CN1231595A - 1－羟基－2－吡啶酮类化合物用于治疗皮脂溢性皮炎的用途 - Google Patents
1－羟基－2－吡啶酮类化合物用于治疗皮脂溢性皮炎的用途 Download PDFInfo
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- CN1231595A CN1231595A CN97198266A CN97198266A CN1231595A CN 1231595 A CN1231595 A CN 1231595A CN 97198266 A CN97198266 A CN 97198266A CN 97198266 A CN97198266 A CN 97198266A CN 1231595 A CN1231595 A CN 1231595A
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- Prior art keywords
- surfactant
- pyridone
- formula
- alkyl
- methyl
- Prior art date
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- 208000008742 seborrheic dermatitis Diseases 0.000 title claims abstract description 12
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- 210000005069 ears Anatomy 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
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- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 1
- 230000035984 keratolysis Effects 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- NSKIPIAUYVRHTO-UHFFFAOYSA-N morpholine-3,4-diamine Chemical compound NC1COCCN1N NSKIPIAUYVRHTO-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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Abstract
式Ⅰ的化合物适用于生产用于治疗皮脂溢性皮炎的药物。
Description
皮脂溢性皮炎是指头皮的疾病，该疾病与单纯头皮屑的不同之处在于：它存在红斑作为炎症的征兆，头皮的剥落的程度更大并且有时伴有瘙痒和灼热感，以及在身体的其它部位出现湿疹。该疾病可以以斑块的形式发生，但经常也会影响到整个头皮并且超过发际线，经常包括前额、颈部周围以及两耳。对于严重的患者，头皮可能会发生二次感染，变化可能表现为海绵状的质地、形成水疱和痂并且可能渗出水。
皮脂溢性皮炎在婴幼儿期也经常发生并通常在8-12个月时自发缓解。婴儿的头皮变化包括红斑、头皮剥落和偶而出现水疱和痂，这些变化可在数周内自发消退、间歇性地复发或持续整个儿童期。这些变化通常伴有在眼皮、鼻子和两耳周围的相似病变。然后，该病情在青春期后经常发生并且可以持续一生，甚至有可能会更加严重。约1-3％的人群患有该疾病。
已知1-羟基-2-吡啶酮类化合物及其盐对正常头皮屑具有活性，正常头皮屑的特征在于发生于几乎所有人群的临床非炎症性头皮剥落(DE2234009)。
迄今为止，治疗皮脂溢性皮炎的最有前途的方法是局部涂抹皮质类固醇制剂，最近，使用抗真菌物质的局部治疗已越来越受到重视。
皮质类固醇制剂的活性主要表现在对炎症病变的影响，而抗真菌物质如酮康唑主要对糠疹癣菌属的酵母真菌具有活性，糠疹癣菌属被认为是皮脂溢性皮炎的发病原因。但是，本发明的1-羟基-2-吡啶酮类化合物同时具有了以上两种物质的特性，并且同时表现出抗炎作用和对糠疹癣菌属的抗真菌活性。
与酮康唑相比，本发明的物质(即使仅局部接触很短的时间)在与真菌生长有关的皮肤层迅速集中，从而有助于迅速治愈。
酮康唑在体外对革兰氏阳性菌无活性(Kinsman等，医学微生物学杂志(J.Med.Microbiol.)(1993)16,2,Ⅳ)，而本发明的羟基-吡啶酮类化合物对革兰氏阳性菌和革兰氏阴性需氧和厌氧菌具有活性(Dittmar等，Arzneim.-Forschung,(1981)31(Ⅱ),8a,1317-1322页)。就治疗二次感染的患者而言，这是极为重要的发现。
与酮康唑相比，本发明所用的化合物的另一个非常重要的优点在于其在药物制剂中的加工可能性。基于它们在水、醇和含水醇溶液中的可溶性，可以毫无困难地制备头发洗液和透明凝胶制剂。
本发明的制剂还可用于治疗花斑癣，一种发生于躯干的表面非炎症性皮肤真菌疾病。
因此，本发明涉及游离或盐形式的式Ⅰ的1-羟基-2-吡啶酮类化合物在生产用于治疗皮脂溢性皮炎的药物中的用途：
其中R1、R2和R3彼此相同或不同，分别是氢原子或含有1-4个碳原子的烷基，R4是含有6-9个碳原子的饱和烃基，或式Ⅱ的基团
其中X 是S或O，Y 是氢原子或最多2个卤原子如氯和/或溴，Z 是单键或二价基团O、S、-CR2-(R=H或(C1-C4)-烷基)或含有2-10个碳的其它二价基团，并且，如果适宜的话，氧和/或硫原子以
链的形式连接，其中-如果基团中含有2个或多个氧和/或硫原子的
话-后者必须被至少两个碳原子隔开，并且其中两个邻近的碳原子
也可以通过双键彼此连接在一起并且碳原子的自由价键被H和/或
(C1-C4)-烷基饱和，Ar 是含有最多两个环的芳环系统，所述环可被最多三个选自氟、氯、
溴、甲氧基、(C1-C4)-烷基、三氟甲基或三氟甲氧基的取代基取代。
在基团“Z”中，碳链成员优选为CH2基团。如果CH2基团被C1-C4-烷基取代，CH3和C2H5是优选的取代基。基团“Z”的例子是：
-O-,-S-,-CH2-,-(CH2)m-(m=2-10),-C(CH3)2-,-CH2O-,-OCH2-,-CH2S-,
-SCH2-,-SCH(C2H5)-,-CH=CH-CH2O-,-O-CH2-CH=CH-CH2O-,
-OCH2-CH2O-,-OCH2-CH2CH2O-,-SCH2CH2CH2S-,
-SCH2CH2CH2CH2O-,-SCH2CH2OCH2CH2O-,
-SCH2CH2OCH2CH2O-CH2CH2S-or-S-CH2-C(CH3)2-CH2-S-.
基团“S”是硫原子，基团“O”是氧原子。符号“Ar”指苯基或稠合的系统如萘基、四氢萘基和茚基，以及分离的系统，例如从联苯基、二苯基烷烃、二苯基醚和二苯基硫醚衍生的系统。
式Ⅰ中，烃基R4是烷基或环己基，所述环己基也可以通过亚甲基或亚乙基与吡啶酮环连接，或可以含有一个内甲基。R4还可以是芳族基团，但是，优选该芳族基团通过至少一个脂族碳原子与吡啶酮基团相连。
式Ⅰ化合物的重要例子是：
6-[4-(4-氯苯氧基)苯氧基甲基]-1-羟基-4-甲基-2-吡啶酮，6-[4-(2,4-二氯苯氧基)苯氧基甲基]-1-羟基-4-甲基-2-吡啶酮，6-(联苯基-4-氧甲基)-1-羟基4-甲基-2-吡啶酮，6-(4-苄基-苯氧基甲基)-1-羟基-4-甲基-2-吡啶酮，6-[4-(2,4-二氯苄氧基)苯氧基甲基]-1-羟基-4-甲基-2-吡啶酮，6-[4-(4-氯苯氧基)苯氧基甲基]-1-羟基-3,4-二甲基-2-吡啶酮，6-[4-(2,4-二氯苄基)苯氧基甲基]-1-羟基-3,4-二甲基-2-吡啶酮，6-[4-(肉桂基氧基)苯氧基甲基]-1-羟基-4-甲基-2-吡啶酮，1-羟基-4-甲基-6-[4-(4-三氟甲基苯氧基)苯氧基甲基]-2-吡啶酮，1-羟基-4-甲基-6-环己基-2-吡啶酮，1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2-吡啶酮，1-羟基-4-甲基-6-正己基-、-6-异己基-、-6-正庚基-、-6-异庚基-2-吡啶酮，1-羟基-4-甲基-6-辛基-或-6-异辛基-2-吡啶酮，特别是1-羟基-4-甲基-6-环己基甲基-或-6-环己基乙基-2-吡啶酮，其中的各环己基还可以带有一个甲基，1-羟基-4-甲基-6-(2-二环[2,2,1]庚基)-2-吡啶酮，1-羟基-3,4-二甲基-6-苄基-或-6-二甲基-苄基-2-吡啶酮或1-羟基-4-甲基-6-(β-苯乙基)-2-吡啶酮。
术语“饱和的”是指不含脂族多重键、即不含烯键或炔键的基团。
上述式Ⅰ化合物可以以游离的形式或盐的形式使用，优选以游离的形式使用。
如果使用有机碱，优选采用低挥发性的碱，例如低分子量的链烷醇胺如乙醇胺、二乙醇胺、N-乙基乙醇胺、N-甲基二乙醇胺、三乙醇胺、二乙氨基乙醇、2-氨基-2-甲基-正丙醇、二甲氨基-丙醇、2-氨基-2-甲基丙二醇、三异丙醇胺。其它低挥发性碱的例子是，例如乙二胺、己二氨、吗啉、哌啶、哌嗪、环己基胺、三丁基胺、十二烷胺、N,N-二甲基十二烷胺、十八烷胺、9-十八碳烯胺、苄胺、二苄基胺、N-乙基苄基胺、二甲基十八烷胺、N-甲基吗啉、N-甲基哌嗪、4-甲基环己基胺、N-羟乙基吗啉。也可以使用季铵氢氧化物的盐如三甲基苄基氢氧化铵、四甲基氢氧化铵或四乙基氢氧化铵，此外，还可以使用胍及其衍生物、特别是其烷基化产物。但是，也可以使用例如低分子量烷胺如甲胺、乙胺或三乙胺作为成盐试剂。本发明所用的化合物适宜的盐还包括与无机阳离子形成的盐，例如碱金属盐，特别是钠盐、钾或铵盐；碱土金属盐如镁盐或钙盐；以及与二价或三价阳离子形成的盐，例如锌、铝或锆盐。
在式Ⅰ化合物的制剂中所用的活性化合物可以根据，例如US2540218中所述的方法制备。
对于所述化合物的本发明的用途，适宜的制剂是液体至半固体药物制剂，特别是头发洗液、香波、液体香皂，以及霜剂、软膏和凝胶制剂。
在该情况下，依据它们的实际用途，这些制剂通常是涂抹于皮肤和/或头皮上一段或长或短的时间。由于加入了本发明的化合物，可以对皮脂溢性皮炎进行有效的治疗。
如果本发明的制剂是以香波的形式存在，它们可以是透明液体或不透明液体的形式、霜剂的形式或是凝胶状的。这些香波所用的表面活性剂可以是阴离子、阳离子、非离子或两性的，并且可以以这些物质的混合物的形式存在。
但是，优选使用阴离子表面活性剂或多种阴离子表面活性剂的混合物作为基础表面活性剂，如需要，可加入两性表面活性剂作为辅助表面活性剂。
作为单独的洗涤剂，两性表面活性剂并不十分重要，因为它们的发泡作用、增稠性以及皮肤和眼粘膜的耐受性很一般。但是，如果与各种阴离子表面活性剂联用，这些特性将得到协同性改善。这就解释了两性表面活性剂对于优化阴离子香波的重要意义。
也可以使用非离子表面活性剂作为辅助表面活性剂。
这种类型的阴离子洗涤剂的例子包括：(C10-C20)-烷基-和亚烷基羧酸盐、烷基醚羧酸盐、脂肪醇硫酸盐、脂肪醇醚硫酸盐、烷醇酰胺硫酸盐和磺酸盐、脂肪酸烷醇酰胺聚乙二醇醚硫酸盐、链烷磺酸盐和羟基链烷磺酸盐、烯属磺酸盐、异硫代硫酸盐(isothionate)的酰基酯、α-磺基脂肪酸酯、烷基苯磺酸酯、烷基苯酚乙二醇醚磺酸盐、磺基琥珀酸盐、磺基琥珀酸半酯和二酯、脂肪醇醚磷酸酯(盐)、蛋白-脂肪酸缩合产物、烷基单甘油酯硫酸盐和磺酸酯盐、烷基甘油酯醚磺酸酯盐、脂肪酸甲基牛磺酸酯(methyltauride)、脂肪酸肌氨酸盐或磺化蓖麻醇酸盐。这些化合物及其混合物以它们的水溶性或水可分散盐的形式使用，例如钠盐、钾盐、镁盐、铵盐、单-、二-和三乙醇铵盐以及类似的链烷醇铵盐。
可以加入到香波中的两性表面活性剂的例子是：N-((C12-C18)-烷基)-β-氨基丙酸和N-((C12-C18)-烷基)-β-亚氨基二丙酸的碱金属盐和单、二-和三链烷醇铵盐；N-酰氨基烷基-N,N-二甲基乙酰甜菜碱，优选N-((C8-C18)-酰基)氨基丙基-N,N-二甲基乙酰甜菜碱；(C12-C18)-烷基-二甲基磺基丙基甜菜碱；基于咪唑啉的两性表面活性剂(商品名：Miranol、Steinapon)，优选1-(β-羧甲基氧乙基)-1-(羧甲基)-2-月桂基咪唑啉鎓的钠盐；胺氧化物，例如(C12-C18)-烷基二甲胺氧化物或脂肪酸酰氨基烷基二甲胺氧化物。
可用作洗涤剂的适宜的非离子表面活性剂是，例如脂肪醇乙氧基化物(烷基聚乙二醇)；烷基苯酚聚乙二醇；烷基硫醇聚乙二醇；脂肪胺乙氧基化物(烷基氨基聚乙二醇)；脂肪酸乙氧基化物(酰基聚乙二醇)，聚丙二醇乙氧基化物(Pluronic)；脂肪酸烷醇酰胺(脂肪酸酰胺聚乙二醇)；蔗糖酯；烷基聚葡糖苷；山梨醇酯和聚乙二醇醚。
适宜的阳离子表面活性剂是，例如季铵盐如二-((C10-C24)-烷基)二甲基氯化铵或溴化铵，优选二-((C12-C18)-烷基)二甲基氯化铵或溴化铵；(C10-C24)-烷基二甲基乙基氯化铵或溴化铵；(C10-C24)-烷基三甲基氯化铵或溴化铵，优选鲸蜡基三甲基氯化铵或溴化铵和(C20-C22)-烷基三甲基氯化铵或溴化铵；(C10-C24)-烷基二甲基苄基氯化铵或溴化铵，优选(C12-C18)-烷基二甲基苄基氯化铵；N-((C10-C18)-烷基)吡啶鎓氯化物或溴化物，优选N-((C12-C16)-烷基)吡啶鎓氯化物或溴化物；N-((C10-C18)-烷基)异喹啉鎓氯化物、溴化物或单烷基硫酸盐；N-((C12-C18)-烷基羟乙氨基甲酰基甲基)吡啶鎓氯化物；N-((C12-C18)-烷基)-N-甲基吗啉鎓氯化物、溴化物或单烷基硫酸盐；N-((C12-C18)-烷基)-N-乙基吗啉鎓氯化物、溴化物或单烷基硫酸盐；(C16-C18)-烷基-五氧乙基氯化铵；二异丁基苯氧基乙氧基乙基二甲基苄基氯化铵；N,N-二乙氨基乙基硬脂酰胺和-油酰胺与盐酸、乙酸、乳酸、柠檬酸、磷酸形成的盐；N-酰氨基乙基-N,N-二乙基-N-甲基铵氯化物、溴化物或单烷基硫酸盐和N-酰氨基乙基-N,N-二乙基-N-苄基铵氯化物、溴化物或单烷基硫酸盐，其中的酰基优选硬脂酰基或油酰基。
本发明的制剂还可含有其它添加剂，例如芳香物质；着色剂；遮光剂和珍珠上光剂，例如脂肪酸和多元醇的酯、脂肪酸的镁盐和锌盐；基于共聚物的分散剂；增稠剂，例如氯化钠、氯化钾、氯化铵、硫酸钠、脂肪酸烷醇酰胺、天然胶的纤维素衍生物、胶原水解物、其它脂肪、油、脂肪醇、聚硅氧烷、具有角质层分离和角膜成形(keratoplastic)作用的物质，例如硫、水杨酸或酶。
根据本身已知的方式通过将各成分混合在一起制得香波，如需要，可进行适于制剂具体类型的进一步加工。在实施例中以举例说明的方式对一些可能的制剂进行了描述。
本发明的制剂还可以是水或水-醇性头发洗液的形式，也可以是凝胶的形式和作为喷雾或泡沫的气雾剂的形式。所用的醇优选为乙醇和异丙醇。
可以提到的其它可以根据本发明应用1-羟基-2-吡啶酮类化合物的制剂是，例如霜剂和软膏制剂，主要用于治疗秃头和身体部分的产品。
正如在香波中所描述的，所有这些制剂的制备也是根据本身已知的方式通过加入本发明所用的活性化合物进行制备。对于上述的1-羟基-2-吡啶酮类化合物，本发明的制剂可含有一种化合物或将多种化合物联合使用。
制剂的pH值在约4.5-6.5的皮肤生理学的范围内。当使用盐形式的化合物时，上述pH范围的调节需用有机酸进行，而当使用游离化合物时，则该测定无需进行。
在本发明的制剂中，活性化合物的掺入量通常在约0.05-约10％之间。在该范围内，具体制剂的浓度取决于其应用目的。某些制剂形式，例如需要在使用前稀释的浓缩液，可以具有相当高的浓度。
如果是保留在皮肤和头皮上的制剂，例如凝胶制剂、软膏、霜剂或头发洗液，应采用低浓度，例如约0.05％-约1％，优选0.1-0.5％。高浓度适用于在选择性地稀释后仅短时间作用于头皮的制剂，例如香波或液体香皂。在这些情况下，可以使用例如约0.2-约10％的浓度，优选约0.5-约2％。
若无相反说明，以下数据是就重量而言的。实施例1
本发明的制剂具有如下组成：香波(基于阴离子洗涤剂)1-羟基-4-甲基-6-环己基-2-(1H)-吡啶酮 1.00％月桂基二甘醇醚硫酸钠(浓度为27％的溶液) 40.00％月桂基聚乙二醇醚磺基琥珀酸二钠(浓度为33％的溶液) 10.00％氯化钠 2.50％水 46.50％实施例2
本发明的制剂具有如下组成：香波(基于阴离子洗涤剂并含有两性表面活性剂作为辅助表面活性剂)1-羟基-4-甲基-6-环己基-2-(1H)-吡啶酮 1.00％月桂基二甘醇醚硫酸钠(浓度为27％的溶液) 36.00％椰油酰胺基(cocamido)丙基甜菜碱(浓度为30％的溶液) 6.00％氯化钠 3.30％水 53.70％实施例3
本发明的制剂具有如下组成：香波(基于阴离子洗涤剂并含有非离子表面活性剂作为辅助表面活性剂)1-羟基-4-甲基-6-环己基-2-(1H)-吡啶酮 1.50％月桂基二甘醇醚硫酸钠(浓度为27％的溶液) 30.00％月桂醇聚葡糖苷 8.00％氯化钠 2.00％水 58.50％实施例4
本发明的制剂具有如下组成：液体香皂1-羟基-4-甲基-6-环己基-2-(1H)-吡啶酮 1.00％月桂基二甘醇醚硫酸钠(浓度为27％的溶液) 35.00％椰油酰胺基聚乙二醇醚硫酸镁(浓度为30％的溶液) 8.00％椰油酰胺基丙基甜菜碱(浓度为30％的溶液) 10.00％月桂醇甘醇醚 2.00％氯化钠 2.00％水 42.00％实施例5
本发明的制剂具有如下组成：头发洗液1-羟基-4-甲基-6-[4-(4-氯苯氧基)苯氧基甲基]-2-(1H)-吡啶酮 0.05％2-丙醇 60.00％水 39.95％实施例6
本发明的制剂具有如下组成：凝胶制剂1-羟基-4-甲基环己基-2-(1H)-吡啶酮 0.75％2-丙醇 15.00％2-辛基十二烷醇 7.50％卡波姆4,000,000 0.50％吐温60 1.50％氢氧化钠 0.18％水 74.57％实施例7
本发明的制剂具有如下组成：霜剂1-羟基-4-甲基-6-环己基-2-(1H)-吡啶酮，氨基乙醇盐1∶1 1.00％2-辛基十二烷醇 7.50％液体石蜡 7.50％硬脂醇 7.50％鲸蜡醇 7.50％吐温60 3.00％脱水山梨醇单硬脂酸酯 2.00％乳酸，浓度为90％ 0.51％水 63.49％实施例8
在总共180名患者的临床研究中可以观察到，在用1％浓度的环己吡酮乙醇胺香波制剂以每周1-2次治疗4周后，头皮的皮脂溢性皮炎症状(严重的头皮剥落、炎症、瘙痒)得到了有效的治疗。实施例9
在临床研究中，通过涂抹0.77％环己吡酮乙醇胺凝胶制剂4周，成功地治疗了180患者脸部和上身的皮脂溢性皮炎。
Claims (13)
1．游离或盐形式的式Ⅰ的1-羟基-2-吡啶酮在生产用于治疗皮脂溢性皮炎的药物中的用途：
其中R1、R2和R3彼此相同或不同，分别是氢原子或含有1-4个碳原子的烷基，R4是含有6-9个碳原子的饱和烃基，或式Ⅱ的基团
其中X 是S或O，Y 是氢原子或最多2个卤原子如氯和/或溴，Z 是单键或二价基团O、S、-CR2-(R=H或(C1-C4)-烷基)或含有2-10个碳的其它二价基团，并且，如果适宜的话，氧和/或硫原子以链的形式连接，其中-如果基团中含有2个或多个氧和/或硫原子的话-后者必须被至少两个碳原子隔开，并且其中两个邻近的碳原子也可以通过双键彼此连接在一起并且碳原子的自由价键被H和/或(C1-C4)-烷基饱和，Ar 是含有最多两个环的芳环系统，所述环可被最多三个选自氟、氯、溴、甲氧基、(C1-C4)-烷基、三氟甲基或三氟甲氧基的取代基取代。
2．权利要求1的用途，其中，所用的式Ⅰ化合物中Ar是从联苯基、二苯基烷烃或二苯基醚衍生的二环系统。
3．权利要求1或2的用途，其中，式Ⅰ化合物在R4位置含有环己基。
4．权利要求1-3中一项或多项所述的用途，其中，式Ⅰ化合物在R4位置含有结构式为-CH2-CH(CH3)-CH2-C(CH3)3的辛基。
5．权利要求1所述的用途，其中，所用的化合物为1-羟基-4-甲基-6-[4-(4-氯苯氧基)苯氧基甲基]-2(1H)-吡啶酮、1-羟基-4-甲基-6-环己基-2(1H)-吡啶酮或1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2(1H)-吡啶酮。
6．权利要求1-5中一项或多项所述的用途，其中的药物是头发洗液、香波或霜剂、软膏或凝胶制剂。
7．权利要求6所述的用途，其中，阴离子表面活性剂、阳离子表面活性剂、非离子表面活性剂或两性表面活性剂单独使用或与其它表面活性剂混合使用。
8．权利要求7所述的用途，其中所用的表面活性剂是至少一种单独使用的阴离子表面活性剂或其与其它阴离子表面活性剂和/或两性表面活性剂的混合物。
9．权利要求1-8中一项或多项所述的用途，其中，药物的pH为4.5-6.5。
10．含有权利要求1所述式Ⅰ的1-羟基-2-吡啶酮和至少一种阴离子表面活性剂、阳离子表面活性剂、非离子表面活性剂或两性表面活性剂或这些表面活性剂的混合物的药物制剂。
11．权利要求10所述的药物制剂，其中所用的表面活性剂是至少一种单独使用的阴离子表面活性剂或其与其它阴离子表面活性剂和/或两性表面活性剂的混合物。
12．权利要求10或11所述的药物制剂，其中，所述制剂的pH为4.5-6.5。
13．权利要求10-12中的一项或多项所述的药物制剂，其中，式Ⅰ的1-羟基-2-吡啶酮的使用浓度为0.2％-10％，优选0.5-2％。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19639818.5 | 1996-09-27 | ||
| DE19639818A DE19639818A1 (de) | 1996-09-27 | 1996-09-27 | Verwendung von 1-Hydroxy-2-pyridonen zur Behandlung der Seborrhoischen Dermatitis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1231595A true CN1231595A (zh) | 1999-10-13 |
| CN1104231C CN1104231C (zh) | 2003-04-02 |
Family
ID=7807118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97198266A Expired - Lifetime CN1104231C (zh) | 1996-09-27 | 1997-09-16 | 1－羟基－2－吡啶酮类化合物用于治疗皮脂溢性皮炎的用途 |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP0928183B1 (zh) |
| JP (2) | JP2001500884A (zh) |
| KR (1) | KR100494207B1 (zh) |
| CN (1) | CN1104231C (zh) |
| AR (1) | AR008860A1 (zh) |
| AT (1) | ATE209891T1 (zh) |
| AU (1) | AU716208B2 (zh) |
| BG (1) | BG64365B1 (zh) |
| BR (1) | BR9711575A (zh) |
| CA (1) | CA2267165C (zh) |
| CY (1) | CY2362B1 (zh) |
| CZ (1) | CZ291485B6 (zh) |
| DE (2) | DE19639818A1 (zh) |
| DK (1) | DK0928183T3 (zh) |
| ES (1) | ES2167721T3 (zh) |
| HK (1) | HK1022267A1 (zh) |
| HU (1) | HU226955B1 (zh) |
| ID (1) | ID21874A (zh) |
| IL (1) | IL129141A0 (zh) |
| MA (1) | MA24333A1 (zh) |
| MY (1) | MY125674A (zh) |
| NO (1) | NO312492B1 (zh) |
| NZ (1) | NZ334850A (zh) |
| OA (1) | OA11028A (zh) |
| PL (1) | PL188033B1 (zh) |
| PT (1) | PT928183E (zh) |
| RS (1) | RS49801B (zh) |
| TR (1) | TR199900662T2 (zh) |
| TW (1) | TW519491B (zh) |
| UA (1) | UA57754C2 (zh) |
| WO (1) | WO1998013009A2 (zh) |
| ZA (1) | ZA978640B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103974937A (zh) * | 2011-12-08 | 2014-08-06 | 皮埃尔·法布尔皮肤化妆品公司 | 新的脂肪生成抑制剂化合物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19639816A1 (de) | 1996-09-27 | 1998-04-02 | Hoechst Ag | Antimykotische Mittel mit hoher Wirkstofffreisetzung |
| US20040039030A1 (en) | 1996-09-27 | 2004-02-26 | Hoechst Akeengesellschaft | Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis |
| US20050095215A1 (en) * | 2003-11-03 | 2005-05-05 | Popp Karl F. | Antimicrobial shampoo compositions |
| WO2009027473A1 (en) | 2007-08-31 | 2009-03-05 | Janssen Pharmaceutica Nv | Combinations of imazalil and hydroxypyridones |
| NZ585433A (en) | 2007-11-30 | 2011-11-25 | Janssen Pharmaceutica Nv | Combinations of fungicidal azoles and pyrion compounds |
| EP2252147B1 (en) | 2008-02-06 | 2012-12-05 | Janssen Pharmaceutica NV | Combinations of fludioxonil and pyrion compounds |
| ES2602481T3 (es) | 2010-07-01 | 2017-02-21 | Janssen Pharmaceutica, N.V. | Combinaciones antimicrobianas de compuestos de piriona con polietileniminas |
| ES2573116T3 (es) * | 2010-12-02 | 2016-06-06 | The University Of Kansas | Profármacos de 6-ciclohexil-1-hidroxi-4-metilpiridin-2(1H)-ona y sus derivados |
| WO2013011996A1 (ja) * | 2011-07-19 | 2013-01-24 | リジェンティス株式会社 | 酵母菌から抽出されたポリリン酸，ポリリン酸の塩又はポリリン酸の溶媒和物を含むポリリン酸組成物及びその製造方法。 |
| CN104744359B (zh) * | 2015-03-06 | 2017-10-10 | 上药康丽（常州）药业有限公司 | 一种环吡酮的精制方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2234009C3 (de) * | 1972-07-11 | 1979-01-11 | Hoechst Ag, 6000 Frankfurt | Kosmetische Zubereitungen |
| NL8601762A (nl) * | 1986-07-07 | 1988-02-01 | Bouke Jan Lange | Werkwijze voor de reiniging en conditionering en eventuele medicinale behandeling van het haar en de hoofdhuid, een voor dit doel bruikbare tweefasen shampoo, alsmede een verpakking daarvoor. |
| ATE159169T1 (de) * | 1992-09-08 | 1997-11-15 | Procter & Gamble | Milde, im wesentlichen farblose shampoozusammensetzung |
| DE4333893A1 (de) * | 1993-10-05 | 1995-04-06 | Hoechst Ag | Kosmetische Zubereitungen |
| FR2722689B1 (fr) * | 1994-07-20 | 1996-10-04 | Fabre Pierre Dermo Cosmetique | Nouveau produit de combinaison comprenant un agent antifongique et du crotamiton comme potentialisateur de l'activite de l'agent antifongique, et compositions dermatologiques et/ou cosmetiques le comprenant |
-
1996
- 1996-09-27 DE DE19639818A patent/DE19639818A1/de not_active Withdrawn
-
1997
- 1997-09-16 AU AU47746/97A patent/AU716208B2/en not_active Expired
- 1997-09-16 CZ CZ19991075A patent/CZ291485B6/cs not_active IP Right Cessation
- 1997-09-16 PT PT97910294T patent/PT928183E/pt unknown
- 1997-09-16 ID IDW990129A patent/ID21874A/id unknown
- 1997-09-16 DK DK97910294T patent/DK0928183T3/da active
- 1997-09-16 ES ES97910294T patent/ES2167721T3/es not_active Expired - Lifetime
- 1997-09-16 TR TR1999/00662T patent/TR199900662T2/xx unknown
- 1997-09-16 JP JP10515223A patent/JP2001500884A/ja active Pending
- 1997-09-16 NZ NZ334850A patent/NZ334850A/en not_active IP Right Cessation
- 1997-09-16 WO PCT/EP1997/005070 patent/WO1998013009A2/de active IP Right Grant
- 1997-09-16 DE DE59705697T patent/DE59705697D1/de not_active Expired - Lifetime
- 1997-09-16 UA UA99042351A patent/UA57754C2/uk unknown
- 1997-09-16 KR KR10-1999-7002553A patent/KR100494207B1/ko not_active IP Right Cessation
- 1997-09-16 EP EP97910294A patent/EP0928183B1/de not_active Expired - Lifetime
- 1997-09-16 HU HU9903811A patent/HU226955B1/hu unknown
- 1997-09-16 CA CA002267165A patent/CA2267165C/en not_active Expired - Lifetime
- 1997-09-16 IL IL12914197A patent/IL129141A0/xx not_active IP Right Cessation
- 1997-09-16 AT AT97910294T patent/ATE209891T1/de active
- 1997-09-16 RS YUP-134/99A patent/RS49801B/sr unknown
- 1997-09-16 BR BR9711575A patent/BR9711575A/pt not_active Application Discontinuation
- 1997-09-16 PL PL33260397A patent/PL188033B1/pl unknown
- 1997-09-16 CN CN97198266A patent/CN1104231C/zh not_active Expired - Lifetime
- 1997-09-25 TW TW086113944A patent/TW519491B/zh not_active IP Right Cessation
- 1997-09-25 AR ARP970104432A patent/AR008860A1/es not_active Application Discontinuation
- 1997-09-26 MY MYPI97004501A patent/MY125674A/en unknown
- 1997-09-26 ZA ZA9708640A patent/ZA978640B/xx unknown
- 1997-09-29 MA MA24814A patent/MA24333A1/fr unknown
-
1999
- 1999-03-17 BG BG103260A patent/BG64365B1/bg unknown
- 1999-03-25 NO NO19991460A patent/NO312492B1/no not_active IP Right Cessation
- 1999-03-26 OA OA9900071A patent/OA11028A/fr unknown
-
2000
- 2000-02-28 HK HK00101194A patent/HK1022267A1/xx not_active IP Right Cessation
-
2003
- 2003-05-26 CY CY0300044A patent/CY2362B1/xx unknown
-
2006
- 2006-03-22 JP JP2006078057A patent/JP2006176540A/ja not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103974937A (zh) * | 2011-12-08 | 2014-08-06 | 皮埃尔·法布尔皮肤化妆品公司 | 新的脂肪生成抑制剂化合物 |
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