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    Process for the production of thiazolines-(3)
    1.
    发明授权
    Process for the production of thiazolines-(3) 失效
    生产噻唑啉的方法 - （3）

    公开(公告)号：US3931208A

    公开(公告)日：1976-01-06

    申请号：US413048

    申请日：1973-11-05

    申请人： Heribert Offermanns ,  Friedrich Asinger ,  Wolf-Dieter Pfeifer ,  Paul Scherberich ,  Gerd Schreyer

    发明人： Heribert Offermanns ,  Friedrich Asinger ,  Wolf-Dieter Pfeifer ,  Paul Scherberich ,  Gerd Schreyer

    IPC分类号： C07D277/10 ,  C07D277/60

    CPC分类号： C07D277/60 ,  C07D277/10

    摘要： 2 AND 5 SUBSTITUTED THIAZOLINE-(3) COMPOUNDS OF THE FORMULA: ##EQU1## in which R.sub.1, R.sub.2, and R.sub.3 and R.sub.4 are the same or different, R.sub.1 and R.sub.2 are straight or branched chain lower alkyl, alkenyl or aralkyl groups or together are a straight or branched chain alkylene or ethylenically unsaturated divalent aliphatic hydrocarbon group which joins with the adjacent carbon atom to form a ring and R.sub.3 and R.sub.4 are similarly defined except R.sub.3 can also be hydrogen by reaching a 2,2' dioxodisulfide of the formula ##EQU2## with an oxo compound of the formula ##EQU3## and with ammonia and hydrogen sulfide in the presence of an amine and an ammonium salt.

    摘要翻译： 2和5取代的噻唑啉 - （3）式的化合物：其中R 1，R 2和R 3和R 4相同或不同，R 1和R 2是直链的 或支链低级烷基，烯基或芳烷基或一起是与相邻碳原子连接以形成环的直链或支链亚烷基或烯键式不饱和二价脂族烃基，并且R 3和R 4类似地定义，除了R 3也可以是氢 通过到达式OO C的二氧杂二硫化物。方法C将C 1 -C 6（C 1 -C 6）环烷基（R 2）R 2 R 2与式R 3的氧代化合物反应。 和氨和硫化氢在胺和铵盐的存在下反应。

    Process of making penicillamine
    2.
    发明授权
    Process of making penicillamine 失效
    制作青霉胺的过程

    公开(公告)号：US4061674A

    公开(公告)日：1977-12-06

    申请号：US657605

    申请日：1976-02-12

    申请人： Friedrich Asinger ,  Wolf-Dieter Pfeifer ,  Heribert Offermanns ,  Paul Scherberich ,  Gerd Schreyer

    发明人： Friedrich Asinger ,  Wolf-Dieter Pfeifer ,  Heribert Offermanns ,  Paul Scherberich ,  Gerd Schreyer

    IPC分类号： C07D277/06 ,  C07C99/00

    CPC分类号： C07D277/06

    摘要： Penicillamine or a homolog thereof is obtained by reacting a 2-disubstituted-5,5-alkyl-thiazolidine nitrile, alkyl having 1 to 6 carbon atoms, with a mineral acid in a two-stage proceeding wherein in the first stage relatively low temperatures and a relatively high concentration of the mineral acid are employed while in the second stage the concentration of the acid is relatively low and the temperatures are relatively high, the term "relatively" referring to the relationship of said two stages of the reaction with mineral acid.

    摘要翻译： 青霉胺或其同系物是通过2-二取代-5,5-烷基 - 噻唑烷腈，具有1至6个碳原子的烷基与无机酸反应得到的，其中在两阶段进行，其中在第一阶段相对低的温度和 使用相对高浓度的无机酸，而在第二阶段酸的浓度相对较低并且温度相对较高，术语“相对”是指反应两个阶段与无机酸的关系。

    Process of making penicillamine
    4.
    发明授权
    Process of making penicillamine 失效
    制作青霉胺的过程

    公开(公告)号：US4060548A

    公开(公告)日：1977-11-29

    申请号：US642572

    申请日：1975-12-19

    申请人： Friedrich Asinger ,  Heribert Offermanns ,  Miklos Ghyczy

    发明人： Friedrich Asinger ,  Heribert Offermanns ,  Miklos Ghyczy

    IPC分类号： C07D277/06 ,  C07C99/10

    CPC分类号： C07D277/06

    摘要： Penicillamine and its hydrochloride are made by reacting i-butyraldehyde with elemental sulfur or a sulfur-containing compound and with gaseous ammonia so as to form 2-isopropyl-5.5-dimethyl-thiazoline-.DELTA..sup.3, then reacting the latter compound with substantially anhydrous hydrogen cyanide so as to form the corresponding thiazolidine 4-carbonitrile, thereupon treating the latter compound with an excess of concentrated hydrochloric acid at an elevated temperature and separating the components of the mixture formed and recovering the penicillamine hydrochloride which may then be converted to the free D,L-penicillamine.

    摘要翻译： 青霉胺及其盐酸盐通过使异丁醛与元素硫或含硫化合物和气态氨反应形成2-异丙基-5-二甲基 - 噻唑啉-TATA 3，然后使后一种化合物与基本上无水的氢 氰化物以形成相应的噻唑烷-4-腈，然后在升高的温度下用过量的浓盐酸处理后一化合物，并分离形成的混合物的组分并回收盐酸青霉胺，然后将其转化为游离D ，L-青霉胺。

    Process for the splitting of the racemate of d-1-phenylpropanolamine
    5.
    发明授权
    Process for the splitting of the racemate of d-1-phenylpropanolamine 失效
    分离d-1-苯基丙醇胺外消旋体的方法

    公开(公告)号：US3959302A

    公开(公告)日：1976-05-25

    申请号：US513725

    申请日：1974-10-10

    申请人： Friedrich Asinger ,  Heribert Offermanns

    发明人： Friedrich Asinger ,  Heribert Offermanns

    IPC分类号： C07D277/56 ,  C07D277/06

    CPC分类号： C07D277/56

    摘要： The d,1-phenylpropanolamine(norephedrine) racemate is split with optically active thiazolidine-4-carboxylic acids of the formula: ##EQU1## where R.sub.1 and R.sub.2 are both methyl or are joined together to form the pentamethylene group.

    摘要翻译： d，1-苯基丙醇胺（去甲麻黄碱）外消旋物与光学活性的噻唑烷-4-羧酸分开，其结构式如下：COOH | H-C-N-Ac || CH 3||R1 ANGLE CC ANGLE ANGLE CH3SR2其中R1 和R2均为甲基或连接在一起形成五亚甲基。

    Salts of phenylpropanolamine with thiazolidine carboxylic acids
    6.
    发明授权
    Salts of phenylpropanolamine with thiazolidine carboxylic acids 失效
    苯丙醇胺与噻唑烷羧酸的盐

    公开(公告)号：US3947464A

    公开(公告)日：1976-03-30

    申请号：US419448

    申请日：1973-11-27

    申请人： Friedrich Asinger ,  Heribert Offermanns

    发明人： Friedrich Asinger ,  Heribert Offermanns

    IPC分类号： C07D277/06 ,  C07D277/04

    CPC分类号： C07D277/06

    摘要： The d,l-phenylpropanolamine racemate is split with optically active thiazolidine-4-carboxylic acids of the formula: ##EQU1## where R.sub.1 R.sub.2 are hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl, aryl or alkylene of at least 2 carbon atoms or R.sub.1 and R.sub.2 together form a ring of alkyl or alkylene with 4 to 12 carbon atoms and AC is acyl, especially benzoyl, tosyl, nitrophenylsulfenyl, acetyl or preferably formyl.

    摘要翻译： D，l-苯基丙醇胺外消旋物与下式的光学活性噻唑烷-4-羧酸分开：COOH | H-C-N-Ac || CH 3 || R ANGLE CC ANGLE CH3 ANGLE R2 S其中R1 R2 1〜8个碳原子的烷基，至少2个碳原子的环烷基，芳基或亚烷基，或者R 1和R 2一起形成具有4〜12个碳原子的烷基或亚烷基的环，AC是酰基，特别是苯甲酰基，甲苯磺酰基， 硝基苯基亚磺酰基，乙酰基或优选甲酰基。

    Process of preparing penicillamine
    7.
    发明授权
    Process of preparing penicillamine 失效
    制备青霉胺的方法

    公开(公告)号：US4045479A

    公开(公告)日：1977-08-30

    申请号：US598995

    申请日：1975-07-25

    申请人： Friedrich Asinger ,  Heribert Offermanns ,  Karl-Heinz Gulzek

    发明人： Friedrich Asinger ,  Heribert Offermanns ,  Karl-Heinz Gulzek

    IPC分类号： C07D277/06 ,  C07D277/10 ,  C07C99/00

    CPC分类号： C07D277/06 ,  C07D277/10

    摘要： Penicillamine or a homolog thereof is made by reacting an aldehyde branched at the .alpha.-carbon atom, sulfur and ammonia to form a thiazoline- .DELTA..sup.3 ; converting the latter compound by reaction with anhydrous hydrogen cyanide into the corresponding thiazolidine-4-carbonitrile; hydrolyzing the nitrile with an aqueous concentrated hydrochloric acid containing at least 30% by weight of hydrogen chloride at a temperature between 40.degree. and 70.degree. C to form the hydrochloric salt of the thiazolidine-4-acid amide and then, at a higher temperature continuing the hydrolysis to form the salt of the thiazolidine-4-carboxylic acid together with the ammonium salt. The ammonium salt is then separated from the mixture and the carboxylic acid hydrochloride is hydrolytically decomposed whereby the penicillamine is obtained.

    摘要翻译： 青霉胺或其同系物通过使在α-碳原子上分支的醛，硫和氨反应形成噻唑啉-TATA 3而制备; 通过与无水氰化氢反应将后一种化合物转化成相应的噻唑烷-4-腈; 在40℃〜70℃的温度下，用含有至少30重量％氯化氢的浓盐酸水解腈，形成噻唑烷-4-酸酰胺的盐酸盐，然后在更高的温度下继续 水解形成噻唑烷-4-羧酸的盐与铵盐一起。 然后将铵盐与混合物分离，并将羧酸盐酸盐水解分解，从而得到青霉胺。

    Process of making penicillamine
    8.
    发明授权
    Process of making penicillamine 失效
    制作青霉胺的过程

    公开(公告)号：US3948984A

    公开(公告)日：1976-04-06

    申请号：US346825

    申请日：1973-03-29

    申请人： Friedrich Asinger ,  Heribert Offermanns ,  Miklos Ghyczy

    发明人： Friedrich Asinger ,  Heribert Offermanns ,  Miklos Ghyczy

    IPC分类号： C07D277/06 ,  C07C99/10

    CPC分类号： C07D277/06

    摘要： Penicillamine and its hydrochloride are made by reacting isobutyraldehyde with elemental sulfur or a sulfur-containing compound and with gaseous ammonia so as to form 2-isopropyl-5.5-dimethyl-thiazoline-.DELTA..sup.3, then reacting the latter compound with substantially anhydrous hydrogen cyanide so as to form the corresponding thiazolidine 4-carbonitrile, thereupon treating the latter compound with an excess of concentrated hydrochloric acid at an elevated temperature and separating the components of the mixture formed and recovering the penicillamine hydrochloride which may then be converted to the free D,L-penicillamine.

    摘要翻译： 青霉胺及其盐酸盐通过使异丁醛与元素硫或含硫化合物和气态氨反应形成2-异丙基-5-二甲基 - 噻唑啉-TATA 3，然后使后一种化合物与基本上无水的氰化氢反应制得。 为了形成相应的噻唑烷4-甲腈，随后在高温下用过量的浓盐酸处理后一种化合物，分离所形成的混合物的组分并回收盐酸青霉胺，然后将其转化为游离的D，L 青霉胺

    Process of preparing penicillamine
    9.
    发明授权
    Process of preparing penicillamine 失效
    制备青霉胺的方法

    公开(公告)号：US4028406A

    公开(公告)日：1977-06-07

    申请号：US657835

    申请日：1976-02-13

    申请人： Friedrich Asinger ,  Heribert Offermanns ,  Karl-Heinz Gluzek

    发明人： Friedrich Asinger ,  Heribert Offermanns ,  Karl-Heinz Gluzek

    IPC分类号： C07D277/06 ,  C07C99/00

    CPC分类号： C07D277/06 ,  Y10S426/807

    摘要： Improvements in the process of preparing penicillamine or a homolog thereof by reacting an .alpha.-carbon atom branched aldehyde, sulfur and ammonia to form a thiazoline-.DELTA..sup.3, reacting the thiazoline-.DELTA..sup.3 with anhydrous hydrogen cyanide to form a thiazolidine-4-carbonitrile, hydrolyzing the nitrile to form a mixture of the salt of the thiazolidine-4-carboxylic acid and ammonium salts, separating off the ammonium salts and hydrolytically decomposing the thiazolidine-4-carboxylic acid, wherein under the action of a mineral acid the thiazolidine-4-carbonitrile is in the first stage converted at low temperatures into the salt of the thiazolidine-4-carbonamide and then at higher temperatures converted into the salt of the thiazolidine-4-carboxylic acid.

    摘要翻译： 通过使α-碳原子支链醛，硫和氨反应形成噻唑啉-DTA 3，制备青霉胺或其同系物的方法的改进，使噻唑啉-DTA 3与无水氰化氢反应形成噻唑烷-4-腈 水解腈形成噻唑烷-4-羧酸盐和铵盐的混合物，分离出铵盐并水解分解噻唑烷-4-羧酸，其中在无机酸的作用下，噻唑烷-4-酮 4-甲腈在第一阶段在低温下转化成噻唑烷-4-碳酰胺的盐，然后在更高的温度下转化成噻唑烷-4-羧酸的盐。