JPH0680567A - Agent for prevention and treatment of dandruff - Google Patents
Agent for prevention and treatment of dandruffInfo
- Publication number
- JPH0680567A JPH0680567A JP4233607A JP23360792A JPH0680567A JP H0680567 A JPH0680567 A JP H0680567A JP 4233607 A JP4233607 A JP 4233607A JP 23360792 A JP23360792 A JP 23360792A JP H0680567 A JPH0680567 A JP H0680567A
- Authority
- JP
- Japan
- Prior art keywords
- dandruff
- compound
- agent
- azole derivative
- 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.)
- Pending
Links
- 208000001840 Dandruff Diseases 0.000 title claims abstract description 16
- 238000011282 treatment Methods 0.000 title abstract description 5
- 230000002265 prevention Effects 0.000 title abstract 2
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000000069 prophylactic effect Effects 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- -1 imino, methylimino Chemical group 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- MQILKXUBPIQNQI-RQZCQDPDSA-N 1-[2-(2,4-dichlorophenyl)-2-[(2e)-3,7-dimethylocta-2,6-dienyl]sulfanylethyl]imidazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(SC/C=C(C)/CCC=C(C)C)CN1C=CN=C1 MQILKXUBPIQNQI-RQZCQDPDSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000006071 cream Substances 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
- JAUFWPNLLLUYNV-UHFFFAOYSA-N 3-(16-methylheptadecoxy)propane-1,2-diol Chemical compound CC(C)CCCCCCCCCCCCCCCOCC(O)CO JAUFWPNLLLUYNV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JBBRZDLNVILTDL-XNTGVSEISA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 16-methylheptadecanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCCCCCC(C)C)C1 JBBRZDLNVILTDL-XNTGVSEISA-N 0.000 description 4
- ASGSROHYBOETMM-UHFFFAOYSA-N alpha-monoisostearyl glycerylether Natural products CC(C)CCCCCCCCCCCCCCCCC(=O)OCC(O)CO ASGSROHYBOETMM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000004761 scalp Anatomy 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 239000004909 Moisturizer Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000001333 moisturizer Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BJDAUCLANVMIOB-UHFFFAOYSA-N (3-decanoyloxy-2,2-dimethylpropyl) decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)(C)COC(=O)CCCCCCCCC BJDAUCLANVMIOB-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 2
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 235000015961 tonic Nutrition 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000003871 white petrolatum Substances 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- KUJPUHSUDJSBKU-RQZCQDPDSA-N 1-[2-(2,4-dichlorophenyl)-2-[(2e)-3,7-dimethylocta-2,6-dienoxy]ethyl]imidazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC/C=C(C)/CCC=C(C)C)CN1C=CN=C1 KUJPUHSUDJSBKU-RQZCQDPDSA-N 0.000 description 1
- KUJPUHSUDJSBKU-MFOYZWKCSA-N 1-[2-(2,4-dichlorophenyl)-2-[(2z)-3,7-dimethylocta-2,6-dienoxy]ethyl]imidazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC\C=C(C)/CCC=C(C)C)CN1C=CN=C1 KUJPUHSUDJSBKU-MFOYZWKCSA-N 0.000 description 1
- SETLNUTYJWLMCN-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)-2-(2,4-dichlorophenyl)ethyl]triazole Chemical compound C1CC1COC(CN2C=CN=N2)C3=C(C=C(C=C3)Cl)Cl SETLNUTYJWLMCN-UHFFFAOYSA-N 0.000 description 1
- XXTUHZSIWQWXSX-WOJGMQOQSA-N 1-[2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-2-(2-nitrophenyl)ethyl]imidazole Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(OC/C=C(C)/CCC=C(C)C)CN1C=CN=C1 XXTUHZSIWQWXSX-WOJGMQOQSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 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
- PZAXAPQXFVSGHM-PISQQLRESA-N ClC1=C(C=CC(=C1)Cl)/C(/C(ON1C=NC=C1)C\C=C(\CCC=C(C)C)/C)=N/O Chemical compound ClC1=C(C=CC(=C1)Cl)/C(/C(ON1C=NC=C1)C\C=C(\CCC=C(C)C)/C)=N/O PZAXAPQXFVSGHM-PISQQLRESA-N 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- 239000004166 Lanolin Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 239000006096 absorbing agent Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
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- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VFRPYBIGSSNAJS-UHFFFAOYSA-N methyl 2-benzoyloxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 VFRPYBIGSSNAJS-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 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
- 210000003491 skin Anatomy 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000001993 wax 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
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はフケの予防・治療剤に関
する。FIELD OF THE INVENTION The present invention relates to a prophylactic / therapeutic agent for dandruff.
【０００２】[0002]
【従来の技術】一般にフケは皮脂腺の分泌物、汗腺の分
泌物、表皮層の剥離・脱離物等からなり、皮脂腺等の分
泌昴進、細菌、酵母等が関与することにより発生すると
言われている。このため、従来より一般にフケ防止手段
として、分泌された皮脂の洗浄と微生物の増殖抑制を目
的として、抗菌剤を配合したフケ取りシャンプー等の頭
髪化粧料を使用する等の方法が取られてきた。BACKGROUND ART Dandruff is generally composed of secretions of sebaceous glands, secretions of sweat glands, exfoliation and detachment of epidermal layers, etc. ing. Therefore, conventionally, as a means for preventing dandruff, methods such as using hair cosmetics such as dandruff shampoo containing an antibacterial agent have been used for the purpose of cleaning secreted sebum and suppressing the growth of microorganisms. .
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、従来こ
のようなフケ予防・治療手段として使用されている抗菌
剤は、中には刺激等の安全性上問題があるものもいくつ
か見られるうえに、そのフケ防止効果という点において
も充分に満足できるものではなかった。従って本発明の
目的は、これまで以上に従来フケ防止剤として使用され
ている抗菌剤のこれらの問題点を改善し、これまで以上
に有効性及び安全性の高い新規なフケ予防・治療剤を提
供することにある。However, among the antibacterial agents conventionally used as the preventive / therapeutic means for dandruff, some of them have safety problems such as irritation, and The anti-dandruff effect was not sufficiently satisfactory. Therefore, the object of the present invention is to improve these problems of the antibacterial agents conventionally used as antidandruff agents, and to provide a novel antidandruff agent with higher efficacy and safety than ever before. To provide.
【０００４】[0004]
【課題を解決するための手段】そこで、本発明者らはか
かる課題を解決すべく種々検討した結果、下記一般式
（１）で表わされるアゾール誘導体またはその酸付加塩
を頭皮等に適用すればフケの発生が極めて顕著に防止さ
れ、かつ副作用もないことを見出し、本発明を完成し
た。Therefore, as a result of various studies to solve the above problems, the present inventors have found that if an azole derivative represented by the following general formula (1) or an acid addition salt thereof is applied to the scalp and the like. The present invention has been completed by finding that the occurrence of dandruff is extremely remarkably prevented and there is no side effect.
【０００５】すなわち、本発明は次の一般式（１）That is, the present invention has the following general formula (1):
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】で表わされるアゾール誘導体またはその酸
付加塩を有効成分とするフケの予防・治療剤を提供する
ものである。The present invention provides a prophylactic / therapeutic agent for dandruff, which comprises an azole derivative represented by or an acid addition salt thereof as an active ingredient.
【０００８】本発明に用いられるアゾール誘導体（１）
は、例えば特開平３−１０９３７７号公報や特開平３−
２６４５６３号公報に示す方法により製造される。The azole derivative (1) used in the present invention
Is disclosed in, for example, Japanese Patent Application Laid-Open No. 3-109377 and Japanese Patent Application Laid-Open No. 3-109377.
It is manufactured by the method shown in Japanese Patent No. 264563.
【０００９】すなわち、下記反応式に従って、ハロゲン
化メチルシクロアルカン又はハロゲン化メチルシクロア
ルケン（２）に化合物（３）を反応させることによりア
ゾール誘導体（１）′が得られる。That is, the azole derivative (1) 'is obtained by reacting the halogenated methylcycloalkane or the halogenated methylcycloalkene (2) with the compound (3) according to the following reaction formula.
【００１０】[0010]
【化３】 [Chemical 3]
【００１１】（式中、Ｒ1 は炭素数３〜７のシクロアル
キル基又は炭素数４〜７の１−シクロアルケニル基を示
し、Ｍはナトリウム、カリウム、リチウム等の金属原子
を示し、Ｘ及びＺは前記と同じ意味を示す。）(In the formula, R 1 represents a cycloalkyl group having 3 to 7 carbon atoms or a 1-cycloalkenyl group having 4 to 7 carbon atoms, M represents a metal atom such as sodium, potassium or lithium, and X and Z has the same meaning as above.)
【００１２】また、下記反応式に従って、ハロゲン化ア
ルケン（４）と化合物（５）とを、塩基の存在下又は非
存在下に反応させることによりアゾール誘導体（１）″
が得られる。Further, according to the following reaction formula, the alkene (4) and the compound (5) are reacted in the presence or absence of a base to give an azole derivative (1) ″.
Is obtained.
【００１３】[0013]
【化４】 [Chemical 4]
【００１４】このようにして得られたアゾール誘導体
（１）は、更に必要に応じて、常法により硝酸塩、塩酸
塩等の無機酸塩、またはフマル酸、マレイン酸、酒石
酸、クエン酸等の有機酸塩とすることができる。The azole derivative (1) thus obtained is, if necessary, further added with an inorganic acid salt such as a nitrate or a hydrochloride or an organic acid such as fumaric acid, maleic acid, tartaric acid or citric acid by a conventional method. It can be an acid salt.
【００１５】上記のごとくして得られたアゾール誘導体
（１）又はその酸付加塩は、頭皮等の患部に適用するの
みでフケ症に対して有効であり、本発明のフケ予防・治
療剤の剤型としては、軟膏、クリーム、ローション、ミ
ルク、チンキ、溶液、懸濁液、粉末等の外用剤；シャン
プー、リンス、ヘアコンディショナー、ヘアトニック、
スカルプトリートメント等の頭髪化粧料；養毛料、ヘア
リキッド、ヘアスプレー、ヘアクリーム等の整髪料等の
剤型をとることができる。また、かかるフケの予防・治
療剤には、アゾール誘導体（１）又はその酸付加塩以外
に、必要に応じ、本発明の効果を損なわない範囲で、化
粧品、医薬部外品、医薬品等に一般に用いられている各
種成分、他の薬効剤、油性成分、界面活性剤、保湿剤、
低級アルコール、増粘剤、脂質吸収剤、酸化防止剤、緩
衝剤、防腐剤、浸透促進剤、キレート剤、香料、色素、
水などを配合することができる。The azole derivative (1) or the acid addition salt thereof obtained as described above is effective against dandruff only when applied to an affected area such as the scalp. Dosage forms include ointments, creams, lotions, milks, tinctures, solutions, suspensions, powders and other external preparations; shampoos, rinses, hair conditioners, hair tonics,
A hair cosmetic such as a scalp treatment; a hair styling agent such as a hair nourishing agent, a hair liquid, a hair spray, or a hair cream can be used. In addition to the azole derivative (1) or its acid addition salt, the prophylactic / therapeutic agent for dandruff is generally used in cosmetics, quasi-drugs, pharmaceuticals, etc., if necessary, within a range not impairing the effects of the present invention. Various ingredients used, other medicinal agents, oily ingredients, surfactants, moisturizers,
Lower alcohols, thickeners, lipid absorbents, antioxidants, buffers, preservatives, penetration enhancers, chelating agents, fragrances, dyes,
Water or the like can be added.
【００１６】他の薬効剤としては、例えば抗炎症剤、ビ
タミン類、消毒剤等が挙げられる。油性成分としては、
各種植物油、ワックス類、パラフィン類、脂肪酸、高級
アルコール、エステル類等が挙げられる。界面活性剤と
してはアニオン、カチオン、両性または非イオン型のい
ずれも挙げられるが、皮膚に対する刺激性の面より例え
ばグリセリンモノステアレート、ソルビタンモノステア
レート、ショ糖脂肪酸エステル、プロピレングリコール
モノステアレート、ポリオキシエチレンオレイルエーテ
ル、ポリエチレングリコールモノステアレート、ポリオ
キシエチレンソルビタンモノパルミテート、ポリオキシ
エチレンヤシ油脂肪酸モノエタノールアミド、ポリオキ
シエチレンポリオキシプロピレングリコール（例えば
「Pluronic」の商標で販売されている材料）、ポリオキ
シエチレンヒマシ油、ポリオキシエチレンラノリン等の
非イオン界面活性剤が好ましい。保湿剤としてはグリセ
リン、１，３−ブチレングリコール、プロピレングリコ
ール等が挙げられ、増粘剤としては、キサンタンゴム、
ヒドロキシプロピルセルロース、ヒドロキシプロピルメ
チルセルロース、ポリエチレングリコール、ナトリウム
カルボキシメチルセルロース等が挙げられ、脂質吸収剤
としては、カオリン、ベントナイト等が挙げられ、酸化
防止剤としては、ブチル化ヒドロキシトルエン、ブチル
化ヒドロキシアニソール、プロピルガレート、クエン酸
等が挙げられる。また、キレート剤としては、ジソジウ
ムエデテート、エタンヒドロキシジホスフェート等が挙
げられ、緩衝剤としては、クエン酸、クエン酸ナトリウ
ム、ホウ酸、硼砂、リン酸水素二ナトリウム等が挙げら
れ、そして防腐剤としては、メチルパラベン、エチルパ
ラベン、デヒドロ酢酸、サリチル酸、安息香酸塩等が挙
げられる。Other medicinal agents include, for example, anti-inflammatory agents, vitamins, antiseptics and the like. As an oily component,
Examples include various vegetable oils, waxes, paraffins, fatty acids, higher alcohols, esters and the like. Examples of the surfactant include anion, cation, and amphoteric or nonionic type, but for example, glycerin monostearate, sorbitan monostearate, sucrose fatty acid ester, propylene glycol monostearate from the viewpoint of irritation to skin. Polyoxyethylene oleyl ether, polyethylene glycol monostearate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene coconut oil fatty acid monoethanolamide, polyoxyethylene polyoxypropylene glycol (eg materials sold under the trademark "Pluronic") ), Polyoxyethylene castor oil, polyoxyethylene lanolin and the like nonionic surfactants are preferred. Examples of moisturizers include glycerin, 1,3-butylene glycol, propylene glycol, and the like, and examples of thickeners include xanthan gum and
Hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyethylene glycol, sodium carboxymethyl cellulose and the like, lipid absorbents such as kaolin, bentonite and the like, antioxidants, butylated hydroxytoluene, butylated hydroxyanisole, propyl Examples include gallate and citric acid. Examples of the chelating agent include disodium edetate, ethanehydroxydiphosphate, and the like, and buffering agents include citric acid, sodium citrate, boric acid, borax, disodium hydrogenphosphate, and antiseptic. Examples of the agent include methylparaben, ethylparaben, dehydroacetic acid, salicylic acid, benzoate and the like.
【００１７】また、シャンプー、リンス等の毛髪処理剤
の場合には、アゾール誘導体（１）又はその酸付加塩以
外に、必要に応じて他の薬効剤、界面活性剤、油性成
分、保湿剤、防腐剤、増粘剤、紫外線吸収剤、抗酸化
剤、着色剤、コンディショニング剤、パール剤、水、そ
の他エンサイクロペディア・オブ・コンディショニング
・リンス・イングレディエンツ〔ENCYCLOPEDIA OF COND
ITIONING RINSE INGREDIENTS(MICELLE PRESS 1987年)
〕に収載されている成分等を、本発明の効果を損なわ
ない範囲において、適宜配合することができる。In the case of a hair treatment agent such as shampoo and conditioner, other medicinal agents, surfactants, oily ingredients, moisturizers, if necessary, in addition to the azole derivative (1) or its acid addition salt. Preservatives, thickeners, UV absorbers, antioxidants, colorants, conditioning agents, pearlescent agents, water and other encyclopedia of conditioning rinse incredibles (ENCYCLOPEDIA OF COND
ITIONING RINSE INGREDIENTS (MICELLE PRESS 1987)
The components listed in the above [] can be appropriately blended within a range that does not impair the effects of the present invention.
【００１８】アゾール誘導体（１）またはその塩の本発
明のフケ予防・治療剤への配合量は、その剤型、配合成
分によっても異なるが、通常0.01〜１０重量％、特に
0.1〜５重量％が好ましい。The amount of the azole derivative (1) or a salt thereof to be incorporated into the antidandruff agent of the present invention is usually 0.01 to 10% by weight, particularly preferably 10 to 10% by weight, although it varies depending on its dosage form and components.
0.1 to 5% by weight is preferable.
【００１９】[0019]
【実施例】以下、実施例を挙げて本発明を更に詳細に説
明するが、本発明はこれらに限定されるものではない。The present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
【００２０】実施例１ （臨床試験）脂漏性皮膚炎、フケ症を患っている患者５
人に対し、下記の本発明液剤を患部に１か月間使用し
た。その結果、表２のように従来の治療（ステロイドロ
ーション塗布、ビタミンＢ2 、Ｂ6 内服等）で無効であ
った症状が軽快、治癒した。Example 1 (clinical test) Patient 5 suffering from seborrheic dermatitis and dandruff
The following liquid preparations of the present invention were applied to humans on the affected area for one month. As a result, as shown in Table 2, the symptoms which were ineffective by the conventional treatments (application of steroid lotion, oral administration of vitamin B 2 , B 6 etc.) were relieved and cured.
【００２１】[0021]
【表１】 （液剤） （１）化合物１* １．０（重量％） （２）α−モノイソステアリルグリセリルエーテル ２．５ （３）プロピレングリコール １５．５ （４）エタノール ３５．５ （５）イソプロパノール １２．０ （６）精製水 バランス[Table 1] (Liquid formulation) (1) Compound 1 * 1.0 (wt%) (2) α-monoisostearyl glyceryl ether 2.5 (3) Propylene glycol 15.5 (4) Ethanol 35.5 (5) ) Isopropanol 12.0 (6) Purified water balance
【００２２】*:化合物１；１−〔２−（２，４−ジクロ
ロフェニル）−２−（（Ｅ）−３，７−ジメチルオクタ
−２，６−ジエニロキシ）エチル〕−１Ｈ−イミダゾー
ル*: Compound 1; 1- [2- (2,4-dichlorophenyl) -2-((E) -3,7-dimethylocta-2,6-dienyloxy) ethyl] -1H-imidazole
【００２３】（１）〜（５）を均一に溶解し、（６）を
加えて液剤を調製した。(1) to (5) were uniformly dissolved, and (6) was added to prepare a liquid preparation.
【００２４】[0024]
【表２】 [Table 2]
【００２５】[0025]
【表３】 実施例２ （ヘアトニック） （１）エチルアルコール ５５．０（重量％） （２）ポリオキシエチレン（８モル）オレイル アルコールエーテル ２．０ （３）化合物１* ０．５ （４）香料 ０．５ （５）色素 適量 （６）精製水 バランス *:化合物１；実施例１と同じ。Table 2 Example 2 (hair tonic) (1) Ethyl alcohol 55.0 (wt%) (2) Polyoxyethylene (8 mol) oleyl alcohol ether 2.0 (3) Compound 1 * 0.5 (4 ) Fragrance 0.5 (5) Dye Appropriate amount (6) Purified water Balance *: Compound 1; Same as in Example 1.
【００２６】[0026]
【表４】 実施例３ （抗フケシャンプー） （１）ポリオキシエチレン（２．５モル）ラウリル エーテル硫酸ナトリウム（２５％） ３５．０（重量％） （２）ラウリル硫酸トリエタノール アミン（４０％） １５．０ （３）ヤシ油脂肪酸ジエタノールアミド ２．０ （４）化合物２*1 １．０ （５）カチオン化セルロース*2 ０．３ （６）香料 ０．５ （７）色素 適量 （８）粘度調整剤 適量 （９）精製水 バランスTable 4 Example 3 (Anti-dandruff shampoo) (1) Polyoxyethylene (2.5 mol) Lauryl ether sodium sulfate (25%) 35.0 (wt%) (2) Triethanolamine lauryl sulfate (40%) ) 15.0 (3) Coconut oil fatty acid diethanolamide 2.0 (4) Compound 2 * 1 1.0 (5) Cationized cellulose * 2 0.3 (6) Perfume 0.5 (7) Dye Suitable amount (8 ) Viscosity modifier Appropriate amount (9) Purified water balance
【００２７】*1：化合物２；１−〔２−（シクロプロピ
ルメトキシ）−２−（２，４−ジクロロフェニル）エチ
ル〕−１Ｈ−トリアゾール *2：ポリマーＪＲ４００（ユニオンカーバイド社製）* 1: Compound 2; 1- [2- (cyclopropylmethoxy) -2- (2,4-dichlorophenyl) ethyl] -1H-triazole * 2: Polymer JR400 (manufactured by Union Carbide Co.)
【００２８】[0028]
【表５】 実施例４ （抗フケリンス） （１）ステアリルトリメチルアンモニウムクロリド ２．０（重量％） （２）セチルアルコール ３．０ （３）ポリオキシエチレン（１０モル）オレイル アルコールエーテル １．０ （４）グリセリン ５．０ （５）化合物３* ０．２ （６）香料 ０．５ （７）色素 適量 （８）精製水 バランスTable 5 Example 4 (Anti-Ducerinose) (1) Stearyl trimethyl ammonium chloride 2.0 (wt%) (2) Cetyl alcohol 3.0 (3) Polyoxyethylene (10 mol) oleyl alcohol ether 1.0 ( 4) Glycerin 5.0 (5) Compound 3 * 0.2 (6) Perfume 0.5 (7) Dye Appropriate amount (8) Purified water balance
【００２９】*:化合物３；１−〔２−（２，４−ジクロ
ロフェニル）−２−（（Ｚ）−３，７−ジメチルオクタ
−２，６−ジエニロキシ）エチル〕−１Ｈ−イミダゾー
ル*: Compound 3; 1- [2- (2,4-dichlorophenyl) -2-((Z) -3,7-dimethylocta-2,6-dienyloxy) ethyl] -1H-imidazole
【００３０】[0030]
【表６】 実施例５ （クリーム（Ｗ／Ｏ）） （１）化合物４* ０．０５（重量％） （２）コレステロール ０．５ （３）コレステロールイソステアレート １．０ （４）ポリエーテル変性シリコーン（シリコーン Ｘ−２２−４０１３，信越シリコーン（株）製） １．５ （５）オクタメチルシクロテトラシロキサン １０．０ （６）デカメチルシクロペンタシロキサン １０．０ （７）メチルフェニルポリシロキサン ２．０ （８）メチルポリシロキサン（６cs） ２．０ （９）硫酸マグネシウム ０．５ （10）５５％エタノール ５．０ （11）カルボキシメチルキチン （一丸ファルコス社製、キチンリキッドＨＶ） ０．５ （12）精製水 バランスTable 5 Example 5 (Cream (W / O)) (1) Compound 4 * 0.05 (wt%) (2) Cholesterol 0.5 (3) Cholesterol isostearate 1.0 (4) Polyether Modified silicone (Silicone X-22-4013, manufactured by Shin-Etsu Silicone Co., Ltd.) 1.5 (5) Octamethylcyclotetrasiloxane 10.0 (6) Decamethylcyclopentasiloxane 10.0 (7) Methylphenylpolysiloxane 2 .0 (8) Methyl polysiloxane (6cs) 2.0 (9) Magnesium sulfate 0.5 (10) 55% ethanol 5.0 (11) Carboxymethyl chitin (Ichimaru Falcos Co., Ltd., Chitin Liquid HV) 0.5 (12) Purified water balance
【００３１】*:化合物４；１−〔２−（（Ｅ）−３，７
−ジメチルオクタ−２，６−ジエニロキシ）−２−（２
−ニトロフェニル）エチル〕−１Ｈ−イミダゾール （１）〜（８）を８０℃に加温して溶解し、これに
（９）〜（１２）を加えて均一に混合し、Ｗ／Ｏクリー
ムを調製した。*: Compound 4; 1- [2-((E) -3,7
-Dimethylocta-2,6-dienyloxy) -2- (2
-Nitrophenyl) ethyl] -1H-imidazole (1) to (8) were heated to 80 ° C to dissolve, and (9) to (12) were added to and mixed uniformly to give a W / O cream. Prepared.
【００３２】[0032]
【表７】 実施例６ （クリーム（Ｗ／Ｏ）） （１）化合物５* １．０（重量％） （２）α−モノイソステアリルグリセリルエーテル １．０ （３）ポリエーテル変性シリコーン（シリコーン Ｘ−２２−４０１３，信越シリコーン（株）製） １．５ （４）ステアリン酸アルミニウム ０．２ （５）コレステロールイソステアレート １．０ （６）スクワラン ４．０ （７）オリーブ油 １．０ （８）ジカプリン酸ネオペンチルグリコール ２．５ （９）オクタメチルシクロテトラシロキサン ２．５ （10）デカメチルシクロペンタシロキサン ５．０ （11）メチルポリシロキサン（６cs） １２．５ （12）硫酸マグネシウム ０．５ （13）防腐剤 適量 （14）グリセリン １０．０ （15）精製水 バランスTable 7 Example 6 (Cream (W / O)) (1) Compound 5 * 1.0 (wt%) (2) α-monoisostearyl glyceryl ether 1.0 (3) Polyether-modified silicone (silicone) X-22-4013, manufactured by Shin-Etsu Silicone Co., Ltd. 1.5 (4) Aluminum stearate 0.2 (5) Cholesterol isostearate 1.0 (6) Squalane 4.0 (7) Olive oil 1.0 ( 8) Neopentyl glycol dicaprate 2.5 (9) Octamethylcyclotetrasiloxane 2.5 (10) Decamethylcyclopentasiloxane 5.0 (11) Methylpolysiloxane (6cs) 12.5 (12) Magnesium sulfate 0 .5 (13) Preservative proper amount (14) Glycerin 10.0 (15) Purified water balance
【００３３】*:化合物５；１−〔２−（（Ｅ）−３，７
−ジメチルオクタ−２，６−ジエチロキシ）−２−フェ
ニルエチル〕−１Ｈ−イミダゾール （１）〜（１１）を８０℃に加温して溶解し、これに
（１２）〜（１５）を加えて均一に混合し、Ｗ／Ｏクリ
ームを調製した。*: Compound 5; 1- [2-((E) -3,7
-Dimethylocta-2,6-diethyloxy) -2-phenylethyl] -1H-imidazole (1) to (11) were heated to 80 ° C to dissolve, and (12) to (15) were added thereto. The mixture was uniformly mixed to prepare a W / O cream.
【００３４】[0034]
【表８】 実施例７ （クリーム（Ｏ／Ｗ）） （１）化合物６* ５．０（重量％） （２）ポリオキシエチレン（１０）硬化 ヒマシ油 １．０ （３）モノステアリン酸ソルビタン ０．５ （４）ステアロイルメチルタウリンナトリウム ０．５ （５）セトステアリルアルコール ２．０ （６）ステアリン酸 １．８ （７）コレステロール １．５ （８）コレステロールイソステアレート １．０ （９）ジカプリン酸ネオペンチルグリコール ８．０ （10）メチルポリシロキサン（６cs） ５．０ （11）グリセリン ５．０ （12）精製水 バランスTable 8 Example 7 (Cream (O / W)) (1) Compound 6 * 5.0 (wt%) (2) Polyoxyethylene (10) Hardened castor oil 1.0 (3) Sorbitan monostearate 0.5 (4) Sodium stearoylmethyl taurine 0.5 (5) Cetostearyl alcohol 2.0 (6) Stearic acid 1.8 (7) Cholesterol 1.5 (8) Cholesterol isostearate 1.0 (9) Neopentyl glycol dicaprate 8.0 (10) Methyl polysiloxane (6cs) 5.0 (11) Glycerin 5.0 (12) Purified water balance
【００３５】*:化合物６；１−〔２−（４−ブロモフェ
ニル）−２−（（Ｅ）−３，７−ジメチルオクタ−２，
６−ジエチロキシ）エチル〕−１Ｈ−トリアゾール （１）〜（１０）を８０℃に加温して溶解し、これに
（１１）、（１２）を加えて均一に混合し、Ｏ／Ｗクリ
ームを調製した。*: Compound 6; 1- [2- (4-bromophenyl) -2-((E) -3,7-dimethylocta-2,
6-Diethyloxy) ethyl] -1H-triazole (1) to (10) are heated to 80 ° C. to dissolve, and (11) and (12) are added to and mixed uniformly to form an O / W cream. Prepared.
【００３６】[0036]
【表９】 実施例８ （軟膏） （１）化合物７* １．０（重量％） （２）白色ワセリン バランス （３）コレステロールイソステアレート ３．０ （４）流動パラフィン １０．０ （５）α−モノイソステアリルグリセリルエーテル １．０ （６）グリセリン １０．０Table 8 Example 8 (Ointment) (1) Compound 7 * 1.0 (wt%) (2) White petrolatum balance (3) Cholesterol isostearate 3.0 (4) Liquid paraffin 10.0 (5) α-monoisostearyl glyceryl ether 1.0 (6) glycerin 10.0
【００３７】*:化合物７；１−〔２−（２，４−ジクロ
ロフェニル）−２−（（Ｅ）−３，７−ジメチルオクタ
−２，６−ジエニルチオ）エチル〕−１Ｈ−イミダゾー
ル （１）〜（６）を８０℃に加温して溶解した後冷却し、
軟膏を調製した。*: Compound 7; 1- [2- (2,4-dichlorophenyl) -2-((E) -3,7-dimethylocta-2,6-dienylthio) ethyl] -1H-imidazole (1) ~ (6) is heated to 80 ℃ to dissolve and then cooled,
An ointment was prepared.
【００３８】[0038]
【表１０】 実施例９ （軟膏） （１）化合物８* ２．０（重量％） （２）白色ワセリン バランス （３）プロピレングリコール １５．０ （４）α−モノイソステアリルグリセリルエーテル ２．５Table 9 Example 9 (Ointment) (1) Compound 8 * 2.0 (wt%) (2) White petrolatum balance (3) Propylene glycol 15.0 (4) α-monoisostearyl glyceryl ether 2.5
【００３９】*:化合物８；（Ｚ）−１−（２，４−ジク
ロロフェニル）−２−（１Ｈ−イミダゾール−１−イ
ル）−Ｏ−（（Ｅ）−３，７−ジメチルオクタ−２，６
−ジエニル）エタノンオキシム （１）〜（４）を８０℃に加温して溶解した後冷却し、
軟膏を調製した。*: Compound 8; (Z) -1- (2,4-dichlorophenyl) -2- (1H-imidazol-1-yl) -O-((E) -3,7-dimethylocta-2, 6
-Dienyl) ethanone oxime (1) to (4) were heated to 80 ° C to dissolve and then cooled,
An ointment was prepared.
【００４０】[0040]
【発明の効果】本発明の薬剤を頭皮に塗布すれば優れた
予防・治療効果が得られるとともに、副作用をほとんど
発生せず、フケの予防・治療剤に有用である。EFFECTS OF THE INVENTION By applying the drug of the present invention to the scalp, excellent prophylactic / therapeutic effects can be obtained, and almost no side effects occur, and it is useful as a prophylactic / therapeutic agent for dandruff.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｄ 249/08 Ｚ // Ｃ０７Ｄ 233/60 １０２ 233/61 １０２ (72)発明者 坂口 明 栃木県宇都宮市長岡町616−47 (72)発明者 土屋 秀一 栃木県宇都宮市泉が丘２丁目11−10─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display location C07D 249/08 Z // C07D 233/60 102 233/61 102 (72) Inventor Akira Sakaguchi Tochigi Prefecture 616-47 Nagaoka-cho, Utsunomiya City (72) Inventor Shuichi Tsuchiya 2-11-10 Izumigaoka, Utsunomiya City, Tochigi Prefecture
Claims (1)
成分とするフケの予防・治療剤。1. The following general formula (1): A prophylactic / therapeutic agent for dandruff, which comprises the azole derivative represented by or an acid addition salt thereof as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4233607A JPH0680567A (en) | 1992-09-01 | 1992-09-01 | Agent for prevention and treatment of dandruff |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4233607A JPH0680567A (en) | 1992-09-01 | 1992-09-01 | Agent for prevention and treatment of dandruff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0680567A true JPH0680567A (en) | 1994-03-22 |
Family
ID=16957703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4233607A Pending JPH0680567A (en) | 1992-09-01 | 1992-09-01 | Agent for prevention and treatment of dandruff |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0680567A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004022546A1 (en) * | 2002-09-04 | 2004-03-18 | Keimei Oh | Substances inhibiting biosynthesis of jasmonic acid |
| US7981909B2 (en) | 1996-09-27 | 2011-07-19 | Medicis Pharmaceutical Corporation | Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis |
-
1992
- 1992-09-01 JP JP4233607A patent/JPH0680567A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7981909B2 (en) | 1996-09-27 | 2011-07-19 | Medicis Pharmaceutical Corporation | Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis |
| WO2004022546A1 (en) * | 2002-09-04 | 2004-03-18 | Keimei Oh | Substances inhibiting biosynthesis of jasmonic acid |
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