公开(公告)号：US06348617B1

公开(公告)日：2002-02-19

申请号：US09284263

申请日：1999-06-21

申请人： Hideki Ushio ,  Motoo Hazama ,  Toshikazu Yagi ,  Akihiko Nakamura ,  Masahiko Mizuno

发明人： Hideki Ushio ,  Motoo Hazama ,  Toshikazu Yagi ,  Akihiko Nakamura ,  Masahiko Mizuno

IPC分类号： C09C6966

CPC分类号： C07C67/343 ,  C07C67/60 ,  C07C69/716

摘要： The present invention is directed to a method for purifying pyruvic acid compounds, which method comprises reacting a pyruvic acid compound of general formula (I): wherein R1 is an optionally substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and R2 is a lower alkyl group, with a bisulfite of general formula (II): MHSO3  (II) wherein M is NH4 or an alkali metal, to give a bisulfite adduct of the pyruvic acid compound and then decomposing the adduct with an acid. According to the present invention, pyruvic acid compounds can be purified by simple and easy procedures without using purification techniques such as distillation or column chromatography, and the above method is advantageous as a process for the production on an industrial scale.

摘要翻译： 本发明涉及一种纯化丙酮酸化合物的方法，该方法包括使通式（I）的丙酮酸化合物：其中R 1为任选取代的低级烷基，低级烯基，低级炔基， 环烷基，芳基或杂环基，R2是低级烷基，与通式（II）的亚硫酸氢盐反应：其中M是NH 4或碱金属，得到丙酮酸化合物的亚硫酸氢盐加合物和 然后用酸分解加合物。 根据本发明，丙酮酸化合物可以通过简单且简单的方法纯化，而不使用蒸馏或柱色谱法等纯化技术，上述方法作为工业规模生产的方法是有利的。

公开(公告)号：US5880291A

公开(公告)日：1999-03-09

申请号：US924320

申请日：1997-09-05

申请人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

发明人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

IPC分类号： C07D205/04

CPC分类号： C07D205/04

摘要： The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.

摘要翻译： 本发明提供了使用工业中价格相对较低的容易获得的试剂制备光学活性氮杂环丁烷-2-羧酸的方法。 因此，提供光学活性的氮杂环丁烷-2-羧酸及其制备方法，该方法是使式（1）表示的旋光性N-（烷基苄基）氮杂环丁烷-2-羧酸：（1） 在催化剂存在下氢解。

公开(公告)号：US6114543A

公开(公告)日：2000-09-05

申请号：US128974

申请日：1998-08-04

申请人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

发明人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

IPC分类号： C07D205/04

CPC分类号： C07D205/04

摘要： The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.

摘要翻译： 本发明提供了使用工业中价格相对较低的容易获得的试剂制备光学活性氮杂环丁烷-2-羧酸的方法。 因此，提供光学活性的氮杂环丁烷-2-羧酸及其制备方法，其中式（1）表示的光学活性的N-（烷基苄基）氮杂环丁烷-2-羧酸：在 催化剂

公开(公告)号：US5874593A

公开(公告)日：1999-02-23

申请号：US592375

申请日：1996-02-08

申请人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

发明人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

IPC分类号： C07C251/86 ,  C07C257/18 ,  C07C257/22 ,  C07D257/04 ,  C07D405/04

CPC分类号： C07D257/04 ,  C07C251/86 ,  C07C257/18 ,  C07C257/22 ,  C07D405/04

摘要： There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): ##STR1## characterized in that a nitrile of general formula (2):R.sup.1 CN (2)is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3):ANO.sub.2 (3)or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4):R.sup.4 J (4)with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5):R.sup.1 C(=R.sup.5)R.sup.6 (5)which is useful for the production of the tetrazole compound (in which R.sup.1 to R.sup.6, A and J in the above formulas are as defined in the specification).

摘要翻译： PCT No.PCT / JP95 / 00919 Sec。 371日期1996年2月8日 102（e）日期1996年2月8日PCT提交1995年5月15日PCT公布。 出版物WO95 / 31445 日本公开了1995年11月23日的通式（1）的四唑化合物的工业上有利的方法：其中通式（2）的腈：R1CN（2）与肼 或其盐在催化剂存在下反应，随后与通式（3）的亚硝酸化合物：ANO2（3）或通式（2）的腈反应与硫化氢反应，随后与 通式（4）的烷基卤化物：R4J（4）与肼或其盐，然后与通式（3）的亚硝酸化合物反应; 和通式（5）的中间体：可用于制备四唑化合物的R1C（= R5）R6（5）（上述式中的R1至R6，A和J如说明书中所定义） 。

公开(公告)号：US06191289B1

公开(公告)日：2001-02-20

申请号：US09176198

申请日：1998-10-21

申请人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

发明人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

IPC分类号： C07D25704

CPC分类号： C07D257/04 ,  C07C251/86 ,  C07C257/18 ,  C07C257/22 ,  C07D405/04

摘要： There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): characterized in that a nitrile of general formula (2): R1CN  (2) is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3): ANO2  (3) or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4): R4J  (4) with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5): R1C(═R5)R6  (5) which is useful for the production of the tetrazole compound (in which R1 to R6, A and J in the above formulas are as defined in the specification).

摘要翻译： 公开了用于制备通式（1）的四唑化合物的工业上有利的方法：其特征在于通式（2）的腈与肼或其盐在催化剂存在下反应，然后与 将通式（3）的亚硝酸化合物或通式（2）的腈与硫化氢反应，然后与通式（4）的烷基卤反应：与肼或其盐反应，然后与 通式（3）的亚硝酸化合物; 和通式（5）的中间体：其可用于制备四唑化合物（其中上述式中的R 1至R 6，A和J如说明书中所定义）。

公开(公告)号：US06277998B1

公开(公告)日：2001-08-21

申请号：US09662591

申请日：2000-09-14

申请人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

发明人： Hideki Ushio ,  Takayuki Higashii ,  Masayoshi Minai ,  Akihiko Nakamura

IPC分类号： C07D40504

CPC分类号： C07D257/04 ,  C07C251/86 ,  C07C257/18 ,  C07C257/22 ,  C07D405/04

摘要： There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): characterized in that a nitrile of general formula (2): R1CN  (2) is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3): ANO2  (3) or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4): R4J  (4) with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5): R1C(═R5)R6  (5) which is useful for the production of the tetrazole compound (in which R1 to R6, A and J in the above formulas are as defined in the specification).

公开(公告)号：US20090118519A1

公开(公告)日：2009-05-07

申请号：US12297113

申请日：2006-06-28

申请人： Norihiko Hirata ,  Toshitsugi Uemura ,  Hideki Ushio

发明人： Norihiko Hirata ,  Toshitsugi Uemura ,  Hideki Ushio

IPC分类号： C07D209/48

CPC分类号： C07D209/48 ,  C07D209/52

摘要： A process for producing lactams of formula (1) below, including the step of reacting lactones of formula (2) below with imides of any of formulae (3a), (3b) and (3c) to thereby obtain corresponding carboxylic acids (step A); the step of esterifying the carboxylic acids into corresponding esters (step B); and the step of reacting the esters with amines to thereby obtain lactams of the formula (1) (step C). In the formulae (1)-(2) and (3a)-(3c), when R3 and R4 are simultaneously hydrogen atoms, R is a substituted methylene or optionally substituted polymethylene; when at least one of R3 and R4 is a substituent other than hydrogen atom, R is an optionally substituted methylene or polymethylene; each of R3, R4, R5 and R6 independently is a hydrogen atom, a halogen atom, cyano, etc.; each of A1, A2, A3, A4, A5, A6, A7, A8, A9 and A10 independently is a hydrogen atom, a halogen atom, nitro, etc.; and M is a hydrogen atom or an alkali metal atom.

摘要翻译： 一种生产下式（1）的内酰胺的方法，包括使下式（2）的内酯与式（3a），（3b）和（3c）中任一式的酰亚胺反应的步骤，从而得到相应的羧酸（步骤A ）; 将羧酸酯化成相应的酯（步骤B）的步骤; 以及使酯与胺反应从而得到式（1）的内酰胺（步骤C）的步骤。 在式（1） - （2）和（3a） - （3c）中，当R3和R4同时为氢原子时，R为取代的亚甲基或任选取代的聚亚甲基; 当R 3和R 4中的至少一个是除氢原子以外的取代基时，R是任选取代的亚甲基或聚亚甲基; R 3，R 4，R 5和R 6各自独立地为氢原子，卤原子，氰基等; A1，A2，A3，A4，A5，A6，A7，A8，A9和A10各自独立地为氢原子，卤素原子，硝基等; M是氢原子或碱金属原子。

公开(公告)号：US06653507B2

公开(公告)日：2003-11-25

申请号：US10147966

申请日：2002-05-20

申请人： Miyuki Oikawa ,  Hideki Ushio ,  Isao Kurimoto ,  Takayuki Higashii

发明人： Miyuki Oikawa ,  Hideki Ushio ,  Isao Kurimoto ,  Takayuki Higashii

IPC分类号： C07C21100

CPC分类号： C07C251/24 ,  C07B2200/07 ,  C07C51/412 ,  C07C51/43 ,  C07C59/115 ,  C07C211/27 ,  C07C211/29 ,  C07C217/58

摘要： There are disclosed are A diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):

摘要翻译： 公开了式（1）的非对映异构体盐：其制备方法，制备式（2'）的光学活性3,3,3-三氟-2-羟基-2-甲基丙酸的方法：a 式（4）的新型光学活性胺化合物：式（8）的新型光学活性胺化合物：式（7）或（11）的亚胺化合物：

公开(公告)号：US5675036A

公开(公告)日：1997-10-07

申请号：US673441

申请日：1996-06-28

申请人： Etsuko Fukuda ,  Atsushi Furutani ,  Hideki Ushio ,  Hirokazu Murata

发明人： Etsuko Fukuda ,  Atsushi Furutani ,  Hideki Ushio ,  Hirokazu Murata

IPC分类号： C07C67/31 ,  C07C231/02

CPC分类号： C07C231/02 ,  C07C67/31

摘要： 3-�4-(4-Phenyl-1-butoxy)benzoyl!amino-2-hydroxyacetophenone is prepared by reacting a benzoate ester with a halobutylbenzene in the presence of a basic compound and an aprotic polar compound in an aromatic hydrocarbon solvent to obtain a corresponding ether, alkali hydrolyzing the ether in an aromatic hydrocarbon solvent and precipitating a hydrolysate with an acid to obtain 4-(4-phenyl-1-butoxy)benzoic acid, reacting a halogenating agent with this benzoic acid derivative in an aromatic hydrocarbon solvent to obtain an acid halide, and reacting the acid halide in an aromatic hydrocarbon solvent with a corresponding aromatic amine.

摘要翻译： 通过苯甲酸酯与卤代丁基苯在碱性化合物和非质子极性化合物存在下在芳族烃溶剂中反应制备3- [4-（4-苯基-1-丁氧基）苯甲酰基]氨基-2-羟基苯乙酮，得到 相应的醚，在芳族烃溶剂中碱解水解醚并用酸沉淀水解产物，得到4-（4-苯基-1-丁氧基）苯甲酸，将卤代剂与该苯甲酸衍生物在芳族烃溶剂 以获得酰卤，并使芳族烃溶剂中的酰卤与相应的芳族胺反应。

公开(公告)号：US5659051A

公开(公告)日：1997-08-19

申请号：US273119

申请日：1994-07-11

申请人： Takayuki Higashii ,  Hideki Ushio ,  Yukari Fujimoto ,  Tsutomu Matsumoto ,  Masayoshi Minai ,  Katsuichi Yasunaga ,  Hiroshi Sogabe ,  Takahiro Kotera

发明人： Takayuki Higashii ,  Hideki Ushio ,  Yukari Fujimoto ,  Tsutomu Matsumoto ,  Masayoshi Minai ,  Katsuichi Yasunaga ,  Hiroshi Sogabe ,  Takahiro Kotera

IPC分类号： C07D311/24

CPC分类号： C07D311/24

摘要： There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro or a group of the RCONH wherein R is C.sub.1 -C.sub.20 alkyl, phenyl, phenyl-substituted (C.sub.1 -C.sub.20) alkyl, phenyl (C.sub.1 -C.sub.20)alkoxyphenyl or (C.sub.1 -C.sub.20) alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): ##STR3## wherein A.sup.1 and A.sup.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl. If the final product cannot be obtained as crystals having good filtration properties by ordinary treatments, a novel technique as disclosed herein can provide such crystals by dissolving the reaction product in an organic solvent insoluble or slightly soluble in water; pouring the resultant solution into water; and removing the organic solvent by distillation with stirring to effect the crystallization of the final product.

摘要翻译： 公开了通式（2）的2-氰基-4-氧代-4H-苯并吡喃化合物的制备方法：其中R 1和R 2独立地是氢，卤素，羟基，C 1 -C 5烷基 硝基或其中R为C 1 -C 20烷基，苯基，苯基取代的（C 1 -C 20）烷基，苯基（C 1 -C 20）烷氧基苯基或（C 1 -C 20）烷氧基苯基）的RCONH基团。 该制造方法的特征在于通式（1）的羧酰胺：其中R 1和R 2各自如上所定义，与脱水剂在通式（Ⅴ）的吡啶化合物存在下反应， （4）：其中A1和A2独立地为氢或C1-C5烷基。 如果通过常规处理不能获得具有良好过滤性能的结晶的最终产品，则本文公开的新技术可以通过将反应产物溶解在不溶或微溶于水的有机溶剂中来提供这种晶体; 将所得溶液倒入水中; 并在搅拌下通过蒸馏除去有机溶剂以实现最终产物的结晶。