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    • 3. 发明申请
    • USE OF BENZOTROPOLONE DERIVATIVES AS UV ABSORBERS AND ANTIOXIDANTS AND THEIR USE IN SUNSCREENS AND/OR COSMETIC COMPOSITIONS
    • US20110123468A1
    • 2011-05-26
    • US13000163
    • 2009-06-18
    • Barbara WagnerReinhold OhrleinBernd HerzogKai EichinGabriele BaischStephanie Portmann
    • Barbara WagnerReinhold OhrleinBernd HerzogKai EichinGabriele BaischStephanie Portmann
    • A61K8/49A61K8/37A61K31/235A61K31/351C07C69/76C07D307/34A61K31/375A61K31/665A61Q19/04A61P39/06
    • A61Q17/04A61K8/35A61Q19/08C07C49/747C07C62/38C07C69/712C07C69/757C07C305/18C07C2602/12C07F9/4006C07H15/18C07H15/203C07H15/26
    • Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R2, R3, R4, R5 and R6 independently of one another are hydrogen; OH; C1-C30alkyl, C2-C30al-kenyl, C1-C30alkoxy, C3-C12cycloalkyl or C1C30hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, CN, or —CO—R17; C1-C30mono- or dialkylamino; COR9; COOR9; CONR9R10; CN; SO2R9; OCOOR9; OCOR9; NHCOOR9; NR9COR10; NH2; *—(CO)—NH—(CH2)n1—(PO)—(OR11)2; —(CO)—O—(CH2)n1—(PO)—(OR11)2; sulphate; sulphonate; phosphate; phosphonate; —(CH2)n2—[O—(SO2)]n3—OR11; —O—(CH2)n4(CO)n5—R11; —(O)n6—(CH2)n7—(PO)—(OR9)2; —(O)n6—(CH2)n7—SO2—OR9; halogen; organosilanyl; organo-siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—(X1)1 or 0-benzotropolone system, wherein n=1-10 and X1=—O—; —(CO)—; —O—CO—; —COO—, —NH—; —S—; —SO2—); R1, R7 and R8 independently of one another are hydrogen; C1C12alkyl or C3-C12-cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, or COOR9; COR9; CONR9R10; SO3R9; SO2R9; PO3(R9)2; PO2(R9)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—(X2)1 or 0—*, wherein n=1-10 and X2=—C(═O)—; —O—CO—*); R9 and R10 independently from each other are hydrogen; C1C18alkyl or C3-C12-cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—*, wherein n=1-10); or R9 and R10 together form a five or six membered ring, R11 is hydrogen; or C1-C5alkyl; n1, n2, n4 and n7 independently from each other are a number from 1 to 5; n3, n5 and n6 independently from each other are a 0; or 1; D is —CO—; —COO—; —S—; —SO—; —SO2-; —O—; —NR14—; —S1R19R20—; —POR11—; —CR12═CR13—; or —C≡C—; and E is —OR18; —SR18; —NR14R15; —NR14COR15; —COR17; —COOR16; —CONR14R15; —CN; halogen; Or SO3R18; SO2R18; PO3(R18)2; PO2(R18)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n-(X1)1 or 0—*, wherein n=1-10 and X1=—O—; —C(═O)—; —O—CO—; —COO—; —NH—; —S—; —SO2—); G is E; C1-C18alkyl, which is optionally interrupted by D; C1-C18perfluoroalkyl; C1-C18alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R12, R13, R14 and R15 independently of each other are hydrogen; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; C1-C18alkyl, which is optionally interrupted by —O—; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C1-C18alkyl or d-C18alkoxy; C1-C18alkyl which is optionally interrupted by —O—; R17 is H; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; or d-C18alkyl which is optionally interrupted by —O—; R18 is hydrogen; C6-C18aryl, which is optionally substituted by OH, C1-C18alkyl or d-C18alkoxy; C1-C18alkyl, which is optionally interrupted by —O—; R19 and R20 independently of each other are hydrogen; C1-C18alkyl; C6-C18aryl which is optionally substituted by C1-C18alkyl; and R21 is C1-C18alkyl; or C6-C18aryl, which is substituted by C1-C18alkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.
    • 9. 发明授权
    • Use of benzotropolone derivatives as UV absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions
    • US09707417B2
    • 2017-07-18
    • US13000163
    • 2009-06-18
    • Barbara WagnerReinhold ÖhrleinBernd HerzogKai EichinGabriele BaischStephanie Portmann
    • Barbara WagnerReinhold ÖhrleinBernd HerzogKai EichinGabriele BaischStephanie Portmann
    • A61K8/49A61Q17/04A61K8/35A61Q19/08C07C49/747C07C62/38C07C69/712C07C69/757C07C305/18C07F9/40C07H15/18C07H15/203C07H15/26
    • A61Q17/04A61K8/35A61Q19/08C07C49/747C07C62/38C07C69/712C07C69/757C07C305/18C07C2602/12C07F9/4006C07H15/18C07H15/203C07H15/26
    • Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R2, R3, R4, R5 and R6 independently of one another are hydrogen; OH; C1-C30alkyl, C2-C30al-kenyl, C1-C30alkoxy, C3-C12cycloalkyl or C1C30hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, CN, or —CO—R17; C1-C30mono- or dialkylamino; COR9; COOR9; CONR9R10; CN; SO2R9; OCOOR9; OCOR9; NHCOOR9; NR9COR10; NH2; *—(CO)—NH—(CH2)n1—(PO)—(OR11)2; —(CO)—O—(CH2)n1—(PO)—(OR11)2; sulphate; sulphonate; phosphate; phosphonate; —(CH2)n2—[O—(SO2)]n3—OR11; —O—(CH2)n4(CO)n5—R11; —(O)n6—(CH2)n7—(PO)—(OR9)2; —(O)n6—(CH2)n7—SO2—OR9; halogen; organosilanyl; organo-siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—(X1)1 or 0-benzotropolone system, wherein n=1-10 and X1═—O—; —(CO)—; —O—CO—; —COO—, —NH—; —S—; —SO2—); R1, R7 and R8 independently of one another are hydrogen; C1C12alkyl or C3-C12-cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, or COOR9; COR9; CONR9R10; SO3R9; SO2R9; PO3(R9)2; PO2(R9)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—(X2)1 or 0—*, wherein n=1-10 and X2═—C(═O)—; —O—CO—*); R9 and R10 independently from each other are hydrogen; C1C18alkyl or C3-C12-cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n—*, wherein n=1-10); or R9 and R10 together form a five or six membered ring, R11 is hydrogen; or C1-C5alkyl; n1, n2, n4 and n7 independently from each other are a number from 1 to 5; n3, n5 and n6 independently from each other are a 0; or 1; D is —CO—; —COO—; —S—; —SO—; —SO2-; —O—; —NR14—; —S1R19R20—; —POR11—; —CR12═CR13—; or —C≡C—; and E is —OR18; —SR18; —NR14R15; —NR14COR15; —COR17; —COOR16; —CONR14R15; —CN; halogen; Or SO3R18; SO2R18; PO3(R18)2; PO2(R18)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n-(X1)1 or 0—*, wherein n=1-10 and X1=—O—; —C(═O)—; —O—CO—; —COO—; —NH—; —S—; —SO2—); G is E; C1-C18alkyl, which is optionally interrupted by D; C1-C18perfluoroalkyl; C1-C18alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R12, R13, R14 and R15 independently of each other are hydrogen; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; C1-C18alkyl, which is optionally interrupted by —O—; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C1-C18alkyl or d-C18alkoxy; C1-C18alkyl which is optionally interrupted by —O—; R17 is H; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; or d-C18alkyl which is optionally interrupted by —O—; R18 is hydrogen; C6-C18aryl, which is optionally substituted by OH, C1-C18alkyl or d-C18alkoxy; C1-C18alkyl, which is optionally interrupted by —O—; R19 and R20 independently of each other are hydrogen; C1-C18alkyl; C6-C18aryl which is optionally substituted by C1-C18alkyl; and R21 is C1-C18alkyl; or C6-C18aryl, which is substituted by C1-C18alkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.
    • 10. 发明申请
    • Use of specific bis(biphenyl)triazine derivatives and mixtures thereof as UV absorbers
    • US20130164231A1
    • 2013-06-27
    • US13822014
    • 2011-09-09
    • Barbara WagnerBernd Herzog
    • Barbara WagnerBernd Herzog
    • A61K8/49A61Q17/04C07D251/24
    • A61K8/4966A61K2800/5922A61Q17/04
    • Disclosed is the use of mixtures comprising at least 2 structurally different bis(biphenyl)triazine derivatives of formula (1) wherein X is hydrogen; C1-C50alkyl which may be uninterrupted or interrupted by one or more oxygen atoms and/or substituted by one or more R8 groups; C3-C12-cycloalkyl which is substituted by R8; —CH((CH2)p—R8)—CO—O—(CH2)m—R9; —CH((CH2)p—R8)—CO—(NR10)—(CH2)m—R9; —CO—O—(CH2)p—Ra; —CH2—CH(—O(CO)—R8)—R9; —CO—(NR10)—(Ch2)p—Ra; C6-C20aryl; allyl; C4-C50alkenyl which is uninterrupted or is interrupted by one or more oxygen atoms; C3-C12cycloalkyl which is uninterrupted or interrupted by one or more oxygen atoms; C3-C20alkynyl; C6-C12cycloalkynyl; R1 is hydrogen; unsubstituted or substituted unsubstituted or substituted C3-C12cycloalkyl; unsubstituted or substituted C6-C20aryl; unsubstituted or substituted C2-C20alkenyl; OR7; OH; SR8; SOR7; SO2R7; SO2H; SO3M; or a radical of the formula (c); R2, R3, R4, R5 and R6 independently of one another are hydrogen; hydroxyl; —CN; substituted or unsubstituted C1-C20alkyl; unsubstituted or substituted C3-C12-cycloalkyl; unsubstituted or substituted C1-C18alkoxy; unsubstituted or substituted C4-C20cycloalkoxy; C7-C20phenylalkyl; halogen; halo-C1-C5alkyl; sulfonyl; carboxyl; acylamino; acyloxy; C1-C12alkoxycarbonyl; aminocarbonyl; R7 is substituted or unsubstituted C1-C18alkyl; unsubstituted or substituted C3-C12-cycloalkyl; unsubstituted or substituted C6-C20aryl; unsubstituted or substituted C2-C20alkenyl; or C7-C20phenylalkyl; M is alkali metal; R8 and R9 independently of one another are Rx if attached to a carbon atom and are Ry if attached to an oxygen atom; p is 0 to 20; m is 0 to 20; Rx is hydrogen; hydroxyl; C1-C30alkyl; C3-C12cycloalkyl; C1-C30alkoxy; C3-C12cycloalkoxy; C3-C12-cycloalkyl or C3-C12cycloalkoxy which is interrupted by one or more oxygen atoms; C6-C12aryl; hetero-C3-C12aryl; —ORz; NHRz; Rz; CONR10R11; SO3H; SO3M; OSO3H2; allyl, C2-C30alkenyl; C4-C12-cycloalkenyl which is uninterrupted or interrupted by one or more oxygen atoms; C3-C20-alkynyl; or C6-C12cycloalkynyl; Ry is hydrogen; C1-C30alkyl; C3-C12cycloalkyl which is uninterrupted or interrupted by one or more oxygen atoms; C6-C12aryl; hetero-C3-C12aryl; Rz; allyl, C2-C30alkenyl; C4-C12-cycloalkenyl which is uninterrupted or interrupted by one or more oxygen atoms; C3-C20-alkynyl; or C6-C12cycloalkynyl; Rz is —COR10; —COOR10; —CON-R10R11; —CO—CH═CH2; —CO—C(CH3)═CH2; R10 and R11 independently of one another are hydrogen; C1-C30alkyl; C1-C50alkyl which is interrupted by one or more oxygen atoms; C3-C12cycloalkyl which is uninterrupted or interrupted by one or more oxygen atoms; C2-C20alkenyl which is uninterrupted or is interrupted by one or more oxygen atoms; or C6-C12aryl; or R10 and R11 together form a five or six membered ring; as UV absorbers for increasing the UVA protection factor of cosmetic or dermatological compositions.