公开(公告)号：US5777103A

公开(公告)日：1998-07-07

申请号：US808270

申请日：1997-02-28

申请人： Takaji Matsumoto ,  Toshiyuki Murayama ,  Shigeru Mitsuhashi ,  Takashi Miura

发明人： Takaji Matsumoto ,  Toshiyuki Murayama ,  Shigeru Mitsuhashi ,  Takashi Miura

IPC分类号： C07D205/08 ,  C07F7/18 ,  C07B49/00

CPC分类号： C07F7/186 ,  C07D205/08 ,  Y02P20/55

摘要： A process for producing cyclohexylazetidinone expressed by the formula(IV) comprises condensing the magnesium enolate compound expressed by the formula (II) with acyloxyazetidinone expressed by the formula (III), wherein Me is a methyl group; R.sup.1 is a hydroxyl-protecting group, R.sup.2 is an acyl group, and X is a halogen atom. ##STR1##

摘要翻译： 由式（IV）表示的环己基氮杂环丁酮的制备方法包括将由式（II）表示的烯醇镁化合物与由式（III）表示的酰氧基氮杂环丁酮缩合，其中Me为甲基; R1是羟基保护基，R2是酰基，X是卤素原子。 （IMA）>（IV）

公开(公告)号：US5756863A

公开(公告)日：1998-05-26

申请号：US730021

申请日：1996-10-11

申请人： Toshiyuki Murayama ,  Takaji Matsumoto ,  Takashi Miura

发明人： Toshiyuki Murayama ,  Takaji Matsumoto ,  Takashi Miura

IPC分类号： B01J31/22 ,  C07B61/00 ,  C07C29/145 ,  C07C35/08 ,  C07C41/26 ,  C07C43/196

CPC分类号： C07C41/26 ,  C07C29/145 ,  C07B2200/07 ,  C07C2101/14

摘要： A process for producing an optically active cyclohexanol derivative represented by formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, or a protected hydroxyl group, comprising asymmetrically hydrogenating a cyclohexanone derivative in the presence of a catalyst system composed of a transition metal compound (e.g., transition metal complex), a base (e.g., KOH), and a nitrogen compound (e.g., an amine compound).

摘要翻译： 制备由式（I）表示的光学活性环己醇衍生物的方法：其中R 1表示具有1至4个碳原子的烷基，羟基或被保护的羟基，包括不对称地氢化环己酮 在由过渡金属化合物（例如过渡金属络合物），碱（例如KOH）和氮化合物（例如胺化合物）组成的催化剂体系存在下的衍生物。

公开(公告)号：US06340751B1

公开(公告)日：2002-01-22

申请号：US09357153

申请日：1999-07-19

申请人： Takao Saito ,  Toshiyuki Murayama ,  Takaji Matsumoto ,  Takashi Miura

发明人： Takao Saito ,  Toshiyuki Murayama ,  Takaji Matsumoto ,  Takashi Miura

IPC分类号： C07F718

CPC分类号： C07D413/06 ,  C07D205/08 ,  Y02P20/55

摘要： Disclosed is a process for the preparation of a 4-substituted azetidinone derivative, which comprises reacting an azetidinone derivative and an amide compound in the presence of a magnesium compound such as those represented by the following formulas (II): and (IV): represented by the following formula (III): MgR5R6  (III) wherein R5 represents a C1-12 alkyl group, a C2-5 alkenyl group, a 5- to 8-membered alicyclic group which may be substituted by a lower C1-4 alkyl group, a phenyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom or a benzyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom, and R6 represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, an acetoxy group which may be substituted by a halogen atom or a cyano group or an OR7 group (R7 representing a lower C1-4 alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group). The process provides an industrially excellent process for the preparation of a 4-substituted azetidinone derivative which permits the selective preparation of an intermediate for the synthesis of a carbapenem antibacterial agent having a desired 1-&bgr;′ configuration.

摘要翻译： 公开了制备4-取代的氮杂环丁酮衍生物的方法，该方法包括在镁化合物如下式（II）和（IV）所示的那些镁化合物存在下使氮杂环丁酮衍生物与酰胺化合物反应：代表 通过下式（III）表示：其中R5表示C1-12烷基，C2-5烯基，可被低级C1-4烷基取代的5至8元脂环基，苯基 可以被低级C 1-4烷基，低级C 1-4烷氧基或卤素原子取代的苯基，或可以被低级C 1-4烷基取代的苄基，低级C 1-4烷氧基或 卤原子，R6表示卤原子，甲磺酰氧基，苯磺酰氧基，对甲苯磺酰氧基，三氟甲磺酰氧基，可被卤素原子或氰基取代的乙酰氧基或OR7基（R7表示 低级C 1-4烷基，取代的o R未取代的苯基或取代或未取代的苄基）。 该方法提供了制备4-取代的氮杂环丁酮衍生物的工业上优异的方法，其允许选择性制备用于合成具有所需1-β'构型的碳青霉烯类抗菌剂的中间体。

公开(公告)号：US5712388A

公开(公告)日：1998-01-27

申请号：US648516

申请日：1996-05-13

申请人： Takaji Matsumoto ,  Toshiyuki Murayama ,  Takashi Miura

发明人： Takaji Matsumoto ,  Toshiyuki Murayama ,  Takashi Miura

IPC分类号： C07D205/08 ,  C07C229/22 ,  C07F7/18

CPC分类号： C07F7/1852 ,  C07C229/22 ,  C07F7/188 ,  C07F7/1892

摘要： To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.

摘要翻译： 为了制备化合物（1'R，3S）-3-（1'-三取代的甲硅烷氧基乙基）氮杂环丁烷-2-酮，将（2S，3R）-2-氨基甲基-3-羟基丁酸与醇反应 存在至少一种选自亚硫酰氯，氯化氢和对甲苯磺酸的化合物，从而得到相应酯的盐。 在金属催化剂的存在下，使盐与三取代的硅烷反应，从而保护酯的羟基，然后与碱反应，从而得到（2S，3R）-2-氨基甲基-3- （三取代甲硅烷氧基）丁酸。 随后，在格氏试剂或金属酰胺存在下，将酯转化成内酰胺，从而得到（1'R，3S）-3-（1'-三取代的甲硅烷氧基乙基）氮杂环丁-2-酮。 该化合物为制备β-内酰胺型抗微生物剂如碳青霉烯类药物提供了有用的基础。

公开(公告)号：US06608214B2

公开(公告)日：2003-08-19

申请号：US10199136

申请日：2002-07-19

申请人： Tsukasa Sotoguchi ,  Takaji Matsumoto ,  Motonobu Takenaka ,  Takashi Miura

发明人： Tsukasa Sotoguchi ,  Takaji Matsumoto ,  Motonobu Takenaka ,  Takashi Miura

IPC分类号： C07D30733

CPC分类号： C07D307/33 ,  C07B2200/07 ,  C07C67/31 ,  Y02P20/55 ,  C07C69/734

摘要： This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

摘要翻译： 本发明提供了一种在短时间内制备光学活性3-羟基-γ-丁内酯的新方法，其经济性和效率都优异，在工业上适用于便宜且易于获得的试剂和易于处理的试剂。 本发明涉及一种由式I表示的光学活性3-羟基-γ-丁内酯的制备方法：其中符号*表示不对称碳原子，其包括将由式II表示的光学活性的4-取代的氧基-3-羟基丁酸 ：其中R1表示C1-4低级烷基，R2表示通过异相氢化催化剂氢化脱保护的羟基的保护基，符号*具有与上述相同的含义，在非均相加氢催化剂存在下 和酸性物质，然后脱保护并同时闭环。

公开(公告)号：US06403804B1

公开(公告)日：2002-06-11

申请号：US09456950

申请日：1999-12-07

申请人： Kenzo Sumi ,  Takashi Imai ,  Shigeru Mitsuhashi ,  Hideki Nara ,  Takashi Miura

发明人： Kenzo Sumi ,  Takashi Imai ,  Shigeru Mitsuhashi ,  Hideki Nara ,  Takashi Miura

IPC分类号： C07D26304

CPC分类号： C07D263/20 ,  C07D263/22 ,  C07D263/24

摘要： Disclosed is a process for preparing an optically active oxazolidinone derivative comprising allowing hydrazine to react on an optically active ester having a hydroxyl group at the 3-position which is represented by formula (II): wherein R1 represents a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, a methoxymethyl group, a benzyloxymethyl group, a benzyloxycarbonylaminomethyl group which may have a substituent or substituents on the benzene ring thereof, an acylaminomethyl group having 3 to 10 carbon atoms, or an alkyloxycarbonylaminomethyl group having 3 to 6 carbon atoms; R2 and R3, which may be the same or different, each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, an acetylaminomethyl group, a benzoylaminomethyl group, or a benzyl group; and * indicates an asymmetric carbon atom, and subjecting the resulting hydrazide to Curtius rearrangement.

摘要翻译： 公开了一种制备光学活性恶唑烷酮衍生物的方法，其包括使肼在由式（II）表示的3-位具有羟基的光学活性酯上反应：其中R1表示具有1-4个碳原子的低级烷基 碳原子，苯基，甲氧基甲基，苄氧基甲基，苯环上可以具有取代基的苄氧羰基氨基甲基，碳原子数3〜10的酰氨基甲基或碳原子数3〜6的烷氧基羰基氨基甲基 原子 R 2和R 3可以相同或不同，分别表示氢原子，碳原子数1〜4的低级烷基，苯基，乙酰氨基甲基，苯甲酰基氨基甲基或苄基。 和*表示不对称碳原子，并将所得酰肼进行柯氏重排。

公开(公告)号：US5204461A

公开(公告)日：1993-04-20

申请号：US789604

申请日：1991-11-08

申请人： Toshiyuki Murayama ,  Takashi Miura ,  Toyohiko Kobayashi

发明人： Toshiyuki Murayama ,  Takashi Miura ,  Toyohiko Kobayashi

IPC分类号： C07D205/08

CPC分类号： C07D205/08 ,  Y02P20/55

摘要： A process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-one or a derivative thereof represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a hydroxyl-protective group, is disclosed, comprising reacting (2S,3R)-2-aminomethyl-3-hydroxybutyric acid or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, with a sulfenamide represented by formula (III): ##STR3## wherein R.sup.2 represents ##STR4## and R.sup.3 and R.sup.4 each represent a hydrogen atom or a cyclic or acyclic hydrocarbon group, provided that they do not simultaneously represent a hydrogen atom, or R.sup.3 and R.sup.4 are taken together with the adjacent nitrogen atom to form a heterocyclic group, and triphenylphosphine. The reaction yield is high, and the sulfenamide (III) used as a lactamization reagent is cheap and can be recovered after the reaction.

公开(公告)号：US5371214A

公开(公告)日：1994-12-06

申请号：US987779

申请日：1992-12-09

申请人： Takashi Miura ,  Toshiyuki Murayama ,  Akifumi Yoshida ,  Toyohiko Kobayashi

发明人： Takashi Miura ,  Toshiyuki Murayama ,  Akifumi Yoshida ,  Toyohiko Kobayashi

IPC分类号： C07D205/08

CPC分类号： C07D205/08 ,  Y02P20/55

摘要： A 4-(1,1-dialkoxycarbonylalkyl )azetidin-2-one derivative represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and each represents an alkyl group, an alkenyl group, or an aralkyl group, R.sup.3 represents a lower alkyl group, R.sup.4 represents a hydrogen atom or a hydroxyl-protective group, and R.sup.5 represents a hydrogen atom or an amino-protective group, and a process for producing a 4-(1-carboxyalkyl)azetidin-2-one derivative represented by formula (II) useful as an intermediate for 1.beta.-alkylcarbapenem-type antibacterials: ##STR2## wherein R.sup.3 represents a lower alkyl group and R.sup.4 represents a hydrogen atom or a hydroxyl-protective group, which comprises de-esterifying and decarboxylating the derivative represented by formula (I), and in the case where an amino-protective group is present in the derivative of formula (I), eliminating the protective group from the derivative, are disclosed.

摘要翻译： 由式（I）表示的4-（1,1-二烷氧基羰基烷基）氮杂环丁-2-酮衍生物：其中R 1和R 2相同或不同，各自表示烷基，烯基或 芳烷基，R3表示低级烷基，R4表示氢原子或羟基保护基，R5表示氢原子或氨基保护基，以及制备4-（1-羧基烷基）氮杂环丁烷基的方法， 可用作1β-烷基碳青霉烯型抗菌剂的中间体的式（II）表示的2-酮衍生物：其中R3表示低级烷基，R4表示氢原子或羟基保护基，其中 包括使由式（I）表示的衍生物脱酯化和脱羧，并且在式（I）的衍生物中存在氨基保护基的情况下，从衍生物中除去保护基。

公开(公告)号：US5574152A

公开(公告)日：1996-11-12

申请号：US277319

申请日：1994-07-25

申请人： Takashi Miura ,  Toshiyuki Murayama ,  Akifumi Yoshida ,  Toyohiko Kobayashi

发明人： Takashi Miura ,  Toshiyuki Murayama ,  Akifumi Yoshida ,  Toyohiko Kobayashi

IPC分类号： C07D205/08 ,  C07D705/08 ,  C07B37/06

CPC分类号： C07D205/08 ,  Y02P20/55

摘要： A process for preferentially producing a 4-(1-carboxyalkyl) azetidin-2-one derivative represented by formula (II.beta.): ##STR1## wherein R.sup.3 represents a lower alkyl group and R.sup.4 represents a hydrogen atom or a hydroxy-protective group, which involves deesterifying and decarboxylating a 4-(1,1-dialkoxycarbonylalkyl) azetidin-2-one derivative represented by formula (I): ##STR2## wherein R.sup.1 and R.sup.2 are identical or different and each represents an alkyl group, an alkenyl group, or an aralkyl group, R.sup.3 and R.sup.4 each has the meaning as defined above, and R.sup.5 represents an amino-protective group, and after that, eliminating the amino-protective group from the derivative, where the 4-(1-carboxyalkyl)azetidin-2-one derivative of formula (II.beta.) is present in an amount of at least 61% by mol of all 4-(1-carboxyalkyl)azetidin-2-one derivatives produced.

摘要翻译： 优选制备由式（IIβ）表示的4-（1-羧基烷基）氮杂环丁-2-酮衍生物的方法：其中R 3表示低级烷基，R 4表示氢原子或羟基 保护基，其包括使由式（I）表示的4-（1,1-二烷氧基羰基烷基）氮杂环丁-2-酮衍生物脱酯和脱羧基：其中R 1和R 2相同或不同，并且各自表示 烷基，烯基或芳烷基，R 3和R 4各自具有如上所定义的含义，R 5表示氨基保护基，之后，从衍生物中除去氨基保护基， 式（IIβ）的（1-羧基烷基）氮杂环丁-2-酮衍生物的存在量为所产生的所有4-（1-羧基烷基）氮杂环丁烷-2-酮衍生物的至少61摩尔％。

公开(公告)号：US08312162B2

公开(公告)日：2012-11-13

申请号：US12869153

申请日：2010-08-26

申请人： Tsuyoshi Honma ,  Akihiko Kinoshita ,  Hiroyuki Chiba ,  Takashi Miura

发明人： Tsuyoshi Honma ,  Akihiko Kinoshita ,  Hiroyuki Chiba ,  Takashi Miura

IPC分类号： G06F15/16

CPC分类号： H04L29/08729 ,  H04L67/2819 ,  H04N21/42661 ,  H04N21/44004 ,  H04N21/44209 ,  H04N21/458 ,  H04N21/8456

摘要： There is provided an information processing apparatus including a communication unit which communicates with a distribution server that contains content data for streaming delivery, a buffer unit which temporarily stores stream data obtained from the distribution server, a storage unit which stores an inserting content, a reproduction unit which reproduces the content inserted by the storage unit, and a control unit which measures a bandwidth of the network, determines whether it is possible to reproduce until the end of a next chapter defined by a chapter point set in the content based on a buffer volume of the buffer unit and the bandwidth, and when determined it is impossible, switches the content to be produced by the reproduction unit to the inserting content.

摘要翻译： 提供了一种信息处理设备，包括：通信单元，其与包含用于流传送的内容数据的分发服务器进行通信;临时存储从分发服务器获得的流数据的缓冲单元，存储插入内容的存储单元， 再现由存储单元插入的内容的单元和测量网络带宽的控制单元，确定是否可以再现直到由基于缓冲器的内容中设置的章节点定义的下一章节的结尾 缓冲单元的体积和带宽，并且当确定不可能时，将由再现单元产生的内容切换到插入内容。