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1. 发明授权

US4914199A Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives 失效
公开(公告)号：US4914199A
公开(公告)日：1990-04-03
申请号：US156873
申请日：1988-02-18
申请人： Isao Sada , Kazunori Kan , Noboru Ueyama , Shingo Matsumoto , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Isao Sada , Kazunori Kan , Noboru Ueyama , Shingo Matsumoto , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07F7/186 , C07D205/08 , Y02P20/55
摘要： A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reactig a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as difined above and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is a lower alkyl group having 1 to 4 carbon atoms or an aralkyl group, with acetic anhydride in the presence of a base and a catalyst selected from the group consisting of an organic strong acid, a mineral acid, a Lewis acid, a halogenated acyl compound having the formula (IV):R.sup.8 --CO--X (IV)wherein R.sup.8 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, a halogenated sulfonyl compound having the formula (V):R.sup.9 --SO.sub.2 --X (V)wherein R.sup.9 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, and a compound having the formula (VI):(R.sup.10).sub.4-n --Si(X').sub.n (VI)wherein R.sup.10 is a lower alkyl group having 1 to 6 carbon atoms or phenyl group, X' is a halogen atom or CF.sub.3 SO.sub.2 O group and n is an integer of 1 to 4. According to the present invention, there can be obtained 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem .beta.-lactam antibiotics, in high yield.

2. 发明授权

US4914200A Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives 失效
标题翻译： 4-乙酰氧基-3-羟乙基氮杂环丁-2-酮衍生物的制备方法
公开(公告)号：US4914200A
公开(公告)日：1990-04-03
申请号：US309935
申请日：1989-02-14
申请人： Kazunori Kan , Noboru Ueyama , Isao Sada , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Kazunori Kan , Noboru Ueyama , Isao Sada , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07D205/08 , C07F7/186 , Y02P20/55
摘要： A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2, R.sup.3 and R.sup.4 are a lower alkyl group having 1 to 6 carbon atoms, phenyl group or an aralkyl group, with acetic anhydride in an organic solvent in the presence of a low concentration of a substituted pyridine. According to the present invention, there can be obtained 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem .beta.-lactam antibiotics.

3. 发明授权

US4791198A Beta-lactam compound and preparation thereof 失效
标题翻译： β-内酰胺化合物及其制备方法
公开(公告)号：US4791198A
公开(公告)日：1988-12-13
申请号：US810
申请日：1987-01-06
申请人： Takehisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
发明人： Takehisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07D205/08 , C07F7/186
摘要： The present invention relates to .beta.-lactam compound having the formula (I): ##STR1## wherein R.sup.1 is a trialkylsilyl group, dimethyl-1,1,2-trimethylpropylsilyl group, acetyl group, benzyloxycarbonyl group, O-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group or t-butyl group, R.sup.2, R.sup.3 and R.sup.4 are a member selected from the group consisting of a lower alkyl group having 1 to 6 carbon atoms, phenyl group and an aralkyl group and a process for preparing the compound which comprises reacting enolsilylethers having the formula (III): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. The .beta.-lactam compound of the present invention is a useful intermediate for preparing carbapenem .beta.-lactam compound.
摘要翻译：本发明涉及具有式（I）的β-内酰胺化合物：其中R1是三烷基甲硅烷基，二甲基-1,1,2-三甲基丙基甲硅烷基，乙酰基，苄氧基羰基，O-硝基苄氧基羰基对硝基苄氧羰基或叔丁基，R2，R3和R4是选自具有1至6个碳原子的低级烷基，苯基和芳烷基的成员，以及制备该化合物的方法包括使具有式（III）的烯醇醚：其中R 1，R 2，R 3和R 4如上所述与式（III）化合物反应，得到产物。本发明的β-内酰胺化合物是制备碳青霉烯类β-内酰胺化合物的有用中间体。

4. 发明授权

US4861877A Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives 失效
标题翻译： 4-乙酰氧基-3-羟乙基氮杂环丁-2-酮衍生物的制备方法
公开(公告)号：US4861877A
公开(公告)日：1989-08-29
申请号：US809
申请日：1987-01-06
申请人： Takehisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
发明人： Takehisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07D205/08 , C07F7/186 , Y02P20/55
摘要： A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as defined above, R.sup.2, R.sup.3 and R.sup.4 are a lower alkyl group having 1 to 6 carbon atoms, phenyl group or an aralkyl group and R is a protective group for N, with acetic anhydride in an organic solvent in the presence of a base, and removing the protective group for N.4-Acetoxy-3-hydroxyethylazetidin-2-one derivatives are useful intermediates for preparing carbapenem .beta.-lactam antibiotics such as thienamycin and penem .alpha.-lactam antibiotics.
摘要翻译：制备具有式（II）的4-乙酰氧基-3-羟乙基氮杂环丁-2-酮衍生物的方法：其中R1是羟基的保护基，其包括使具有式（I）：其中R 1如上定义，其中R 1，R 3和R 4为具有1至6个碳原子的低级烷基，苯基或芳烷基，R为N的保护基在乙酸酐的存在下，在有机溶剂中，在碱的存在下，除去N-（4-乙酰氧基-3-羟乙基氮杂环丁烷-2-酮）衍生物的保护基是制备碳青霉烯类β-内酰胺抗生素如噻吩霉素和青霉素的有用中间体 α-内酰胺抗生素。

5. 发明授权

US5061817A Enolsilyl ether compound 失效
标题翻译： ENOLSILYL醚化合物
公开(公告)号：US5061817A
公开(公告)日：1991-10-29
申请号：US200205
申请日：1988-05-31
申请人： Takeisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
发明人： Takeisa Ohashi , Kazunori Kan , Noboru Ueyama , Isao Sada , Akimasa Miyama , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07D205/08 , C07F7/186
摘要： The present invention relates to .beta.-lactam compound having the formula (I): ##STR1## wherein R.sup.1 is a trialkylsilyl group, dimethyl-1,1,2-trimethylpropylsilyl group, acetyl group, benzyloxycarbonyl group, O-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group or t-butyl group, R.sup.2, R.sup.3 and R.sup.4 are a member selected from the group consisting of a lower alkyl group having 1 to 6 carbon atoms, phenyl group and an aralkyl group and a process for preparing the compound which comprises reacting enolsilylethers having the formula (III): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. The .beta.-lactam compound of the present invention is a useful intermediate for preparing carbapenem .beta.-lactam compound.

6. 发明授权

US4371699A Process for preparation of optically active N-mercaptoalkanoylamino acids 失效
标题翻译：光学活性N-巯基烷酰氨基酸的制备方法
公开(公告)号：US4371699A
公开(公告)日：1983-02-01
申请号：US214780
申请日：1980-12-09
申请人： Takehisa Ohashi , Masami Shimazaki , Kazunori Kan , Hideo Kondo , Kiyoshi Watanabe
发明人： Takehisa Ohashi , Masami Shimazaki , Kazunori Kan , Hideo Kondo , Kiyoshi Watanabe
IPC分类号： C07C51/60 , C07D207/16 , C07D211/60 , C07D277/06 , C07K5/078
CPC分类号： C07K5/06165 , C07C51/60 , C07D207/16 , C07D211/60 , C07D277/06
摘要： A process is disclosed wherein an optically active N-mercaptoalkanoylamino acid is prepared by(1) reacting an optically active .beta.-hydroxyalkanoic acid, with a halogenating reagent to prepare an optically active .beta.-haloalkanoyl halide(2) reacting the .beta.-haloalkanoyl halide with an amino acid to produce an optically active N-.beta.-haloalkanoylamino acid and(3) reacting the N-.beta.-haloalkanoylamino acid with a reagent capable of converting the halogen into the thiol group, the configuration of the formulas (II), (III), (IV), (V), and (VI) being retained in all the optically active compounds throughout the process to prepare the compound represented by formula (I). The product of the present invention, for example, N-(3-mercapto-2-D-methylpropanoyl)-L-proline inhibits the enzymatic conversion of angiotensin I into angiotensin II and therefore is useful for relieving angiotensin-related hypertension.
摘要翻译：公开了一种方法，其中光学活性N-巯基烷酰基氨基酸通过（1）使光学活性β-羟基链烷酸与卤化试剂反应制备光学活性β-卤代烷酰基卤化物（2）使β-卤代烷酰卤与氨基酸以产生光学活性的N-β-卤代烷酰基氨基酸和（3）使N-β-卤代烷酰基氨基酸与能够将卤素转化成硫醇基团的试剂反应，式（II），（III ），（IV），（V）和（VI）在整个过程中保留在所有光学活性化合物中以制备由式（I）表示的化合物。本发明的产物，例如N-（3-巯基-2-D-甲基丙酰基）-L-脯氨酸抑制血管紧张素I的酶促转化为血管紧张素II，因此可用于缓解血管紧张素相关的高血压。

7. 发明授权

US4384139A Process for preparation of an optically active .beta.-mercaptoalkanoic acid 失效
标题翻译：光学活性β-巯基链烷酸的制备方法
公开(公告)号：US4384139A
公开(公告)日：1983-05-17
申请号：US294028
申请日：1981-08-18
申请人： Takehisa Ohashi , Masami Shimazaki , Kenji Nomura , Kazunori Kan , Kiyoshi Watanabe
发明人： Takehisa Ohashi , Masami Shimazaki , Kenji Nomura , Kazunori Kan , Kiyoshi Watanabe
IPC分类号： C07B53/00 , C07B31/00 , C07C53/19 , C07C53/50 , C07C67/00 , C07C313/00 , C07C319/02 , C07C319/14 , C07C323/52 , C07C51/363
CPC分类号： C07C53/50 , C07C323/00 , C07C53/19
摘要： A process is disclosed wherein an optically active .beta.-mercaptoalkanoic acid represented by formula (I): ##STR1## wherein R.sub.1 is lower alkyl having from 1 to 4 carbon atoms, is prepared by(1) reacting an optically active .beta.-hydroxyalkanoic acid represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above, with a halogenating reagent to prepare an optically active .beta.-haloalkanoyl halide represented by formula (III): ##STR3## wherein X is halogen and R.sub.1 is the same as defined above; (2) reacting the .beta.-haloalkanoyl halide with water or an aqueous alkaline solution to prepare an optically active .beta.-haloalkanoic acid represented by formula (IV): ##STR4## wherein X and R.sub.1 are each the same as defined above, or a salt thereof, respectively; and(3) reacting the .beta.-haloalkanoic acid or the salt thereof with a reagent capable of converting the halogen into the thiol group, the configuration of the compound (II), (III), and (IV) being retained throughout the process to prepare the compound represented by formula (I). The product of the present invention is useful as an intermediate for preparation of an antihypertensive agent such as N-(3-mercapto-2-D-methylpropanoyl)-L-proline.
摘要翻译：公开了一种方法，其中式（I）表示的光学活性β-巯基链烷酸：其中R1是具有1-4个碳原子的低级烷基，其通过以下步骤制备：（1）使光学活性β- （II）表示的羟基链烷酸：其中R1与上述定义相同，与卤化试剂反应，制备式（III）表示的光学活性β-卤代烷酰基卤化物：（III）其中X是卤素且R 1与上述定义相同; （2）使β-卤代烷酰基卤化物与水或碱性水溶液反应以制备由式（Ⅳ）表示的光学活性β-卤代链烷酸：其中X和R 1各自与上述定义相同，或其盐; 和（3）使β-卤代烷酸或其盐与能够将卤素转化成硫醇基的试剂反应，化合物（II），（III）和（IV）的构型在整个过程中被保留制备由式（I）表示的化合物。本发明的产品可用作制备抗高血压药如N-（3-巯基-2-D-甲基丙酰基）-L-脯氨酸的中间体。

8. 发明授权

US5003083A Process for preparing optically active cyano compound 失效
标题翻译：光学活性氰基化合物的制备方法
公开(公告)号：US5003083A
公开(公告)日：1991-03-26
申请号：US131230
申请日：1987-12-10
申请人： Kenji Inoue , Mitsunori Matsumoto , Satomi Takahashi , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Kenji Inoue , Mitsunori Matsumoto , Satomi Takahashi , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07B53/00 , B01J31/00 , B01J31/02 , C07B31/00 , C07B43/08 , C07B61/00 , C07C67/00 , C07C253/00 , C07C253/08 , C07C255/16 , C07C255/36 , C07C255/53 , C07D333/24
CPC分类号： C07C255/00 , C07D333/24
摘要： A novel process for effectively preparing an optically active cyanohydrin comprising asymmetrically cyanating an aldehyde by reacting the aldehyde with a cyanating agent in the presence of a titanate of an optically active tartaric acid derivative.

9. 发明授权

US4994600A Process for preparing trans-.beta.-benzoylacrylic acid ester 失效
标题翻译：反式β-苯甲酰丙烯酸酯的制备方法
公开(公告)号：US4994600A
公开(公告)日：1991-02-19
申请号：US869782
申请日：1986-06-02
申请人： Satomi Takahashi , Yasuyoshi Ueda , Yoshifumi Yanagida , Namito Yoshio , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Satomi Takahashi , Yasuyoshi Ueda , Yoshifumi Yanagida , Namito Yoshio , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07C69/738 , B01J27/02 , B01J31/02 , B01J31/14 , C07B61/00 , C07C67/327
CPC分类号： C07C67/327
摘要： A process for preparing trans-.beta.-benzoylacrylic acid ester having the general formula (I): ##STR1## wherein R is alkyl group or aralkyl group, which comprises dealcoholizing .beta.-benzoyl-.alpha.-alkoxypropionic acid ester having the general formula (II): ##STR2## wherein R is above, in the presence of an acid catalyst to give trans-.beta.-benzoylacrylic acid ester having the general formula (I).According to the process of the present invention, the by-product (II) produced in the esterification reaction of .beta.-benzoylacrylic acid (III) with the alcohol (V) by the dehydration reaction can be converted into the compound (I) by the dealcoholization reaction in the presence of the acid catalyst and thus trans-.beta.-benzoylacrylic acid ester (I) with a high purity can be produced in an industrially advantageous manner.
摘要翻译：制备具有通式（I）的反式-β-苯甲酰基丙烯酸酯的方法：其中R是烷基或芳烷基，其包括使具有通式（I）的β-苯甲酰基-α-烷氧基丙酸酯脱醇（II）：其中R在上面，在酸催化剂存在下，得到具有通式（I）的反式-β-苯甲酰基丙烯酸酯。根据本发明的方法，通过脱水反应在β-苯甲酰基丙烯酸（III）与醇（V）的酯化反应中产生的副产物（II）可以通过在酸催化剂存在下脱醇反应，从而可以以工业上有利的方式生产具有高纯度的反式-β-苯甲酰基丙烯酸酯（I）。

10. 发明授权

US4745066A Method for producing optically active glycol derivatives 失效
标题翻译：光学活性二醇衍生物的制备方法
公开(公告)号：US4745066A
公开(公告)日：1988-05-17
申请号：US846766
申请日：1986-04-01
申请人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07B31/00 , C07C67/00 , C07C301/00 , C07C303/22 , C07C309/72 , C12P11/00 , C12P41/00 , C12R1/01 , C12R1/38 , C12R1/66 , C12R1/785 , C12R1/845
CPC分类号： C12P41/004 , C07C309/00 , C12P11/00
摘要： A method for producing optically active glycol derivatives by biochemical resolution which comprises contacting a racemic ester of the general formula 1 ##STR1## (wherein R.sub.1 is an aliphatic hydrocarbon group of 1 to 16 carbon atoms, R.sub.2 is an aliphatic hydrocarbon group of 1 to 8 carbon atoms, and R.sub.3 is an aromatic hydrocarbon group such as phenyl, tolyl or naphtyl) with a microorganism- or animal organ-derived enzyme having stereoselective hydrolytic activity to asymmetrically hydrolyze said racemic ester of general formula 1 to produce an optically active alcohol of general formula 2* ##STR2## (wherein R.sub.1 and R.sub.3 have the same meanings as defined above) and an unreacted ester of the general formula 1* ##STR3## (wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as defined hereinbefore), separating the optically active compounds from each other, hydrolyzing said ester of general formula 1* to give an optically active glycol derivative which is antipodal to the alcohol of general formula 2* and, then, isolating the same optically active glycol derivative. The invention provides a method for producing optically active glycol derivatives, which is expedient, does not require costly reagents and is suited to commercial scale production.
摘要翻译：一种通过生物化学拆分制备光学活性二醇衍生物的方法，其包括使通式1的外消旋酯1（其中R 1是1至16个碳原子的脂族烃基，R 2是1的脂族烃基， 8个碳原子，并且R 3是芳族烃基如苯基，甲苯基或萘基）与具有立体选择性水解活性的微生物或动物器官衍生的酶不对称地水解所述通式1的外消旋酯以产生光学活性的醇通式2 * 2 *（其中R 1和R 3具有与上述相同的含义）和通式1 *未反应的酯*（其中R 1，R 2和R 3具有与定义相同的含义）将光学活性化合物彼此分离，水解所述通式1 *的酯，得到对通式为醇的对映体的光学活性二醇衍生物 2 *，然后分离相同的光学活性二醇衍生物。本发明提供了一种制备光学活性二醇衍生物的方法，这是有利的，不需要昂贵的试剂并且适于商业规模生产。

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