LU86865A1 - Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie - Google Patents

Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie Download PDF

Info

Publication number: LU86865A1
Authority: LU; Luxembourg
Prior art keywords: retinoate; trans; garlic; formula; denotes
Prior art date: 1987-05-06

Application number

LU86865A

Other languages

English (en)

French (fr)

Inventor

Jean-Luc Leveque

Michel Philippe

Henri Sebag

Didier Saint-Leger

Original Assignee

Oreal

Priority date (The priority date 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 date listed.)

1987-05-06

Filing date

1987-05-06

Publication date

1989-01-19

1987-05-06 Application filed by Oreal filed Critical Oreal

1987-05-06 Priority to LU86865A priority Critical patent/LU86865A1/fr

1988-04-29 Priority to CA000565553A priority patent/CA1304740C/fr

1988-05-05 Priority to AT88107228T priority patent/ATE74591T1/de

1988-05-05 Priority to US07/190,441 priority patent/US4857525A/en

1988-05-05 Priority to DE8888107228T priority patent/DE3869825D1/de

1988-05-05 Priority to ES198888107228T priority patent/ES2039496T3/es

1988-05-05 Priority to EP88107228A priority patent/EP0290020B1/de

1988-05-06 Priority to JP63110272A priority patent/JP2595036B2/ja

1989-01-19 Publication of LU86865A1 publication Critical patent/LU86865A1/fr

Links

-1 AMMONIUM RETINOATES Chemical class 0.000 title claims description 19
239000002537 cosmetic Substances 0.000 title claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
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 claims description 53
239000000203 mixture Substances 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 39
240000002234 Allium sativum Species 0.000 claims description 38
235000004611 garlic Nutrition 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 13
206010000496 acne Diseases 0.000 claims description 11
239000006210 lotion Substances 0.000 claims description 11
208000002874 Acne Vulgaris Diseases 0.000 claims description 10
239000000499 gel Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
SHGAZHPCJJPHSC-XFYACQKRSA-M 13-cis-retinoate Chemical compound [O-]C(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-XFYACQKRSA-M 0.000 claims description 6
230000000699 topical effect Effects 0.000 claims description 5
230000000844 anti-bacterial effect Effects 0.000 claims description 4
229940088710 antibiotic agent Drugs 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
239000000058 anti acne agent Substances 0.000 claims description 2
229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
239000002260 anti-inflammatory agent Substances 0.000 claims description 2
230000003110 anti-inflammatory effect Effects 0.000 claims description 2
229940124340 antiacne agent Drugs 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
239000006260 foam Substances 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
239000004530 micro-emulsion Substances 0.000 claims description 2
235000013336 milk Nutrition 0.000 claims description 2
210000004080 milk Anatomy 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
239000000344 soap Substances 0.000 claims description 2
239000007921 spray Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
ZRIILUSQBDFVNY-UHFFFAOYSA-N 4-dodecylmorpholine Chemical compound CCCCCCCCCCCCN1CCOCC1 ZRIILUSQBDFVNY-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000003892 C18 acyl group Chemical group 0.000 abstract description 2
SHGAZHPCJJPHSC-YCNIQYBTSA-M all-trans-retinoate Chemical compound [O-]C(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-M 0.000 abstract 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 9
238000006073 displacement reaction Methods 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
150000001450 anions Chemical class 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
210000003491 skin Anatomy 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
241000186427 Cutibacterium acnes Species 0.000 description 4
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000001863 hydroxypropyl cellulose Substances 0.000 description 4
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
229940049964 oleate Drugs 0.000 description 4
229940055019 propionibacterium acne Drugs 0.000 description 4
229930002330 retinoic acid Natural products 0.000 description 4
208000017520 skin disease Diseases 0.000 description 4
229960001727 tretinoin Drugs 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001342522 Vampyrum spectrum Species 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000002995 comedolytic effect Effects 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
230000001530 keratinolytic effect Effects 0.000 description 3
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
208000020154 Acnes Diseases 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000001840 Dandruff Diseases 0.000 description 2
SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 2
229940124091 Keratolytic Drugs 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
XSPWEZBRYVQZST-UHFFFAOYSA-L benzyl-hexadecyl-dimethylazanium;carbonate Chemical compound [O-]C([O-])=O.CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1.CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XSPWEZBRYVQZST-UHFFFAOYSA-L 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229960002227 clindamycin Drugs 0.000 description 2
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960003276 erythromycin Drugs 0.000 description 2
238000009472 formulation Methods 0.000 description 2
UZLANKRGXIJVHI-UHFFFAOYSA-L hexadecyl(trimethyl)azanium;carbonate Chemical compound [O-]C([O-])=O.CCCCCCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCCCCCC[N+](C)(C)C UZLANKRGXIJVHI-UHFFFAOYSA-L 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229960005280 isotretinoin Drugs 0.000 description 2
239000003410 keratolytic agent Substances 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
210000004761 scalp Anatomy 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
FPPBCRLXUHYGHR-UHFFFAOYSA-N 2-tert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=C(O)C(=O)C=CC1=O FPPBCRLXUHYGHR-UHFFFAOYSA-N 0.000 description 1
VXYGFTZDXZHPHP-UHFFFAOYSA-N 4-dodecyl-4-methylmorpholin-4-ium Chemical compound CCCCCCCCCCCC[N+]1(C)CCOCC1 VXYGFTZDXZHPHP-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
201000004384 Alopecia Diseases 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002101 Chitin Polymers 0.000 description 1
229920001661 Chitosan Polymers 0.000 description 1
229920002907 Guar gum Polymers 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
102000001974 Hyaluronidases Human genes 0.000 description 1
108050009363 Hyaluronidases Proteins 0.000 description 1
229920000161 Locust bean gum Polymers 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
241000364528 Phyllosiphon ari Species 0.000 description 1
239000004365 Protease Substances 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000011162 ammonium carbonates Nutrition 0.000 description 1
230000003255 anti-acne Effects 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
210000004207 dermis Anatomy 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
BPSQMWSZGQGXHF-UHFFFAOYSA-N dodecyl-ethyl-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC BPSQMWSZGQGXHF-UHFFFAOYSA-N 0.000 description 1
VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
230000004090 etiopathogenesis Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000003325 follicular Effects 0.000 description 1
210000001061 forehead Anatomy 0.000 description 1
230000002070 germicidal effect Effects 0.000 description 1
239000000665 guar gum Substances 0.000 description 1
235000010417 guar gum Nutrition 0.000 description 1
229960002154 guar gum Drugs 0.000 description 1
208000024963 hair loss Diseases 0.000 description 1
230000003676 hair loss Effects 0.000 description 1
230000003659 hair regrowth Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000003903 lactic acid esters Chemical class 0.000 description 1
LZCLXQDLBQLTDK-UHFFFAOYSA-N lactic acid ethyl ester Natural products CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 1
230000003902 lesion Effects 0.000 description 1
239000000711 locust bean gum Substances 0.000 description 1
235000010420 locust bean gum Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
FBUWSYHNBKUMSA-UHFFFAOYSA-N n,n-dimethyl-17-phenylheptadecan-1-amine Chemical compound CN(C)CCCCCCCCCCCCCCCCCC1=CC=CC=C1 FBUWSYHNBKUMSA-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
210000002374 sebum Anatomy 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000029305 taxis Effects 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000003871 white petrolatum 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Dermatology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)

LU86865A 1987-05-06 1987-05-06 Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie LU86865A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU86865A LU86865A1 (fr)	1987-05-06	1987-05-06	Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie
CA000565553A CA1304740C (fr)	1987-05-06	1988-04-29	Retinoates d'ammonium quaternaires, leur utilisation en cosmetique et endermopharmacie
AT88107228T ATE74591T1 (de)	1987-05-06	1988-05-05	Quaternaere ammonium-retinoate, ihre verwendung in der kosmetik und dermopharmazie.
US07/190,441 US4857525A (en)	1987-05-06	1988-05-05	Quaternary ammonium retinoates, their use in cosmetics and in dermopharmacy
DE8888107228T DE3869825D1 (de)	1987-05-06	1988-05-05	Quaternaere ammonium-retinoate, ihre verwendung in der kosmetik und dermopharmazie.
ES198888107228T ES2039496T3 (es)	1987-05-06	1988-05-05	Procedimiento de preparacion de retinoatos de amonio cuaternarios.
EP88107228A EP0290020B1 (de)	1987-05-06	1988-05-05	Quaternäre Ammonium-Retinoate, ihre Verwendung in der Kosmetik und Dermopharmazie
JP63110272A JP2595036B2 (ja)	1987-05-06	1988-05-06	第４級アンモニウムレチノエートおよびこれを含む組成物

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU86865A LU86865A1 (fr)	1987-05-06	1987-05-06	Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie
LU86865		1987-05-06

Publications (1)

Publication Number	Publication Date
LU86865A1 true LU86865A1 (fr)	1989-01-19

Family

ID=19730914

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86865A LU86865A1 (fr)	1987-05-06	1987-05-06	Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie

Country Status (8)

Country	Link
US (1)	US4857525A (de)
EP (1)	EP0290020B1 (de)
JP (1)	JP2595036B2 (de)
AT (1)	ATE74591T1 (de)
CA (1)	CA1304740C (de)
DE (1)	DE3869825D1 (de)
ES (1)	ES2039496T3 (de)
LU (1)	LU86865A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5057502A (en) *	1987-06-02	1991-10-15	Walsh William E	Composition and topical and systemic treatments of conditions caused by heavy, oily or greasy secretions
FR2647015B1 (fr) *	1989-05-17	1994-05-06	Cird	Gel aqueux a base d'acide retinoique et son utilisation en medecine humaine et en cosmetique
US5470567A (en) *	1989-08-24	1995-11-28	Bristol Myers Squibb Company	Synergistic skin depigmentation composition
FR2653015B1 (fr) *	1989-10-12	1993-10-29	Oreal	Composition cosmetique ou pharmaceutique pour application topique contenant au moins un derive retinouide et au moins un derive de pyrimidine, son utilisation comme medicament et procede de traitement correspondant.
US5053024A (en) *	1989-10-23	1991-10-01	Israel Dvoretzky	Application system and method for treating warts
ZA943999B (en) *	1993-06-09	1995-02-03	Lonza Ag	Quaternary ammonium and waterproofing/preservative compositions
KR20050026401A (ko) *	2002-06-17	2005-03-15	비큐론 파마세티컬스 인코포레이티드	여드름 치료를 위한 ｇｅ 2270 인자 ａ3의 아미드유도체의 용도
US8048919B2 (en) *	2004-06-28	2011-11-01	Archer Daniels Midland Company	Use of ethyl lactate as an excipient for pharmaceutical compositions
CN115232048B (zh) *	2021-04-22	2024-02-27	南京毓浠医药技术有限公司	一种离子液体及其制备方法和应用
CN117384073A (zh) *	2022-07-11	2024-01-12	南京毓浠医药技术有限公司	一种维a酸醇胺类复合物及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL58296C (de) *	1943-02-26	1946-08-16
FR1297730A (fr) *	1960-11-04	1962-07-06	Hoffmann La Roche	Préparation cosmétique
US4214000A (en) *	1978-10-30	1980-07-22	Johnson & Johnson	Zinc salt of all-trans-retinoic acid for the treatment of acne

1987
- 1987-05-06 LU LU86865A patent/LU86865A1/fr unknown
1988
- 1988-04-29 CA CA000565553A patent/CA1304740C/fr not_active Expired - Lifetime
- 1988-05-05 ES ES198888107228T patent/ES2039496T3/es not_active Expired - Lifetime
- 1988-05-05 EP EP88107228A patent/EP0290020B1/de not_active Expired - Lifetime
- 1988-05-05 AT AT88107228T patent/ATE74591T1/de active
- 1988-05-05 US US07/190,441 patent/US4857525A/en not_active Expired - Fee Related
- 1988-05-05 DE DE8888107228T patent/DE3869825D1/de not_active Expired - Lifetime
- 1988-05-06 JP JP63110272A patent/JP2595036B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0290020B1 (de)	1992-04-08
US4857525A (en)	1989-08-15
ATE74591T1 (de)	1992-04-15
JPS63287763A (ja)	1988-11-24
ES2039496T3 (es)	1993-10-01
EP0290020A1 (de)	1988-11-09
DE3869825D1 (de)	1992-05-14
JP2595036B2 (ja)	1997-03-26
CA1304740C (fr)	1992-07-07

Publication	Publication Date	Title
CA1299572C (fr)	1992-04-28	Salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie
EP0317846B1 (de)	1991-10-16	Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und lipophilen quaternären Ammoniumsalizylaten und ihre Verwendung, insbesondere bei der Behandlung von Akne
EP0335115B1 (de)	1991-11-06	Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen
EP0402266B1 (de)	1994-02-02	N-substituierte Lauramide, ihre Herstellung und sie enthaltende Zusammensetzungen
WO1986006064A1 (fr)	1986-10-23	Derives naphtaleniques a action de type retinoide, leur procede de preparation et compositions medicamenteuse et cosmetique les contenant
LU87308A1 (fr)	1990-03-13	Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux
EP0540629A1 (de)	1993-05-12	Verwendung von pyrimidin-3-oxydderivaten zur verhütung von haarausfall und deren anwendung in topischen zusammensetzungen.
LU85558A1 (fr)	1986-04-03	Nouveaux derives naphtaleniques a action retinoique,leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant
EP0498728A1 (de)	1992-08-12	Glycyl-Serine Amide und diese enthaltende kosmetische und pharmazeutische Zusammensetzungen oder Röhrmittel
EP0916652B1 (de)	2001-10-31	Neue N-Aryl-2-hydroxy-alkylamide
CA1294971C (fr)	1992-01-28	Derives benzofuranniques, leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant
LU86865A1 (fr)	1989-01-19	Nouveaux retinoates d'ammonium quaternaires,leur utilisation en cosmetique et en dermopharmacie
CA1341278C (fr)	2001-07-31	Association de derives de pyrimidine et de retinoides en composants separes pour induire et stimuler la croissance des cheveux et diminuer leur chute
FR2649697A1 (fr)	1991-01-18	Nouveaux derives d'urethanne, leur preparation et leur application notamment comme agents hydratants dans des compositions cosmetiques ou pharmaceutiques destinees au traitement des peaux seches
EP0179697B1 (de)	1989-03-22	Vitamin A-säure Derivate, Verfahren zu ihrer Herstellung und pharmazeutische und kosmetische Präparate die sie enthalten
CA2261095C (fr)	2004-01-27	Composes de la famille des 3-aryl 2,4 dioxo oxazolidines et leur utilisation en cosmetique et en pharmacie
EP0304649B1 (de)	1991-03-20	Salze von 6-Piperidino-2,4-diaminopyrimidin-3-oxyd und von Derivaten der Thiamorpholin-3-on-5-carbonsäure und deren Verwendung in kosmetischen Stoffen und als Heilmittel
EP0117176A1 (de)	1984-08-29	Zink L-Thiazolidin-4-Carboxylate, ihre Herstellung, ihre Anwendung und Zusammensetzungen die sie enthalten
CH667452A5 (fr)	1988-10-14	Derives substitues en 1 du methoxy-4 trimethyl-2,3,6 benzene, leur procede de preparation et compositions medicamenteuse et cosmetique les contenant.
BE887671A (fr)	1981-08-25	Preparations pharmaceutiques topiques contenant des sels d'acides alcane-carboxyliques ainsi que de nouveaux sels d'acides carboxyliques et leurs procedes de preparation
CH499323A (fr)	1970-11-30	Procédé de dépilation et composition cosmétique pour sa mise en oeuvre
FR2745717A1 (fr)	1997-09-12	Utilisation de n-aryl-2-hydroxyalkylamides pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute