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1. 发明授权

US06894170B2 Process for the preparation of substituted thiazolines and their intermediates 失效
标题翻译：制备取代噻唑啉及其中间体的方法
公开(公告)号：US06894170B2
公开(公告)日：2005-05-17
申请号：US10270324
申请日：2002-10-15
申请人： Sylvia Krich , Alexander Rieder , Ferdinand Heu , Gerhard Steinbauer
发明人： Sylvia Krich , Alexander Rieder , Ferdinand Heu , Gerhard Steinbauer
IPC分类号： C12P41/00 , C07B55/00 , C07B57/00 , C07C319/02 , C07C319/28 , C07C323/58 , C07D277/12 , C07D417/04 , C07D277/10
CPC分类号： C07D417/04 , C07C319/02 , C07D277/12 , C07C323/58
摘要： Process for the preparation of substituted thiazolines of the formula (I) in which Ar is a phenyl, naphthyl, thienyl, pyridyl or quinolinyl radical which can optionally be substituted by one or more substituents from the group consisting of halogen, OH, benzyloxy, C1-C4-alkyl, C1-C4-alkoxy, COOR1 where R1 is H or C1-C4-alkyl, by coupling of (S)-α-methylcysteine hydrochloride of the formula (II) with a nitrile of the formula (III) Ar—CN in which Ar is as defined above, or a corresponding C1-C4-alkyl imidate, in which (S)-α-methylcysteine hydrochloride of the formula (II) is reacted in a suitable solvent with a nitrile of the formula (III) or a corresponding C1-C4-alkyl imidate in the presence of a tertiary base at a pH of 6.5 to 10 at 50° C. up to the reflux temperature to give the corresponding thiazoline of the formula (I), and processes for the preparation of (S)-α-methylcysteine hydrochloride and its use for the preparation of thiazolines of the formula (I).
摘要翻译：制备式（I）的取代噻唑啉的方法，其中Ar是苯基，萘基，噻吩基，吡啶基或喹啉基，其可以任选地被一个或多个选自卤素，OH，苄氧基，C C 1 -C 4 - 亚烷基，C 1 -C 4 - 烷氧基，COOR 1 - 其中R 1是H或C 1 -C 4 - 烷基，通过将（S）-α-甲基半胱氨酸盐酸盐与式（II）与式（III）的腈<？in-line-formula description =“In-line formula”end =“lead”？> Ar-CN <？in-line-formula description =“In- 其中Ar如上所定义，或其相应的C 1 -C 4 - 亚烷基亚氨酸酯，其中（S） - 式（II）的α-甲基半胱氨酸盐酸盐在合适的溶剂中与式（III）的腈或相应的C 1 -C 4 - 亚烷基亚氨基酯反应在pH为6.5t的叔碱存在下进行 o 10在50℃直到回流温度，得到相应的式（I）噻唑啉，以及制备（S）-α-甲基半胱氨酸盐酸盐的方法及其用于制备式（I）的噻唑啉的用途一世）。

2. 发明申请

US20050101782A1 Process for the preparation of substituted thiazolines and their intermediates 审中-公开
标题翻译：制备取代噻唑啉及其中间体的方法
公开(公告)号：US20050101782A1
公开(公告)日：2005-05-12
申请号：US11011110
申请日：2004-12-15
申请人： Sylvia Krich , Alexander Rieder , Ferdinand Heu , Gerhard Steinbauer
发明人： Sylvia Krich , Alexander Rieder , Ferdinand Heu , Gerhard Steinbauer
IPC分类号： C12P41/00 , C07B55/00 , C07B57/00 , C07C319/02 , C07C319/28 , C07C323/58 , C07D277/12 , C07D417/04
CPC分类号： C07D417/04 , C07C319/02 , C07D277/12 , C07C323/58
摘要： Process for the preparation of substituted thiazolines of the formula (I) in which Ar is a phenyl, naphthyl, thienyl, pyridyl or quinolinyl radical which can optionally be substituted by one or more substituents from the group consisting of halogen, OH, benzyloxy, C1-C4-alkyl, C1-C4-alkoxy, COOR1 where R1 is H or C1-C4-alkyl, by coupling of (S)-α-methylcysteine hydrochloride of the formula (II) with a nitrile of the formula (III) Ar—CN in which Ar is as defined above, or a corresponding C1-C4-alkyl imidate, in which (S)-α-methylcysteine hydrochloride of the formula (II) is reacted in a suitable solvent with a nitrile of the formula (III) or a corresponding C1-C4-alkyl imidate in the presence of a tertiary base at a pH of 6.5 to 10 at 50° C. up to the reflux temperature to give the corresponding thiazoline of the formula (I), and processes for the preparation of (S)-α-methylcysteine hydrochloride and its use for the preparation of thiazolines of the formula (I).
摘要翻译：制备式（I）的取代噻唑啉的方法，其中Ar是苯基，萘基，噻吩基，吡啶基或喹啉基，其可以任选地被一个或多个选自卤素，OH，苄氧基，C C 1 -C 4 - 亚烷基，C 1 -C 4 - 烷氧基，COOR 1 - 其中R 1是H或C 1 -C 4 - 烷基，通过将（S）-α-甲基半胱氨酸盐酸盐与式（II）与式（III）的腈<？in-line-formula description =“In-line formula”end =“lead”？> Ar-CN <？in-line-formula description =“In- 其中Ar如上所定义，或其相应的C 1 -C 4 - 亚烷基亚氨酸酯，其中（S） - 式（II）的α-甲基半胱氨酸盐酸盐在合适的溶剂中与式（III）的腈或相应的C 1 -C 4 - 亚烷基亚氨基酯反应在pH为6.5的叔碱存在下进行至10℃，直到回流温度，得到相应的式（I）噻唑啉，以及制备（S）-α-甲基半胱氨酸盐酸盐的方法及其用于制备式（I）的噻唑啉的用途一世）。

3. 发明申请

US20070112216A1 Method for producing chiral mercapto amino acids 审中-公开
公开(公告)号：US20070112216A1
公开(公告)日：2007-05-17
申请号：US10581790
申请日：2004-11-15
申请人： Martina Kotthaus , Herbert Mayrhofer , Christian Rogl , Sylvia Krich , Michael Simetzberger
发明人： Martina Kotthaus , Herbert Mayrhofer , Christian Rogl , Sylvia Krich , Michael Simetzberger
IPC分类号： C07C323/29
CPC分类号： C07C319/06 , C07B2200/07 , C07C323/58
摘要： The invention relates to a method for producing chiral mercapto amino acids of formula (I) wherein R1, R2 and R3 can represent hydrogen, C6-C12 aryl, C1-C6-alkyl-C6-C12-aryl, C6-C12-aryl-C1-C6-alkyl, C1-C18-alkyl or C2-C18-alkenyl, R2 and R3 forming a saturated or unsaturated ring. According to said method, a) an oxo compound of formula (II), wherein X represents a leaving group, is reacted in the presence of ammonia or ammonium hydroxide and a sulfide, optionally under phase transfer catalysis or addition of a solubiliser, with a ketone or an aldehyde of formula (III) wherein R4 and R5 can represent a C1-C12 alkyl radical or a C6-C20 aryl radical or one of the two radicals H, or R4 and R5 together form a C4-C7 ring, to form the compound of formula (IV), that b) reacts with HCN to form the corresponding nitrile, whereupon c) the crystallised nitrile is converted, by selective hydrolysis by means of a mineral acid, into the corresponding amide of formula (VI), and d) is then converted into the corresponding chiral amide of formula (VI*) by means of an L amidase or a chiral dissociating acid, whereupon by reaction with an acid, the desired chiral mercapto amino acid of formula (I) is obtained, or e) first the reaction with an acid is carried out, and then the conversion into the chiral mercapto amino acid takes place.

4. 发明授权

US06787654B2 Method for producing 2-chloro-5-chloromethyl-1,3-thiazole 失效
标题翻译： 2-氯-5-氯甲基-1,3-噻唑的制备方法
公开(公告)号：US06787654B2
公开(公告)日：2004-09-07
申请号：US10296488
申请日：2003-03-27
申请人： Sylvia Krich , Christian Burger , Johann Altreiter , Birgit Zwölfer
发明人： Sylvia Krich , Christian Burger , Johann Altreiter , Birgit Zwölfer
IPC分类号： C07D27732
CPC分类号： C07D277/32
摘要： A process for the preparation of 2-chloro-5-chloromethyl-1,3-thiazole, in which allyl isothiocyanate of formula CH2═CH—CH2—NCS is reacted at from −40° C. to +30° C., in a solvent that is inert under the reaction conditions, with from 1 to 2 mol of a chlorinating agent per mol of allyl isothiocyanate; to the reaction mixture so obtained there is added, at a reaction temperature of from 0° C. to the boiling temperature of the solvent used, from 1 to 5 mol of oxidising agent per mol of allyl isothiocyanate, and then 2-chloro-5-chloromethyl-1,3-thiazole is isolated from the reaction mixture and is optionally converted by crystallisation into high-purity 2-chloro-5-chloromethyl-1,3-thiazole.
摘要翻译：制备2-氯-5-氯甲基-1,3-噻唑的方法，其中式CH 2 = CH-CH 2 -NCS的异硫氰酸烯丙酯在-40℃至+ 30℃下反应，在在反应条件下为惰性的溶剂，每摩尔异硫氰酸烯丙酯为1至2摩尔氯化剂; 向如此获得的反应混合物中，在0℃至所用溶剂的沸点的反应温度下，每摩尔异硫氰酸烯丙基酯加入1至5摩尔氧化剂，然后加入2-氯-5 - 氯甲基-1,3-噻唑从反应混合物中分离出来，任选地通过结晶转化为高纯度2-氯-5-氯甲基-1,3-噻唑。

5. 发明申请

US20050131246A1 Method for producing 2,2-dichloro or dibromo-phenyl alkyl acetates 审中-公开
标题翻译： 2,2-二氯或二溴 - 苯基烷基乙酸酯的制备方法
公开(公告)号：US20050131246A1
公开(公告)日：2005-06-16
申请号：US10507305
申请日：2003-03-10
申请人： Sylvia Krich , Bernhard Holub
发明人： Sylvia Krich , Bernhard Holub
IPC分类号： C07C67/22 , C07C69/76
CPC分类号： C07C67/22 , C07C69/65
摘要： The invention relates to an improved method for producing 2,2-dichloro or dibromo-phenyl alkyl acetates of formula (1), in which X represents Cl or Br, n represents a whole number from 1 to 5, R represents hydrogen, C1-C8 alkyl, aryl, heteroaryl, C1-C8 alkoxy, aryloxy or halogen and R1 represents C1-C8 alkyl. According to said method, a 2,2-dichloro- or dibromo-phenylacetonitrile of formula (II) is reacted in 0.8 to 2 mol water per mol nitrile of formula (II), 1 to 8 mol alcohol of formula R1OH (III) per mol nitrile of formula (II) and in the presence of 1 to 3 mol HCl or HBr per mol nitrile of formula (II), optionally in the presence of a solvent that is inert in the reaction conditions, to form the corresponding 2,2-dichloro- or dibromo-phenyl alkyl acetates of formula (I), whereby the reaction temperature in the first phase lies between 30 and 60° C. and in the second phase between 60 and 100° C. Once the reaction has taken place, the reaction mixture is cooled to between 20 and 40° C., diluted with water and the 2,2-dichloro- or dibromo-phenyl alkyl acetate of formula (I) is isolated.
摘要翻译：本发明涉及一种制备式（1）的2,2-二氯或二溴 - 苯基烷基乙酸酯的改进方法，其中X表示Cl或Br，n表示1至5的整数，R表示氢， C 1 -C 8烷基，芳基，杂芳基，C 1 -C 8烷氧基，芳氧基或卤素，R 1表示 C 1 -C 8烷基。根据所述方法，式（II）的2,2-二氯或二溴 - 苯基乙腈在0.8-2摩尔水/摩尔的式（II）腈，1至8摩尔的式R 1 OH（III）的醇/ 式（II）的咪唑腈和在1至3mol HCl或HBr / mol式（II）腈存在下，任选地在反应条件下为惰性的溶剂存在下，形成相应的2,2 （I）的二氯或二溴 - 苯基烷基乙酸酯，其中第一相中的反应温度为30至60℃，第二相为60至100℃。一旦发生反应，将反应混合物冷却至20-40℃，用水稀释，分离式（I）的2,2-二氯或二溴 - 苯基烷基乙酸酯。

6. 发明授权

US06812348B1 Method for producing 2-chloro-5-chloromethyl-1,3-thiazol 失效
标题翻译： 2-氯-5-氯甲基-1,3-噻唑的制备方法
公开(公告)号：US06812348B1
公开(公告)日：2004-11-02
申请号：US10111011
申请日：2002-04-19
申请人： Wolfram Hendel , Sylvia Krich
发明人： Wolfram Hendel , Sylvia Krich
IPC分类号： C07D27720
CPC分类号： C07C331/20 , C07D277/32 , C07D277/40 , Y02P20/55
摘要： The invention relates to a method for producing 2-chloro-5-chloromethyl-1,3-thiazol from compounds of formula (I), wherein X means Cl, —OR, —SR or NR2, R being H or a suitable protective group; Y means H or Cl and Z means Cl or O, the compounds of formula (I) having at most one double bond between C* and C″ or between C″ and Z, on the condition that the bond between C″ and Z is a double bond when Z is the same as O and a single bond when Z is the same as Cl; with the following intermediate stage: A1) reacting 2,3-dichloropropanal with rhodanide and acetalising to 3-chloro-1,1-dialkoxy-2-isothiocyanato-propane or a2) reacting 2,3-dichloropropanal with thiourea to form a mixture of the hydrochlorides of the compounds N-[[5-(2-aminothiazol)yl]methyl]thiourea and [5-(2-aminothiazol)yl]methylthioformamidine and splitting to obtain the corresponding thiol or amine or b) reacting a compound of formula (I) wherein X means OR, SR or NR2, Y means clorine and Z means oxygen with thiourea to produce the compound of formula (V), or c) reacting a compound of formula (I), wherein X means OR, SR or NR2, Y means chlorine and Z means oxygen with ammoniumdithiocarbamate or ammoniumthiocarbamate, to produce the compound (VIa) or (VIb); d) converting 1,2,3-trichloropropane to the corresponding thiazolidine and then dehydrogenating or e) converting 1,3-dichloro-prop-1-ene to the corresponding epoxide and then reacting said epoxide with thiourea (e1) or ammoniumdithiocarbamate or ammoniumthiocarbamate (e2).
摘要翻译：本发明涉及由式（I）化合物制备2-氯-5-氯甲基-1,3-噻唑的方法，其中X表示Cl，-OR，-SR或NR2，R为H或合适的保护基 ; Y表示H或Cl，Z表示Cl或O，式（I）化合物在C *和C“之间至多有一个双键或C”和Z之间，条件是C“ 当Z与O相同时Z为双键，当Z与Cl相同时，Z为双键; 具有以下中间阶段：A1）使2,3-二氯丙醛与硫氰酸盐反应并缩醛化为3-氯-1,1-二烷氧基-2-异硫氰酸根合丙烷或a2）使2,3-二氯丙醛与硫脲反应，形成化合物N - [[5-（2-氨基噻唑）基]甲基]硫脲和[5-（2-氨基噻唑）基]甲硫基甲脒的盐酸盐，并分离得到相应的硫醇或胺，或b）使式（I）其中X表示OR，SR或NR2，Y表示氯，Z表示氧与硫脲反应生成式（Ⅴ）化合物，或c）使式（Ⅰ）化合物（其中X表示OR，SR或 NR2，Y表示氯，Z表示氧与二硫代氨基甲酸铵或硫代氨基甲酸铵反应，生成化合物（Ⅵa）或（Ⅵb）。 d）将1,2,3-三氯丙烷转化为相应的噻唑烷，然后脱氢或e）将1,3-二氯丙基-1-烯转化为相应的环氧化物，然后使所述环氧化物与硫脲（e1）或二硫代氨基甲酸铵或硫代氨基甲酸铵反应（e2）。

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