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1. 发明授权

US06218586B1 Method for preparing perhalogenated five-membered cyclic compound 失效
标题翻译：制备全卤代五元环化合物的方法
公开(公告)号：US06218586B1
公开(公告)日：2001-04-17
申请号：US09434277
申请日：1999-11-05
申请人： Naoto Takada , Masatomi Kanai , Hideaki Imura , Takeo Komata
发明人： Naoto Takada , Masatomi Kanai , Hideaki Imura , Takeo Komata
IPC分类号： C07C1708
CPC分类号： C07C23/08 , C07C17/04 , C07C17/206 , C07C17/21
摘要： The invention relates to a method for preparing a fluorinated product that is a first perhalogenated five-membered cyclic compound (e.g., 1,2-dichlorohexafluorocyclopentene and 1,1-dichlorooctafluorocyclopentane). This method includes reacting in a gas phase a starting material that is a second perhalogenated five-membered cyclic compound having at least one unsaturated bond, at substantially the same time with chlorine and hydrogen fluoride, in the presence of a fluorination catalyst containing an activated carbon optionally carrying thereon a metal compound, thereby to decrease the number of the at least one unsaturated bond and to increase the number of fluorine atoms of the second compound. The method is appropriate for the production of the first perhalogenated five-membered cyclic compound in an industrial scale.
摘要翻译：本发明涉及一种制备作为第一全卤代五元环化合物（例如1,2-二氯六氟环戊烯和1,1-二氯八氟环戊烷）的氟化产物的方法。该方法包括在气相中，在含有活性炭的氟化催化剂的存在下，将基本上同时具有至少一个不饱和键的第二全卤化五元环化合物的起始物质与氯和氟化氢反应任选地带有金属化合物，从而减少至少一个不饱和键的数目并增加第二化合物的氟原子数。该方法适用于以工业规模生产第一全卤代五元环化合物。

2. 发明授权

US06395940B1 Method for producing perhalogenated cyclopentene 有权
标题翻译：生产全卤代环戊烯的方法
公开(公告)号：US06395940B1
公开(公告)日：2002-05-28
申请号：US09486608
申请日：2000-03-01
申请人： Takeo Komata , Takayuki Nishimiya , Fuyuhiko Sakyu , Hideaki Imura , Mikio Ujiie , Masatomi Kanai
发明人： Takeo Komata , Takayuki Nishimiya , Fuyuhiko Sakyu , Hideaki Imura , Mikio Ujiie , Masatomi Kanai
IPC分类号： C07C1720
CPC分类号： C07C23/08 , C07C17/206 , C07C17/208 , C07C17/21
摘要： The invention relates to a method for producing a first perhalogenated cyclopentene represented by the general formula: C5ClBF8−B where B is an integer of from 0 to 7. The method includes a step of (a) fluorinating a second perhalogenated cyclopentene by hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. The second perhalogenated cyclopentene is represented by general formula: C5ClAF8−A where A is an integer of from 1 to 8, and A is not smaller than B. With this method, the first perhalogenated cyclopentene (e.g., 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene, another chlorofluorinated cyclopentene, or octafluorocyclopentene) can continuously easily be produced, for example, from octachlorocyclopentene obtained by chlorination of hexachlorocyclopentadiene that is easily available. Therefore, the above method is very useful as an industrial scale production method. In case that the first perhalogenated cyclopentene is octafluorocyclopentene, the method may further include a step of (b) fluorinating a reaction product of the step (a) in a way that is different from that of the step (a), thereby to convert said reaction product of the step (a) into octafluoropentene. The step (a) may be conducted by a multistep reaction wherein there are provided “m” of reaction zones in number where m is an integer of from 2 to 10. In this case, the reaction zones are arranged in series and such that a reaction temperature of each reaction zone is independently controllable.
摘要翻译：本发明涉及一种制备由通式C5ClBF8-B表示的第一全卤代环戊烯的方法，其中B为0-7的整数。该方法包括以下步骤：（a）通过氟化氢将第二全卤代环戊烯氟化在氟化催化剂存在下的气相。第二全卤代环戊烯由通式C5ClAF8-A表示，其中A为1至8的整数，A不小于B.使用该方法，将第一全卤代环戊烯（例如1,2-二氯-3 ，3,4,4,5,5-六氟环戊烯，另一种氯氟化环戊烯或八氟环戊烯）可以连续容易地制备，例如由可以容易获得的六氯环戊二烯氯化获得的八氯环戊烯。因此，上述方法作为工业规模生产方法是非常有用的。在第一全卤代环戊烯是八氟环戊烯的情况下，该方法还可以包括以下步骤：（b）以与步骤（a）不同的方式氟化步骤（a）的反应产物，从而将所述步骤（a）的反应产物进入八氟戊烯。步骤（a）可以通过多步反应进行，其中m为2〜10的整数的“m”个反应区。在这种情况下，反应区串联排列，使得每个反应区的反应温度是独立可控的。

3. 发明申请

US20070191639A1 Optically active 1-Aryl-2-fluoro-substituted ethylamine and method for producing same 有权
标题翻译：光活性1-芳基-2-氟取代的乙胺及其制备方法
公开(公告)号：US20070191639A1
公开(公告)日：2007-08-16
申请号：US10591669
申请日：2005-02-21
申请人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Katsuhide Suto , Koji Ueda
发明人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Katsuhide Suto , Koji Ueda
IPC分类号： C07C209/26
CPC分类号： C07C251/24 , C07C209/52 , C07C209/62 , C07C211/29 , C07C249/02
摘要： The present invention relates to a method of producing an optically active 1-aryl-2-fluoro-substituted ethylamine compound of the formula [2] or a salt thereof by hydrogenolysis of an optically active secondary amine compound of the formula [1] or a salt thereof in the presence of a transition metal catalyst of Group VIII [Chem. 59] [where Ar represents an aryl group; n represents an integer of 1 or 2; and * represents an asymmetric carbon] [Chem. 60] [where Ar represents an aryl group; n represents an integer of 1 or 2; and * represents an asymmetric carbon].
摘要翻译：本发明涉及通过氢解式[1]的光学活性仲胺化合物或式[1]的光学活性的1-芳基-2-氟取代的乙胺化合物或其盐，其盐在第VIII族的过渡金属催化剂存在下[Chem。 59]其中Ar表示芳基; n表示1或2的整数; 和*表示不对称碳] 60] [其中Ar表示芳基; n表示1或2的整数，和*表示不对称碳]。

4. 发明授权

US07393979B2 Process for producing optically active 1-alkyl-substituted 2,2,2-trifluoroethylamine 有权
标题翻译：光学活性1-烷基取代的2,2,2-三氟乙胺的制备方法
公开(公告)号：US07393979B2
公开(公告)日：2008-07-01
申请号：US10560251
申请日：2004-06-08
申请人： Akihiro Ishii , Yokusu Kuriyama , Manabu Yasumoto , Masatomi Kanai , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
发明人： Akihiro Ishii , Yokusu Kuriyama , Manabu Yasumoto , Masatomi Kanai , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
IPC分类号： C07C209/62 , C07C211/05
CPC分类号： C07C209/62 , C07B2200/07 , C07C209/52 , C07C211/15 , C07C249/02 , C07C251/08
摘要： The present invention relates to a process for producing an optically active 1-alkyl-substituted 2,2,2-trifluoroethylamine, which is an important intermediate of medicines and agricultural chemicals, and which is represented by the formula [3] [in the formula R represents a lower alkyl group of a carbon and * represents an asymmetric carbon], or its salt by subjecting an optically active imine represented by the formula [1] to an asymmetric reduction under hydrogen atmosphere using a metal catalyst of Group VIII to convert it into an optically active secondary amine represented by the formula [2] and then by subjecting the secondary amine or its salt to hydrogenolysis.[Chem. 23]
摘要翻译：本发明涉及一种制备光学活性的1-烷基取代的2,2,2-三氟乙基胺的方法，它是药物和农药的重要中间体，由式[3] [式 R表示碳的低级烷基，*表示不对称碳]或其盐，通过使用式（1）表示的光学活性亚胺在氢气氛下使用VIII族金属催化剂进行不对称还原，将其转化为由式[2]表示的光学活性仲胺，然后通过使仲胺或其盐进行氢解。 [Chem。 23]

5. 发明授权

US07388094B2 Processing for producing 2′-deoxy-2′-fluorouridine 失效
标题翻译： 2'-脱氧-2'-氟尿苷的制备方法
公开(公告)号：US07388094B2
公开(公告)日：2008-06-17
申请号：US10552463
申请日：2004-04-09
申请人： Akihiro Ishii , Takashi Ootsuka , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
发明人： Akihiro Ishii , Takashi Ootsuka , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
IPC分类号： C07H19/073
CPC分类号： C07H19/067 , Y02P20/55
摘要： 1-β-D-Arabinofuranosyluracil in 3′,5′-hydroxyl-protected form is reacted with a trifluoromethanesulfonylating agent in the presence of an organic base to convert it into a 2′-triflate form, and then it is reacted with a fluorinating agent containing “a salt or complex formed by an organic base and hydrofluoric acid” to produce 2′-deoxy-2′-fluorouridine in 3′,5′-hydroxyl-protected form. A deprotecting agent is further caused to act thereon to obtain 2′-deoxy-2′-fluorouridine. The 2′-deoxy-2′-fluorouridine obtained can efficiently be purified by temporarily converting it into a 3′,5′-diacetyl form, recrystallizing the 3′,5′-diacetyl form, and then deacetylating it. Thus, high-purity 2′-deoxy-2′-fluorouridine can be produced.
摘要翻译： 3'，5'-羟基保护形式的1-β-D-阿拉伯呋喃糖尿嘧啶在有机碱的存在下与三氟甲磺酰化剂反应，将其转化为2,3-三氟甲磺酸酯形式，然后与氟化含有“由有机碱和氢氟酸形成的盐或络合物”的试剂以产生3'，5'-羟基保护形式的2'-脱氧-2'-氟尿苷。进一步使脱保护剂作用于其上，得到2'-脱氧-2'-氟尿苷。所得到的2'-脱氧-2'-氟尿苷可以通过暂时转化为3'，5'-二乙酰基形式，重结晶3'，5'-二乙酰基形式，然后脱乙酰化而有效地纯化。因此，可以制备高纯度2'-脱氧-2'-氟尿苷。

6. 发明授权

US07186865B2 Optically active 1-(fluoro-, trifluoromethyl-or trifluoromethoxy-substituted phenyl) alkylamine n-monoalkyl derivatives and process for producing same 有权
标题翻译：光学活性1-（氟 - ，三氟甲基 - 或三氟甲氧基取代的苯基）烷基胺n-单烷基衍生物及其制备方法
公开(公告)号：US07186865B2
公开(公告)日：2007-03-06
申请号：US10476650
申请日：2003-09-05
申请人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
发明人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
IPC分类号： C07C211/00
CPC分类号： C07C209/62 , C07B2200/07 , C07C211/29 , C07C217/58 , C07C249/02 , C07C251/24
摘要： An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R2—X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1 and R2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.
摘要翻译：由式4表示的光学活性1-（氟 - ，三氟甲基 - 或三氟甲氧基取代的苯基）烷基胺N-单烷基衍生物通过以下方法制备，该方法包括：（a）使由式1表示的光学活性仲胺与式烷基化剂R 2 -X在碱的存在下，由此将仲胺转化成由式3表示的光学活性叔胺; 和（b）使叔胺进行氢解，从而制备N-单烷基衍生物，其中R表示氟原子，三氟甲基或三氟甲氧基，n表示1〜5的整数，R 1 独立地表示碳原子数1〜6的烷基，Me表示甲基，Ar表示苯基或1-或2-萘基， *表示手性碳，X表示离去基团。

7. 发明申请

US20060247433A1 Process for producing 2'-deoxy-2'-fluorouridine 失效
标题翻译：制备2'-脱氧-2'-氟尿苷的方法
公开(公告)号：US20060247433A1
公开(公告)日：2006-11-02
申请号：US10552463
申请日：2004-04-09
申请人： Akihiro Ishii , Takashi Ootsuka , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
发明人： Akihiro Ishii , Takashi Ootsuka , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Koji Ueda
IPC分类号： C07H19/12
CPC分类号： C07H19/067 , Y02P20/55
摘要： 1-β-D-Arabinofuranosyluracil in 3′,5′-hydroxyl-protected form is reacted with a trifluoromethanesulfonylating agent in the presence of an organic base to convert it into a 2′-triflate form, and then it is reacted with a fluorinating agent containing “a salt or complex formed by an organic base and hydrofluoric acid” to produce 2′-deoxy-2′-fluorouridine in 3′,5′-hydroxyl-protected form. A deprotecting agent is further caused to act thereon to obtain 2′-deoxy-2′-fluorouridine. The 2′-deoxy-2′-fluorouridine obtained can efficiently be purified by temporarily converting it into a 3′,5′-diacetyl form, recrystallizing the 3′,5′-diacetyl form, and then deacetylating it. Thus, high-purity 2′-deoxy-2′-fluorouridine can be produced.
摘要翻译： 3'，5'-羟基保护形式的1-β-D-阿拉伯呋喃糖尿嘧啶在有机碱的存在下与三氟甲磺酰化剂反应，将其转化为2,3-三氟甲磺酸酯形式，然后与氟化含有“由有机碱和氢氟酸形成的盐或络合物”的试剂以产生3'，5'-羟基保护形式的2'-脱氧-2'-氟尿苷。进一步使脱保护剂作用于其上，得到2'-脱氧-2'-氟尿苷。所得到的2'-脱氧-2'-氟尿苷可以通过暂时转化为3'，5'-二乙酰基形式，重结晶3'，5'-二乙酰基形式，然后脱乙酰化而有效地纯化。因此，可以制备高纯度2'-脱氧-2'-氟尿苷。

8. 发明申请

US20060128976A1 Process for producing trifluoromethyl-substituted 2-alkoxyacetophenone derivatives 失效
标题翻译：制备三氟甲基取代的2-烷氧基苯乙酮衍生物的方法
公开(公告)号：US20060128976A1
公开(公告)日：2006-06-15
申请号：US11347390
申请日：2006-02-06
申请人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
发明人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
IPC分类号： C07D317/00 , C07D309/00
CPC分类号： C07D317/22 , C07C43/315 , C07C45/57 , C07C45/59 , C07C45/60 , C07C49/84 , C07D317/16 , C07C49/80
摘要： A process for producing a brominated acetal (represented by the formula 3) includes (a) brominating a trifluoromethyl-substituted acetophenone by Br2 in the presence of an alkylene diol. It is optional to produce a trifluoromethyl-substituted 2-alkoxyacetophenone derivative (represented by the formula 9) by (b) reacting the brominated acetal with a metal alkoxide, thereby converting the brominated acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove an acetal group from the ether, thereby producing the 2-alkoxyacetophenone derivative. Alternatively, the 2-alkoxyacetophenone can be produced by (a) reacting a trifluoromethyl-substituted phenacyl halide with an acetalization agent, thereby converting the phenacyl halide into an acetal; (b) reacting the acetal with a metal alkoxide, thereby converting the acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove the acetal group from the ether.
摘要翻译：制备溴化缩醛的方法（由式3表示）包括（a）在亚烷基二醇的存在下用Br 2 H 3溴化三氟甲基取代的苯乙酮。（b）使溴化缩醛与金属醇盐反应，从而将溴化缩醛转化成醚，任选地制备三氟甲基取代的2-烷氧基苯乙酮衍生物（由式9表示）和（c）在酸催化剂的存在下水解醚，以从乙醚中除去缩醛基，从而制备2-烷氧基苯乙酮衍生物。或者，2-烷氧基苯乙酮可以通过以下方法制备：（a）使三氟甲基取代的苯甲酰甲基卤化物与缩醛化剂反应，从而将苯甲酰甲酰卤转化成缩醛; （b）使缩醛与金属醇盐反应，从而将缩醛转化成醚; 和（c）在酸催化剂存在下水解该醚，以从乙醚中除去缩醛基。

9. 发明授权

US07053248B2 Process for producing trifluoromethyl- substituted 2- alkoxyacetophenone derivatives 有权
标题翻译：制备三氟甲基取代的2-烷氧基苯乙酮衍生物的方法
公开(公告)号：US07053248B2
公开(公告)日：2006-05-30
申请号：US10473399
申请日：2003-08-08
申请人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
发明人： Akihiro Ishii , Masatomi Kanai , Yokusu Kuriyama , Manabu Yasumoto , Kenjin Inomiya , Takashi Ootsuka , Koji Ueda
IPC分类号： C07C45/61
CPC分类号： C07D317/22 , C07C43/315 , C07C45/57 , C07C45/59 , C07C45/60 , C07C49/84 , C07D317/16 , C07C49/80
摘要： A process for producing a brominated acetal (represented by the formula 3) includes (a) brominating a trifluoromethyl-substituted acetophenone by Br2 in the presence of an alkylene diol. It is optional to produce a trifluoromethyl-substituted 2-alkoxyacetophenone derivative (represented by the formula 9) by (b) reacting the brominated acetal with a metal alkoxide, thereby converting the brominated acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove an acetal group from the ether, thereby producing the 2-alkoxyacetophenone derivative. Alternatively, the 2-alkoxyacetophenone can be produced by (a) reacting a trifluoromethyl-substituted phenacyl halide with an acetalization agent, thereby converting the phenacyl halide into an acetal; (b) reacting the acetal with a metal alkoxide, thereby converting the acetal into an ether; and (c) hydrolyzing the ether in the presence of an acid catalyst to remove the acetal group from the ether.
摘要翻译：制备溴化缩醛的方法（由式3表示）包括（a）在亚烷基二醇的存在下用Br 2 H 3溴化三氟甲基取代的苯乙酮。（b）使溴化缩醛与金属醇盐反应，从而将溴化缩醛转化成醚，任选地制备三氟甲基取代的2-烷氧基苯乙酮衍生物（由式9表示）和（c）在酸催化剂的存在下水解醚，以从乙醚中除去缩醛基，从而制备2-烷氧基苯乙酮衍生物。或者，2-烷氧基苯乙酮可以通过以下方法制备：（a）使三氟甲基取代的苯甲酰甲基卤化物与缩醛化剂反应，从而将苯甲酰甲酰卤转化成缩醛; （b）使缩醛与金属醇盐反应，从而将缩醛转化成醚; 和（c）在酸催化剂存在下水解该醚，以从乙醚中除去缩醛基。

10. 发明授权

US5905174A Method for producing 3,3-dichloro-1,1,1-triflouroacetone 失效
标题翻译： 3,3-二氯-1,1,1-三氟丙酮的制备方法
公开(公告)号：US5905174A
公开(公告)日：1999-05-18
申请号：US60180
申请日：1998-04-15
申请人： Masatomi Kanai , Takashi Sakaya , Mineo Watanabe , Yoshihiko Goto , Ryo Nadano
发明人： Masatomi Kanai , Takashi Sakaya , Mineo Watanabe , Yoshihiko Goto , Ryo Nadano
IPC分类号： B01J27/08 , B01J27/125 , C07C45/63 , C07C45/82 , C07C45/83 , C07C45/00
CPC分类号： C07C45/82 , B01J27/08 , B01J27/125 , C07C45/63 , C07C45/83
摘要： The invention relates to a method for producing 3,3-dichloro-1,1,1-trifluoroacetone. This method includes a step of fluorinating pentachloroacetone by hydrogen fluoride in the presence of a fluorination catalyst. This fluorination may be conducted in a liquid phase in the presence of an antimony compound as the fluorination catalyst. Alternatively, the fluorination may be conducted in a gas phase in the presence of a fluorination catalyst which may be a fluorinated alumina or at least one compound of at least one metal selected from Al, Cr, Mn, Ni, and Co. The method is suited to an industrial scale production of 3,3-dichloro-1,1,1-trifluoroacetone. The invention further relates to another method for producing 3,3-dichloro-1,1,1-trifluoroacetone. This method includes a step of purifying a crude 3,3-dichloro-1,1,1-trifluoroacetone by a distillation in the presence of water, thereby to produce 3,3-dichloro-1,1,1-trifluoroacetone which is substantially free of organic matters other than 3,3-dichloro-1,1,1-trifluoroacetone. This crude 3,3-dichloro-1,1,1-trifluoroacetone may be the reaction products of the fluorination of pentachloroacetone in a gas phase. Due to the provision of the another method, 3,3-dichloro-1,1,1-trifluoroacetone can be produced with high yield.
摘要翻译：本发明涉及一种生产3,3-二氯-1,1,1-三氟丙酮的方法。该方法包括在氟化催化剂存在下用氟化氢氟化五氯丙酮的步骤。该氟化可以在作为氟化催化剂的锑化合物的存在下在液相中进行。或者，氟化可以在可以是氟化氧化铝或至少一种选自Al，Cr，Mn，Ni和Co的至少一种金属的化合物的氟化催化剂的存在下在气相中进行。该方法是适合工业规模生产3,3-二氯-1,1,1-三氟丙酮。本发明还涉及制备3,3-二氯-1,1,1-三氟丙酮的另一种方法。该方法包括在水存在下通过蒸馏纯化粗制3,3-二氯-1,1,1-三氟丙酮的步骤，从而产生3,3-二氯-1,1,1-三氟丙酮，其基本上不含3,3-二氯-1,1,1-三氟丙酮以外的有机物。该粗的3,3-二氯-1,1,1-三氟丙酮可以是五氯丙酮在气相中氟化的反应产物。由于提供另一种方法，可以高产率制备3,3-二氯-1,1,1-三氟丙酮。

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