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1. 发明授权

US08217196B2 Process for producing α-fluoro-β-amino acids 有权
标题翻译：制备α-氟代 - 氨基酸的方法
公开(公告)号：US08217196B2
公开(公告)日：2012-07-10
申请号：US12919108
申请日：2009-04-21
申请人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
发明人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
IPC分类号： C07C227/16
CPC分类号： C07C227/16 , C07B55/00 , C07C227/32 , C07C229/20
摘要： By reacting a β-hydroxy-α-amino acid with sulfuryl fluoride (SO2F2) in the presence of an organic base, it is possible to produce an α-fluoro-β-amino acid of the formula [2]. By using a C8-12 tertiary amine having two or more alkyl groups of C3 or higher, and especially diisopropylethylamine, as the organic base, by-production of quantery ammonium salts is effectively suppressed. By applying the production process of the present invention, it is possible to very easily produce (2R)-3-(dibenzylamino)-2-fluoropropionic acid methyl ester, which is extremely important as a pharmaceutical intermediate, with high positional selectivity even on an industrial scale.
摘要翻译：通过在有机碱的存在下使β-羟基-α-氨基酸与硫酰氟（SO2F2）反应，可以制备式[2]的α-氟 - 二 - 氨基酸。通过使用具有两个以上具有3个以上的烷基的C8-12叔胺，特别是二异丙基乙胺作为有机碱，有效地抑制了副铵盐的副产物。通过应用本发明的制备方法，可以非常容易地制备作为药物中间体极其重要的（2R）-3-（二苄基氨基）-2-氟丙酸甲酯，即使在工业规模。

2. 发明申请

US20110015428A1 Process for Producing Alpha-Fluoro-Beta-Amino Acids 有权
标题翻译：生产α-氟-β-氨基酸的方法
公开(公告)号：US20110015428A1
公开(公告)日：2011-01-20
申请号：US12919108
申请日：2009-04-21
申请人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
发明人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
IPC分类号： C07C227/16
CPC分类号： C07C227/16 , C07B55/00 , C07C227/32 , C07C229/20
摘要： By reacting a β-hydroxy-α-amino acid with sulfuryl fluoride (SO2F2) in the presence of an organic base, it is possible to produce an α-fluoro-β-amino acid of the formula [2]. By using a C8-12 tertiary amine having two or more alkyl groups of C3 or higher, and especially diisopropylethylamine, as the organic base, by-production of quantery ammonium salts is effectively suppressed. By applying the production process of the present invention, it is possible to very easily produce (2R)-3-(dibenzylamino)-2-fluoropropionic acid methyl ester, which is extremely important as a pharmaceutical intermediate, with high positional selectivity even on an industrial scale.
摘要翻译：通过在有机碱的存在下使β-羟基-α-氨基酸与硫酰氟（SO2F2）反应，可以制备式[2]的α-氟 - 二 - 氨基酸。通过使用具有两个以上具有3个以上的烷基的C8-12叔胺，特别是二异丙基乙胺作为有机碱，有效地抑制了副铵盐的副产物。通过应用本发明的制备方法，可以非常容易地制备作为药物中间体极其重要的（2R）-3-（二苄基氨基）-2-氟丙酸甲酯，即使在工业规模。

3. 发明申请

US20110152536A1 Process for Production of Alpha-Trifluoromethyl-Beta-Substituted-Beta-Amino Acid 有权
标题翻译： α-三氟甲基-β-取代的β-氨基酸的制备方法
公开(公告)号：US20110152536A1
公开(公告)日：2011-06-23
申请号：US13002595
申请日：2009-08-27
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
IPC分类号： C07C229/08 , C07D261/02
CPC分类号： C07D261/04 , C07B53/00 , C07C229/20
摘要： α-Trifluoromethyl-β-substituted-β-amino acids can be produced by allowing α-trifluoromethyl-β-substituted-α,β-unsaturated esters to react with hydroxylamine to convert α-trifluoromethyl-β-substituted-α,β-unsaturated esters into dehydrogenated closed-ring body of α-trifluoromethyl-β-substituted-β-amino acid, and by hydrogenolyzing the dehydrogenated closed-ring body. According to this production process, novel α-trifluoromethyl-β-substituted-β-amino acids which are free amino acids whose functional groups are not protected can be produced, in which β-position substituent is not limited to aromatic ring group or substituted aromatic ring group while the relative stereochemistry of α-position and β-position can be also controlled.
摘要翻译： α-三氟甲基 - 和取代的 - 氨基酸可以通过使α-三氟甲基 - 取代的α，β-不饱和酯与羟胺反应以转化α-三氟甲基 - α，β-不饱和酯转化为α-三氟甲基 - 取代的 - 氨基酸的脱氢闭环体，并通过氢化脱氢闭环体。根据该制造方法，可以制备作为官能团未被保护的游离氨基酸的新型α-三氟甲基 - 取代 - 取代的 - 氨基酸，其中，取代基不限于芳环基或取代的芳族环基团，同时也可以控制相对的立体化学位置和位置。

4. 发明申请

US20110160477A1 Process for Producing alpha-Trifluoromethyl-alpha,beta-Unsaturated Ester 有权
标题翻译：生产α-三氟甲基-α，β-不饱和酯的方法
公开(公告)号：US20110160477A1
公开(公告)日：2011-06-30
申请号：US13060565
申请日：2009-09-24
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
IPC分类号： C07C67/327
CPC分类号： C07C67/317 , C07C67/327 , C07C69/65
摘要： An α-trifluoromethyl-α,β-unsaturated ester can be produced by reacting an α-trifluoromethyl-α-hydroxy ester with sulfuryl fluoride (SO2F2) in the presence of an organic base. It is preferable that the raw substrate has a hydrogen atom as one β-position substituent group and either an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aromatic ring group or a substituted aromatic ring group as the other β-position substituent group. It is more preferable that an ester moiety of the raw substrate is an alkyl ester. This raw substrate is readily available. Further, the desired reaction can proceed favorably with the use of this raw substrate. It is also preferable to use either 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the organic base. The desired reaction can proceed more favorably with the use of this organic base.
摘要翻译： α-三氟甲基-α，β-不饱和酯可以通过α-三氟甲基-α-羟基酯与硫酰氟（SO 2 F 2）在有机碱的存在下反应来制备。原料优选为氢原子作为一个位置取代基和烷基，取代的烷基，链烯基，取代的烯基，芳族环基或取代的芳环基作为另一个位置取代基。原料的酯部更优选为烷基酯。该原料基材容易获得。此外，期望的反应可以有利地利用该原始基底进行。还优选使用1,5-二氮杂双环[4.3.0]壬-5-烯（DBN）或1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为有机碱。使用该有机碱可以更有利地进行所需的反应。

5. 发明授权

US08653295B2 Process for producing α-trifluoromethyl-α,β-unsaturated ester 有权
标题翻译： α-三氟甲基-α，β-不饱和酯的制备方法
公开(公告)号：US08653295B2
公开(公告)日：2014-02-18
申请号：US13060565
申请日：2009-09-24
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
IPC分类号： C07C69/76
CPC分类号： C07C67/317 , C07C67/327 , C07C69/65
摘要： An α-trifluoromethyl-α,β-unsaturated ester can be produced by reacting an α-trifluoromethyl-α-hydroxy ester with sulfuryl fluoride (SO2F2) in the presence of an organic base. It is preferable that the raw substrate has a hydrogen atom as one β-position substituent group and either an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aromatic ring group or a substituted aromatic ring group as the other β-position substituent group. It is more preferable that an ester moiety of the raw substrate is an alkyl ester. This raw substrate is readily available. Further, the desired reaction can proceed favorably with the use of this raw substrate. It is also preferable to use either 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the organic base. The desired reaction can proceed more favorably with the use of this organic base.
摘要翻译： α-三氟甲基-α，β-不饱和酯可以通过在有机碱存在下使α-三氟甲基-α-羟基酯与硫酰氟（SO 2 F 2）反应来制备。原料优选为具有作为一个β位取代基的氢原子，烷基，取代烷基，链烯基，取代烯基，芳香环基或取代芳环基作为其他β位取代基。原料的酯部更优选为烷基酯。该原料基材容易获得。此外，期望的反应可以有利地利用该原始基底进行。还优选使用1,5-二氮杂双环[4.3.0]壬-5-烯（DBN）或1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为有机碱。使用该有机碱可以更有利地进行所需的反应。

6. 发明授权

US08524913B2 Process for production of α-trifluoromethyl-β-substituted-β-amino acid 有权
标题翻译： α-三氟甲基-β-取代的β-氨基酸的制备方法
公开(公告)号：US08524913B2
公开(公告)日：2013-09-03
申请号：US13002595
申请日：2009-08-27
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
IPC分类号： C07D261/04 , C07C229/20
CPC分类号： C07D261/04 , C07B53/00 , C07C229/20
摘要： α-Trifluoromethyl-β-substituted-β-amino acids can be produced by allowing α-trifluoromethyl-β-substituted-α,β-unsaturated esters to react with hydroxylamine to convert α-trifluoromethyl-β-substituted-α,β-unsaturated esters into dehydrogenated closed-ring body of α-trifluoromethyl-β-substituted-β-amino acid, and by hydrogenolyzing the dehydrogenated closed-ring body. According to this production process, novel α-trifluoromethyl-β-substituted-β-amino acids which are free amino acids whose functional groups are not protected can be produced, in which β-position substituent is not limited to aromatic ring group or substituted aromatic ring group while the relative stereochemistry of α-position and β-position can be also controlled.
摘要翻译： α-三氟甲基-β-取代的β-取代的β-氨基酸可以通过使α-三氟甲基-β-取代的α，β-不饱和酯与羟胺反应以转化α-三氟甲基-β-取代的α，β-不饱和的酯转化成α-三氟甲基-β-取代的β-氨基酸的脱氢闭环体，并通过氢化脱氢闭环体。根据该制造方法，可以制备作为官能团未被保护的游离氨基酸的新型α-三氟甲基-β-取代的β-氨基酸，其中β位取代基不限于芳环或取代芳族环组，而α位和β位的相对立体化学也可以被控制。

7. 发明授权

US08058412B2 Dehydroxyfluorination agent 有权
标题翻译：脱羟基氟化剂
公开(公告)号：US08058412B2
公开(公告)日：2011-11-15
申请号：US12306826
申请日：2007-06-25
申请人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
发明人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
IPC分类号： C07D478/00 , C09K3/00 , C07C17/00 , C07C19/08 , C07C21/18
CPC分类号： C07B39/00 , C07B55/00 , C07B2200/07 , C07C17/16 , C07C67/307 , C07D207/16 , C07D209/48 , C07D405/04 , C07H19/09 , C07C19/08 , C07C69/63
摘要： There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SO2F2) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.
摘要翻译：提供了含有硫酰氟（SO 2 F 2）和分子中不含游离羟基的有机碱的新型有用的脱羟基氟化剂。根据现有的脱羟基氟化剂，不需要使用全氟烷基磺酰氟，其在大规模使用中是不优选的，并且可以有利地制备作为药物，农药和光学的重要中间体的光学活性氟衍生物材料，例如4-氟脯氨酸衍生物，2'-脱氧-2'-氟尿苷衍生物，光学活性α-氟代羧酸酯衍生物和单氟甲基衍生物，甚至大规模。

8. 发明申请

US20080103327A1 Process For Production Of Optically Active Alpha-Fluoro-Carboxylic Ester Derivatives 失效
标题翻译：光活性α-氟羧酸酯衍生物的制备方法
公开(公告)号：US20080103327A1
公开(公告)日：2008-05-01
申请号：US11597105
申请日：2005-08-05
申请人： Akihiro Ishii , Hideyuki Tsuruta , Takashi Ootsuka , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
发明人： Akihiro Ishii , Hideyuki Tsuruta , Takashi Ootsuka , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
IPC分类号： C07C69/63 , C07C31/38 , C07C69/635
CPC分类号： C07C67/307 , C07B2200/07 , C07C29/147 , C07C69/65 , C07C69/63 , C07C31/38
摘要： The present invention relates to a process for producing an optically active α-fluorocarboxylate derivative represented by the formula [2], by reacting an optically active α-hydroxycarboxylate derivative with trifluoromethanesulfonyl fluoride (CF3SO2F) in the presence of an organic base, in the formula [2], R represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 12; one of or two by any combination of aromatic hydrocarbon groups, unsaturated hydrocarbon groups, straight-chain or branched alkoxy groups of a carbon number of 1 to 6, aryloxy groups, halogen atoms (fluorine, chlorine, bromine and iodine), protected carboxyl groups, protected amino groups or protected hydroxyl group can be substituted on any carbon atoms of the alkyl group; R1 represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 8; any carbon atoms of the alkyl groups of R and R1 may form a covalent bond; and * represents an asymmetric carbon.
摘要翻译：本发明涉及通过使光学活性α-羟基羧酸酯衍生物与三氟甲磺酰氟（CF 3 SO 3）反应制备由式[2]表示的光学活性α-氟代羧酸酯衍生物的方法， 2 F）在有机碱存在下，在式[2]中，R表示碳数为1至12的直链或支链烷基; 碳数为1至6的芳族烃基，不饱和烃基，直链或支链烷氧基，芳氧基，卤素原子（氟，氯，溴和碘）的任意组合中的一个或两个，被保护的羧基被保护的氨基或被保护的羟基可以在烷基的任何碳原子上被取代; R 1表示碳数为1至8的直链或支链烷基; R和R 1的烷基的任何碳原子可以形成共价键; 和*表示不对称碳。

9. 发明授权

US07807858B2 Process for production of fluoro derivative 有权
标题翻译：氟衍生物生产工艺
公开(公告)号：US07807858B2
公开(公告)日：2010-10-05
申请号：US11795378
申请日：2006-03-17
申请人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
发明人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
IPC分类号： C07C19/08 , C07C205/00 , C07C69/63 , C07C51/58 , C07D239/02 , C07D207/00
CPC分类号： C07D209/48 , C07B39/00 , C07B2200/07 , C07C17/16 , C07C67/307 , C07D207/16 , C07H19/073 , C07C19/08 , C07C69/63
摘要： It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and the like, even in a large scale.
摘要翻译：发现氟衍生物可以通过羟基衍生物与硫酰氟（SO 2 F 2）在有机碱的存在下或在有机碱和“含有机碱和氟化氢的盐或络合物”的存在下反应来制备，。根据本制造方法，不需要使用在工业上不优选的全氟烷基磺酰氟，可以有利地制造作为药物，农药，光学材料的重要中间体的光学活性氟衍生物，特别是4-氟脯氨酸衍生物，2'-脱氧-2'-氟尿苷衍生物，光学活性α-氟代羧酸酯衍生物等，甚至大规模。

10. 发明申请

US20080125589A1 Process for Production of Fluoro Derivative 有权
标题翻译：氟衍生物的生产工艺
公开(公告)号：US20080125589A1
公开(公告)日：2008-05-29
申请号：US11795378
申请日：2006-03-17
申请人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
发明人： Akihiro Ishii , Takashi Ootsuka , Manabu Yasumoto , Hideyuki Tsuruta , Kenjin Inomiya , Koji Ueda , Kaori Mogi
IPC分类号： C07C19/08 , C07D207/04 , C07D239/54 , C07C69/63 , C07D209/32
CPC分类号： C07D209/48 , C07B39/00 , C07B2200/07 , C07C17/16 , C07C67/307 , C07D207/16 , C07H19/073 , C07C19/08 , C07C69/63
摘要： It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and the like, even in a large scale.
摘要翻译：发现氟衍生物可以通过羟基衍生物与硫酰氟（SO 2 H 2 F 2）在有机碱的存在下或在有机碱存在下反应来制备有机碱和“含有机碱和氟化氢的盐或络合物”。根据本制造方法，不需要使用在工业上不优选的全氟烷基磺酰氟，可以有利地制造作为药物，农药，光学材料的重要中间体的光学活性氟衍生物，特别是4-氟脯氨酸衍生物，2'-脱氧-2'-氟尿苷衍生物，光学活性α-氟代羧酸酯衍生物等，甚至大规模。

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