CN1942163B - 生发剂 - Google Patents
生发剂 Download PDFInfo
- Publication number
- CN1942163B CN1942163B CN2004800428860A CN200480042886A CN1942163B CN 1942163 B CN1942163 B CN 1942163B CN 2004800428860 A CN2004800428860 A CN 2004800428860A CN 200480042886 A CN200480042886 A CN 200480042886A CN 1942163 B CN1942163 B CN 1942163B
- Authority
- CN
- China
- Prior art keywords
- acid
- amino
- ferric
- hair growth
- hair
- 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
- 210000004209 hair Anatomy 0.000 title abstract description 24
- 230000003779 hair growth Effects 0.000 claims abstract description 73
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims abstract description 14
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960002749 aminolevulinic acid Drugs 0.000 claims abstract 6
- 239000007952 growth promoter Substances 0.000 claims description 53
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 42
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 150000002506 iron compounds Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 13
- 235000013877 carbamide Nutrition 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229960003330 pentetic acid Drugs 0.000 claims description 11
- UEHRTZASQAWUOJ-UHFFFAOYSA-J sodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;hydron;iron(3+) Chemical compound [Na+].[Fe+3].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEHRTZASQAWUOJ-UHFFFAOYSA-J 0.000 claims description 10
- 239000011640 ferrous citrate Substances 0.000 claims description 9
- 235000019850 ferrous citrate Nutrition 0.000 claims description 9
- YNVZDODIHZTHOZ-UHFFFAOYSA-K 2-hydroxypropanoate;iron(3+) Chemical compound [Fe+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O YNVZDODIHZTHOZ-UHFFFAOYSA-K 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 229950010481 5-aminolevulinic acid hydrochloride Drugs 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000004222 ferrous gluconate Substances 0.000 claims description 7
- 235000013924 ferrous gluconate Nutrition 0.000 claims description 7
- 229960001645 ferrous gluconate Drugs 0.000 claims description 7
- VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 claims description 7
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 5
- MDXRFOWKIZPNTA-UHFFFAOYSA-L butanedioate;iron(2+) Chemical compound [Fe+2].[O-]C(=O)CCC([O-])=O MDXRFOWKIZPNTA-UHFFFAOYSA-L 0.000 claims description 5
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 claims description 5
- 229960001604 ferrous succinate Drugs 0.000 claims description 5
- SRFKWQSWMOPVQK-UHFFFAOYSA-K sodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate;iron(2+) Chemical compound [Na+].[Fe+2].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O SRFKWQSWMOPVQK-UHFFFAOYSA-K 0.000 claims description 5
- YITYVXUAFSMRJI-BYPYZUCNSA-N (2s)-2-(carboxymethylamino)pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NCC(O)=O YITYVXUAFSMRJI-BYPYZUCNSA-N 0.000 claims description 4
- 229920002307 Dextran Polymers 0.000 claims description 4
- 229960004642 ferric ammonium citrate Drugs 0.000 claims description 4
- 150000003278 haem Chemical class 0.000 claims description 4
- 239000004313 iron ammonium citrate Substances 0.000 claims description 4
- 235000000011 iron ammonium citrate Nutrition 0.000 claims description 4
- ATEAWHILRRXHPW-UHFFFAOYSA-J iron(2+);phosphonato phosphate Chemical compound [Fe+2].[Fe+2].[O-]P([O-])(=O)OP([O-])([O-])=O ATEAWHILRRXHPW-UHFFFAOYSA-J 0.000 claims description 4
- 235000015424 sodium Nutrition 0.000 claims description 4
- AEDLILNWEXDEHC-UHFFFAOYSA-M sodium;butanedioic acid;3-carboxy-3,5-dihydroxy-5-oxopentanoate Chemical compound [Na+].OC(=O)CCC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O AEDLILNWEXDEHC-UHFFFAOYSA-M 0.000 claims description 4
- XNSQZBOCSSMHSZ-UHFFFAOYSA-K azane;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate;iron(3+) Chemical compound [NH4+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O XNSQZBOCSSMHSZ-UHFFFAOYSA-K 0.000 claims description 2
- FRHBOQMZUOWXQL-UHFFFAOYSA-L ammonium ferric citrate Chemical compound [NH4+].[Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FRHBOQMZUOWXQL-UHFFFAOYSA-L 0.000 claims 1
- APVZWAOKZPNDNR-UHFFFAOYSA-L iron(ii) citrate Chemical group [Fe+2].OC(=O)CC(O)(C([O-])=O)CC([O-])=O APVZWAOKZPNDNR-UHFFFAOYSA-L 0.000 claims 1
- -1 5-aminolevulinic acid compound Chemical class 0.000 abstract description 36
- 238000000034 method Methods 0.000 abstract description 21
- 239000000203 mixture Substances 0.000 abstract description 15
- 150000003839 salts Chemical class 0.000 abstract description 13
- 238000011282 treatment Methods 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- OOIOHEBTXPTBBE-UHFFFAOYSA-N [Na].[Fe] Chemical compound [Na].[Fe] OOIOHEBTXPTBBE-UHFFFAOYSA-N 0.000 abstract 1
- 230000001133 acceleration Effects 0.000 abstract 1
- UMEAURNTRYCPNR-UHFFFAOYSA-N azane;iron(2+) Chemical compound N.[Fe+2] UMEAURNTRYCPNR-UHFFFAOYSA-N 0.000 abstract 1
- 230000003813 thin hair Effects 0.000 abstract 1
- 230000002087 whitening effect Effects 0.000 abstract 1
- 201000004384 Alopecia Diseases 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 23
- 231100000360 alopecia Toxicity 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 13
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241001597008 Nomeidae Species 0.000 description 11
- 230000001737 promoting effect Effects 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- 230000003676 hair loss Effects 0.000 description 6
- 210000003128 head Anatomy 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000006210 lotion Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
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- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 4
- 229940043276 diisopropanolamine Drugs 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229960003632 minoxidil Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 210000004761 scalp Anatomy 0.000 description 4
- OMZPMJRGLDHPDU-QTNFYWBSSA-N 2-aminoacetic acid;(2s)-2-aminopentanedioic acid Chemical class NCC(O)=O.NCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O OMZPMJRGLDHPDU-QTNFYWBSSA-N 0.000 description 3
- TUFYVOCKVJOUIR-UHFFFAOYSA-N 2-hydroxy-3-propan-2-ylcyclohepta-2,4,6-trien-1-one Chemical compound CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 239000000051 antiandrogen Substances 0.000 description 3
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- AUALKMYBYGCYNY-UHFFFAOYSA-E triazanium;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [NH4+].[NH4+].[NH4+].[Fe+3].[Fe+3].[Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O AUALKMYBYGCYNY-UHFFFAOYSA-E 0.000 description 3
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Abstract
本发明的课题是关于对脱发、毛发枯细、毛发分叉、白发化等具有生发促进作用的生发剂，提供了与公知的以5-氨基乙酰丙酸类作为有效成分的生发剂相比，具有更高的稳定性、安全性的生发剂。通过将含有5-氨基乙酰丙酸或其盐或其衍生物与二乙撑三胺五乙酸铁钠或二乙撑三胺五乙酸铁铵的组合物作为有效成分，提供了具有良好的促进毛发伸张作用及具有稳定性和安全性的生发剂和生发方法。
Description
技术领域
本发明涉及应用于药品、准药品或化妆品领域的、具有良好的防止脱发、生发效果等养发作用的生发剂，具体涉及以5-氨基乙酰丙酸类为有效成分的生发剂的改良、将5-氨基乙酰丙酸类与铁化合物合用的生发剂。
背景技术
以往，已开始开发以防止、改善脱发症为目的的毛发用化妆品。从脱发症中男性脱发症所占比例较高考虑，特别对具有抗雄激素作用的成分的应用进行了研究，揭示了可竞争性抑制活化型睾酮——二氢睾酮与受体结合的物质，以及可抑制催化睾酮向二氢睾酮转化的酶——睾酮5α-还原酶的物质。前者可举出乙酸环丙氯地孕酮，后者可举出雄甾酮衍生物、双环庚酮衍生物、苯氧基丁烷衍生物、生育醌、草酚酮衍生物、辅酶Q等，以及以紫苏科植物、菊科植物为代表的多种植物的提取物(例如特开平5-339133号公报、特开平7-330555号公报、Tokushima Journal of Experimental Medicine(德岛实验药物杂志)，9，37-59(1962))、蘑菇类提取物(例如参见特开平11-193220号公报)。
并且，还对6-(1-哌啶基)-2，4-嘧啶二胺-3-氧化物(米诺地尔)(例如参见美国专利第4139619号说明书)、千金藤素、维生素E衍生物、卡普氯铵、尿素(例如参见特开平7-267830号公报)等具有促进头皮血液循环作用的物质以及对三磷酸腺苷、尿抑胃素、黄芩黄素、泛硫乙胺-S-磺酸、奇数链脂肪酸衍生物等具有活化以毛母细胞为代表的毛囊的作用的物质的应用进行了研究。进而已知有将已经作为除草剂、植物调节剂等而周知的以5-氨基乙酰丙酸类作为有效成分的头部用外用剂(例如参见特开平11-116446)。
但是，脱发症的发病除睾酮依赖性的男性型脱发症外，也常见有因老化或营养不良、现代社会中特别是应激等的种种原因而引起。对这样的男性型以外的脱发症来说，是无法期待具有抗雄激素作用的成分产生效果，而且上述具有抗雄激素作用的成分中，有时有产生不良反应的危险、有时在化妆品基质中的稳定性差、有时作用效果不充分的物质不在少数。另外，对于以植物提取物等天然产物为来源的物质，难以得到品质稳定的物质，与化妆品配合使用时颜色不好或有不良气味的物质也较多。因此，尽管有些物质被报道具有促进头皮血液循环作用或活化毛囊作用，但能在低浓度下获得充分作用效果的物质较少，同时也有一些物质存在稳定性和安全性方面的问题。
以往所知的以5-氨基乙酰丙酸类为有效成分的头部用外用剂(生发剂)，存在因用量或用法错误反而使头发受到损伤、头发分叉、头发数量减少等问题，而且还是使用时以避光为绝对条件之类的不能稳定使用的物质。本发明的课题是解决以5-氨基乙酰丙酸类为有效成分的头部用外用剂在使用上的问题，提供稳定性、安全性更高，且用法简便，并且对脱发、头发枯细、毛发分叉、白发化等具有良好的促进生发作用的生发剂。
本发明人等为解决使用5-氨基乙酰丙酸类时产生的上述问题，设想若将5-氨基乙酰丙酸与其他各种化合物合用，可能会用法简便、且产生安全、稳定的生发效果，在此基础上，对大量化合物进行实验、深入研究的结果发现，单独使用5-氨基乙酰丙酸时的脱发问题或使用时为避光条件等问题，能够通过将5-氨基乙酰丙酸类与铁化合物合用来避免，至此完成本发明。
发明内容
即，本发明涉及一种生发剂，其特征在于，含有选自5-氨基乙酰丙酸或其盐、或其衍生物中的1种或2种以上的化合物及铁化合物作为有效成分(第1项发明)；以及根据第1项发明所述的生发剂，其特征在于，还含有尿素作为有效成分(第2项发明)；以及根据第1或2项发明所述的生发剂，其特征在于，铁化合物为选自柠檬酸亚铁、柠檬酸铁钠、柠檬酸铁铵、乙酸铁、草酸铁、琥珀酸亚铁、琥珀酸柠檬酸铁钠、焦磷酸亚铁、焦磷酸铁、血红素铁、葡聚糖铁、乳酸铁、葡糖酸亚铁、二乙撑三胺五乙酸铁钠、二乙撑三胺五乙酸铁铵、乙二胺四乙酸铁钠、乙二胺五乙酸铁铵、三乙撑四胺铁、二羧甲基谷氨酸铁钠、二羧甲基谷氨酸铵中的1种或2种以上的化合物(第3项发明)；以及一种生发方法，其特征在于，从头部经皮给予含有选自5-氨基乙酰丙酸或其盐、或其衍生物中的1种或2种以上的化合物及铁化合物作为有效成分的生发剂(第4项发明)；以及根据第4项发明所述的生发方法，其特征在于，从头部经皮给予还含有尿素作为有效成分的生发剂(第5项发明)；以及根据第4或5项发明所述的生发方法，其特征在于，作为铁化合物，使用选自柠檬酸亚铁、柠檬酸铁钠、柠檬酸铁铵、乙酸铁、草酸铁、琥珀酸亚铁、琥珀酸柠檬酸铁钠、焦磷酸亚铁、焦磷酸铁、血红素铁、葡聚糖铁、乳酸铁、葡糖酸亚铁、二乙撑三胺五乙酸铁钠、二乙撑三胺五乙酸铁铵、乙二胺四乙酸铁钠、乙二胺五乙酸铁铵、三乙撑四胺铁、二羧甲基谷氨酸铁钠、二羧甲基谷氨酸铵中的1种或2种以上的化合物(第6项发明)。
附图说明
图1是本发明生发剂的临床实验例照片。左上为涂敷开始时，左下为4周后，右上为5周后，右下为7周后(7月12日)拍摄的照片。
图2是本发明生发剂的临床实验例照片。左为涂敷开始时，右为4周后拍摄的照片。
图3是本发明生发剂的临床实验例照片。左为涂敷开始时，右为4周后拍摄的照片。
图4是显示小鼠涂敷本发明生发组合物后第20日毛发的照片。左上为未处理小鼠，右上为涂敷5％米诺地尔的小鼠，左下为涂敷本发明的No.14的组合物的小鼠。
具体实施方式
作为本发明的生发剂，只要是含有选自5-氨基乙酰丙酸或其盐、或其衍生物中的1种或2种以上的化合物及铁化合物作为有效成分就无特殊限定，同时，作为本发明的生发方法，只要是从头部经皮给予含有选自5-氨基乙酰丙酸或其盐、或其衍生物中的1种或2种以上的化合物及铁化合物作为有效成分的生发剂的方法即可，无特殊限定，上述5-氨基乙酰丙酸也可以称作是δ-氨基乙酰丙酸，是以式HOOC-(CH2)2-(CO)-CH2-NH2表示的一种氨基酸(以下也称为5-ALA)。该5-氨基乙酰丙酸广泛分布于各种生物中，通常是在5-氨基乙酰丙酸合酶作用下，由琥珀酰CoA和甘氨酸生物合成得到。已知该5-氨基乙酰丙酸也可作为卟啉的生物合成的中间体。
作为本发明的5-氨基乙酰丙酸的盐，例如可举出盐酸盐、磷酸盐、硝酸盐、硫酸盐、乙酸盐、丙酸盐、丁酸盐、戊酸盐、柠檬酸盐、富马酸盐、马来酸盐、苹果酸盐等酸加成盐及钠盐、钾盐、钙盐等金属盐。此外，这些盐在使用时可以水溶液、混悬液或粉体的形式来使用，优选其作用效果与5-氨基乙酰丙酸相同的形式。
作为本发明生发剂的有效成分所用的5-氨基乙酰丙酸衍生物的代表形式，可举出5-氨基乙酰丙酸的酯或N-酰基-5-氨基乙酰丙酸等。作为5-氨基乙酰丙酸的酯的形式，可举出例如可具有取代基的直链、支链或环状的碳数1～2 4的烷基酯，优选例如甲基、乙基、异丙基、正己基、环己基、正庚基、正辛基、正壬基、正十二烷基、正十六烷基、苯甲基、苯乙基、3-苯丙基、羟乙基、乙氧乙基等作为酯残基的5-氨基乙酰丙酸酯。同时，作为这些烷基可具有的取代基，可举出例如羟基、烷氧基、苯基、苯甲基、羟甲基等。另外，作为N-酰基-5-氨基乙酰丙酸，可举出5-氨基乙酰丙酸的氨基被例如碳数1～24的烷酰基、芳酰基、苯甲氧羰基等酰化的化合物。进一步地，作为具体优选的N-酰基形式，可举出例如乙酰基、正戊酰基、正己酰基、正壬酰基、苯甲酰基、苯甲氧羰基等。
这些5-氨基乙酰丙酸的酯和N-酰基-5-氨基乙酰丙酸，可以通过例如特开平4-9360号公报等记载的方法等公知的化学合成方法制备。除该化学合成外，也可以用微生物生产、酶生产的任意方法进行制备。并且，在其制备工序中所得含目标产物的粗纯化物，只要不含有害物质，可不必分离纯化直接使用。5-氨基乙酰丙酸及其盐、衍生物可分别单独使用，也可将其中2种以上物质混合使用。
作为本发明的铁化合物，只要是分子内含铁的化合物就无特殊限定，可举出例如柠檬酸亚铁、柠檬酸铁钠、柠檬酸铁铵、乙酸铁、草酸铁、琥珀酸亚铁、琥珀酸柠檬酸铁钠、焦磷酸亚铁、焦磷酸铁、血红素铁、葡聚糖铁、乳酸铁、葡糖酸亚铁、二乙撑三胺五乙酸铁钠、二乙撑三胺五乙酸铁铵、乙二胺四乙酸铁钠、乙二胺四乙酸铁铵、三乙撑四胺铁、二羧甲基谷氨酸铁钠、二羧甲基谷氨酸铵、柠檬酸铁胆碱、甲酸亚铁、甲酸铁、草酸钾铁铵、硫酸亚铁、硫酸铁、硫酸铁铵、碳酸铁、氯化亚铁、氯化铁、焦磷酸铁、氧化铁等，其中优选二乙撑三胺五乙酸铁钠或二乙撑三胺五乙酸铁铵。
在本发明的生发剂中，作为有效成分，优选还含有尿素。尿素为无色～白色结晶或结晶性的粉末，可溶于水，稍易溶于乙醇，作为外用剂，可制成洗剂或乳剂等多种剂型。因此，其与皮肤的亲和性高，具有适合作为生发剂成分的物性。尿素的含量随所合用的基材及其他成分的不同而不同，可在本发明生发剂中以0.01～40％(W/W％：重量比)、优选0.1～10％的比例进行配合。作为所用的尿素，可直接使用市售的尿素。
本发明中，通常用于生发剂的赋形剂、血管扩张剂(卡普氯铵、烟酸苄酯、当药提取液、人参提取物、维生素E乙酸酯、辣椒酊等)、抗组胺剂(盐酸苯海拉明、盐酸氮异丙嗪等)、抗炎剂(甘草亭酸、愈创薁等)、杀菌剂(葡糖酸氯已定、异丙基甲酚、季铵盐、日扁柏醇、吡啶酮乙醇胺盐等)、保湿剂(透明质酸钠、硫酸软骨素等)、各种动植物(红豆杉、牡丹皮、甘草、藤黄、附子、枇杷、茵陈蒿、雏菊(comfrey)、咸草、藏红花、山栀子、迷迭香、鼠尾草、木香、青木香、麻蛇草、胎盘等)的提取物、维生素类(乙酸视黄醇、盐酸吡哆素、抗坏血酸、硝酸硫胺素、氰钴氨素、生物素等)、水、低级醇(甲醇、乙醇、变性乙醇、异丙醇等)、抗氧化剂(二丁羟基甲苯、焦亚硫酸钠、生育酚、依地酸钠、抗坏血酸、没食子酸异丙酯等)、助溶剂(己二酸二异丙酯、肉豆蔻酸异丙酯、聚乙二醇、中链脂肪酸三甘油酯、脂肪酸酯类、各种植物油、各种动物油、脂肪酸多元醇酯、烷基甘油醚、烃类、乳酸、氢氧化钠等)、代谢赋活剂(泛酰醇等)、表面活性剂(山梨糖醇酐脂肪酸酯、脂肪酸甘油酯、聚甘油脂肪酸酯、丙二醇脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇脂肪酸酯、聚氧乙烯甘油脂肪酸酯、聚乙二醇脂肪酸酯、聚氧乙烯烷基醚、聚氧乙烯聚氧丙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯氢化蓖麻油、聚氧乙烯蓖麻油、聚氧乙烯蜂蜡衍生物、聚氧乙烯含水羊毛脂衍生物、聚氧乙烯烷酰胺、聚氧乙烯烷基胺、卵磷脂衍生物、高分子乳化剂等)、乳化稳定剂(高级醇等)、凝胶化剂(水溶性高分子等)、粘合剂、香料、清凉剂(薄荷醇、薄荷油、樟脑等)、染料等通常使用的成分，可在不影响本发明效果的范围内配合使用。
如上所述，本发明的生发剂以含有5-氨基乙酰丙酸或其盐、或其衍生物及铁化合物为特征，其剂型为粉剂、液体制剂、软膏均可。可根据常规方法(例如第12版日本药局方规定的方法等)配制成洗剂、乳液、乳剂(软膏)、凝胶剂、喷雾剂等剂型。应予说明，5-氨基乙酰丙酸或其盐、或其衍生物及铁化合物，可以以各自的剂型施加于同一患部。
配制成洗剂这样的水溶液、乳剂(软膏)的情况下，为防止5-氨基乙酰丙酸或其盐、或其衍生物分解，优选注意不将之配制为碱性。碱性情况下，可通过除氧方法防止分解。只要注意这一点，就可与通常使用的液体制剂或软膏成分组合使用。
本发明的生发方法，优选通过对患部喷雾、涂敷、湿敷等方法经皮给予上述本发明的生发剂，也可对整个头皮进行适当的经皮给药。通常对成人每人的整个头皮进行涂敷时，将有效成分5-氨基乙酰丙酸或其盐及衍生物换算成5-氨基乙酰丙酸盐酸盐为10μg～10mg，优选100μg～5mg，更优选1mg～5mg的比例进行给予。与5-氨基乙酰丙酸等组合的铁化合物的给予量在同等条件下相当于换算为铁50μg～50mg，优选500μg～25mg，更优选5mg～25mg。
作为本发明生发剂的给予方式，例如可优选自傍晚至夜间用涂敷等方法经皮给予本发明的生发剂，并在晚间冲洗的方法，但不限定于所述给药方式。
尽管本发明的生发剂、生发方法的特征之一是无需单独给予(涂敷等)5-氨基乙酰丙酸时所必需的严密避光处理，但仍希望避开烈日下等的强光照射。本发明的给予方法是以3个月为一疗程进行实施，多数情况下从第3日起产生脱发减少和出现新发等生发效果。本发明生发剂也可以连续使用，当效果稳定的情况下暂停给药，在3个月中，之后再次开始给药时可期待再次产生效果。
下面通过实施例更具体地说明本发明，但本发明的技术范围并不局限于这些实施例。
实施例
(实施例1)
在溶有1，3-丁二醇4％、羟苯甲酯0.15％的纯化水20ml中，充分地混合5-氨基乙酰丙酸盐酸盐1.5g、尿素3g及柠檬酸亚铁1g。每晚将其以共计3ml涂敷于有稀发、脱发部分的人的头顶部位。涂敷后放置2小时，该晚冲洗头发。不实行以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。开始后第3日时，确认枕套上附着的脱发量减少。2周后，新发开始明显增长。在涂敷开始时、4周后、5周后(6/28)、7周后(7/2)进行拍照。拍摄结果见图1(照片)。如图1所示，与开始涂敷时相比，确认第7周后有明显的硬发增加，视觉观察可见明显的增发。
(实施例2)
除将实施例1的5-氨基乙酰丙酸盐酸盐变更为3g外，配制与实施例1同样的生发剂，结果，得到与实施例1基本相同的效果。
(实施例3)
除将实施例1的柠檬酸亚铁变更为2g外，配制与实施例1同样的生发剂，结果，得到与实施例1基本相同的效果。
(实施例4)
除将实施例1的柠檬酸亚铁1g变更为二乙撑三胺五乙酸铁铵4g外，配制与实施例1同样的生发剂，结果，得到与实施例1基本相同或之上的效果。
(实施例5)
除未配合有实施例1的尿素外，配制与实施例1同样的生发剂，结果，除生发效果稍微降低外，得到与实施例1基本相同的效果。
(实施例6)
将乙醇45重量份、5-氨基乙酰丙酸盐酸盐2重量份和二乙撑三胺五乙酸铁铵5.6重量份混合溶解，使其分散至羧乙烯聚合物0.7重量份中后，加入纯化水4 6.6重量份溶解。向该溶液中添加二异丙醇胺0.7重量份，搅拌混合、配成凝胶型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。开始后第3日时，确认枕套上附着的脱发量减少。2周后，新发开始明显增长。对涂敷开始时及4周后拍摄照片。拍摄结果见图2(照片)。如图2所示，与开始涂敷时相比，第4周后确认有明显的硬发增加，视觉观察可见明显的增发。
(实施例7)
除将实施例6的5-氨基乙酰丙酸盐酸盐变更为5-氨基乙酰丙酸甲酯外，用与实施例6同样的方法配制凝胶型生发剂，结果，得到与实施例6同等程度的效果。
(实施例8)
除将实施例6的二乙撑三胺五乙酸铁铵变更为二乙撑三胺五乙酸铁钠外，用与实施例6同样的方法配制凝胶型生发剂，得到与实施例6同等或其上的效果。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。开始后第3日时，确认枕套上附着的脱发量减少。2周后，新发开始明显增长。对涂敷开始时及4周后拍摄照片。拍摄结果见图3(照片)。如图3所示，与开始涂敷时相比，第4周后确认有明显的硬发增加，视觉观察可见明显的增发。
(实施例9)
除将实施例6的5-氨基乙酰丙酸盐酸盐变更为5-氨基乙酰丙酸苯乙酯外，用与实施例6同样的方法配制凝胶型生发剂，结果，得到与实施例6同等程度的效果。
(实施例10)
将单硬脂酸甘油酯5重量份、肉豆蔻酸异丙酯2重量份、液体石蜡5重量份、聚氧乙烯(20)山梨糖醇酐单硬脂酸酯4重量份、单异硬脂酸丙二醇酯4重量份、鲸蜡醇2重量份、硬脂醇2重量份、维生素E乙酸酯0.2重量份、日扁柏醇0.1重量份、甘草亭酸0.2重量份及乳酸铁5重量份在加热的同时搅拌、溶解。另外，向5-氨基乙酰丙酸2重量份、丙二醇7重量份、对羟基苯甲酸乙酯0.1重量份中加入纯化水至总计100重量份，加热的同时搅拌溶解，将该溶液加入到前述溶液中，搅拌、混合，配成乳剂型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。同时，生发效果与单独使用5-氨基乙酰丙酸类时相同或在其上。
(实施例11)
除将实施例10的乳酸铁5重量份变更为葡糖酸亚铁1重量份外，用与实施例10同样的方法，配制乳剂型生发剂，结果，得到与实施例10同等程度的效果。
(实施例12)
将5-氨基乙酰丙酸甲酯1重量份、琥珀酸亚铁5重量份、β-雌二醇0.0008重量份、日扁柏醇0.2重量份、甘草亭酸0.2重量份、维生素E乙酸酯0.1重量份、乙醇55重量份、聚乙二醇4005重量份、甘油单异硬脂酸酯5重量份及1-薄荷醇0.3重量份搅拌溶解。预先将聚氧乙烯(20)聚氧丙烯(6)癸基十四烷基醚4重量份、纯化水24.7重量份搅拌、溶解，将该溶液加入到前述溶液中，搅拌混合，配成洗剂型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。同时，生发效果与单独使用5-氨基乙酰丙酸类时相同或在其上。
(实施例13)
向聚氧乙烯(20)山梨糖醇酐单油酸酯3重量份、丙二醇5重量份、乙醇15重量份、5-氨基乙酰丙酸1重量份、乙二胺四乙酸铁钠中加入纯化水至合计量为100重量份，混合、搅拌溶解。将其放入喷雾筒中，向其中加压填充液化石油气4重量份，配成喷雾型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。同时，生发效果与单独使用5-氨基乙酰丙酸类时相同或在其上。
(实施例14)
除将实施例13的5-氨基乙酰丙酸1重量份变更为5-氨基乙酰丙酸甲酯1重量份外，用与实施例13同样的方法，配制喷雾型生发剂，结果，得到与实施例13同等程度的效果。
(实施例15)
向乙醇70重量份中加入丙二醇5重量份、5-氨基乙酰丙酸0.5重量份、三乙撑四胺铁2重量份和使其合计量为100重量份的纯化水，搅拌溶解，配成洗剂型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。同时，生发效果与单独使用5-氨基乙酰丙酸类时相同或在其上。
(实施例16)
加入乙醇45重量份、5-氨基乙酰丙酸1重量份、乙酸铁2重量份、1，3-丁二醇5重量份和使其合计量为100重量份的纯化水，搅拌溶解，向其中分散羧乙烯聚合物0.7重量份后，添加二异丙醇胺0.7重量份，搅拌混合配成凝胶型生发剂。该生发剂不实施以往单独使用5-氨基乙酰丙酸类时的严密避光条件，而且部分用量过剩时未见脱发现象。同时，生发效果与单独使用5-氨基乙酰丙酸类时相同或在其上。
(实施例17)
除将实施例16的乙酸铁变更为草酸铁外，用与实施例16同样的方法，配制凝胶型生发剂，结果，得到与实施例16同等程度的效果。
(实施例18)
[生发试验]
表1中，本发明的5-氨基乙酰丙酸(有时简称为ALA)和铁化合物，以及它们与尿素的配比组成用重量％表示。予以说明，相对于ALA1g，分别配合柠檬酸亚铁0.4g，乳酸铁2.81g，二乙撑三胺五乙酸铁钠5.7g，二乙撑三胺五乙酸铁铵5.6g，葡糖酸亚铁0.36g。对处于毛发生长停止周期的C3H/HeNCr J小鼠(各组n＝3)背部用推子剃毛，以1日1次0.2ml样品量喷涂表1所示各混悬液至均匀。2周后从各小鼠背部拔毛，在显微镜下测定毛的长度。结果如表1所示。
表1
| 样品No. | 组成 | 2周后的毛长(mm) | ||
| ALA | 铁化合物 | 尿素 | ||
| 1 | 2％溶液 | 柠檬酸亚铁 | 0％ | 1.12 |
| 2 | 同上 | 同上 | 10％ | 1.48 |
| 3 | 同上 | 乳酸铁 | 0％ | 1.00 |
| 4 | 同上 | 同上 | 10％ | 1.20 |
| 5 | 同上 | 二乙撑三胺五乙酸铁钠 | 0％ | 1.82 |
| 6 | 同上 | 同上 | 10％ | 2.96 |
| 7 | 同上 | 二乙撑三胺五乙酸铁铵 | 0％ | 1.68 |
| 8 | 同上 | 同上 | 10％ | 2.14 |
| 9 | 同上 | 葡糖酸亚铁 | 0％ | 1.48 |
| 10 | 同上 | 同上 | 10％ | 1.46 |
| 对照 | 同上 | 无 | 0％ | 1.08 |
| 对照 | 0.1％巴豆油 | 1.90 | ||
| 对照 | 5％米诺地尔 | 1.70 | ||
| 对照 | 蒸馏水 | 1.22 | ||
另外，在涂敷后第20日，对本发明的样品No.8组、5％米诺地尔组(阳性对照)、蒸馏水组(阴性对照)的小鼠背部拍摄照片。结果见图2(照片)。如图4所示，本发明组与蒸馏水组(阴性对照)相比，可知毛量、毛长、毛色有显著差异，其具有良好的生发效果。而且可知，即使与以往使用的米诺地尔相比，本发明生发剂也在毛量、毛长、毛色上显示了与之同等程度的效果，效果良好。
工业实用性
本发明通过将5-氨基乙酰丙酸类与铁化合物、尤其是二乙撑三胺五乙酸铁钠或二乙撑三胺五乙酸铁铵合用，能够提供与单独使用5-氨基乙酰丙酸类时相比，不存在脱发、毛发枯细、毛发分叉、白发化等问题、且使用时不以避光为绝对条件、不仅用法简便、而且具有同等程度或其上的显著生发效果的生发剂。
Claims (3)
1.铁化合物，以及
选自5-氨基乙酰丙酸、5-氨基乙酰丙酸盐、5-氨基乙酰丙酸的酯、和N-酰基-5-氨基乙酰丙酸中的1种或2种以上的化合物的组合在制备生发剂中的应用，其中，
所述铁化合物为选自柠檬酸亚铁、柠檬酸铁钠、柠檬酸铁铵、乙酸铁、草酸铁、琥珀酸亚铁、琥珀酸柠檬酸铁钠、焦磷酸亚铁、焦磷酸铁、血红素铁、葡聚糖铁、乳酸铁、葡糖酸亚铁、二乙撑三胺五乙酸铁钠、二乙撑三胺五乙酸铁铵、乙二胺四乙酸铁钠、乙二胺四乙酸铁铵、三乙撑四胺铁和二羧甲基谷氨酸铁钠中的1种或2种以上的化合物，
其中，选自5-氨基乙酰丙酸、5-氨基乙酰丙酸盐、5-氨基乙酰丙酸的酯、5-氨基乙酰丙酸盐的酯、N-酰基-5-氨基乙酰丙酸和N-酰基-5-氨基乙酰丙酸盐中的1种或2种以上的化合物的给予量以换算成5-氨基乙酰丙酸盐酸盐计为10μg～10mg，铁化合物的给予量以换算成铁计为50μg～50mg。
2.权利要求1所述的应用，其特征在于，所述生发剂还含有尿素。
3.权利要求1或2所述的应用，其特征在于，铁化合物为二乙撑三胺五乙酸铁钠或二乙撑三胺五乙酸铁铵。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004134709 | 2004-04-28 | ||
| JP134709/2004 | 2004-04-28 | ||
| PCT/JP2004/009894 WO2005105022A1 (ja) | 2004-04-28 | 2004-07-06 | 育毛剤 |
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| Publication Number | Publication Date |
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| CN1942163A CN1942163A (zh) | 2007-04-04 |
| CN1942163B true CN1942163B (zh) | 2010-11-24 |
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| JP (1) | JP3810018B2 (zh) |
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| ES2464169T3 (es) * | 2004-04-28 | 2014-05-30 | Cosmo Oil Co., Ltd. | Restaurador capilar |
| CA2606140C (en) * | 2005-04-28 | 2011-07-19 | Cosmo Oil Co., Ltd. | External preparation for skin |
| FR2911495B1 (fr) * | 2007-01-23 | 2014-06-27 | Oreal | Utilisation cosmetique d'associations de fer pour le soin de la peau. |
| JP5098051B2 (ja) | 2007-04-05 | 2012-12-12 | Ｓｂｉファーマ株式会社 | ミトコンドリア障害脳疾患治療剤及び診断剤 |
| DK2272538T3 (da) | 2008-04-22 | 2020-10-26 | Sbi Pharmaceuticals Co Ltd | Fremgangsmåde til påvisning af blærecancer |
| EP2305237B1 (en) * | 2008-05-14 | 2014-04-30 | SBI Pharmaceuticals Co., Ltd. | Therapeutic agent for male sterility |
| KR20100122952A (ko) * | 2008-05-30 | 2010-11-23 | 제이에프이 스틸 가부시키가이샤 | 선철 제조 방법 |
| JP5295652B2 (ja) * | 2008-06-16 | 2013-09-18 | Ｓｂｉファーマ株式会社 | 光障害の軽減剤 |
| JP5081121B2 (ja) * | 2008-10-17 | 2012-11-21 | 株式会社ミルボン | 育毛剤組成物 |
| CA2935654C (en) | 2008-10-27 | 2019-01-08 | Sbi Pharmaceuticals Co., Ltd. | Prophylactic/ameliorating agent for adult diseases comprising 5-aminolevulinic acid, its ester, or salt thereof as active ingredient |
| KR101034567B1 (ko) * | 2009-11-13 | 2011-05-12 | 이소영 | 탈모 방지 및 발모 촉진용 약물 전달 시스템 |
| CN106109455A (zh) | 2010-05-19 | 2016-11-16 | 思佰益药业股份有限公司 | 以5‑氨基乙酰丙酸或其衍生物作为有效成分的抗疟药 |
| WO2012092628A2 (en) * | 2010-12-31 | 2012-07-05 | Incube Labs, Llc | Patches and methods for the transdermal delivery of agents to treat hair loss |
| JP5782327B2 (ja) * | 2011-08-03 | 2015-09-24 | 株式会社ミルボン | 育毛剤組成物 |
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Also Published As
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| US20120122974A1 (en) | 2012-05-17 |
| AU2004318989B2 (en) | 2007-08-09 |
| US8133479B2 (en) | 2012-03-13 |
| CA2564043C (en) | 2012-01-31 |
| US20070249721A1 (en) | 2007-10-25 |
| US8632759B2 (en) | 2014-01-21 |
| CA2564043A1 (en) | 2005-11-10 |
| JP3810018B2 (ja) | 2006-08-16 |
| MXPA06012636A (es) | 2007-03-21 |
| EP1743621A4 (en) | 2009-05-06 |
| NZ550853A (en) | 2009-04-30 |
| AU2004318989A1 (en) | 2005-11-10 |
| EP1743621B1 (en) | 2014-03-05 |
| ES2464169T3 (es) | 2014-05-30 |
| KR100873664B1 (ko) | 2008-12-11 |
| BRPI0418784A2 (pt) | 2010-11-23 |
| BRPI0418784B1 (pt) | 2014-08-19 |
| CN1942163A (zh) | 2007-04-04 |
| WO2005105022A1 (ja) | 2005-11-10 |
| KR20070087488A (ko) | 2007-08-28 |
| EP1743621A1 (en) | 2007-01-17 |
| PL1743621T4 (pl) | 2014-11-28 |
| JPWO2005105022A1 (ja) | 2007-09-13 |
| PL1743621T3 (pl) | 2014-08-29 |
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