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    Geometrical isomers of acrylonitrile compounds, mixture thereof, and process for producing these
    31.
    发明授权
    Geometrical isomers of acrylonitrile compounds, mixture thereof, and process for producing these 有权
    丙烯腈化合物的几何异构体，其混合物，及其制备方法

    公开(公告)号：US06624179B1

    公开(公告)日：2003-09-23

    申请号：US10030122

    申请日：2002-01-24

    申请人： Toru Koyanagi ,  Yuji Nakamura ,  Masayuki Morita ,  Tsuyoshi Ueda ,  Akihiro Hisamatsu ,  Mayumi Kanamori

    发明人： Toru Koyanagi ,  Yuji Nakamura ,  Masayuki Morita ,  Tsuyoshi Ueda ,  Akihiro Hisamatsu ,  Mayumi Kanamori

    IPC分类号： A61K3144

    CPC分类号： C07C329/16 ,  C07B2200/09 ,  C07C255/34 ,  C07C255/38 ,  C07C329/04 ,  C07C329/06

    摘要： A geometrical isomer of an acrylonitrile compound represented by the formula (I) or of its salt, or a mixture thereof: [wherein T is phenyl or pyridyl, which is substituted by R2, Q is phenyl, thienyl, pyridyl or benzyl, which may be substituted by R3, R1 is —C(═O)R4 or —C(═S)R4, R4 is alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, —N(R5)R6, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, benzylthio, —J, —O—J or —S—J], wherein the geometrical isomer has a longer retention time when analyzed by reversed phase liquid chromatography in which a packing comprising silica having chemically bonded thereto an alkyl group selected from trimethyl, octyl and octadecyl, is used as the stationary phase, and a polar solvent selected from water, methanol and acetonitrile, is used as the mobile phase, and the geometrical isomer mixture contains such geometrical isomer in a larger proportion.

    摘要翻译： 由式（I）表示的丙烯腈化合物或其盐的几何异构体或其混合物：[其中T是被R 2取代的苯基或吡啶基，Q是苯基，噻吩基，吡啶基或苄基，其可以 被R 3取代，R 1是-C（= O）R 4或-C（= S）R 4，R 4是烷基，烯基，炔基，烷氧基，烯氧基，炔氧基，烷硫基，链烯硫基，炔硫基，环烷基，环烷氧基， N（R 5）R 6，苯基，苯氧基，苯硫基，苄基，苄氧基，苄硫基，-J，-OJ或-SJ]，其中几何异构体在通过反相液相色谱分析时具有更长的保留时间， 化学键合有选自三甲基，辛基和十八烷基的烷基作为固定相，使用选自水，甲醇和乙腈的极性溶剂作为流动相，几何异构体混合物含有这种几何异构体 比例较大。

    Process for producing 4-trifluoromethylnicotinic acid
    33.
    发明授权
    Process for producing 4-trifluoromethylnicotinic acid 失效
    生产4-三氟甲基烟酸的方法

    公开(公告)号：US5708175A

    公开(公告)日：1998-01-13

    申请号：US648761

    申请日：1996-05-16

    申请人： Toru Koyanagi ,  Tetsuo Yoneda ,  Fumio Kanamori ,  Shigehisa Kanbayashi ,  Toyoshi Tanimura ,  Noriyuki Horiuchi

    发明人： Toru Koyanagi ,  Tetsuo Yoneda ,  Fumio Kanamori ,  Shigehisa Kanbayashi ,  Toyoshi Tanimura ,  Noriyuki Horiuchi

    IPC分类号： C07C45/45 ,  C07C49/255 ,  C07C221/00 ,  C07C225/14 ,  C07C229/22 ,  C07C229/30 ,  C07C251/08 ,  C07D213/80 ,  C07D213/12 ,  C07D213/08

    CPC分类号： C07D213/80 ,  C07C221/00 ,  C07C229/22 ,  C07C229/30 ,  C07C251/08 ,  C07C45/455 ,  C07C49/255

    摘要： A process for producing 4-trifluoromethylnicotinic acid of the formula (VIII) or its salt: ##STR1## which comprises (i) a first step of reacting a halide of the formula (I): CF.sub.3 COHal (I) wherein Hal is a halogen atom, with a compound of the formula (II): CH.sub.2 .dbd.CHOR.sup.1 (II) wherein R.sup.1 is an alkyl group, in the presence of a base to obtain a 4-alkoxy-1,1,1-trifluoro-3-buten-2-one of the formula (III): CF.sub.3 CO--CH.dbd.CH--OR.sup.1 (III) wherein R.sup.1 is as defined above, and reacting this compound with ammonia to obtain 4-amino-1,1,1-trifluoro-3-buten-2-one of the formula (IV): ##STR2## and (ii) a second step of subjecting the 4-amino-1,1,1-trifluoro-3-buten-2-one obtained in the first step and a compound of the formula (V): ACO.sub.2 R.sup.2 (V) wherein R.sup.2 is an ester-forming residue, and A is (R.sup.3 O)CH.dbd.CH-- or (R.sup.3 O).sub.2 CHCH.sub.2 --, wherein R.sup.3 is an alkyl group, to a condensation reaction to obtain a compound of the formula (VI) (inclusive of its salt): ##STR3## wherein R.sup.2 is as defined above, and/or a compound of the formula (VII) (inclusive of its salt): ##STR4## wherein R.sup.2 and R.sup.3 are as defined above, as the reaction product, and then subjecting the reaction product to ring closure and hydrolysis.

    摘要翻译： （VIII）的4-三氟甲基烟酸或其盐：（Ⅷ）的方法，其包括（ⅰ）使式（I）的卤化物：CF 3 COHal（I）（其中Hal为 卤素原子与式（II）的化合物：CH 2 = CHOR 1（II）其中R 1是烷基，在碱的存在下，得到4-烷氧基-1,1,1-三氟-3- （III）的丁烯-2-酮：CF 3 CO-CH = CH-OR 1（III）其中R 1如上定义，并使该化合物与氨反应，得到4-氨基-1,1,1-三氟-3 （IV）的2-丁烯-2-酮：（IV）和（ii）第二步，将得到的4-氨基-1,1,1-三氟-3-丁烯-2-酮 第一步和式（V）化合物：其中R 2为酯形成残基，A为（R 3 O）CH = CH-或（R 3 O）2 CHCH 2 - ，其中R 3为烷基， 进行缩合反应，得到式（VI）化合物（包括其盐）：其中R 2如上所定义，和/或式 （VII）（包括其盐）：其中R2和R3如上定义，作为反应产物，然后使反应产物闭环并水解。