公开(公告)号：JPH06279412A

公开(公告)日：1994-10-04

申请号：JP32759093

申请日：1993-12-24

Applicant: UBE INDUSTRIES

Inventor： ATAKA KIKUO ,  OKU MASAYOSHI ,  YONEDA YASUHIRO ,  KONO MASAHIKO ,  YOKOTA NAOYUKI

IPC: B01J31/14 ,  C07B61/00 ,  C07D215/56

Abstract: PURPOSE:To obtain the subject compound useful as an intermediate for a quinolonecarboxylic acid ester containing an oxygen atom at the 8-position useful as an antimicrobial agent for human and animals by a simple operation in high yield without evolving HF. CONSTITUTION:A 3-monoalkylamino-2-(2,4,5-trifluoro-3-hydroxybenzoyl) acrylic ester derivative of formula I [R is substituent group 1 (alkyl or alkenyl); R is H or substituent group 2 (alkyl, alicyclic group or alkylamino); R is H or substituent group 3 (acetyl, benzyl or alkyl] is subjected to ring formation reaction in the presence of a boric ester to give a 8-hydroxyquinolonecarboxlic acid ester of formula II [R is H, substituent group 4 (alkyl, alicyclic group or alkylamino); R is H, substituent group 5 (alkyl)]. The compound of formula I is obtained by reacting a 3-dialkylamino-2-(2,4,5-trifluoro-3-hydroxybenzoyl) acrylic ester derivative of formula III [R and R are substituent group 6 (alkyl)] with a compound of the formula R -NH.

公开(公告)号：JPH1180076A

公开(公告)日：1999-03-23

申请号：JP33849597

申请日：1997-12-09

Applicant: UBE INDUSTRIES

Inventor： YONEDA YASUHIRO ,  YOKOTA NAOYUKI ,  ATAKA KIKUO

IPC: B01J27/24 ,  C07B61/00 ,  C07C51/377 ,  C07C63/70 ,  C07C69/76

Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a raw material for an important intermediate for the syntheses of quinolone carboxylic acids useful as medicines, especially antibacterial agents and antiviral agents. SOLUTION: A compound of the formula (R is H, a 1-10C alkyl, a 3-10C cycloalkyl or the like), e.g. 2,3,4-trifluoro-5-iodobenzoic acid. The compound of the formula is obtained by reacting 1 mole of 5-amino-2,3,5-trifluorobenzoic acid with 2.5-10 moles of hydroiodic acid in the presence of 0.4-1.2 moles of a cuprous halide of the formula: CuX (X is a halogen) (preferably cuprous iodide) and 1.5-3 moles of an alkali metal nitrite (e.g. sodium nitrite) in 0.1-3 liter of a solvent (e.g. water, methanol, acetone, acetonitrile) preferably at 0-30 deg.C for 0. 5-3 hr.

公开(公告)号：JPH06336480A

公开(公告)日：1994-12-06

申请号：JP12746993

申请日：1993-05-28

Applicant: UBE INDUSTRIES

Inventor： YOSHIDA HIROSHI ,  OMORI KIYOSHI ,  YONEDA YASUHIRO ,  FUSE KENSAKU

IPC: C07B63/00 ,  C07B63/02 ,  C07D401/12

Abstract: PURPOSE:To efficiently purify an intermediate for piperidine useful for production, etc., of a piperidine derivative having antihistamic activity in high purity and yield by crystallizing a specific piperidine intermediate in a form of salts with carboxylic acids in an inert solvent. CONSTITUTION:A piperidine intermediate of the formula [either one of Ar and Ar is pyridyl and the other is (substituted)phenyl] is made to react with carboxylic acids of O-nitrobenzoic acid, etc., to form a salt of the piperidine intermediate with the carboxylic acids and the salt is crystallized to carry out purification of the piperidine intermediate.

公开(公告)号：JPH0570441A

公开(公告)日：1993-03-23

申请号：JP23035591

申请日：1991-09-10

Applicant: SANKYO CO ,  UBE INDUSTRIES

Inventor： OMORI KIYOSHI ,  YONEDA YASUHIRO ,  FUSE KENSAKU

IPC: C07D239/70

Abstract: PURPOSE:To obtain the subject compounds useful as a synthetic intemediate for antidepressive agents, cardiotonic agents and ameliorants of cerebropathy at a low cost according to simple operation by reacting a 2-amino-1- cyclopentenecarboxylic acid ester with formamide in the presence of a base. CONSTITUTION:A 2-amino-1-cyclopentenecarboxylic acid ester (e.g. methyl 2- amino-1-cyclopentenecarboxylate) expressed by formula I [R is 1-4C alkyl; X is H or OR (R is 1-4C alkyl)] is reacted with formamide in the presence of a base (preferably an alkali metal alcoholate etc.) to afford 6,7-dihydro-3H, 5H-cyclopenta[d]pyrimidin-4-ones [e.g. 6,7-dihydro-3H, 5H- cyclopenta[d]pryimidin-4-one]. A compound, expressed by formula III and useful as antidepressive agents, cardiotonic agents and ameliorants for cerebropathy can efficiently and advantageously be produced at a low cost by passing a compound expressed by formula II through compounds expressed by formulas IV and V.

公开(公告)号：JPH10237069A

公开(公告)日：1998-09-08

申请号：JP3756597

申请日：1997-02-21

Applicant: UBE INDUSTRIES

Inventor： YOSHIDA HIROSHI ,  OMORI KIYOSHI ,  YONEDA YASUHIRO ,  FUSE KENSAKU

IPC: C07D401/12

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound in a good yield, useful as an intermediate compound for the production of an antiallergic agent by optically resolving racemic piperidine compound and then reacemizing useless one of the optically active piperidine compounds for reuse. SOLUTION: This method for recemizing an optically active piperidine compound is to heat the optically active piperidine compound expressed by the formula in an alcohol in the presence of a base. Further, in detail, e.g. the compound of the formula is preferably heated at 90-110 deg.C reaction temperature in the alcohol such as n-butanol in the presence of the base such as sodium hydroxide, potassium hydroxide, sodium methoxide, etc. The compound of the formula is preferably obtained by optically resolving the corresponding racemic compound, 4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine.

公开(公告)号：JPH10120677A

公开(公告)日：1998-05-12

申请号：JP28218296

申请日：1996-10-24

Applicant: UBE INDUSTRIES

Inventor： YOSHIDA HIROSHI ,  OMORI KIYOSHI ,  YONEDA YASUHIRO ,  FUSE KENSAKU

IPC: C07D401/12 ,  A61K31/4427 ,  A61K31/445 ,  A61P37/08 ,  A61P43/00

Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a synthetic intermediate for a piperidine derivative having antihistaminic and antiallergic activities. SOLUTION: This is a compound expressed by formula I (X is a halogen), e.g. 1-benzyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine. Further, (4- halogenophenyl) (2-pyridyl)methyl halide expressed by formula II (X and Y are each a halogen) is made to react with 1-benzyl-4-piperidinol expressed by formula III, for example, in a solvent such as toluene at a reaction temperature of 100-170 deg.C for about 0.5-10hr to obtain the objective compound.

公开(公告)号：JPH0931059A

公开(公告)日：1997-02-04

申请号：JP18537995

申请日：1995-07-21

Applicant: UBE INDUSTRIES

Inventor： YONEDA YASUHIRO ,  YAMAMOTO YASUHITO ,  OKAMURA SHINJI ,  ATAKA KIKUO

IPC: C07D215/12 ,  C07D215/18

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound capable of readily industrializing and useful as an antiallergic agent having antileukotriene action without using a solvent affecting adverse influence on environment by using an ester-based solvent or amide-based solvent as an organic solvent. SOLUTION: When (A) a quinaldine derivative (e.g. quinaldine) of formula I (R to R are each H or a halogen) is reacted with (C) a brominating agent (e.g. N-bromosuccinimide) in the presence of (B) a free radical initiator (e.g. N,N'-azobisisobutyronitrile), the reaction is carried out in a solvent expressed by the formula R COR [R is H, an alkyl or an alkoxy; R is an alkoxy or NR 2 (R is an alkyl)], preferably an ester-based solvent or an amide-based solvent, especially ethyl acetate or dimethylformamide to provide the objective compound of formula II [e.g. 2-(bromomethyl)quinoline].

公开(公告)号：JPH1180075A

公开(公告)日：1999-03-23

申请号：JP33849197

申请日：1997-12-09

Applicant: UBE INDUSTRIES

Inventor： YONEDA YASUHIRO ,  YAMAMOTO YASUHITO ,  ATAKA KIKUO

IPC: B01J27/122 ,  C07B61/00 ,  C07C63/70 ,  C07C67/343 ,  C07C69/76

Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a starting substance on the syntheses of quinolone carboxylic acid compounds useful as medicines, especially antibacterial agents and antiviral agents. SOLUTION: A compound of formula I (R is H, a 1-10C alkyl, a 3-10C cycloalkyl or the like), e.g. 2,3,4-trifluoro-5-trifluoromethylbenzoic acid ethyl ester. The compound of formula I is obtained by reacting a 2, 3, 4-trifluoro-5- iodobenzoic acid ester of formula II (R is a 1-10C alkyl, a 3-10C cycloalkyl or the like) (preferably 2,3,4-trifluoro-5-iodobenzoic acid 1-4C alkyl ester) with a fluorosulfonyldifluoroacetic ester of formula III (preferably a fluorosulfonyldifluoroacetic acid 1-4C alkyl ester) in the presence of a copper catalyst (preferably cuprous iodide) in an organic solvent (preferably dimethylformamide, dimethylacetamide).

公开(公告)号：JPH10114711A

公开(公告)日：1998-05-06

申请号：JP22264397

申请日：1997-08-19

Applicant: UBE INDUSTRIES

Inventor： YAMAMOTO YASUHITO ,  YONEDA YASUHIRO ,  ATAKA KIKUO

IPC: B01J27/122 ,  C07B61/00 ,  C07C67/343 ,  C07C69/78

Abstract: PROBLEM TO BE SOLVED: To provide a method for producing the subject compound useful as a starting material for antibacterial and antiviral medicines by reacting a specific ester with a 2,4,5-trifluoro-3-iodobenzoate. SOLUTION: This method reacts a 2,4,5-trifluoro-3-iodobenzoate shown by formula I (R is an alkyl, cycloalkyl or the like) with a 2,2-difluoro(fluorosulfonyl) acetate shown by formula II in the presence of a copper catalyst, such as cuprous iodide, in an organic solvent, such as dimethylformamide, to produce a 2,4,5-trifluoro-3-trifluoromethylbenzoate shown by formula III as the objective compound. It can be produced at 0 to 200 deg.C and in a high yield without risk of explosion.

公开(公告)号：JPH0565255A

公开(公告)日：1993-03-19

申请号：JP23020491

申请日：1991-09-10

Applicant: SANKYO CO ,  UBE INDUSTRIES

Inventor： OMORI KIYOSHI ,  YONEDA YASUHIRO ,  FUSE KENSAKU

IPC: C07C227/08 ,  C07C229/48

Abstract: PURPOSE:To obtain a new intermediate capable of inexpensively and efficiently producing a 4-(4-cyanoanilino)-6.7-dihydro-5H-cyclopenta[d]pyrimidines, useful as antidepressant, cardiac and brain disorder improving drug. CONSTITUTION:A 3-alkoxy-2-amino-1-cyclopentenecarboxylic acid ester shown by formula I (R and R are 1-4C alkyl) such as 2-amino-3-methoxy-1- cyclopentenecarboxylic acid methyl ester. The compound is obtained by reacting a 3-alkoxy-2-oxocyclopentacarboxylic acid ester shown by formula Ii with ammonia in the presence of a catalyst.