ES2207023T3 - Composiciones que comprenden una combinacion de una base esfingoide libre y una ceramida y utilizacion de las mismas. - Google Patents
Composiciones que comprenden una combinacion de una base esfingoide libre y una ceramida y utilizacion de las mismas.Info
- Publication number
- ES2207023T3 ES2207023T3 ES98963566T ES98963566T ES2207023T3 ES 2207023 T3 ES2207023 T3 ES 2207023T3 ES 98963566 T ES98963566 T ES 98963566T ES 98963566 T ES98963566 T ES 98963566T ES 2207023 T3 ES2207023 T3 ES 2207023T3
- Authority
- ES
- Spain
- Prior art keywords
- ceramide
- composition
- skin
- composition according
- group
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 229940106189 ceramide Drugs 0.000 title claims abstract description 71
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 title claims abstract description 45
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 title claims abstract description 45
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 title claims abstract description 45
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 title claims abstract description 43
- 150000003410 sphingosines Chemical class 0.000 claims abstract description 26
- 230000000699 topical effect Effects 0.000 claims abstract description 13
- 208000015181 infectious disease Diseases 0.000 claims abstract description 8
- 230000002458 infectious effect Effects 0.000 claims abstract description 8
- 150000001783 ceramides Chemical class 0.000 claims description 27
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 claims description 19
- 229940033329 phytosphingosine Drugs 0.000 claims description 17
- 230000004888 barrier function Effects 0.000 claims description 16
- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 claims description 16
- -1 lipid compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 claims description 3
- OTKJDMGTUTTYMP-UHFFFAOYSA-N dihydrosphingosine Natural products CCCCCCCCCCCCCCCC(O)C(N)CO OTKJDMGTUTTYMP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- 230000009703 regulation of cell differentiation Effects 0.000 claims description 3
- OTKJDMGTUTTYMP-ZWKOTPCHSA-N sphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO OTKJDMGTUTTYMP-ZWKOTPCHSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000033228 biological regulation Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000024245 cell differentiation Effects 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 230000021014 regulation of cell growth Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000004069 differentiation Effects 0.000 abstract description 7
- 208000017520 skin disease Diseases 0.000 abstract description 6
- 230000008591 skin barrier function Effects 0.000 abstract description 2
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 230000008470 skin growth Effects 0.000 abstract 1
- 210000003491 skin Anatomy 0.000 description 30
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 14
- 150000002632 lipids Chemical class 0.000 description 13
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- ATGQXSBKTQANOH-UWVGARPKSA-N N-oleoylphytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(=O)CCCCCCC\C=C/CCCCCCCC ATGQXSBKTQANOH-UWVGARPKSA-N 0.000 description 11
- 239000006071 cream Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 206010040844 Skin exfoliation Diseases 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 229930183167 cerebroside Natural products 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 210000000434 stratum corneum Anatomy 0.000 description 6
- BBAFBDLICMHBNU-MFZOPHKMSA-N N-(2-hydroxyoctadecanoyl)-4-hydroxysphinganine Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC BBAFBDLICMHBNU-MFZOPHKMSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001784 cerebrosides Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000003974 emollient agent Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 210000002510 keratinocyte Anatomy 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 150000003904 phospholipids Chemical class 0.000 description 4
- 230000026267 regulation of growth Effects 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MIUIRGGKIICMBP-NFOZDHADSA-N [27-oxo-27-[[(2s,3s,4r)-1,3,4-trihydroxyoctadecan-2-yl]amino]heptacosyl] octadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC MIUIRGGKIICMBP-NFOZDHADSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229940048864 ceramide 1 Drugs 0.000 description 3
- BHYOQNUELFTYRT-DPAQBDIFSA-N cholesterol sulfate Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 BHYOQNUELFTYRT-DPAQBDIFSA-N 0.000 description 3
- 210000000736 corneocyte Anatomy 0.000 description 3
- 230000035618 desquamation Effects 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 241000235648 Pichia Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 206010048222 Xerosis Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229940099417 ceramide 2 Drugs 0.000 description 2
- 229940044176 ceramide 3 Drugs 0.000 description 2
- RIZIAUKTHDLMQX-UHFFFAOYSA-N cerebroside D Natural products CCCCCCCCCCCCCCCCC(O)C(=O)NC(C(O)C=CCCC=C(C)CCCCCCCCC)COC1OC(CO)C(O)C(O)C1O RIZIAUKTHDLMQX-UHFFFAOYSA-N 0.000 description 2
- 229940073669 ceteareth 20 Drugs 0.000 description 2
- 229940081733 cetearyl alcohol Drugs 0.000 description 2
- 229940080277 cholesteryl sulfate Drugs 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001924 fatty-acyl group Chemical group 0.000 description 2
- 150000002270 gangliosides Chemical class 0.000 description 2
- 229940075529 glyceryl stearate Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- SZUJJDLBXJCDNT-ZCNNSNEGSA-N n-[(2s,3s,4r)-1,3,4-trihydroxyoctadecan-2-yl]acetamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(C)=O SZUJJDLBXJCDNT-ZCNNSNEGSA-N 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229930000756 phytoceramide Natural products 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
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- 239000001294 propane Substances 0.000 description 2
- 235000013849 propane Nutrition 0.000 description 2
- 150000003873 salicylate salts Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 206010040872 skin infection Diseases 0.000 description 2
- 229950011392 sorbitan stearate Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
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- 239000008117 stearic acid Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- HRANPRDGABOKNQ-ORGXEYTDSA-N (1r,3r,3as,3br,7ar,8as,8bs,8cs,10as)-1-acetyl-5-chloro-3-hydroxy-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,7,7a,8,8a,8b,8c,9,10,10a-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-1-yl acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1[C@H](O)C[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 HRANPRDGABOKNQ-ORGXEYTDSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
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- ZQCIPRGNRQXXSK-UHFFFAOYSA-N 1-octadecoxypropan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCOCC(C)O ZQCIPRGNRQXXSK-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 1
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97203824 | 1997-12-05 | ||
| EP97203824 | 1997-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2207023T3 true ES2207023T3 (es) | 2004-05-16 |
Family
ID=8229019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98963566T Expired - Lifetime ES2207023T3 (es) | 1997-12-05 | 1998-12-07 | Composiciones que comprenden una combinacion de una base esfingoide libre y una ceramida y utilizacion de las mismas. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20030059447A1 (enExample) |
| EP (1) | EP0975325B1 (enExample) |
| JP (1) | JP2001510487A (enExample) |
| KR (1) | KR100639531B1 (enExample) |
| CN (1) | CN1112916C (enExample) |
| BR (1) | BRPI9807124B8 (enExample) |
| DE (1) | DE69818242T2 (enExample) |
| ES (1) | ES2207023T3 (enExample) |
| WO (1) | WO1999029293A1 (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6306383B1 (en) * | 1998-09-16 | 2001-10-23 | Wilson T Crandall | Method for topical treatment of scars with protein kinase C inhibitors |
| JP4037577B2 (ja) * | 1999-10-07 | 2008-01-23 | ロレアル | 少なくとも１種のカチオン界面活性剤、液体脂肪アルコールおよびセラミド型の化合物を含む化粧品用組成物およびこれを用いた方法 |
| US6493559B1 (en) * | 2000-01-07 | 2002-12-10 | Motorola, Inc. | Method for receiving SMSCB messages during GPRS/EDGE data transfer mode |
| JP4391668B2 (ja) | 2000-06-06 | 2009-12-24 | 高砂香料工業株式会社 | 液晶構造を有する脂質組成物 |
| JP4619489B2 (ja) * | 2000-06-13 | 2011-01-26 | 花王株式会社 | 抗かゆみ皮膚外用剤 |
| CA2441893C (en) | 2001-03-26 | 2015-01-20 | Dana-Farber Cancer Institute, Inc. | Method of attenuating reactions to skin irritants |
| US6680062B2 (en) | 2001-10-05 | 2004-01-20 | Color Access, Inc. | Anti-irritating rosacea treatment |
| JP2003155231A (ja) * | 2001-11-20 | 2003-05-27 | Kikkoman Corp | 医薬及び抗アレルギー剤 |
| TWI230073B (en) * | 2001-12-10 | 2005-04-01 | Kao Corp | Ceramide emulsifier |
| FR2834216B1 (fr) * | 2001-12-27 | 2004-04-30 | Pharmascience Lab | Composition cosmetique ou pharmaceutique comprenant au moins une oxazoline pour inhiber la migration des cellules de langerhans, et ses utilisations |
| FR2834213B1 (fr) | 2001-12-27 | 2004-06-04 | Pharmascience Lab | Composition cosmetique ou pharmaceutique comprenant au moins une alcanolamide pour inhiber la migration des cellules de langerhans, et ses utilisations |
| KR100487113B1 (ko) * | 2002-08-03 | 2005-05-03 | 대한민국(관리부서:농촌진흥청) | 백강잠 101ａ로부터 분리, 정제한 뇌신경성장 촉진물질(4ｅ, 6ｅ, 2ｓ,3ｒ)-2-ｎ-도코사노일-4,6-테트라데카스핀가디에닌 |
| KR100487112B1 (ko) * | 2002-08-03 | 2005-05-03 | 대한민국(관리부서:농촌진흥청) | 백강잠 101ａ로부터 분리, 정제한 뇌신경성장 촉진물질(4ｅ, 6ｅ, 2ｓ,3ｒ)-2-ｎ-아이코사노일-4,6-테트라데카스핀게닌 |
| JP4504195B2 (ja) * | 2002-11-15 | 2010-07-14 | 株式会社コーセー | 半透明化粧料 |
| DE10255554A1 (de) | 2002-11-28 | 2004-06-17 | Goldschmidt Ag | Emulgator-Wachs-Gele auf Wasserbasis |
| GB0301395D0 (en) * | 2003-01-21 | 2003-02-19 | Univ Aston | Inflammatory disorder treatment |
| FR2855047B1 (fr) * | 2003-05-19 | 2007-11-30 | Oreal | Composition comprenant une base sphingoide, un activateur de la voie des 4-et/ou des 6-hydroxylases et un acide gras, utilisation pour renforcer la fonction barriere de la peau |
| JP3967292B2 (ja) * | 2003-06-10 | 2007-08-29 | 花王株式会社 | 油中水型乳化組成物 |
| KR101153576B1 (ko) * | 2003-06-10 | 2012-06-11 | 가오 가부시키가이샤 | 수중유형 유화 화장료 |
| US20070104774A1 (en) * | 2003-11-11 | 2007-05-10 | Sunki Kim | Method for preparing phytosphingosine liposome composition |
| EP1817004A2 (en) * | 2004-11-15 | 2007-08-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Combination therapy associating preferably a ceramide with a cytotoxic drug |
| JP4832000B2 (ja) * | 2005-06-02 | 2011-12-07 | 花王株式会社 | 油中水型乳化組成物 |
| JP2007001950A (ja) * | 2005-06-27 | 2007-01-11 | Pola Chem Ind Inc | セラミド含有皮膚外用剤 |
| JP2007104926A (ja) * | 2005-10-12 | 2007-04-26 | Hokkaido Univ | セラミド合成酵素ＬＡＳＳ６を用いたフィトセラミドおよびαハイドロキシセラミドの製造方法 |
| EP2056824A4 (en) * | 2006-08-09 | 2009-09-23 | Lipo Chemicals Inc | TOPICAL CERAMIDE COMPOSITIONS AND METHODS OF USE |
| ATE468100T1 (de) * | 2006-10-13 | 2010-06-15 | Evonik Goldschmidt Gmbh | Hautbehandlungszusammensetzung |
| CA2699454C (en) * | 2007-08-27 | 2012-07-24 | Auxagen, Inc. | Methods for inhibiting tgf-.beta. |
| CN101288640B (zh) * | 2008-05-23 | 2010-12-22 | 海南京润珍珠生物技术股份有限公司 | 一种添加珍珠水解液脂质体的祛痘精华液 |
| WO2010033507A1 (en) * | 2008-09-16 | 2010-03-25 | St. Louis University | Method of enhancing tgf-beta signalling |
| US9445975B2 (en) | 2008-10-03 | 2016-09-20 | Access Business Group International, Llc | Composition and method for preparing stable unilamellar liposomal suspension |
| JP5503130B2 (ja) * | 2008-10-20 | 2014-05-28 | ユニチカ株式会社 | コラーゲン産生促進剤 |
| FR2963233B1 (fr) | 2010-07-28 | 2014-03-14 | Oreal | Procede pour diminuer les hyperpigmentations post-reactionnelles |
| FR2972112B1 (fr) * | 2011-03-01 | 2020-11-06 | Oreal | Utilisation d'un compose pour le traitement des dermatoses inflammatoires |
| FR2972110B1 (fr) * | 2011-03-01 | 2013-11-15 | Oreal | Procede de traitement cosmetique des rougeurs cutanees |
| NZ701958A (en) * | 2012-05-16 | 2016-08-26 | Archer Daniels Midland Co | Emulsifier for solubilizing polar solvents in oils and polyols |
| EP2948004A1 (en) * | 2013-01-24 | 2015-12-02 | Danstar Ferment AG | Yeast cell walls comprising vitamin d2, uses thereof and method of producing the same |
| US9511144B2 (en) | 2013-03-14 | 2016-12-06 | The Proctor & Gamble Company | Cosmetic compositions and methods providing enhanced penetration of skin care actives |
| KR101682452B1 (ko) * | 2015-03-04 | 2016-12-05 | 주식회사 지오코스 | 피부장벽 회복을 위한 액정 베이스 및 이를 포함하는 화장료 조성물 |
| AU2016100423A4 (en) * | 2015-11-05 | 2016-07-21 | Macau University Of Science And Technology | Method of isolating sphingolipids from cordyceps and their use |
| CN105496886B (zh) * | 2015-12-29 | 2019-06-25 | 苏州工业园区安诺科斯化妆品研发有限公司 | 植物鞘氨醇护肤液 |
| CN106420605A (zh) * | 2016-09-23 | 2017-02-22 | 苏州药基美研医药科技有限公司 | 基于拟神经酰胺和丹皮酚的皮肤外用制剂及其生产方法 |
| ES2832555T3 (es) | 2017-03-27 | 2021-06-10 | Evonik Operations Gmbh | Procedimiento y producto para la preparación de formulaciones con contenido en ceramida |
| CN109966179A (zh) * | 2017-12-27 | 2019-07-05 | 太阳星光齿磨公司 | 化妆水组合物 |
| KR101899413B1 (ko) * | 2018-05-03 | 2018-09-18 | 주식회사 케어사이드 | 피부 감염의 예방 또는 치료용 조성물 |
| JP6602945B1 (ja) * | 2018-12-18 | 2019-11-06 | 株式会社ジェヌインＲ＆Ｄ | セラミド分散組成物 |
| US20200345611A1 (en) * | 2019-04-30 | 2020-11-05 | Evonik Operations Gmbh | Composition comprising at least one ceramide, at least one sphingoid base and triethyl citrate |
| CN110742842B (zh) * | 2019-11-12 | 2022-09-13 | 医美生物科技(上海)有限公司 | 一种延缓皮肤老化的精华组合物及其制备方法 |
| CA3172272A1 (en) * | 2020-03-17 | 2021-09-23 | Enzo Biochem, Inc. | Sphingosine pathway modulating compounds for the treatment of coronavirus infection |
| KR102592150B1 (ko) * | 2020-07-09 | 2023-10-20 | 크로다코리아 주식회사 | 살리실산 유도체를 포함하는 신규한 스핑고지질 및 이를 포함하는 조성물 |
| KR102503769B1 (ko) * | 2020-07-10 | 2023-02-27 | 솔루스바이오텍 주식회사 | 측쇄 지방산을 포함하는 신규한 스핑고지질과 그의 용도 |
| KR102502487B1 (ko) * | 2020-07-14 | 2023-02-23 | 솔루스바이오텍 주식회사 | 신규한 스핑고지질 및 이를 포함하는 피부외용제 조성물 |
| EP3981378A1 (de) * | 2020-10-09 | 2022-04-13 | Evonik Operations GmbH | Zusammensetzungen enthaltend ceramid, polyglycerincarbonsäureester und cholesterol |
| JP2024504517A (ja) * | 2021-01-20 | 2024-01-31 | 味の素株式会社 | 化粧料組成物 |
| WO2022231448A1 (en) | 2021-04-30 | 2022-11-03 | Carbocode S.A. | Topical compositions comprising (glyco)sphingolipids and/or (glyco)ceramides |
| JP2023033269A (ja) * | 2021-08-28 | 2023-03-10 | ブルネエズ株式会社 | 外用組成物 |
| CN115894270B (zh) * | 2022-10-10 | 2024-09-06 | 深圳市迪克曼生物科技有限公司 | 一种神经酰胺及其制备方法和应用 |
| CN117285432A (zh) * | 2023-02-02 | 2023-12-26 | 深圳市迪克曼生物科技有限公司 | 亚麻籽油神经酰胺及其合成方法与用途 |
| CN116003288A (zh) * | 2023-02-02 | 2023-04-25 | 深圳市迪克曼生物科技有限公司 | 南美油藤油神经酰胺及其合成方法与用途 |
| CN116041205A (zh) * | 2023-02-02 | 2023-05-02 | 深圳市迪克曼生物科技有限公司 | 琉璃苣油神经酰胺及其合成方法与用途 |
| EP4512485A1 (en) | 2023-08-25 | 2025-02-26 | Evonik Operations GmbH | Composition comprising ceramide, glycerol and organic acid |
| WO2025119790A1 (en) | 2023-12-07 | 2025-06-12 | Evonik Operations Gmbh | Composition comprising ceramide and triglyceride |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6126000A (ja) | 1984-07-14 | 1986-02-05 | Furuta Denki Kk | 高温気体移送用送風機 |
| US5565207A (en) * | 1990-09-19 | 1996-10-15 | Pola Kasei Kogyo Kabushiki Kaisha | Scalp moisturizer and external skin preparation |
| DE69307131T2 (de) | 1992-04-03 | 1997-04-24 | Gist Brocades Nv | Selektive n-acylation von aminoalkoholen |
| ATE192928T1 (de) | 1992-06-19 | 2000-06-15 | Univ California | Lipide zur epidermalen befeuchtung und zur wiederherstellung der barrierefunktion |
| NZ257361A (en) * | 1992-11-03 | 1996-11-26 | Quest Int | Cosmetic composition containing a phytosphingosine-containing ceramide |
| GB9308103D0 (en) * | 1993-04-20 | 1993-06-02 | Unilever Plc | Cosmetic composition |
| EP0725772B1 (en) | 1993-10-28 | 2003-08-20 | Cosmoferm B.V. | Phytosphingosine-based ceramide i analogs |
| WO1995025716A1 (en) | 1994-03-18 | 1995-09-28 | Gist-Brocades B.V. | Linoleoylamide based ceramide derivative and its use in cosmetic preparations for the treatment of dry skin |
| JPH08512060A (ja) * | 1994-04-27 | 1996-12-17 | ギスト ブロカデス ベスローテン フェンノートシャップ | 短鎖２−ヒドロキシカルボン酸をベースにしたセラミド誘導体 |
| AU3699695A (en) | 1994-09-30 | 1996-04-26 | Gist-Brocades B.V. | Ceramide 3 derivatives based on monounsaturated fatty acids |
| JPH09508925A (ja) * | 1994-11-28 | 1997-09-09 | ギスト ブロカデス ベスローテン フェンノートシャップ | セラミド類の局所適用 |
| FR2730410B1 (fr) * | 1995-02-15 | 1997-03-21 | Oreal | Composition cosmetique comprenant une association de ceramides et son utilisation |
| FR2732680B1 (fr) * | 1995-04-05 | 1997-05-09 | Oreal | Composes de type ceramides, leur procede de preparation et leur utilisation |
| AU6986496A (en) * | 1995-09-01 | 1997-03-27 | Gist-Brocades B.V. | Retinoylamide based derivatives of sphingoid bases |
-
1998
- 1998-12-07 CN CN98802328A patent/CN1112916C/zh not_active Expired - Lifetime
- 1998-12-07 EP EP98963566A patent/EP0975325B1/en not_active Expired - Lifetime
- 1998-12-07 KR KR1019997006968A patent/KR100639531B1/ko not_active Expired - Lifetime
- 1998-12-07 JP JP53009599A patent/JP2001510487A/ja active Pending
- 1998-12-07 US US09/367,033 patent/US20030059447A1/en not_active Abandoned
- 1998-12-07 BR BRPI9807124A patent/BRPI9807124B8/pt not_active IP Right Cessation
- 1998-12-07 ES ES98963566T patent/ES2207023T3/es not_active Expired - Lifetime
- 1998-12-07 DE DE69818242T patent/DE69818242T2/de not_active Expired - Lifetime
- 1998-12-07 WO PCT/EP1998/008121 patent/WO1999029293A1/en not_active Ceased
-
2003
- 2003-06-17 US US10/463,277 patent/US7597899B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9807124A (pt) | 2000-01-25 |
| JP2001510487A (ja) | 2001-07-31 |
| BR9807124B1 (pt) | 2013-07-09 |
| US20030215414A1 (en) | 2003-11-20 |
| WO1999029293A1 (en) | 1999-06-17 |
| EP0975325A1 (en) | 2000-02-02 |
| BRPI9807124B8 (pt) | 2021-05-25 |
| KR100639531B1 (ko) | 2006-10-27 |
| DE69818242T2 (de) | 2004-07-01 |
| CN1246789A (zh) | 2000-03-08 |
| DE69818242D1 (de) | 2003-10-23 |
| KR20000070718A (ko) | 2000-11-25 |
| US20030059447A1 (en) | 2003-03-27 |
| CN1112916C (zh) | 2003-07-02 |
| US7597899B2 (en) | 2009-10-06 |
| EP0975325B1 (en) | 2003-09-17 |
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