulina, arginina y asparraguina, en forma racémica o en forma de isómero D o L, y/o sus sales, para uso en el tratamiento y/o la prevención de la dermatitis atópica.
Description
Tabla 1: Condiciones operativas
- Prueba
- Parámetros
- Valor del parámetro
- Programa de calor
- Desecación estándar
- Temperatura final
- 32°C
- Comienzo del análisis
- Con estabilidad
- Final del análisis
- 480 min.
- Resultados
- Extractos secos (%)
Estas condiciones operativas han sido seleccionadas con objeto de simular las condiciones de la piel (la temperatura 5 de la piel es de alrededor de 30-32°C).
3. Resultados y discusiones
10 Todos los productos estudiados se basan en una formulación que contiene el agente gelificante Natrosol 250HHX (nombre INCI Hidroxietilcelulosa) al 0,5%. El pH de los productos está comprendido entre 5,0 y 5,5 (ajustado mediante ácido cítrico y citrato de sodio). La siguiente Tabla 2 presenta la composición cualitativa y cuantitativa de los productos estudiados:
15 Tabla 2: Presentación de las formulaciones
- Excipientes (%)
- A B C D
- Denominación comercial
- Nombre INCI
- Natrosol 250HHX
- Hidroxietilcelulosa 0,5 0,5 0,5 0,5
- Ácido cítrico/citrato de sodio USP 2H20
- Ácido cítrico/citrato de sodio pH 5,5 +/-0,5
- Nalidona
- PCA Na (ácido pirrolidonocarboxílico sodio) - 4,0 4,0 4,0
- L-Citrulina
- Citrulina - - 12,0 -
- L-Arginina
- Arginina - 12,0 - -
- L-Asparraguina
- Asparraguina - - - 12,0
- Agua purificada
- Agua 97,1 81,1 81,1 81,1
20 El análisis termogravimétrico demuestra una caída abrupta del índice de extractos secos entre los 0 y alrededor de los 150 minutos, lo que indica que la evaporación se produce muy rápidamente. A continuación, se observa una evaporación estable entre los 150 y los 480 min.
25 La velocidad de evaporación al final del análisis es menos importante cuando hay aminoácidos en el producto.
Para seguir cuantificando las propiedades higroscópicas de los aminoácidos, se calculó la pendiente/el gradiente entre los 0 y los 150 min. (cf. figura 6). Cuanto menor es la pendiente/el gradiente para un producto, mejores son sus propiedades higroscópicas.
30 Se observa la velocidad de desecación más alta para el producto A (sin aminoácidos). Esto significa que el producto A no retiene evaporación de agua, a diferencia de los productos que contienen aminoácidos. La adición de aminoácidos reduce la velocidad de pérdida de agua, como se observa por la menor velocidad de desecación de los productos B, C, y D, que contienen aminoácidos.
35
4. Conclusión
Para resumir, el análisis termogravimétrico demostró que la velocidad de evaporación es menor para productos que contienen aminoácidos.
40 Los aminoácidos son capaces de reducir la velocidad de pérdida de agua.
Los resultados descritos en las secciones I y II nos permitieron documentar que los aminoácidos son agentes higroscópicos y, particularmente si se combinan, pueden desempeñar un papel significativo en la hidratación cutánea.
45
8
- Alcohol estearílico
- 1
- EDTA
- 0,1
- Pirrolidono-5-carboxilato de sodio
- 3
- Asparraguina
- 3
- Ajustador del pH
- Cs pH 6
3) Gel
- Ingredientes
- Concentración %
- Agua
- Cs 100
- Carboximetilcelulosa
- 1,25
- Glicerol
- 5
- Agente conservante
- 0,3
- EDTA
- 0,1
- Pirrolidono-5-carboxilato de sodio
- 2
- Arginina
- 3
- Citrulina
- 2
- Asparraguina
- 2
4) Crema-gel
- Ingredientes
- Concentración %
- Agua
- Cs 100
- Glicerol
- 5
- Carbómero
- 0,15
- Crospolímero de acrilatos/alquil(C10-30)acrilato (Pemulen TR1)
- 0,3
- Polisorbato 80
- 1
- EDTA
- 0,1
- Propilenglicol
- 3
- Agente conservante
- 0,3
- Pirrolidono-5-carboxilato de sodio
- 1
- Asparraguina
- 2
- Citrulina
- 2
10
Claims (1)
-
imagen1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0755186 | 2007-05-22 | ||
| FR0755186A FR2916351B1 (fr) | 2007-05-22 | 2007-05-22 | Composition pharmaceutique comprenant au moins deux composes choisis parmi l'acide pyrrolidone-5-carboxylique, la citrulline, l'arginine et l'asparagine et leur utilisation dans le traitement de la dermatite atopique |
| US92471207P | 2007-05-29 | 2007-05-29 | |
| US924712P | 2007-05-29 | ||
| PCT/EP2008/056333 WO2008142147A1 (en) | 2007-05-22 | 2008-05-22 | Combination comprising pyrrolidone-5-carboxylic acid and at least one compound from citrulline, arginine and asparagine, and use thereof in the treatment of atopic dermatitis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2554776T3 true ES2554776T3 (es) | 2015-12-23 |
Family
ID=38606551
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08759934.6T Active ES2554776T3 (es) | 2007-05-22 | 2008-05-22 | Combinación consistente en ácido pirrolidono-5-carboxílico y al menos un compuesto de citrulina, arginina y asparraguina y su uso en el tratamiento de la dermatitis atópica |
| ES10165250.1T Active ES2554834T3 (es) | 2007-05-22 | 2008-05-22 | Combinación consistente en ácido pirrolidono-5-carboxílico y al menos un compuesto de citrulina, arginina y asparraguina y su uso en el tratamiento de la dermatitis atópica |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10165250.1T Active ES2554834T3 (es) | 2007-05-22 | 2008-05-22 | Combinación consistente en ácido pirrolidono-5-carboxílico y al menos un compuesto de citrulina, arginina y asparraguina y su uso en el tratamiento de la dermatitis atópica |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8795705B2 (es) |
| EP (2) | EP2164482B1 (es) |
| JP (2) | JP2010527970A (es) |
| KR (1) | KR20100017202A (es) |
| CN (1) | CN101686957A (es) |
| BR (1) | BRPI0810323A2 (es) |
| CA (1) | CA2687324A1 (es) |
| ES (2) | ES2554776T3 (es) |
| FR (1) | FR2916351B1 (es) |
| HU (2) | HUE025824T2 (es) |
| MX (1) | MX2009012472A (es) |
| PL (2) | PL2218452T3 (es) |
| PT (2) | PT2218452E (es) |
| RU (1) | RU2476214C2 (es) |
| WO (1) | WO2008142147A1 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5689026B2 (ja) * | 2010-06-17 | 2015-03-25 | 株式会社 資生堂 | 水中油型乳化皮膚化粧料 |
| KR101066859B1 (ko) * | 2010-12-10 | 2011-09-26 | 전명자 | 패드 및 이를 포함하는 깔창 |
| JP6009147B2 (ja) * | 2011-03-15 | 2016-10-19 | 株式会社 資生堂 | ブレオマイシン水解酵素産生促進剤 |
| RU2538084C1 (ru) * | 2013-07-25 | 2015-01-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Уральская государственная медицинская академия Министерства здравоохранения и социального развития Российской Федерации" (ГБОУ ВПО УГМА Минздрава России) | Средство для лечения и профилактики атопического дерматита |
| KR101732428B1 (ko) | 2015-06-25 | 2017-05-24 | 이정재 | 탄성 리포좀 조성물 및 이를 포함하는 화장료 조성물 |
| KR102396603B1 (ko) | 2015-09-16 | 2022-05-11 | 원광대학교산학협력단 | 시트룰린을 유효성분으로 함유하는 간 기능 개선용 조성물 |
| US9909427B2 (en) | 2015-12-22 | 2018-03-06 | General Electric Company | Turbine airfoil with trailing edge cooling circuit |
| CN115671098A (zh) * | 2016-06-17 | 2023-02-03 | 药物递送解决方案私人有限责任公司 | 用于治疗尿毒性瘙痒症的制剂 |
| CN112137995A (zh) | 2019-06-28 | 2020-12-29 | 默克专利股份有限公司 | 增加皮肤细胞中钙的细胞利用率的方法和混合物 |
| CN112569162B (zh) * | 2019-09-27 | 2024-04-12 | 默克专利股份有限公司 | 麦冬提取物、氨基酸、氨基酸衍生物和乳酸钙水合物的协同作用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61215308A (ja) | 1985-03-20 | 1986-09-25 | Shiseido Co Ltd | 皮膚外用剤 |
| JPS61215307A (ja) | 1985-03-20 | 1986-09-25 | Shiseido Co Ltd | 皮膚外用剤 |
| JPH0729911B2 (ja) | 1986-05-15 | 1995-04-05 | 株式会社資生堂 | 皮膚外用剤 |
| US4837019A (en) * | 1986-08-11 | 1989-06-06 | Charles Of The Ritz Group Ltd. | Skin treatment composition and method for treating burned skin |
| DE4341000A1 (de) * | 1993-12-02 | 1995-06-08 | Beiersdorf Ag | Verwendung von L-Arginin, L-Ornithin oder L-Citrullin und topischen Zubereitungen mit diesen Stoffen |
| JPH0820525A (ja) | 1994-07-06 | 1996-01-23 | Nendo Kagaku Kenkyusho:Kk | ボディシャンプ |
| ES2132855T3 (es) | 1995-09-07 | 1999-08-16 | Oreal | Extracto de iridaceas y composiciones que lo contienen. |
| EP0761204B1 (fr) | 1995-09-07 | 1998-04-15 | L'oreal | Utilisation d'un extrait d'une bactérie filamenteuse non photosynthétique et composition le contenant |
| JP3525233B2 (ja) | 1995-09-20 | 2004-05-10 | 味の素株式会社 | 化粧料 |
| FR2768622B1 (fr) | 1997-09-22 | 1999-11-26 | Oreal | Extrait de rosacees en tant qu'antagoniste de bradykinine |
| FR2778562B1 (fr) * | 1998-05-14 | 2000-08-04 | Sephra | Composition pharmaceutique, hygienique et/ou cosmetique contenant de l'eau de mer et de l'arginine |
| DE19831798A1 (de) * | 1998-07-15 | 2000-01-27 | Mandorlo Investment Gmbh Luxem | Mittel zur Pflege und/oder Behandlung von Haut und Gewebe |
| JP2002053428A (ja) | 2000-08-12 | 2002-02-19 | Tadashi Fukiya | 皮膚外用剤 |
| JP4681132B2 (ja) | 2001-01-29 | 2011-05-11 | 味の素株式会社 | 一酸化窒素合成酵素産生促進剤および化粧料若しくは医薬組成物 |
| DE10111049A1 (de) * | 2001-03-06 | 2002-09-12 | Beiersdorf Ag | Verwendung von Substanzen, die verhindern, daß die NO-Synthese des warmblütigen Organismus ihre Wirkung entfaltet, zur Herstellung von kosmetischen oder dermatologischen Zubereitungen, zur Prophylaxe und Behandlung von entzündlichen Hautzuständen und/oder zum Hautschutz bei empfindlich determinierter trockener Haut |
| JP4851046B2 (ja) | 2002-06-19 | 2012-01-11 | 味の素株式会社 | 細胞への塩基性アミノ酸取り込み促進剤および医薬組成物 |
| JP2004168763A (ja) * | 2002-10-30 | 2004-06-17 | Dsr Corp | 皮膚化粧料 |
| US20060063827A1 (en) * | 2004-09-23 | 2006-03-23 | Yu Ruey J | Systemic administration of therapeutic amino acids and N-acetylamino acids |
| JPWO2005077349A1 (ja) | 2004-02-17 | 2007-10-18 | 大塚製薬株式会社 | ヒトβディフェンシン産生促進剤 |
-
2007
- 2007-05-22 FR FR0755186A patent/FR2916351B1/fr not_active Expired - Fee Related
-
2008
- 2008-05-22 PL PL10165250T patent/PL2218452T3/pl unknown
- 2008-05-22 PT PT101652501T patent/PT2218452E/pt unknown
- 2008-05-22 PL PL08759934T patent/PL2164482T3/pl unknown
- 2008-05-22 HU HUE08759934A patent/HUE025824T2/en unknown
- 2008-05-22 RU RU2009147465/15A patent/RU2476214C2/ru active
- 2008-05-22 BR BRPI0810323-2A2A patent/BRPI0810323A2/pt not_active Application Discontinuation
- 2008-05-22 US US12/601,113 patent/US8795705B2/en active Active
- 2008-05-22 WO PCT/EP2008/056333 patent/WO2008142147A1/en not_active Ceased
- 2008-05-22 EP EP08759934.6A patent/EP2164482B1/en active Active
- 2008-05-22 HU HUE10165250A patent/HUE026388T2/en unknown
- 2008-05-22 CA CA002687324A patent/CA2687324A1/en not_active Abandoned
- 2008-05-22 PT PT87599346T patent/PT2164482E/pt unknown
- 2008-05-22 JP JP2010508859A patent/JP2010527970A/ja active Pending
- 2008-05-22 CN CN200880016754A patent/CN101686957A/zh active Pending
- 2008-05-22 KR KR1020097024242A patent/KR20100017202A/ko not_active Ceased
- 2008-05-22 ES ES08759934.6T patent/ES2554776T3/es active Active
- 2008-05-22 EP EP10165250.1A patent/EP2218452B1/en active Active
- 2008-05-22 ES ES10165250.1T patent/ES2554834T3/es active Active
- 2008-05-22 MX MX2009012472A patent/MX2009012472A/es active IP Right Grant
-
2014
- 2014-01-10 JP JP2014003184A patent/JP2014065742A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN101686957A (zh) | 2010-03-31 |
| AU2008252925A1 (en) | 2008-11-27 |
| BRPI0810323A2 (pt) | 2014-10-14 |
| KR20100017202A (ko) | 2010-02-16 |
| EP2164482A1 (en) | 2010-03-24 |
| CA2687324A1 (en) | 2008-11-27 |
| US8795705B2 (en) | 2014-08-05 |
| PT2164482E (pt) | 2016-02-03 |
| HUE026388T2 (en) | 2016-06-28 |
| RU2476214C2 (ru) | 2013-02-27 |
| EP2218452A1 (en) | 2010-08-18 |
| PL2164482T3 (pl) | 2016-05-31 |
| HUE025824T2 (en) | 2016-05-30 |
| PL2218452T3 (pl) | 2016-04-29 |
| ES2554834T3 (es) | 2015-12-23 |
| EP2164482B1 (en) | 2015-10-07 |
| PT2218452E (pt) | 2016-01-27 |
| FR2916351A1 (fr) | 2008-11-28 |
| US20100291002A1 (en) | 2010-11-18 |
| JP2010527970A (ja) | 2010-08-19 |
| FR2916351B1 (fr) | 2012-12-07 |
| RU2009147465A (ru) | 2011-06-27 |
| EP2218452B1 (en) | 2015-09-30 |
| JP2014065742A (ja) | 2014-04-17 |
| MX2009012472A (es) | 2009-12-01 |
| WO2008142147A1 (en) | 2008-11-27 |
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