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    • 24. 发明授权
    • Tripeptides and derivatives thereof for cosmetic application in order to improve skin structure
    • 用于化妆品应用的三肽及其衍生物,以改善皮肤结构
    • US07863417B2
    • 2011-01-04
    • US10555994
    • 2004-05-07
    • Hugo ZieglerMarc HeidlDominik Imfeld
    • Hugo ZieglerMarc HeidlDominik Imfeld
    • C07K5/08
    • C07K7/08A61K8/64A61Q19/08
    • The invention relates to compounds and to the cosmetically acceptable salts thereof, which correspond to general formula (I), wherein: R1 represents H, —C(O)—R6, —SO2—R6 or —C(O)—XR6; R2 and R4, independent of one another, represent (CH2)n—NH2 or (CH2)3—NHC(NH)NH2; n equals 1 4; R3 represents linear or branched C1-C4 alkyl that is optionally substituted by hydroxy; R5 and R6, independent of one another, represent hydrogen, optionally substituted (C1-C24) alkyl, optionally substituted C2-C24 alkenyl, optionally substituted phenyl, optionally substituted phenyl-C1-C4 alkyl or 9-fluorenyl-methyl; X represents oxygen (—O—) or —NH—; or XR5 with X═O also represents the esters of a-tocopherol, tocotrienol or retinol, with the provision that R1 and R5 do not represent hydrogen and X does not represent oxygen at the same time. The invention also relates to the production of the compounds of general formula (I) and to a cosmetically active composition that contains at least one compound of formula (I).
    • 本发明涉及对应于通式(I)的化合物及其化学上可接受的盐,其中:R 1表示H,-C(O)-R 6,-SO 2 -R 6或-C(O)-XR 6; R 2和R 4彼此独立地表示(CH 2)n -NH 2或(CH 2)3 -NHC(NH)NH 2; n等于1 4; R3表示任选被羟基取代的直链或支链C 1 -C 4烷基; R 5和R 6彼此独立地表示氢,任选取代的(C 1 -C 24)烷基,任选取代的C 2 -C 24烯基,任选取代的苯基,任选取代的苯基-C 1 -C 4烷基或9-芴基 - 甲基; X表示氧(-O-)或-NH-; 或具有X = O的XR5也表示α-生育酚,生育三烯酚或视黄醇的酯,其条件是R1和R5不表示氢,X不同时代表氧。 本发明还涉及通式(I)的化合物的生产和含有至少一种式(I)化合物的化妆品活性组合物。
    • 27. 发明申请
    • Method for producing 3-amidinophenylalanine derivatives
    • 制备3-脒基苯丙氨酸衍生物的方法
    • US20070123706A1
    • 2007-05-31
    • US11699228
    • 2007-01-29
    • Hugo ZieglerPeter Wikstroem
    • Hugo ZieglerPeter Wikstroem
    • A61K31/495C07C311/45
    • C07D295/205C07D211/60
    • The present invention describes a method for the synthesis of enantiomerically pure 3-amidinophenylalanine derivatives, which are used as pharmaceutically effective urokinase inhibitors, by starting from 3-cyanophenylalanine derivatives. The methods of manufacture comprising only one synthesis step lead to new intermediates, namely 3-hydroxyamidino- and 3-amidrazonophenylalanine derivatives. These intermediates or their acetyl derivatives can be reduced into the desired 3-amidinophenylalanine derivatives under gentle conditions (H2 or ammonium formiate, Pd/C (approx. 10%), ethanol/water, room temperature, normal pressure or also H2, Pd/C, AcOH or HCl/ethanol, 1-3 bar) in excellent yields and in an enantiomeric excess of up to 99.9%.
    • 本发明描述了通过从3-氰基苯丙氨酸衍生物开始合成用作药物有效的尿激酶抑制剂的对映体纯的3-脒基苯丙氨酸衍生物的方法。 仅包含一个合成步骤的制备方法导致新的中间体,即3-羟基脒基 - 和3-酰胺基苯丙氨酸衍生物。 这些中间体或它们的乙酰基衍生物可以在温和条件(H 2 N 2或甲酸铵,Pd / C(约10%),乙醇/水,室温)下还原成所需的3-脒基苯丙氨酸衍生物, 正常压力或者H 2 Cl 2,Pd / C,AcOH或HCl /乙醇,1-3巴),产率高,对映体过量高达99.9%。
    • 28. 发明申请
    • Dermopharmaceutically and cosmetically active oligopeptides
    • 药物和化妆品活性寡肽
    • US20050065090A1
    • 2005-03-24
    • US10493856
    • 2002-10-30
    • Christian LudinMarc HeidlHugo Ziegler
    • Christian LudinMarc HeidlHugo Ziegler
    • A61K38/00A61P17/00C07K5/068C07K14/78A61K38/08C07K7/06
    • C07K14/78A61K38/00C07K5/06086
    • Oligopeptides and derivatives thereof, peptide analogs and derivatives thereof as well as pharmaceutically acceptable salts of these compounds, which correspond to general formula (I) wherein R1 represents H, —C(O)—R7, —SO2—R7, —C(O)—OR7 or —C(O)—N(R7)2 R2 represents, independent of one another, H or —(C1-C4)-alkyl, R3 and R6 represent, independent of one another, —(CH2)q—N(R1)R8 R4 and R5 represent, independent of one another, —CH2—OR2, —CH(CH3)OR8 or —CH2—CH2—OR8 R7 represents hydrogen, optionally substituted (C1-C19)-alkyl; optionally substituted (C1-C19)-alkenyl; phenyl-(C1-C4)-alkyl whose phenyl radical is optionally substituted with amino in the para position R8 represents H, —(C1-C4)-alkyl, —C(O)—R7, —C(O)—OR7, —C(O)—N(R7)2 or —SO2—R7 X represents oxygen (—O—) or —NH—; or XR7, with X=O, also represents the esters of α-tocopherol, tocotrienol or retinol or the carboxylic acid (with R7=H) m, n, p represent, independent of one another, zero or 1 and q in R3 and R6 represent, independent of one another, an integer from 1 to 4, with the provision that the following conditions do not simultaneously occur: R4=—CH(CH3)—OH and R5=—CH(CH3)—OH and R6=—(CH2)4—NH2; dermopharmaceutically and/or cosmetically active compositions containing at least one compound of formula (I).
    • 对应于通式(I)的寡肽及其衍生物,肽类似物及其衍生物以及这些化合物的药学上可接受的盐,其中R 1表示H,-C(O)-R 7,-SO 2 - R 7,-C(O)-OR 7或-C(O)-N(R 7)2 R 2彼此独立地表示H或 - (C 1 -C 4) - 烷基,R 3和R 6彼此独立地表示 - (CH 2)q N(R 1)R 8 R 4和R 5彼此独立地表示 - CH2-OR2,-CH(CH3)OR8或-CH2-CH2-OR8表示氢,任选取代的(C 1 -C 19) - 烷基; 任选取代的(C 1 -C 19) - 烯基; 苯基 - (C 1 -C 4) - 烷基,其苯基任选被对位R 8中的氨基取代,代表H, - (C 1 -C 4) - 烷基,-C(O)-R 7,-C (O)-OR 7,-C(O)-N(R 7)2或-SO 2 -R 7表示氧(-O-)或-NH-; 或XR 7,X = O也表示α-生育酚,生育三烯酚或视黄醇或羧酸(R 7 = H)m,n,p彼此独立地为0或 1和q在R 3和R 6中彼此独立地表示1至4的整数,条件是不同时发生以下条件:R 4 = -CH(CH 3) - OH和R 5 = -CH(CH 3)-OH,R 6 = - (CH 2)4 -NH 2; 含有至少一种药物的药物和/或化妆品活性组合物
    • 29. 发明授权
    • N-alkoxy-n-phenylcarbamate derivatives
    • N-烷氧基 - 正 - 苯基氨基甲酸酯衍生物
    • US06486341B1
    • 2002-11-26
    • US09889024
    • 2001-07-10
    • Hugo Ziegler
    • Hugo Ziegler
    • C07C26100
    • C07C251/88
    • Compounds of formula (I) wherein R1 is C1-C4-alkyl or cyclopropyl; R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl; or C1-C6-alkyl substituted by 1 to 5 fluorine atoms; R3 is C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C2-C6-alkinyloxy, C1-C6-alkoxycarbonyl, CN, or aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by identical of different substituents, R5 signifies hydrogen or methyl; R6 and R7 are C1-C4-alkyl; have microbicidal, insecticidal and acaricidal activity and may be used for the control of pests and plant-pathogenic fungi in agriculture, horticulture and in the field of hygiene.
    • 其中R1是C1-C4烷基或环丙基的式(Ⅰ)化合物; R2是C1-C6-烷基,C2-C6-烯基,C2-C6-炔基; 或被1至5个氟原子取代的C 1 -C 6烷基; R3是C1-C6-烷基,C1-C6-烷氧基,C3-C6-环烷基,C3-C6-环烷氧基,C2-C6-烯基,C2-C6-烯氧基,C2-C6-炔基,C2-C6-烷氧基, C 1 -C 6烷氧基羰基,CN或芳基,杂芳基,杂环基,芳氧基,杂芳氧基或杂环氧基,其中上述基团可以被相同的不同取代基取代,R 5表示氢或甲基; R6和R7是C1-C4-烷基; 具有杀菌,杀虫和杀螨活性,可用于控制农业,园艺和卫生领域的害虫和植物致病真菌。
    • 30. 发明授权
    • Dihydrotriazolone derivatives as pesticides
    • 二氢三唑酮衍生物作为农药
    • US06436981B1
    • 2002-08-20
    • US09736694
    • 2000-12-13
    • Hugo Ziegler
    • Hugo Ziegler
    • A01N43653
    • C07D401/12A01N43/653C07D249/12C07D403/12C07D405/12C07D409/12C07D413/12C07D417/12
    • Compounds of formula 1 wherein: Y signifies halogen, C1-C4-alkoxy, C1-C4-alkylthio or hydroxy; R1 signifies methyl, ethyl or cyclopropyl; R2 signifies C1-C6-alkyl or C1-C6-alkyl substituted by 1 to 5 fluorine atoms; R3 is C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C2-C6-alkinyloxy, C1-C6-alkoxycarbonyl or CN, whereby, with the exception of CN, the above-mentioned groups may be substituted by identical or different substituents; or R3 is aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by identical or different substituents, R5 signifies hydrogen or methyl; have microbicidal, insecticidal and acaricidal activity and may be used to control insects and plant-pathogenic fungi in agriculture, horticulture and in the field of hygiene.
    • 式1的化合物,其中Y表示卤素,C 1 -C 4 - 烷氧基,C 1 -C 4 - 烷硫基或羟基; R 1表示甲基,乙基或环丙基; R 2表示被1至5个氟取代的C 1 -C 6 - 烷基或C 1 -C 6烷基 原子; R 3是C 1 -C 6烷基,C 1 -C 6 - 烷氧基,C 3 -C 6 - 环烷基,C 3 -C 6环烷氧基,C 2 -C 6 - 烯基,C 2 -C 6 - 烯氧基,C 2 -C 6 - 炔基,C 2 -C 6 - 烷氧基,C 1 -C 6烷氧基羰基或CN,其中除CN之外,上述基团可以被相同或不同的取代基取代; 或R 3为芳基,杂芳基,杂环基,芳氧基,杂芳氧基或杂环氧基,其中上述基团可被相同或不同的取代基取代,R 5表示氢或甲基; 具有杀菌,杀虫和杀螨活性,可用于控制农业,园艺和卫生领域的昆虫和植物致病真菌。