CA2622468A1 - Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition - Google Patents
Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition Download PDFInfo
- Publication number
- CA2622468A1 CA2622468A1 CA002622468A CA2622468A CA2622468A1 CA 2622468 A1 CA2622468 A1 CA 2622468A1 CA 002622468 A CA002622468 A CA 002622468A CA 2622468 A CA2622468 A CA 2622468A CA 2622468 A1 CA2622468 A1 CA 2622468A1
- Authority
- CA
- Canada
- Prior art keywords
- naphthoic acid
- composition according
- acne
- composition
- adapalene
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 242
- 229920000642 polymer Polymers 0.000 title claims abstract description 57
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 52
- 239000004814 polyurethane Substances 0.000 title claims abstract description 52
- 150000005209 naphthoic acids Chemical class 0.000 title claims abstract description 42
- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims description 152
- 206010000496 acne Diseases 0.000 claims description 67
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 49
- 239000012071 phase Substances 0.000 claims description 36
- 239000008213 purified water Substances 0.000 claims description 30
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 27
- 239000006210 lotion Substances 0.000 claims description 23
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 22
- 229960002216 methylparaben Drugs 0.000 claims description 22
- 239000003349 gelling agent Substances 0.000 claims description 21
- 239000003995 emulsifying agent Substances 0.000 claims description 20
- 239000000839 emulsion Substances 0.000 claims description 19
- 239000003755 preservative agent Substances 0.000 claims description 16
- 239000002738 chelating agent Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000000080 wetting agent Substances 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 13
- 239000006071 cream Substances 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000003974 emollient agent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 235000013336 milk Nutrition 0.000 claims description 7
- 239000008267 milk Substances 0.000 claims description 7
- 210000004080 milk Anatomy 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004945 emulsification Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000000375 suspending agent Substances 0.000 claims description 6
- 206010000501 Acne conglobata Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 230000003780 keratinization Effects 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 239000007764 o/w emulsion Substances 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 201000004700 rosacea Diseases 0.000 claims description 4
- 240000006661 Serenoa repens Species 0.000 claims description 3
- 235000005318 Serenoa repens Nutrition 0.000 claims description 3
- 235000021028 berry Nutrition 0.000 claims description 3
- 230000024245 cell differentiation Effects 0.000 claims description 3
- 230000004663 cell proliferation Effects 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 238000000265 homogenisation Methods 0.000 claims description 3
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- 230000001338 necrotic effect Effects 0.000 claims description 3
- 230000000306 recurrent effect Effects 0.000 claims description 3
- 239000010018 saw palmetto extract Substances 0.000 claims description 3
- TVIKMHRYESWHCR-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-decoxyphenyl]naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OCCCCCCCCCC)=CC=C21 TVIKMHRYESWHCR-UHFFFAOYSA-N 0.000 claims description 2
- BCLMUIMQCLRLNV-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-hexoxyphenyl]naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OCCCCCC)=CC=C21 BCLMUIMQCLRLNV-UHFFFAOYSA-N 0.000 claims description 2
- LDGIHZJOIQSHPB-UHFFFAOYSA-N CD437 Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)O)=CC=C1O LDGIHZJOIQSHPB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 abstract description 20
- 229960002916 adapalene Drugs 0.000 description 138
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 105
- 238000009472 formulation Methods 0.000 description 98
- 239000000499 gel Substances 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000000902 placebo Substances 0.000 description 48
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 43
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 42
- 229940068196 placebo Drugs 0.000 description 41
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 40
- 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 31
- 238000000034 method Methods 0.000 description 30
- 210000003491 skin Anatomy 0.000 description 30
- 239000003981 vehicle Substances 0.000 description 22
- 239000000470 constituent Substances 0.000 description 19
- -1 especially Chemical class 0.000 description 18
- 229920001983 poloxamer Polymers 0.000 description 18
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 17
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 17
- 229960003415 propylparaben Drugs 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 15
- 239000002085 irritant Substances 0.000 description 15
- 229920002125 Sokalan® Polymers 0.000 description 14
- 231100000021 irritant Toxicity 0.000 description 13
- 239000002736 nonionic surfactant Substances 0.000 description 13
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 11
- 210000002615 epidermis Anatomy 0.000 description 11
- 238000003556 assay Methods 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 8
- 229960005323 phenoxyethanol Drugs 0.000 description 8
- 230000036572 transepidermal water loss Effects 0.000 description 8
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 7
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 229940075510 carbopol 981 Drugs 0.000 description 6
- 230000002995 comedolytic effect Effects 0.000 description 6
- STORWMDPIHOSMF-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O STORWMDPIHOSMF-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 6
- 229920000053 polysorbate 80 Polymers 0.000 description 6
- 239000013641 positive control Substances 0.000 description 6
- 210000000434 stratum corneum Anatomy 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 5
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 5
- 238000011725 BALB/c mouse Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 5
- 238000012801 analytical assay Methods 0.000 description 5
- 210000004207 dermis Anatomy 0.000 description 5
- 230000001804 emulsifying effect Effects 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- VMGLLMDIYIPVHX-UHFFFAOYSA-N 1-benzothiophene-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CSC2=C1 VMGLLMDIYIPVHX-UHFFFAOYSA-N 0.000 description 4
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
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- 230000007794 irritation Effects 0.000 description 4
- 229960001727 tretinoin Drugs 0.000 description 4
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 3
- 208000032544 Cicatrix Diseases 0.000 description 3
- 229920003102 Methocel™ E4M Polymers 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 2
- VYBLDUKQAWIMMM-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC2=C1 VYBLDUKQAWIMMM-UHFFFAOYSA-N 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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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
-
- 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
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- 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
- A61P17/10—Anti-acne agents
-
- 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
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- 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
-
- 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
- A61Q19/008—Preparations for oily 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Inorganic Chemistry (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0509493 | 2005-09-16 | ||
FR0509493A FR2890861B1 (fr) | 2005-09-16 | 2005-09-16 | Compositions comprenant au moins un derive de l'acide naphtoique et au moins un compose de type polymeres de polyurethanes ou des derives de celui-ci, leurs procede de preparation, et leur utilisation |
US72527905P | 2005-10-12 | 2005-10-12 | |
US60/725,279 | 2005-10-12 | ||
PCT/IB2006/003852 WO2007031883A2 (fr) | 2005-09-16 | 2006-09-15 | Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2622468A1 true CA2622468A1 (fr) | 2007-03-22 |
Family
ID=37865321
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002622468A Abandoned CA2622468A1 (fr) | 2005-09-16 | 2006-09-15 | Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1933827A2 (fr) |
JP (2) | JP5074401B2 (fr) |
AU (1) | AU2006290364B2 (fr) |
CA (1) | CA2622468A1 (fr) |
MX (1) | MX2008003422A (fr) |
RU (1) | RU2421216C2 (fr) |
WO (1) | WO2007031883A2 (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7820186B2 (en) | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
FR2916966B1 (fr) * | 2007-06-11 | 2011-01-14 | Galderma Res & Dev | Compositions comprenant au moins un compose retinoide, un compose anti-irritant et du peroxyde de benzoyle, et leurs utilisations |
FR2916975B1 (fr) * | 2007-06-11 | 2009-09-04 | Galderma Res & Dev | Compositions comprenant au moins un compose retinoide, un compose anti-irritant et du peroxyde de benzoyle, et leurs utilisations |
WO2009007341A2 (fr) * | 2007-07-06 | 2009-01-15 | Galderma Research & Development | Compositions destinées à l'application topique pour le traitement des troubles de la kératinisation |
EP2065032A1 (fr) * | 2007-11-27 | 2009-06-03 | Galderma Research & Development | Procédé pour la production de gels d'adapalène |
BRPI0819047A2 (pt) * | 2007-11-30 | 2015-05-05 | Galderma Res & Dev | "composição, seu processo de preparação e seus usos" |
US9463158B2 (en) | 2009-06-24 | 2016-10-11 | Strategic Science & Technologies, Llc | Treatment of erectile dysfunction and other indications |
US11684624B2 (en) | 2009-06-24 | 2023-06-27 | Strategic Science & Technologies, Llc | Treatment of erectile dysfunction and other indications |
US12138268B2 (en) | 2009-06-24 | 2024-11-12 | Strategic Science & Technologies, Llc | Treatment of erectile dysfunction and other indications |
EP2445492B1 (fr) * | 2009-06-24 | 2016-09-28 | Strategic Science & Technologies, LLC | Composition topique contenant de l'ibuprofène |
JP5521190B2 (ja) * | 2009-10-01 | 2014-06-11 | 国立大学法人東京工業大学 | コラーゲン組成物及びその製造方法 |
US20130203850A1 (en) * | 2010-04-29 | 2013-08-08 | Galderma Research & Development | Method for treating scars with adapalene 0.3% |
US20150080352A1 (en) * | 2012-03-09 | 2015-03-19 | Bayer Materialscience Llc | Aqueous polyurethane dispersion in the treatment of acne |
JPWO2019240290A1 (ja) * | 2018-06-16 | 2021-06-24 | ロート製薬株式会社 | 外用組成物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE115553T1 (de) * | 1987-07-16 | 1994-12-15 | Univ California | Mittel zur steigerung der hautpenetration von pharmakologisch aktiven verbindungen. |
JPH061851A (ja) * | 1992-06-19 | 1994-01-11 | Toyo Ink Mfg Co Ltd | 顔料組成物および水性顔料分散体 |
US6358541B1 (en) * | 2000-05-03 | 2002-03-19 | David S. Goodman | Topical preparation for the treatment of hair loss |
EP1485080B1 (fr) * | 2002-03-12 | 2009-05-27 | Galderma Research & Development | Emploi d'adapalene pour le traitement de troubles dermatologiques |
-
2006
- 2006-09-15 AU AU2006290364A patent/AU2006290364B2/en active Active
- 2006-09-15 RU RU2008114840/15A patent/RU2421216C2/ru active
- 2006-09-15 EP EP06831837A patent/EP1933827A2/fr not_active Withdrawn
- 2006-09-15 JP JP2008530661A patent/JP5074401B2/ja active Active
- 2006-09-15 MX MX2008003422A patent/MX2008003422A/es active IP Right Grant
- 2006-09-15 CA CA002622468A patent/CA2622468A1/fr not_active Abandoned
- 2006-09-15 WO PCT/IB2006/003852 patent/WO2007031883A2/fr active Application Filing
-
2012
- 2012-06-20 JP JP2012138489A patent/JP2012184258A/ja active Pending
Also Published As
Publication number | Publication date |
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EP1933827A2 (fr) | 2008-06-25 |
JP2012184258A (ja) | 2012-09-27 |
RU2008114840A (ru) | 2009-10-27 |
JP2009508843A (ja) | 2009-03-05 |
JP5074401B2 (ja) | 2012-11-14 |
RU2421216C2 (ru) | 2011-06-20 |
MX2008003422A (es) | 2008-03-27 |
WO2007031883A3 (fr) | 2007-09-13 |
WO2007031883A2 (fr) | 2007-03-22 |
AU2006290364A1 (en) | 2007-03-22 |
AU2006290364B2 (en) | 2012-07-05 |
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