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21. 发明专利

JPH09176130A OPTICALLY ACTIVE 4,5-DIPHENYL-2-IMIDAZOLIDINONE DERIVATIVE 失效
公开(公告)号：JPH09176130A
公开(公告)日：1997-07-08
申请号：JP34100995
申请日：1995-12-27
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , FUKUDA KEIKO
IPC分类号： C07D233/70 , C07F9/6506
摘要： PROBLEM TO BE SOLVED: To obtain 4,5-diphenyl-2-imidazolidinone derivative useful as a reagent for asymmetric synthesis to be used for selectively producing optically active compound. SOLUTION: This new compound is expressed by formula I (R is an alkyl; R is a dialkoxyphosphoryl or halogen; * denotes a site bearing an asymmetric carbon atom), e.g. (4S,5S)-1-chloroacetyl-4,5-diphenyl-3-methyl-2-imidazolidinone. The compound of formula I is obtained by the following process: starting from optically active 1,2-diphenyl-1,2-ethanediamine of formula III, a 4,5-diphenyl-1- alkyl-2-imidazolidinone of formula III is produced through four processes, and is then reacted with a halogenocarboxylic acid halogenide of formula IV (X and X are each a halogen).

22. 发明专利

JPH0827132A PRODUCTION OF 5-OXAZOLONES 失效
公开(公告)号：JPH0827132A
公开(公告)日：1996-01-30
申请号：JP15841494
申请日：1994-07-11
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , HOSOGAI AKIHIKO
IPC分类号： C07D263/42
摘要： PURPOSE:To industrially advantageously obtain compounds, useful as a medicine having physiological activities such as anticancer actions under nearly neutral mild conditions by reacting N-acyl-alpha-amino acids with a haloiminium salt as a dehydrating agent. CONSTITUTION:This method for producing 5-oxazolones of formula III (R and R are each H or an organic group) is to react (A) N-acyl-alpha-amino acids of formula I with (B) a haloiminium salt of formula II [R and R are each a lower alkyl; X is a halogen; (n) is 2 or 3] (preferred example: 2-chloro-1,3- dimethylimidazolium chloride) as a dehydrating agent. Furthermore, a mixture of N-acylglycines of the formula R -CONH-CH2COOH (R is H or an organic group) with aldehydes of the formula R -CHO (R is H or an organic group) may be used in place of the component (A). 2-(4-Methylphenyl)-4-methyl-5- oxazolone is cited as an example of the compound of formula III.

23. 发明专利

JPH0789924A PRODUCTION OF CARBAMATE COMPOUNDS 失效
公开(公告)号：JPH0789924A
公开(公告)日：1995-04-04
申请号：JP23447193
申请日：1993-09-21
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , HOSOGAI AKIHIKO
IPC分类号： C07D233/28 , C07C271/12 , C07C327/22 , C07D233/34 , C07D239/08
摘要： PURPOSE:To industrially and advantageously obtain the compound under almost neutral and mild conditions by reacting a hydroxamic acid compound with a specific haloiminium salt in the presence of a base and subsequently reacting the reaction product with an alcohol or thiol. CONSTITUTION:A hydroxamic acid compound of formula 2 (R is organic group) is reacted with a haloiminium salt of formula 1 (R , R are lower alkyl; X is halogen; n is 2-3) in the presence of a base of formula 4 and subsequently with an alcohol or thiol of formula: R YH (R is organic group; Y is O, S) to obtain a carbamate compound of formula 5. The carbamate compound is utilized in the fields of medicines, fibers and plastic industries, etc., and furthermore useful as a solvent.

24. 发明专利

JPH0597714A PRODUCTION OF NITRILES 失效
公开(公告)号：JPH0597714A
公开(公告)日：1993-04-20
申请号：JP25549091
申请日：1991-10-02
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , SAITO MASAAKI
IPC分类号： C07D233/32 , C07B43/08 , C07C253/00 , C07C255/03 , C07C255/32 , C07C255/50 , C07C255/54
摘要： PURPOSE:To produce nitriles from aldehydoximes under nearly neutral and mild conditions in high efficiency by using a haloiminium salt as a dehydration agent. CONSTITUTION:A nitrile (e.g. 3-nitrobenzonitrile) is produced by using a compound of formula (R and R are lower alkyl; X is halogen; (n) is 2 or 3), e.g. 2-chloro-1,3-dimethylimidazolinium chloride or 2-chloro-1,3-dimethyl-3,4,5,6- tetrahydropyrimidium chloride as a dehydration agent, adding about 1mol of the compound of formula and about 2mol of a base (e.g. pyridine or triethylamine) to 1mol of an aldehydoxime compound (e.g. 3- nitrobenzaldehydoxime) and making the components to react with each other at room temperature or thereabout.

25. 发明专利

JPH0525155A PRODUCTION OF CARBOXYLIC ACID ANHYDRIDE 失效
公开(公告)号：JPH0525155A
公开(公告)日：1993-02-02
申请号：JP18237191
申请日：1991-07-23
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , SAITO MASAAKI
IPC分类号： C07D233/28 , C07B41/10 , C07C51/56 , C07C53/124 , C07C57/03 , C07C57/30 , C07C229/36 , C07D239/08 , C07D307/60
摘要： PURPOSE:To obtain the subject compound useful as a synthetic intermediate for pharmaceuticals and agricultural chemicals under nearly neutral and mild condition in high efficiency by reacting a carboxylic acid with a haloiminium salt as a condensation agent. CONSTITUTION:The objective compound can be produced by reacting a carboxylic acid with a condensation agent consisting of a haloiminium salt of formula I (R and R are lower alkyl; X is halogen; (n) is 2 or 3) in the presence of a base (e.g. triethylamine) at about room temperature optionally using a solvent (e.g. methylene chloride). The amounts of the haloiminium salt and the base are 1mol and 2mol based on 2mol of the carboxylic acid, respectively. The haloiminium salt (e.g. 2-chloro-1,3-dimethylimidazolinium chloride) is produced by reacting a compound of formula II (an easily available solvent) with a halogenation agent (e.g. oxalyl halogenide).

26. 发明专利

JPH04308547A PRODUCTION OF 3-HALOGENO-2,3-UNSATURATED KETONE 失效
公开(公告)号：JPH04308547A
公开(公告)日：1992-10-30
申请号：JP7162091
申请日：1991-04-04
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , SOEDA YUKIO , SAITO MASAAKI , SUZUKI SHIGEKO
IPC分类号： C07C45/63 , C07C49/227 , C07C49/235 , C07C49/255 , C07C49/567
摘要： PURPOSE:To efficiently obtain a 3-halogeno-2,3-unsaturated ketone useful as an intermediate for medicines and agricultural chemicals in high yield under nearly neutral mild conditions. CONSTITUTION:1,3-Drones expressed by formula 2 (R and R are organic group or R and R together may form a cyclic form) are made to react with a haloiminium salt expressed by formula 1 [R and R are lower alkyl; X is halogen; (n) is 2 or 3], preferably 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethyl-3,4,5,6-tetrahydropyrimidinium chloride, etc., to advantageously afford the objective 3-halogeno-2,3-unsaturated ketone expressed by formula 4.

27. 发明专利

JPH04308538A HALOGENATION 失效
公开(公告)号：JPH04308538A
公开(公告)日：1992-10-30
申请号：JP7161991
申请日：1991-04-04
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , SOEDA YUKIO , SAITO MASAAKI , TAKASHI YOSHIHO
IPC分类号： C07C17/16 , C07C19/01
摘要： PURPOSE:To efficiently halogenate a primary alcohol by a mild condition such as at almost neutral pH and to selectively halogenate only the primary alcohol even in the existence of an impurity such as a secondary alcohol contained in the raw material. CONSTITUTION:In halogenation of a primary alcohol, a haloiminium salt represented by the formula (R and R are lower alkyl; X is halogen; (n) is 2 or 3), preferably 1,3-dimethyl-2-chloro-imidazolium chloride is used as a halogenation agent to advantageously halogenate the primary alcohol in a high yield.

28. 发明专利

JPH025737B2 失效
公开(公告)号：JPH025737B2
公开(公告)日：1990-02-05
申请号：JP20058682
申请日：1982-11-16
申请人： SHIRATORI PHARM
发明人： MUKOYAMA MITSUAKI , ISOBE TOSHIO , KATO MASAATSU , MYAGAKI MITSUHIRO , KOGO SHINSHIRO
IPC分类号： C07C67/08 , B01J31/02 , C07B61/00 , C07C69/025 , C07C69/78 , C07D239/08

29. 发明专利

JPS5993030A ESTERIFICATION 失效
公开(公告)号：JPS5993030A
公开(公告)日：1984-05-29
申请号：JP20058682
申请日：1982-11-16
申请人： SHIRATORI PHARM
发明人： MUKOUYAMA MITSUAKI , ISOBE TOSHIO , KATOU MASAATSU , MIYAGAKI MITSUHIRO , KOUGO SHINSHIROU
IPC分类号： C07C67/08 , B01J31/02 , C07B61/00 , C07C69/025 , C07C69/78 , C07D239/08
摘要： PURPOSE:To obtain an ester in high yield, by reacting an alcohol with a carboxylic acid in the presence of a 1,3-dialkyl-2-halogeno-3,4,5,6-tetrahyropyrimidinium halogenide as a condensation agent. CONSTITUTION:In esterifying an alcohol with a carboxylic acid, a compound shown by the formula (R1 and R2 are lower alkyl; X is halogen atom) is used as a condensation agent at carry out the reaction. In the concrete, 1mol alcohol is blended with 1mol carboxylic acid, 1mol compound shown by the formula, and 2mol base such as pyridine, trithylemine, tributylamine, etc. and reacted at room temperature.

30. 发明专利

JPH10279565A OPTICALLY ACTIVE GUANIDINE DERIVATIVE 失效
公开(公告)号：JPH10279565A
公开(公告)日：1998-10-20
申请号：JP8795397
申请日：1997-04-07
申请人： SHIRATORI PHARM
发明人： ISOBE TOSHIO , FUKUDA KEIKO , TAKASHI YOSHIHO , TAKAHASHI TOMOKO
IPC分类号： C07D233/46 , C07B53/00 , C07C67/035 , C07C69/78 , C07D233/48 , C07D233/50 , C07D401/12
摘要： PROBLEM TO BE SOLVED: To obtain a novel compound that is useful as an asymmetric synthesis reagent for selectively producing an optically active compound in high yield. SOLUTION: This novel compound is represented by formula I (R and R are each an alkyl; R is H, an alkyl, an aryl; * mark means an asymmetric carbon atom), typically-(4S,5S)-1,3-dimethyl-4,5-disphenyl-1-2-(n-propylimino) imidazolidine. The objective compound is prepared, for example, by using optically active 1,2-diphenyl-1,2-ethanediamine as a starting substance to form a 4,5-diphenyl-1,3-dialkyl-2-halogenoimidazolinium halogenide of formula III through 3 steps, followed by the reaction of the resultant imidazolinium halogenide with primary amines.

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