AU2009331526B2 - Polyunsaturated fatty acid and diol ester as an anti-acne agent - Google Patents
Polyunsaturated fatty acid and diol ester as an anti-acne agent Download PDFInfo
- Publication number
- AU2009331526B2 AU2009331526B2 AU2009331526A AU2009331526A AU2009331526B2 AU 2009331526 B2 AU2009331526 B2 AU 2009331526B2 AU 2009331526 A AU2009331526 A AU 2009331526A AU 2009331526 A AU2009331526 A AU 2009331526A AU 2009331526 B2 AU2009331526 B2 AU 2009331526B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- compound
- polyunsaturated fatty
- formula
- fatty 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.)
- Ceased
Links
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 52
- -1 diol ester Chemical class 0.000 title claims description 17
- 239000000058 anti acne agent Substances 0.000 title description 3
- 229940124340 antiacne agent Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 206010000496 acne Diseases 0.000 claims abstract description 38
- 208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002537 cosmetic Substances 0.000 claims abstract description 16
- 208000008742 seborrheic dermatitis Diseases 0.000 claims abstract description 14
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 15
- 235000021342 arachidonic acid Nutrition 0.000 claims description 12
- 229940114079 arachidonic acid Drugs 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 11
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 10
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 claims description 9
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 claims description 8
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims description 8
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 claims description 8
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 7
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 7
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 235000020778 linoleic acid Nutrition 0.000 claims description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 7
- 229960004488 linolenic acid Drugs 0.000 claims description 7
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims description 6
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 6
- 235000021292 Docosatetraenoic acid Nutrition 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 6
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 5
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229940012843 omega-3 fatty acid Drugs 0.000 claims description 5
- 229940033080 omega-6 fatty acid Drugs 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 4
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 4
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 claims description 3
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 claims description 3
- HPSWUFMMLKGKDS-DNKOKRCQSA-N (2e,4e,6e,8e,10e,12e)-tetracosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O HPSWUFMMLKGKDS-DNKOKRCQSA-N 0.000 claims description 3
- FPRKGXIOSIUDSE-SYACGTDESA-N (2z,4z,6z,8z)-docosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C(O)=O FPRKGXIOSIUDSE-SYACGTDESA-N 0.000 claims description 3
- KXVFBCSUGDNXQF-DZDBOGACSA-N (2z,4z,6z,8z,10z)-tetracosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C=C/C(O)=O KXVFBCSUGDNXQF-DZDBOGACSA-N 0.000 claims description 3
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 claims description 3
- DQGMPXYVZZCNDQ-KBPWROHVSA-N (8E,10E,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O DQGMPXYVZZCNDQ-KBPWROHVSA-N 0.000 claims description 3
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 3
- DQGMPXYVZZCNDQ-UVZPLDOLSA-N Calendinsaeure Natural products CCCCCC=C/C=C/C=C/CCCCCCC(=O)O DQGMPXYVZZCNDQ-UVZPLDOLSA-N 0.000 claims description 3
- 235000021297 Eicosadienoic acid Nutrition 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 claims description 3
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 claims description 3
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 3
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 3
- XDGRAWWEIOPNRC-UHFFFAOYSA-N 3-hydroxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound OS(=O)(=O)C1(O)CC(=O)NC1=O XDGRAWWEIOPNRC-UHFFFAOYSA-N 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 241000186427 Cutibacterium acnes Species 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000002757 inflammatory effect Effects 0.000 description 13
- 230000003902 lesion Effects 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 230000000844 anti-bacterial effect Effects 0.000 description 11
- 102000004890 Interleukin-8 Human genes 0.000 description 10
- 108090001007 Interleukin-8 Proteins 0.000 description 10
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 10
- 229940096397 interleukin-8 Drugs 0.000 description 10
- 102000004882 Lipase Human genes 0.000 description 9
- 108090001060 Lipase Proteins 0.000 description 9
- 239000004367 Lipase Substances 0.000 description 9
- 235000019421 lipase Nutrition 0.000 description 9
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- HIYAVKIYRIFSCZ-CYEMHPAKSA-N 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid Chemical compound O=C([C@@H](C)[C@H]1O[C@@]2([C@@H](C[C@H]1C)C)O[C@@H]([C@@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C1=CC=CN1 HIYAVKIYRIFSCZ-CYEMHPAKSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 210000002510 keratinocyte Anatomy 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000003385 bacteriostatic effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 230000028709 inflammatory response Effects 0.000 description 5
- 229940040452 linolenate Drugs 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229940031723 1,2-octanediol Drugs 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000003974 emollient agent Substances 0.000 description 4
- 230000003325 follicular Effects 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 4
- 229940055019 propionibacterium acne Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000034309 Bacterial disease carrier Diseases 0.000 description 3
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 210000002374 sebum Anatomy 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000035985 Body Odor Diseases 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 102000034527 Retinoid X Receptors Human genes 0.000 description 2
- 108010038912 Retinoid X Receptors Proteins 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002066 eicosanoids Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 230000003960 inflammatory cascade Effects 0.000 description 2
- 150000002617 leukotrienes Chemical class 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- CGNJFUJNEYIYRZ-UHFFFAOYSA-N nonane-1,3-diol Chemical compound CCCCCCC(O)CCO CGNJFUJNEYIYRZ-UHFFFAOYSA-N 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229940068977 polysorbate 20 Drugs 0.000 description 2
- 230000000770 proinflammatory effect Effects 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- FBWMYSQUTZRHAT-HZJYTTRNSA-N (9z,12z)-octadeca-9,12-dienoyl chloride Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O FBWMYSQUTZRHAT-HZJYTTRNSA-N 0.000 description 1
- MXOAEAUPQDYUQM-QMMMGPOBSA-N (S)-chlorphenesin Chemical compound OC[C@H](O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-QMMMGPOBSA-N 0.000 description 1
- UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- PBPJPXBULMMAEB-UHFFFAOYSA-N 1-[(e)-diazomethyl]anthracene Chemical compound C1=CC=C2C=C3C(C=[N+]=[N-])=CC=CC3=CC2=C1 PBPJPXBULMMAEB-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 1
- CGNXUYGEXJMXDY-LNCSVHMCSA-N 2-hydroxyoctyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CCCCCCC(O)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC CGNXUYGEXJMXDY-LNCSVHMCSA-N 0.000 description 1
- NKFMDKGUVAMJFH-MURFETPASA-N 2-hydroxypentyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(O)CCC NKFMDKGUVAMJFH-MURFETPASA-N 0.000 description 1
- YEWUJYJHVRTNQK-AGRJPVHOSA-N 2-hydroxypentyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CCCC(O)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC YEWUJYJHVRTNQK-AGRJPVHOSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- OSRNFRZCFYTXSF-YSTUJMKBSA-N 3-hydroxybutyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCCC(C)O OSRNFRZCFYTXSF-YSTUJMKBSA-N 0.000 description 1
- GDSZFHRSSZGYJV-LNCSVHMCSA-N 3-hydroxynonyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CCCCCCC(O)CCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC GDSZFHRSSZGYJV-LNCSVHMCSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241001340526 Chrysoclista linneella Species 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- 241000555676 Malassezia Species 0.000 description 1
- 241000555688 Malassezia furfur Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 101150091206 Nfkbia gene Proteins 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 101150014691 PPARA gene Proteins 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 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 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003255 anti-acne Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HOZZFGSUJJRSNV-UHFFFAOYSA-N butane-1,3-diol nonane-1,3-diol octane-1,2-diol pentane-1,2-diol Chemical compound C(CC(CCCCCC)O)O.C(C(CCCCCC)O)O.C(C(CCC)O)O.C(CC(C)O)O HOZZFGSUJJRSNV-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003993 chlorphenesin Drugs 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- PKPOVTYZGGYDIJ-UHFFFAOYSA-N dioctyl carbonate Chemical compound CCCCCCCCOC(=O)OCCCCCCCC PKPOVTYZGGYDIJ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical class CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 108091008569 nuclear steroid hormone receptors Proteins 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000006014 omega-3 oil Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- RPENMORRBUTCPR-UHFFFAOYSA-M sodium;1-hydroxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].ON1C(=O)CC(S([O-])(=O)=O)C1=O RPENMORRBUTCPR-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0858967 | 2008-12-22 | ||
| FR0858967A FR2940281B1 (fr) | 2008-12-22 | 2008-12-22 | Ester de diol et d'acide gras polyinsature comme agent anti-acne |
| PCT/EP2009/067701 WO2010072738A1 (fr) | 2008-12-22 | 2009-12-21 | Ester de diol et d'acide gras polyinsature comme agent anti-acne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009331526A1 AU2009331526A1 (en) | 2010-07-01 |
| AU2009331526B2 true AU2009331526B2 (en) | 2013-10-24 |
Family
ID=40875013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009331526A Ceased AU2009331526B2 (en) | 2008-12-22 | 2009-12-21 | Polyunsaturated fatty acid and diol ester as an anti-acne agent |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8623916B2 (enExample) |
| EP (1) | EP2379484B1 (enExample) |
| JP (1) | JP5587333B2 (enExample) |
| KR (1) | KR101676055B1 (enExample) |
| CN (1) | CN102256930B (enExample) |
| AU (1) | AU2009331526B2 (enExample) |
| BR (1) | BRPI0923494B1 (enExample) |
| CA (1) | CA2747681C (enExample) |
| CL (1) | CL2011001539A1 (enExample) |
| CO (1) | CO6390033A2 (enExample) |
| ES (1) | ES2424088T3 (enExample) |
| FR (1) | FR2940281B1 (enExample) |
| GE (1) | GEP20135820B (enExample) |
| IL (1) | IL213646A (enExample) |
| MA (1) | MA32810B1 (enExample) |
| MX (1) | MX2011006659A (enExample) |
| MY (1) | MY151002A (enExample) |
| NZ (1) | NZ593781A (enExample) |
| PL (1) | PL2379484T3 (enExample) |
| PT (1) | PT2379484E (enExample) |
| RU (1) | RU2524779C2 (enExample) |
| SG (1) | SG172342A1 (enExample) |
| TN (1) | TN2011000237A1 (enExample) |
| UA (1) | UA103645C2 (enExample) |
| WO (1) | WO2010072738A1 (enExample) |
| ZA (1) | ZA201103509B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9907812B2 (en) | 2011-06-22 | 2018-03-06 | Vyome Biosciences Pvt. Ltd. | Conjugate-based antifungal and antibacterial prodrugs |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2983858B1 (fr) * | 2011-12-08 | 2014-01-03 | Fabre Pierre Dermo Cosmetique | Nouveaux composes inhibiteurs de la lipogenese |
| CA2920457A1 (en) * | 2013-08-08 | 2015-02-12 | Galderm Therapeutics Ltd. | Anti-acne compositions comprising bile acid-fatty acid conjugates |
| FR3033135B1 (fr) * | 2015-02-27 | 2018-03-16 | Pierre Fabre Dermo-Cosmetique | Association d'un retinoide et d'un ester de diol et d'acide gras polyinsature |
| FR3053253B1 (fr) * | 2016-07-01 | 2020-01-17 | Pierre Fabre Dermo-Cosmetique | Nouvel extrait d'akenes de silybum marianum et ses utilisations en dermatologie et dermo-cosmetique |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998013330A1 (en) * | 1996-09-26 | 1998-04-02 | Scotia Holdings Plc | Esters of unsaturated fatty acids |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5534762B2 (enExample) | 1975-02-07 | 1980-09-09 | ||
| DE4240674C2 (de) | 1992-11-26 | 1999-06-24 | Schuelke & Mayr Gmbh | Desodorierende Wirkstoffe |
| AU683027B2 (en) * | 1993-01-27 | 1997-10-30 | Scotia Holdings Plc | Triglycerides |
| MY118354A (en) | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| JPH09110818A (ja) * | 1995-10-16 | 1997-04-28 | Sanshin Chem Ind Co Ltd | 1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド塩酸塩の製造方法 |
| ES2176692T3 (es) | 1996-02-21 | 2002-12-01 | Stoa Sa | Composiciones cosmeticas, dermofarmaceuticas o veterinarias para el tratamiento aseptico de la piel humana o animal. |
| GB9622636D0 (en) | 1996-10-30 | 1997-01-08 | Scotia Holdings Plc | Presentation of bioactives |
| GB9710351D0 (en) * | 1997-05-20 | 1997-07-16 | Scotia Holdings Plc | Glucosamine fatty acids |
| WO2001001980A1 (en) * | 1999-07-06 | 2001-01-11 | The Regents Of The University Of California | Methods for the amelioration of neuropsychiatric disorders by inhibiting the inactivating transport of endogenous cannabinoid substances |
| GB9927629D0 (en) * | 1999-11-24 | 2000-01-19 | Croda Int Plc | Compounds |
| ES2208498T3 (es) | 2001-06-22 | 2004-06-16 | SYMRISE GMBH & CO. KG | Uso de 1,2-decanodiol contra germenes causantes de olores corporales desagradables. |
| US20070265352A1 (en) | 2002-02-19 | 2007-11-15 | Joachim Roeding | Synergistic mixtures of at least one 1,2 alkanediol such as 1,2-hexanediol and 1,2-octanediol with a further compound having antimicrobial properties |
| DE10206759A1 (de) | 2002-02-19 | 2003-08-28 | Dragoco Gerberding Co Ag | Synergistische Mischungen von 1,2-Alkandiolen |
| SE0301862D0 (sv) | 2003-06-26 | 2003-06-26 | Jan Faergeman | Sätt att inhibera tillväxten av mot antibiotika resistenta bakterier |
| DE102004031210A1 (de) * | 2004-06-28 | 2006-02-09 | Trommsdorff Gmbh & Co. Kg | MLV-Kosmetikum |
| DE10341179A1 (de) | 2003-09-06 | 2005-03-31 | Beiersdorf Ag | Wirkstoffkombination gegen Akne |
| US7935732B2 (en) | 2004-04-08 | 2011-05-03 | Isp Investments Inc. | Antimicrobial compositions |
| ES2352744T3 (es) * | 2004-04-27 | 2011-02-22 | Akzo Nobel Coatings International Bv | Pintura pigmentada que se desprende a tiras. |
| JP2006056795A (ja) * | 2004-08-18 | 2006-03-02 | Suntory Ltd | 6−o−pufaアスコルビン酸エステルを含有する皮膚化粧料並びに飲食品 |
| DE102006044849A1 (de) * | 2006-09-22 | 2008-04-03 | Symrise Gmbh & Co. Kg | Dekonjugierte Alkadiensäureester als Riech- und/oder Aromastoffe |
-
2008
- 2008-12-22 FR FR0858967A patent/FR2940281B1/fr not_active Expired - Fee Related
-
2009
- 2009-12-21 CA CA2747681A patent/CA2747681C/fr active Active
- 2009-12-21 ES ES09797045T patent/ES2424088T3/es active Active
- 2009-12-21 NZ NZ593781A patent/NZ593781A/xx not_active IP Right Cessation
- 2009-12-21 JP JP2011541506A patent/JP5587333B2/ja active Active
- 2009-12-21 CN CN200980151867.4A patent/CN102256930B/zh active Active
- 2009-12-21 UA UAA201108993A patent/UA103645C2/uk unknown
- 2009-12-21 SG SG2011046067A patent/SG172342A1/en unknown
- 2009-12-21 BR BRPI0923494A patent/BRPI0923494B1/pt not_active IP Right Cessation
- 2009-12-21 MY MYPI20112827 patent/MY151002A/en unknown
- 2009-12-21 AU AU2009331526A patent/AU2009331526B2/en not_active Ceased
- 2009-12-21 EP EP09797045.3A patent/EP2379484B1/fr active Active
- 2009-12-21 RU RU2011128264/04A patent/RU2524779C2/ru not_active IP Right Cessation
- 2009-12-21 PT PT97970453T patent/PT2379484E/pt unknown
- 2009-12-21 KR KR1020117013471A patent/KR101676055B1/ko active Active
- 2009-12-21 MX MX2011006659A patent/MX2011006659A/es active IP Right Grant
- 2009-12-21 PL PL09797045T patent/PL2379484T3/pl unknown
- 2009-12-21 GE GEAP200912313A patent/GEP20135820B/en unknown
- 2009-12-21 US US13/130,900 patent/US8623916B2/en active Active
- 2009-12-21 WO PCT/EP2009/067701 patent/WO2010072738A1/fr not_active Ceased
-
2011
- 2011-05-12 TN TN2011000237A patent/TN2011000237A1/fr unknown
- 2011-05-13 ZA ZA2011/03509A patent/ZA201103509B/en unknown
- 2011-05-20 MA MA33865A patent/MA32810B1/fr unknown
- 2011-06-15 CO CO11074814A patent/CO6390033A2/es not_active Application Discontinuation
- 2011-06-19 IL IL213646A patent/IL213646A/en active IP Right Grant
- 2011-06-21 CL CL2011001539A patent/CL2011001539A1/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998013330A1 (en) * | 1996-09-26 | 1998-04-02 | Scotia Holdings Plc | Esters of unsaturated fatty acids |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9907812B2 (en) | 2011-06-22 | 2018-03-06 | Vyome Biosciences Pvt. Ltd. | Conjugate-based antifungal and antibacterial prodrugs |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2009331526B2 (en) | Polyunsaturated fatty acid and diol ester as an anti-acne agent | |
| HU226010B1 (en) | Cosmetical compositions containing unsaturated aliphatic dicarboxylic acids and/or derivates thereof, process for their preparation and their cosmetical use | |
| US8835496B2 (en) | Dermatological compositions comprising a fat or oil of an essential fatty acid triglyceride for treating of skin, mucosa, hair, nails, or scalp | |
| KR20180124432A (ko) | 항산화, 항균 및 항염증 효능을 지닌 여드름 개선용 조성물 | |
| WO2018084112A1 (ja) | アクネ菌株選択的抗菌剤 | |
| KR101851010B1 (ko) | 항염증 및 항균활성을 가지는 조성물 | |
| KR101430084B1 (ko) | 프로피오니박테리움 아크네스에 작용하는 신규한 항생 펩타이드 및 이의 용도 | |
| CN115381803A (zh) | 类视黄醇组合物及其应用 | |
| JP2020514307A (ja) | 化合物及び使用方法 | |
| WO2010041417A1 (ja) | 皮膚外用剤 | |
| WO2014117056A1 (en) | Therapeutic compounds | |
| JP2009132645A (ja) | アシル化ハイドロキノン配糖体及びそれを含有する皮膚外用剤 | |
| JP2009132644A (ja) | 面皰炎症抑制剤及びこれを含む皮膚外用剤 | |
| KR102160306B1 (ko) | 피부미백제 | |
| WO2013085346A1 (ko) | 신규한 피토스핑고신 유도체 및 이를 포함하는 염증성 피부질환, 자가면역질환 및 피부과다각화증질환 예방 및 치료용 조성물 | |
| US8729312B2 (en) | Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne | |
| WO2023131362A1 (en) | Phenylpropanoid derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |