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1. 发明授权

US06894190B2 Process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, and salt thereof 失效
标题翻译：光学活性3,3,3-三氟-2-羟基-2-甲基丙酸的制备方法及其盐
公开(公告)号：US06894190B2
公开(公告)日：2005-05-17
申请号：US10603941
申请日：2003-06-26
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： C07C51/41 , C07C51/43 , C07C59/115 , C07C211/27 , C07C211/29 , C07C217/58 , C07C251/24 , C07C211/00
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 imine compounds of formula (7) and (11), and processes for preparing the same:
摘要翻译：公开了式（7）和（11）的亚胺化合物及其制备方法：

2. 发明授权

US06403832B1 Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof 失效
标题翻译：光学活性3,3,3-三氟-2-羟基-2-甲基丙酸的制备方法及其盐
公开(公告)号：US06403832B1
公开(公告)日：2002-06-11
申请号：US09632804
申请日：2000-08-04
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）的区域非对映体盐：其制备方法，式（2'）的光学活性3,3,3-三氟-2-羟基-2-甲基丙酸的制备方法：一种新颖的式（4）的光学活性胺化合物：式（8）的新型光学活性胺化合物：式（7）或（11）的亚胺化合物：

3. 发明授权

US06653507B2 Process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, and salt thereof 失效
标题翻译：光学活性3,3,3-三氟-2-羟基-2-甲基丙酸的制备方法及其盐
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：

4. 发明授权

US06191289B1 Production process and intermediate of tetrazole compound 失效
标题翻译：四唑化合物的生产工艺和中间体
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）。

5. 发明授权

US5597929A Production process of 2-(tetrazol-5-yl)-4-oxo-4H-benzopyran 失效
标题翻译： 2-（四唑-5-基）-4-氧代-4H-苯并吡喃的制备方法
公开(公告)号：US5597929A
公开(公告)日：1997-01-28
申请号：US601029
申请日：1996-02-23
申请人： Hideki Ushio , Takayuki Higashii
发明人： Hideki Ushio , Takayuki Higashii
IPC分类号： C07D405/04
CPC分类号： C07D405/04
摘要： There is disclosed a process for producing a 2-(tetrazol-5-yl)-4-oxo-4H-benzopyran of general formula (1): ##STR1## which comprises reacting a hydroxyacetophenone of general formula (2): ##STR2## with a tetrazole compound of general formula (3): ##STR3## in the presence of a base in a solvent composed mainly of at least one selected from hydrocarbons, halogenated hydrocarbons and alcohols, and then treating the reaction mixture under acidic conditions.
摘要翻译： PCT No.PCT / JP95 / 01261 Sec。 371日期1996年2月23日 102（e）日期1996年2月23日PCT提交1995年6月23日PCT公布。出版物WO96 / 日本1996年1月4日公开了一种制备通式（1）的2-（四唑-5-基）-4-氧代-4H-苯并吡喃的方法：其中包括使一般的羟基苯乙酮式（2）：式（3）：（3）在碱存在下，在主要由至少一种选自烃，卤代烃和醇组成的溶剂中，然后在酸性条件下处理反应混合物。

6. 发明授权

US5659051A Process of producing 2-cyano-4-oxo-4H-benzopyran compounds 失效
标题翻译：制备2-氰基-4-氧代-4H-苯并吡喃化合物的方法
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。

7. 发明授权

US5874593A Production process and intermediate of tetrazole compound 失效
标题翻译：四唑化合物的生产工艺和中间体
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）。

8. 发明授权

US06277998B1 Production process and intermediate of tetrazole compound 失效
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).

9. 发明授权

US5637736A Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof 失效
标题翻译：制备1-溴烷基苯衍生物的方法及其中间体
公开(公告)号：US5637736A
公开(公告)日：1997-06-10
申请号：US286411
申请日：1994-08-05
申请人： Hiroaki Fujishima , Yasunobu Miyamoto , Masayoshi Minai , Tsutomu Matsumoto , Hideki Ushio , Takayuki Higashii
发明人： Hiroaki Fujishima , Yasunobu Miyamoto , Masayoshi Minai , Tsutomu Matsumoto , Hideki Ushio , Takayuki Higashii
IPC分类号： C07C15/44 , C07C17/08 , C07C17/087 , C07C17/26 , C07C41/22 , C07F3/02 , C07D319/14
CPC分类号： C07C17/2632 , C07C15/44 , C07C17/08 , C07C17/087 , C07C41/22 , C07F3/02
摘要： A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.
摘要翻译：通过在非极性溶剂存在下使苯基烯烃衍生物与溴化氢反应来制备1-溴烷基苯衍生物。苯基烯烃衍生物通过烯基卤化物与金属镁反应形成格氏试剂制备，然后使格利雅试剂与苄基卤衍生物反应。通过连续将烯丙基卤衍生物与金属镁在有机溶剂中连续反应制备烯丙基格氏试剂，其中将烯丙基卤衍生物和金属镁连续加入到反应体系中，形成的烯丙基格氏试剂从反应体系中连续除去。这些方法以高产率，高选择性和高纯度提供目标化合物。

10. 发明授权

US06753431B2 Production of mixed acid anhydride and amide compound 失效
标题翻译：混合酸酐和酰胺化合物的生产
公开(公告)号：US06753431B2
公开(公告)日：2004-06-22
申请号：US09870676
申请日：2001-06-01
申请人： Takashi Miki , Hideki Ushio , Isao Kurimoto
发明人： Takashi Miki , Hideki Ushio , Isao Kurimoto
IPC分类号： C07D21122
CPC分类号： C07K5/06026 , A61K38/00 , C07C269/06 , C07D277/46 , C07F9/096 , C07F9/3294 , C07C271/22
摘要： There is disclosed an advantageous mixed acid anhydride production method of formula (1): R1C(O)OY(O)n(R2)p (1) wherein R1, R2 and Y denote the same as defined below, n and p denote an integer of 1 or 2, which is characterized by adding a carboxylic acid of formula (2); R1COOH (2) wherein R1 denotes a hydrogen atom, an optionally substituted alkyl group or the like, an organic base to a solution of a carboxylic acid activating agent of formula (3); (R2)pY(O)nX (3) wherein R2 denotes an optionally substituted aliphatic hydrocarbyl group or the like, Y denotes a carbon atom, a phosphorus atom, or a sulfur atom, and X denotes a chlorine atom or the like.
摘要翻译：公开了式（1）的有利的混合酸酐的制备方法：其中R 1，R 2和Y表示与下面定义的相同，n和p表示1或2的整数，其特征在于加入式（2）的羧酸;其中R 1表示氢原子，任选取代的烷基等，式（3）的羧酸活化剂的溶液中的有机碱：其中R 1， 2>表示任选取代的脂族烃基等，Y表示碳原子，磷原子或硫原子，X表示氯原子等。

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