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    CANNABINOIDCARBONSÄUREN, SALZE VON CANNABINOIDCARBONSÄUREN, DEREN HERSTELLUNG UND ANWENDUNGEN
    4.
    发明公开
    CANNABINOIDCARBONSÄUREN, SALZE VON CANNABINOIDCARBONSÄUREN, DEREN HERSTELLUNG UND ANWENDUNGEN 审中-公开
    大麻素碳氢酸，大麻素碳氢酸，生产和应用的盐

    公开(公告)号：EP2760444A1

    公开(公告)日：2014-08-06

    申请号：EP12778040.1

    申请日：2012-10-01

    申请人： The Health Concept GmbH

    发明人： HERKENROTH, Thomas ,  STEUP, Christian

    IPC分类号： A61K31/352 ,  C07D311/80 ,  A61P17/00

    CPC分类号： C07C65/19 ,  C07C51/412 ,  C07C51/42 ,  C07C51/493 ,  C07D311/80

    摘要： The invention relates to a compound selected from the group consisting of all stereoisomers and their mixtures of the compounds of general formulas (1)-(4), in which R
    1 is a straight-chained, branched or cyclic hydrocarbon group with up to 12 C-atoms and X
    + is selected from the group consisting of H
    + , NH
    4
    + , mono, di or trivalent metal cations, NH
    4
    + , primary, secondary, tertiary or quaternary organic ammonium ions with up to 48 C-atoms, which can carry even more functional groups, hydrazinium ion (N
    2 H
    5
    + ), hydroxylammonium ion (NH
    3 OH
    + ), guanidinium ion (CN
    3 H
    6
    + ), and organic derivatives of (N
    2 H
    5
    + ), NH
    3 OH
    + , and CN
    3 H
    6
    + , which can carry even more functional groups, and similar. A method is also provided for producing these compounds, comprising the following steps: producing synthetic cannabinoid carboxylic acids in a chemical reaction, or extracting natural cannabinoid carboxylic acids from plant material or cell cultures of
    Cannabis sativa , and adding a suitable inorganic base, a suitable organic base and/or a suitable inorganic or organic salt in a suitable solvent, to the cannabinoid carboxylic acids or cannabinoid carboxylic acid-rich extracts produced in this manner.

    Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
    8.
    发明公开
    Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities 失效
    具有负激素和/或拮抗剂活性的视黄酸类化合物的合成和用途

    公开(公告)号：EP0931786A3

    公开(公告)日：1999-09-01

    申请号：EP98204074.3

    申请日：1996-08-23

    申请人： Vision Pharmaceuticals L.P.

    发明人： Klein, Elliot S. ,  Johnson, Alan T. ,  Standeven, Andrew M. ,  Beard, Richard L. ,  Gillet, Samuel J. ,  Duong, Tien T. ,  Nagpal, Sunil ,  Vilugonda, Vidyasagar ,  Teng, Min ,  Chandraratna, Roshantha A.

    IPC分类号： C07C65/38 ,  C07D311/92 ,  A61K31/215

    CPC分类号： C07D335/06 ,  C07C57/50 ,  C07C63/33 ,  C07C63/49 ,  C07C63/66 ,  C07C63/72 ,  C07C63/74 ,  C07C65/19 ,  C07C65/28 ,  C07C65/38 ,  C07C69/618 ,  C07C69/76 ,  C07C69/90 ,  C07C69/94 ,  C07C233/81 ,  C07C245/10 ,  C07C327/48 ,  C07C2602/10 ,  C07D213/55 ,  C07D277/30 ,  C07D307/54 ,  C07D333/24 ,  C07F7/0818

    摘要： The invention provides a compound of the formula
    wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons, or X is [C(R 1 ) 2 ] n where R 1 is independently H or alkyl of 1 to 6 carbons, and n is an integer between 0 and 2; R 2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF 3 , fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons; R 3 is hydrogen, lower alkyl of 1 to 6 carbons or F; m is an integer having the value 0-3; o is an integer having the value 0-3; Y is a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl and heteroaryl groups being optionally substituted with one or two R 2 groups; A is (CH 2 ) q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 10 , -CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, -COR 7 , CR 7 (OR 12 ) 2 , CR 7 OR 13 O, or tri-lower alkylsilyl, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, and R 14 is (R 15 ) r -phenyl, (R 15 ) r -naphthyl, or (R 15 ) r -heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and R 15 is independently H, F, Cl, Br, I, NO 2 , N(R 8 ) 2 , N(R 8 )COR 8 , NR 8 CON(R 8 ) 2 , OH, OCOR 8 , OR 8 , CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons; R 16 is H, lower alkyl of 1 to 6 carbons; R 17 is H, lower alkyl of 1 to 6 carbons, OH or OCOR 11 , and p is zero or 1, with the proviso that when p is 1 then there is no R 17 substituent group, and m is an integer between 0 and 2.

    摘要翻译： 本发明提供下式化合物，其中X是S，O，NR'，其中R'是H或1-6个碳原子的烷基，或者X是[C（R1）2] n，其中R1独立地是H或1的烷基 至6个碳，并且n是0至2之间的整数; R2为氢，1-6个碳的低级烷基，F，Cl，Br，I，CF3，1-6个碳的氟取代的烷基，OH，SH，1-6个碳的烷氧基或1-6个碳的烷硫基; R3是氢，1至6个碳的低级烷基或F; m是值为0-3的整数; o是值为0-3的整数; Y是苯基或萘基，或选自吡啶基，噻吩基，呋喃基，哒嗪基，嘧啶基，吡嗪基，噻唑基，恶唑基，咪唑基和吡唑基的杂芳基，所述苯基和杂芳基任选被一个或两个R2基团取代 ; A是（CH 2）q，其中q是0-5，具有3-6个碳的低级支链烷基，具有3-6个碳的环烷基，具有2-6个碳和1或2个双键的烯基，具有2-6个碳的炔基和 1或2个三键; B为氢，COOH或其药学上可接受的盐，COOR8，CONR9R10，-CH2OH，CH2OR11，CH2OCOR11，CHO，CH（OR12）2，CHOR13O，-COR7，CR7（OR12）2，CR7OR13O或三低级烷基甲硅烷基， 其中R7为含有1至5个碳的烷基，环烷基或链烯基，R8为1至10个碳的烷基或三甲基甲硅烷基烷基，其中烷基具有1至10个碳或5至10个碳的环烷基，或R8 为苯基或低级烷基苯基，R9和R10独立地为氢，1-10个碳的烷基或5-10个碳的环烷基，或苯基或低级烷基苯基，R11为低级烷基，苯基或低级烷基苯基，R12为 低级烷基，且R 13为2-5个碳的二价烷基，且R 14为（R 15）r - 苯基，（R 15）r - 萘基或（R 15）r - 杂芳基，其中杂芳基具有1至3个选自 由O，S和N组成的组，r是0-5的整数，并且R 15独立地为H，F，Cl，Br，I，NO 2，N（R 8）2，N（R 8） NR8CON（R8） 2，OH，OCOR 8，OR 8，CN，碳原子数1〜10的烷基，碳原子数1〜10的氟取代烷基，碳原子数1〜10的烯基和1〜3个双键，碳原子数1〜10的炔基 碳原子和1至3个三键，或三烷基甲硅烷基或三烷基甲硅烷氧基，其中烷基独立地具有1至6个碳; R16是H，1至6个碳的低级烷基; R17是H，1至6个碳的低级烷基，OH或OCOR11，并且p是0或1，条件是当p是1时，则不存在R17取代基，并且m是0至2之间的整数。