JPH0579643B2 - - Google Patents
Info
- Publication number
- JPH0579643B2 JPH0579643B2 JP3983585A JP3983585A JPH0579643B2 JP H0579643 B2 JPH0579643 B2 JP H0579643B2 JP 3983585 A JP3983585 A JP 3983585A JP 3983585 A JP3983585 A JP 3983585A JP H0579643 B2 JPH0579643 B2 JP H0579643B2
- Authority
- JP
- Japan
- Prior art keywords
- skin
- allantoin
- residue
- present
- formula
- 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 - Fee Related
Links
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 18
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 15
- 229960000458 allantoin Drugs 0.000 claims description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 11
- 229930182470 glycoside Natural products 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 125000003712 glycosamine group Chemical group 0.000 claims 1
- 125000000625 hexosyl group Chemical group 0.000 claims 1
- 125000001805 pentosyl group Chemical group 0.000 claims 1
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229960000271 arbutin Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-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 7
- 210000004761 scalp Anatomy 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 6
- -1 hydroquinone glycosides Chemical class 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000029663 wound healing Effects 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002337 glycosamines Chemical group 0.000 description 3
- 150000002402 hexoses Chemical group 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002972 pentoses Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- AMZWNNKNOQSBOP-UHFFFAOYSA-M [n'-(2,5-dioxoimidazolidin-4-yl)carbamimidoyl]oxyaluminum;dihydrate Chemical compound O.O.NC(=O)NC1N=C(O[Al])NC1=O AMZWNNKNOQSBOP-UHFFFAOYSA-M 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003755 preservative agent Substances 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
- 239000004094 surface-active agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 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
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 description 1
- JVXJFNLEXLGQIO-UHFFFAOYSA-N 2-hexyldecyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(CCCCCC)CCCCCCCC JVXJFNLEXLGQIO-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-DTEWXJGMSA-N D-Galacturonic acid Natural products O[C@@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-DTEWXJGMSA-N 0.000 description 1
- 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 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 description 1
- BJHIKXHVCXFQLS-PUFIMZNGSA-N D-psicose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PUFIMZNGSA-N 0.000 description 1
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 description 1
- LKDRXBCSQODPBY-OEXCPVAWSA-N D-tagatose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-OEXCPVAWSA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 244000116484 Inula helenium Species 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-DHVFOXMCSA-N L-galactose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-DHVFOXMCSA-N 0.000 description 1
- IAJILQKETJEXLJ-SQOUGZDYSA-N L-guluronic acid Chemical compound O=C[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O IAJILQKETJEXLJ-SQOUGZDYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-WVZVXSGGSA-N L-xylulose Chemical compound OC[C@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-WVZVXSGGSA-N 0.000 description 1
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 1
- BPIBTJIERVJXFG-IFWQJVLJSA-N OC1=CC=C(O)C=C1.O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O Chemical compound OC1=CC=C(O)C=C1.O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O BPIBTJIERVJXFG-IFWQJVLJSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010040849 Skin fissures Diseases 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- GZCGUPFRVQAUEE-KAZBKCHUSA-N aldehydo-D-talose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KAZBKCHUSA-N 0.000 description 1
- PYMYPHUHKUWMLA-YUPRTTJUSA-N aldehydo-L-lyxose Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-YUPRTTJUSA-N 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 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 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 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
- 239000000600 sorbitol Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/002—Aftershave preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
［産業上の利用分野］
本発明は、皮膚外用剤基剤に、アラントイン及
び／又はその誘導体とハイドロキノンの配糖体と
を配合することにより、創傷治癒に対して優れた
効果を有する皮膚又は頭皮用の皮膚外用剤に係る
ものである。
［従来の技術］
従来、アラントイン又はその誘導体の数種類は
皮膚科の諸疾患の治療薬として、又化粧品工業の
原料として利用されている。しかしながら、アラ
ントイン、アラントイン誘導体が化粧料、医薬部
外品、例えばアルコール性ローシヨン、クリー
ム、乳液及び化粧水等に0.01〜2.0重量％程度配
合する例が見られるが、有効成分を配合した皮膚
外用剤を実際使用する場合に、同時に配合される
薬剤、界面活性剤、香料等の影響をうけて、その
効果が充分に現れていないことが多い。
［発明が解決しようとする問題点］
本発明者等は上記事情にかんがみ、アラントイ
ンの上記のような効果を損なうことなく、むしろ
相乗的な効果を得るべく鋭意研究した結果、アラ
ントインとハイドロキノンの配糖体とを皮膚外用
剤に配合することにより、この課題を解決しうる
ことを見出し本発明を完成するに至つた。
［問題点を解決するための手段］
即ち、アラントイン及び／又はその誘導体と下
記一般式であらわされるハイドロキノンの配糖体
[Industrial Application Field] The present invention provides a skin or scalp preparation that has an excellent effect on wound healing by incorporating allantoin and/or its derivatives and hydroquinone glycosides into a skin external preparation base. This relates to a topical skin preparation for use. [Prior Art] Allantoin or several types of its derivatives have heretofore been used as therapeutic agents for various dermatological diseases and as raw materials in the cosmetic industry. However, there are cases in which allantoin and allantoin derivatives are incorporated in cosmetics, quasi-drugs, such as alcoholic lotions, creams, milky lotions, and lotions at a level of 0.01 to 2.0% by weight, but external skin preparations containing active ingredients can be seen. When actually used, the effects are often not fully manifested due to the influence of the drugs, surfactants, fragrances, etc. that are added at the same time. [Problems to be Solved by the Invention] In view of the above circumstances, the present inventors conducted intensive research in order to obtain a synergistic effect without impairing the above-mentioned effects of allantoin. The present inventors have discovered that this problem can be solved by incorporating glycosides into external skin preparations, and have completed the present invention. [Means for solving the problem] Namely, allantoin and/or its derivative and a glycoside of hydroquinone represented by the following general formula
【式】
［式中、Ｒは五炭糖残基、六炭糖残基、アミノ
糖残基、ウロン酸残基又はそれらのメチル化物を
示す。］
とを併用して、皮膚外用剤基剤に配合することに
より、皮膚の創傷治癒並びに肌荒防止に効果的に
作用する皮膚外用剤を提供するものである。
以下、本発明の構成について詳述する。
本発明に用いられるアラントインの誘導体とし
ては、ジヒドロキシアルミニウムアラントイネー
ト、クロロヒドロキシアルミニウムアラントイネ
ート等があげられる。
本発明の実施にあたつては、アラントインおよ
びその誘導体のうち一種または二種以上が適宜選
択され配合される。
配合量は皮膚外用剤全量中の0.01〜5.0重量％
であり、好ましくは0.1〜3.0重量％である。
本発明に用いられるハイドロキノンの配糖体は
下記一般式であらわされる。[Formula] [In the formula, R represents a pentose residue, a hexose residue, an amino sugar residue, a uronic acid residue, or a methylated product thereof. ] By combining these with the skin external preparation base, it is possible to provide a skin external preparation that effectively acts on skin wound healing and prevention of skin roughness. Hereinafter, the configuration of the present invention will be explained in detail. Examples of allantoin derivatives used in the present invention include dihydroxyaluminum allantoinate, chlorohydroxyaluminum allantoinate, and the like. In carrying out the present invention, one or more types of allantoin and its derivatives are appropriately selected and blended. The blending amount is 0.01 to 5.0% by weight of the total amount of the skin external preparation.
and preferably 0.1 to 3.0% by weight. The hydroquinone glycoside used in the present invention is represented by the following general formula.
【式】
［式中、Ｒは五炭糖残基、六炭糖残基、アミノ
糖残基、ウロン酸残基又はそれらのメチル化物を
示す。］
式中でＲはＬ−アラビノース、Ｄ−アラビノー
ス、Ｄ−キシロース、Ｄ−リボース、Ｌ−キシル
ロース、Ｌ−リキソース、Ｄ−リブロースの五炭
糖の残基、Ｄ−グルコース、Ｄ−ガラクトース、
Ｌ−ガラクトース、Ｄ−マンノース、Ｄ−タロー
ス、Ｄ−フルクトース、Ｌ−ソルボース、Ｄ−タ
ガトース、Ｄ−プシコースの六炭糖の残基、Ｄ−
グルコサミン、Ｄ−ガラクトサミン、シアル酸、
アミノウロン酸、ムラミン酸等のアミノ糖の残
基、Ｄ−グルクロン酸、Ｄ−ガラクツロン酸、Ｄ
−マンヌロン酸、Ｌ−イズロン酸、Ｌ−グルロン
酸等のウロン酸の残基又はそれらのメチル化物を
示すが、美白効果、入手の仕易さ、安定性、安全
性の両面からＲがＤ−グルコース残基の場合、と
くにハイドロキノンにＤ−グルコース、β−結合
した、すなわちハイドロキノンβ−Ｄ−グルコー
ス（一般名：アルブチン、以後アルブチンとい
う）が最も好ましい。
配合量は皮膚外用剤全量中の0.1〜30重量％で
あり、好ましくは６〜20重量％である。
本発明の皮膚外用剤にはアラントイン及び／又
はその誘導体とハイドロキノンの配糖体とが併用
されることによつて、創傷に対してこれら成分が
相乗的に作用し、その治癒を顕著に促進すること
が知見された。しかも、本発明によれば創傷治癒
に対して抑制的に作用するような基剤を用いても
優れた創傷治癒効果を有する。従つて、所望の基
剤を選択使用して目的に適応した皮膚外用剤の処
方を容易につくることができ、製造が仕易い。
本発明の皮膚外用剤には界面活性剤、油分、湿
潤剤、紫外線吸収剤、酸化防止剤、防腐剤、保湿
剤、香料、水、アルコール剤、キレート剤、PH調
整剤、増粘剤等を必要に応じて適宜配合すること
ができる。
本発明の皮膚外用剤は栄養クリーム、ハンドク
リーム、ボデイクリーム、マツサージクリーム等
のクリーム類、栄養乳液類、パツク類、化粧水類
等の皮膚外用剤は勿論、頭髪用、特に頭皮（スカ
ルプ）用トリートメント等の皮膚外用剤としても
有益である。
［効果］
このように、本発明の皮膚外用剤は創傷治癒促
進効果が優れているため、ひげそり後、シヤンプ
ー後、爪で損傷した頭皮、ひび、あかぎれ、肌荒
などに好適に使用することができる。
［実施例］
以下、実施例をあげて本発明に係る皮膚外用剤
の創傷治癒促進効果、肌荒改善効果について具体
的に説明する。本発明はこれら実施例に限定され
るものではない。
配合量は重量％である。
実施例 １
試験方法
生後６週齢のウイスター系ラツト（SPF）を４
匹１群とし、毛刈りの後試験に供した。ラツトは
ネンブタールにより麻酔後正中線にそつて、約２
cm背部皮膚を切開し、ただちに切開部をミツヘル
縫合器により縫合した。縫合後、試料0.1mlを１
日１回、２週間に渡り、切開部に塗布した。
２週間後、ラツトを撲殺し、縫合針を外した後
断面１cmとなるように皮膚切片を作成した。張力
測定にはテンシロン（Tensilon）UTM−４（東
洋測器株式会社製）を用い皮膚切片の切断張力を
測定した。
なお、コントロールは生理食塩水を用い、実施
例、および比較例はこの生理食塩水にアラントイ
ン、アルブチンを次表の配合量で配合したものを
用いた。
結果を第１表に示す。[Formula] [In the formula, R represents a pentose residue, a hexose residue, an amino sugar residue, a uronic acid residue, or a methylated product thereof. ] In the formula, R is a pentose residue of L-arabinose, D-arabinose, D-xylose, D-ribose, L-xylulose, L-lyxose, D-ribulose, D-glucose, D-galactose,
Hexose residues of L-galactose, D-mannose, D-talose, D-fructose, L-sorbose, D-tagatose, D-psicose, D-
glucosamine, D-galactosamine, sialic acid,
Residues of amino sugars such as aminouronic acid and muramic acid, D-glucuronic acid, D-galacturonic acid, D
-Represents uronic acid residues such as mannuronic acid, L-iduronic acid, and L-guluronic acid, or their methylated products, but R is D- from the viewpoint of whitening effect, ease of availability, stability, and safety. In the case of glucose residues, in particular D-glucose, β-linked to hydroquinone, ie hydroquinone β-D-glucose (common name: arbutin, hereinafter referred to as arbutin) is most preferred. The blending amount is 0.1 to 30% by weight, preferably 6 to 20% by weight, based on the total amount of the skin external preparation. By using allantoin and/or its derivatives and hydroquinone glycoside in the skin external preparation of the present invention, these components act synergistically on the wound, significantly promoting its healing. It was discovered that Moreover, according to the present invention, excellent wound healing effects can be obtained even when a base that acts to suppress wound healing is used. Therefore, it is possible to select and use a desired base to easily formulate a formulation for an external skin preparation suitable for the purpose, and the production process is easy. The skin external preparation of the present invention contains surfactants, oils, humectants, ultraviolet absorbers, antioxidants, preservatives, humectants, fragrances, water, alcohol agents, chelating agents, PH regulators, thickeners, etc. They can be appropriately blended as needed. The external skin preparations of the present invention include creams such as nutritional creams, hand creams, body creams, and pine surge creams, nutritional emulsions, packs, and lotions, as well as external skin preparations for hair, especially for the scalp (scalp). It is also useful as an external skin preparation for treatments and the like. [Effect] As described above, the skin external preparation of the present invention has an excellent effect of promoting wound healing, so it can be suitably used after shaving, shampooing, scalp damaged by nails, cracks, chapped skin, rough skin, etc. can. [Example] Hereinafter, the wound healing promoting effect and rough skin improving effect of the skin external preparation according to the present invention will be specifically explained with reference to Examples. The present invention is not limited to these examples. The blending amount is in weight%. Example 1 Test method Six-week-old Wistar rats (SPF) were
The animals were divided into one group and subjected to the test after being shaved. After the rat was anesthetized with Nembutal, it was placed along the midline for approximately 2 minutes.
An incision was made on the dorsal skin, and the incision was immediately sutured using a Mitsuhel suture device. After suturing, add 0.1 ml of sample to 1
It was applied to the incision once a day for two weeks. Two weeks later, the rat was bludgeoned to death, and a 1 cm skin section was prepared after removing the suture needle. For tension measurement, Tensilon UTM-4 (manufactured by Toyo Sokki Co., Ltd.) was used to measure the cutting tension of the skin section. Note that physiological saline was used as a control, and in Examples and Comparative Examples, this physiological saline was mixed with allantoin and arbutin in the amounts shown in the following table. The results are shown in Table 1.
【表】
第１表の結果から、0.1％，1.0％アラントイン
塗布部位は無塗布部位（コントロール）に比べ張
力が増加し、修復力の促進効果が認められ、アル
ブチン1.0％，10.0％塗布においては張力の増加
がほとんど観察されなかつた。
一方アルブチンとアラントイン併用の本発明品
の場合は、各々単品塗布の比較品に比べて、張力
に増加傾向が認められ、顕著な治癒促進効果が認
められた。
また、以上の動物試験だけでなく、人体パネル
の場合もこのアルブチンとアラントイン及び／又
はその誘導体併用系はこの動物試験の結果と同等
の効果を示した。
実施例２ 化粧水
次の処方に従い、常法により化粧水を製造し
た。
プロピレングリコール 4.0
エタノール 15.0
POE（20）オレイルエーテル 0.5
アルブチン 20.0
アラントイン 0.01
メチルパラベン 0.1
クエン酸 0.01
クエン酸ソーダ 0.1
香料 0.05
イオン交換水 残余
実施例３ クリーム
次の処方に従い、常法によりクリームを製造し
た。
プロピレングリコール 5.0
ミツロウ 5.0
セチルアルコール 4.0
還元ラノリン 5.0
スクワラン 35.0
グリセリルモノステアレート 2.0
POE（20）ソルビタンモノラウレート 2.0
メチルパラベン 0.1
エチルパラベン 0.15
ハイドロキノン−β−Ｄ−アラビノース 1.0
アラントイン 3.0
香料 0.1
イオン交換水 残余
実施例４ パツク
次の処方に従い、常法によりパツクを製造した
ポリビニルアルコール 15.0
ポリエチレングリコール 3.0
プロピレングリコール 7.0
エタノール 10.0
メチルパラベン 0.1
アルブチン 6.0
ジヒドロキシアルミニウムアラントイネート 3.0
香料 0.1
イオン交換水 残余
実施例５ スカルプトリートメント（頭皮用化
粧料）
次の処方に従い、常法によりスカルプトリート
メントを製造した。
１，３ブチレングリコール 7.0
ポリエチレングリコール 5.0
エタノール 10.0
POE（60）硬化ヒマシ油 2.0
苛性カリ 0.05
カルボキシビニルポリマー 0.2
２−ヘキシルデシルパルミテート 10.0
スクワラン 5.0
ミツロウ 0.5
アルブチン 10.0
アラントイン 4.0
防腐剤 0.2
香料 0.1
イオン交換水 残余
実施例６ 軟膏
ワセリン 40.0
ステアリルアルコール 15.0
木ロウ 15.0
POE（10）オレート 0.25
グリセリルモノステアレート 0.25
アルブチン 6.0
アラントイン 1.0
ソルビトール 5.0
プロピレングリコール 5.0
イオン交換水 残余[Table] From the results shown in Table 1, the tension in the areas treated with 0.1% and 1.0% allantoin increased compared to the areas without application (control), and the effect of promoting repair force was observed. Almost no increase in tension was observed. On the other hand, in the case of the product of the present invention in which arbutin and allantoin were used in combination, there was a tendency for the tension to increase compared to the comparative product in which each was applied individually, and a remarkable healing promoting effect was observed. In addition, not only in the above animal test but also in a human panel, this combination system of arbutin and allantoin and/or its derivatives showed effects equivalent to the results of this animal test. Example 2 Lotion A lotion was produced by a conventional method according to the following formulation. Propylene glycol 4.0 Ethanol 15.0 POE (20) Oleylether 0.5 Arbutin 20.0 Allantoin 0.01 Methylparaben 0.1 Citric acid 0.01 Sodium citrate 0.1 Fragrance 0.05 Ion-exchanged water Remaining Example 3 Cream A cream was produced by a conventional method according to the following recipe. Propilen Glycole 5.0 Mitsu Roux 5.0 Cethyl alcohol 4.0 reduction Ranolin 5.0 Squaralan 35.0 Glyceryl Monostaire 2.0 PoE (20) Sorbitan Monora Lowthrate 2.0 methyl paraben 0.1 ethyl paraben 0.15 Hydroquinone -β -D -Arabinose 3.0 Alant Innis 1.0 .0 Fragrance 0.1 ion exchange water residue 4 Pack A pack was manufactured by a conventional method according to the following formulation: Polyvinyl alcohol 15.0 Polyethylene glycol 3.0 Propylene glycol 7.0 Ethanol 10.0 Methylparaben 0.1 Arbutin 6.0 Dihydroxyaluminum allantoinate 3.0 Fragrance 0.1 Ion exchange water Remaining example 5 Scalp treatment (scalp cosmetics) A scalp treatment was prepared by a conventional method according to the following recipe. 1,3 Butylene Glycol 7.0 Polyethylene Glycol 5.0 Ethanol 10.0 POE (60) Hydrogenated Castor Oil 2.0 Caustic Potassium 0.05 Carboxyvinyl Polymer 0.2 2-Hexyldecyl Palmitate 10.0 Squalane 5.0 Beeswax 0.5 Arbutin 10.0 Allantoin 4.0 Preservatives 0.2 Fragrance 0. 1 Ion exchange water Residual implementation Example 6 Ointment petrolatum 40.0 Stearyl alcohol 15.0 Wood wax 15.0 POE (10) oleate 0.25 Glyceryl monostearate 0.25 Arbutin 6.0 Allantoin 1.0 Sorbitol 5.0 Propylene glycol 5.0 Ion exchange water Residual
Claims (1)
般式であらわされるハイドロキノンの配糖体とを
含有することを特徴とする皮膚外用剤。 【式】 ［式中、Ｒは五炭糖残基、六炭糖残基、アミノ
糖残基、ウロン酸残基又はそれらのメチル化物を
示す。］[Scope of Claims] 1. An external skin preparation characterized by containing allantoin and/or a derivative thereof and a glycoside of hydroquinone represented by the following general formula. [Formula] [In the formula, R represents a pentose residue, a hexose residue, an amino sugar residue, a uronic acid residue, or a methylated product thereof. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3983585A JPS61200919A (en) | 1985-02-28 | 1985-02-28 | External drug for skin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3983585A JPS61200919A (en) | 1985-02-28 | 1985-02-28 | External drug for skin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61200919A JPS61200919A (en) | 1986-09-05 |
| JPH0579643B2 true JPH0579643B2 (en) | 1993-11-04 |
Family
ID=12564016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3983585A Granted JPS61200919A (en) | 1985-02-28 | 1985-02-28 | External drug for skin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61200919A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016204307A (en) * | 2015-04-22 | 2016-12-08 | ロート製薬株式会社 | External composition for skin, coloring inhibitor, and coloring inhibition method |
-
1985
- 1985-02-28 JP JP3983585A patent/JPS61200919A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61200919A (en) | 1986-09-05 |
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