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    Process for the production of optically-active 4-amino-3-hydroxycarboxylic acids
    1.
    发明授权
    Process for the production of optically-active 4-amino-3-hydroxycarboxylic acids 失效
    用于制备光学活性4-氨基-3-羟基羧酸的方法

    公开(公告)号：US5286650A

    公开(公告)日：1994-02-15

    申请号：US932587

    申请日：1992-08-20

    申请人： Markus Banziger ,  John McGarrity ,  Thomas Meul

    发明人： Markus Banziger ,  John McGarrity ,  Thomas Meul

    IPC分类号： C07C227/22 ,  C07C269/00 ,  C07D207/26 ,  C07D207/267 ,  C12P17/10 ,  C12P41/00 ,  C12P13/04

    CPC分类号： C07D207/267 ,  C07C227/22 ,  C07C269/00 ,  C07D207/26 ,  C12P17/10 ,  C12P41/004 ,  Y02P20/55

    摘要： Starting from 5-alkylidene or 5-benzylidenetetramic acid, optically-active 4-amino-3-hydroxy-carboxylic acids are produced in the (rel-3R,4R) configuration, especially statine. The synthesis process includes the O-acylation of the tetramic acid to the corresponding 4-acyloxy-3-pyrrolin-2-one, a stereoselective hydrogenation to (rel-4R,5R)-4-acyloxy-5-alkyl or 5-benzylpyrrolidin-2-one and an enantioselective enzymatic hydrolysis of the (4R,5R)-enantiomer to the corresponding 4-hydroxypyrrolidin-2-one. The nonhydrolyzed enantiomer is separated and converted into the target compound with (3S,4S) configuration by hydrolytic cleavage of the lactam ring and the ester function and optionally introduction of an amino protective group. Analogously the (3R,4R)-enantiomer can be obtained from the 4-hydroxypyrrolidin-2-one from the enzymatic hydrolysis. The 4-amino-3-hydroxycarboxylic acids producible according to the invention are the structural elements of enzyme inhibitors.

    摘要翻译： 从5-亚烷基 - 或5-亚苄基四胺酸开始，制备（rel-3R，4R） - 构型中的光学活性的4-氨基-3-羟基羧酸，特别是他汀类。 合成包括将四酸与相应的4-酰氧基-3-吡咯啉-2-酮的O-酰化反应，立体选择性氢化成（rel-4R，5R）-4-酰氧基-5-烷基 - 或-5 （4R，5R） - 对映体与对应的4-羟基吡咯烷-2-酮的对映选择性酶水解。 通过水解裂解内酰胺环和酯官能团，并酌情将（氨基保护基）引入到（3S，4S）构型的目标化合物中，将未水解的对映异构体分离并转化。 （3R，4R） - 对映体可类似地由酶水解的4-羟基吡咯烷-2-酮得到。 根据本发明可制备的4-氨基-3-羟基羧酸是酶抑制剂的组分。

    Process for the production of optically-active 4-amino-3-hydroxycarboxylic acids
    2.
    发明授权
    Process for the production of optically-active 4-amino-3-hydroxycarboxylic acids 失效
    用于制备光学活性4-氨基-3-羟基羧酸的方法

    公开(公告)号：US5352801A

    公开(公告)日：1994-10-04

    申请号：US120793

    申请日：1993-09-15

    申请人： Markus Banziger ,  John McGarrity ,  Thomas Meul

    发明人： Markus Banziger ,  John McGarrity ,  Thomas Meul

    IPC分类号： C07C227/22 ,  C07C269/00 ,  C07D207/26 ,  C07D207/267 ,  C12P17/10 ,  C12P41/00 ,  C07D207/273

    CPC分类号： C07D207/267 ,  C07C227/22 ,  C07C269/00 ,  C07D207/26 ,  C12P17/10 ,  C12P41/004 ,  Y02P20/55

    摘要： Starting from 5-alkylidene or 5-benzylidenetetramic acid optically-active 4-amino-3-hydroxy-carboxylic acids are produced in the (rel-3R,4R) configuration, especially statine. The synthesis process includes the O-acylation of the tetramic acid to the corresponding 4-acyloxy-3-pyrrolin-2-one, a stereoselective hydrogenation to (rel-4R,5R)-4-acyloxy-5-alkyl or 5-benzylpyrrolidin-2-one and an enantioselective enzymatic hydrolysis of the (4R,5R)-enantiomer to the corresponding 4-hydroxypyrrolidin-2-one. The nonhydrolyzed enantiomer is separated and converted into the target compound with (3S,4S) configuration by hydrolytic cleavage of the lactam ring and the ester function and optionally introduction of an amino protective group. Analogously the (3R,4R)-enantiomer can be obtained from the 4-hydroxypyrrolidin-2-one from the enzymatic hydrolysis. The 4-amino-3-hydroxycarboxylic acids producible according to the invention are the structural elements of enzyme inhibitors.

    摘要翻译： 以（rel-3R，4R）构型，特别是statine生产5-亚烷基或5-亚苄基四胺酸光学活性4-氨基-3-羟基 - 羧酸。 合成方法包括将四酸与相应的4-酰氧基-3-吡咯啉-2-酮进行O-酰化，立体选择性氢化成（rel-4R，5R）-4-酰氧基-5-烷基或5-苄基吡咯烷 （4R，5R） - 对映体与对应的4-羟基吡咯烷-2-酮的对映选择性酶水解。 通过水解裂解内酰胺环和酯官能团并任选地引入氨基保护基，分离未水解的对映异构体并用（3S，4S）构型转化成目标化合物。 类似地，（3R，4R） - 对映异构体可以从酶水解得到4-羟基吡咯烷-2-酮。 根据本发明可生产的4-氨基-3-羟基羧酸是酶抑制剂的结构元件。

    Process for the production of biotin precursors
    3.
    发明授权
    Process for the production of biotin precursors 失效
    生物素前体生产工艺

    公开(公告)号：US4851540A

    公开(公告)日：1989-07-25

    申请号：US127052

    申请日：1987-12-01

    申请人： John McGarrity ,  Leander Tenud ,  Thomas Meul

    发明人： John McGarrity ,  Leander Tenud ,  Thomas Meul

    IPC分类号： C07D491/04 ,  C07D491/048 ,  C07D495/04

    CPC分类号： C07D491/04 ,  C07D495/04 ,  Y02P20/55

    摘要： Process for the production of imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, and aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom. A tetronic acid of the formula: ##STR2## wherein A has the above-mentioned meaning, is reacted with a diazonium salt, converting the resultant arylazotetronic acid or the tautomeric arylhydrazone in a further step with a chiral amine into an arylazoamino compound, reducing the arylazoamino compound, converting the resultant diamine, with phosgene or a phosgene-equivalent reagent, into the corresponding imidazole and optionally introducing a protective group by reaction with a substituted or unsubstituted aliphatic or aromatic acid chloride, an aliphatic or aromatic carboxylic acid anhydride, a haloformic acid alkyl ester, a 1-alkoxyalkyl halide, an enol ether, an aromatic or aliphatic sulfonic acid halide, a diarylphosphinic acid halide, a phosphoric acid dialkyl ester halide, a trialkyl silyl halide or a trialkyl silyl acetamide. These imidazole derivatives are suitable as intermediate products for the production of (+) biotin.

    摘要翻译： 制备下式的咪唑衍生物的方法：其中R1是（R） - 或（S）-1-苯基烷基，（R） - 或（S）-1-烷氧基羰基-1-苯基甲基 基团或（R） - 或（S）-1-芳氧基羰基-1-苯基甲基，R2是氢，取代或未取代的烷酰基，未取代或取代的苯甲酰基，取代或未取代的苄基，烷氧基羰基 基团和芳氧基羰基，烷氧基烷基，吡喃基，取代或未取代的苯磺酰基，烷基磺酰基，二芳基氧膦基，二烷氧基氧膦基或三烷基甲硅烷基，A是硫或氧原子。 其中A具有上述含义的特丁酸与重氮盐反应，将得到的芳基氮杂过硫酸或互变异构芳基腙用手性胺转化成芳基偶氮氨基化合物，将还原 芳基偶氮基氨基化合物，将所得二胺与光气或光气当量的试剂转化成相应的咪唑，并任选地通过与取代或未取代的脂族或芳族酰氯，脂族或芳族羧酸酐反应引入保护基， 卤代甲酸烷基酯，1-烷氧基烷基卤化物，烯醇醚，芳族或脂族磺酸卤化物，二芳基次膦酸卤化物，磷酸二烷基酯卤化物，三烷基甲硅烷基卤化物或三烷基甲硅烷基乙酰胺。 这些咪唑衍生物适用于生产（+）生物素的中间产物。

    Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide
    4.
    发明授权
    Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide 失效
    制备4-羟基-2-氧代 - 吡咯烷-1-基乙酰胺的方法

    公开(公告)号：US4824966A

    公开(公告)日：1989-04-25

    申请号：US188702

    申请日：1988-05-04

    申请人： Thomas Meul ,  John McGarrity

    发明人： Thomas Meul ,  John McGarrity

    IPC分类号： C07D207/38 ,  C07D207/27

    CPC分类号： C07D207/38

    摘要： Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide. A 4-(C.sub.1 -C.sub.2)-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester of the formula: ##STR1## wherein R.sub.1 is alkyl having 1 or 2 C atoms and R.sub.2 is alkyl having 1 to 4 C atoms, is reacted with either trichloromethylsilane in the presence of an alkali iodide or in an acid anhydrous medium to a 2,4-dioxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester. The latter is optionally isolated and then hydrogenated with sodium borohydride to a 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester. Finally, the 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester is converted by amidation with ammonia to the desired end product.

    摘要翻译： 制备4-羟基-2-氧代 - 吡咯烷-1-基乙酰胺的方法。 具有下式的4-（C 1 -C 2） - 烷氧基-3-吡咯烷-2-酮-1-基 - 乙酸（C 1 -C 4） - 烷基酯，其中R 1是具有1或2个C原子的烷基 R2是具有1-4个碳原子的烷基，在碱金属碘化物存在下或在酸性无水介质中与三氯甲基硅烷反应成2,4-二氧代 - 吡咯烷-1-基 - 乙酸（C 1 -C 4） - 烷基酯。 后者任选地分离，然后用硼氢化钠氢化成4-羟基-2-氧代 - 吡咯烷-1-基 - 乙酸（C 1 -C 4） - 烷基酯。 最后，通过用氨的酰胺化将4-羟基-2-氧代 - 吡咯烷-1-基 - 乙酸（C 1 -C 4） - 烷基酯转化为所需的最终产物。

    Chiral biotin precursors
    6.
    发明授权
    Chiral biotin precursors 失效
    手性生物素前体

    公开(公告)号：US4873339A

    公开(公告)日：1989-10-10

    申请号：US284021

    申请日：1988-11-30

    申请人： John McGarrity ,  Leander Tenud ,  Thomas Meul

    发明人： John McGarrity ,  Leander Tenud ,  Thomas Meul

    IPC分类号： C07D491/04 ,  C07D491/048 ,  C07D495/04

    CPC分类号： C07D491/04 ,  C07D495/04 ,  Y02P20/55

    摘要： Imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsufonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom. The imidazole derivatives are intermediate products for the production of (+) biotin.

    摘要翻译： 其中R1是（R） - 或（S）-1-苯基烷基，（R） - 或（S）-1-烷氧基羰基-1-苯基甲基或（R ） - 或（S）-1-芳氧基羰基-1-苯基甲基，R2是氢，取代或未取代的烷酰基，取代或未取代的苯甲酰基，取代或未取代的苄基，烷氧基羰基，芳氧基羰基， 烷氧基烷基，吡喃基，取代或未取代的苯磺酰基，烷基磺酰基，二芳基氧膦基，二烷氧基氧膦基或三烷基甲硅烷基，A为硫或氧原子。 咪唑衍生物是用于生产（+）生物素的中间产物。

    Acetylsalicyloyl-L-carnitine and process for its production
    8.
    发明授权
    Acetylsalicyloyl-L-carnitine and process for its production 失效
    乙酰水杨酯-L-肉碱及其生产工艺

    公开(公告)号：US5227513A

    公开(公告)日：1993-07-13

    申请号：US833673

    申请日：1992-02-11

    申请人： Thomas Meul

    发明人： Thomas Meul

    IPC分类号： C07C229/22

    CPC分类号： C07C229/22

    摘要： Acetylsalicylic acid esters of carnitine are distinguished relative to acetylsalicylic acid. The esters can be produced by acetylation of suitable salicylic acid esters of carnitine.

    摘要翻译： 肉碱的乙酰水杨酸酯相对于乙酰水杨酸是有区别的。 酯可以通过适当的肉碱水杨酸酯的乙酰化来制备。

    Process for the production of optically active 3-aminocarboxylic acid esters
    9.
    发明授权
    Process for the production of optically active 3-aminocarboxylic acid esters 失效
    光学活性3-氨基羧酸酯的制备方法

    公开(公告)号：US4585887A

    公开(公告)日：1986-04-29

    申请号：US677986

    申请日：1984-12-04

    申请人： Synese Jolidon ,  Thomas Meul

    发明人： Synese Jolidon ,  Thomas Meul

    IPC分类号： C07B61/00 ,  B01J23/00 ,  C07C67/00 ,  C07C227/00 ,  C07C227/06 ,  C07C227/08 ,  C07C227/16 ,  C07C227/18 ,  C07C227/32 ,  C07C227/34 ,  C07C229/08 ,  C07C229/30 ,  C07C101/18

    CPC分类号： C07C227/32 ,  C07C227/34

    摘要： Process for the production of an optically active 3-aminocarboxylic acid ester from a .beta.-keto acid ester. The .beta.-keto acid ester is converted with a chiral amine into the corresponding enamine. The enamine is converted by hydrogenation in the presence of a platinum catalyst into the corresponding N-substituted amino acid esters. Such ester mix is converted by means of HCl gas into the hydrochlorides. The latter are neutralized. Then by liberation and isolation from the neutralized products by hydrogenolysis in the presence of a palladium catalyst, the desired optically-active 3-aminocarboxylic acid ester is obtained.

    摘要翻译： 从β-酮酸酯制备光学活性3-氨基羧酸酯的方法。 将β-酮酸酯用手性胺转化成相应的烯胺。 烯胺通过在铂催化剂存在下的氢化转化成相应的N-取代的氨基酸酯。 这种酯混合物通过HCl气体转化成盐酸盐。 后者被中和。 然后通过在钯催化剂的存在下通过氢解从中和产物中释放和分离，得到所需的光学活性3-氨基羧酸酯。