Patents by Inventor Teruji Tsuji
Teruji Tsuji has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5106854Abstract: Novel quinolonecarboxylic acids of the formula: ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, R.sup.2 and R.sup.3 each is identically or differently hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.4 is cyclopropyl, phenyl, halo-phenyl, or thienyl optionally substituted by C.sub.1 -C.sub.4 alkyl or halogen, and R.sup.5 is halogen, or pharmaceutically acceptable salts thereof having a more potent and longer lasting antibacterial activities against G(+) and G(-) bacteria than known analogues, useful as antibacterial agents at an oral dose of 1-500 mg, preferably 50-100 mg per day to an adult.Type: GrantFiled: December 13, 1990Date of Patent: April 21, 1992Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Hisao Sato, Tetsuo Okada
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Patent number: 4731362Abstract: An antibacterial 3-(alkylcarbamoyloxymethyl)-3-cephem-4-carboxylic acid or its derivatives represented by the following formula ##STR1## (wherein R is hydrogen or an amino-protecting group,R.sup.1 and R.sup.2 each is the same or different 1C to 8C alkyl,R.sup.3 is hydrogen, a salt or ester forming atom or group, andX is sulfur or sulfinyl),a pharmaceutical composition containing the same, a method for treating a bacterial infection with the same, and a method for preparing the same are disclosed.Type: GrantFiled: July 23, 1986Date of Patent: March 15, 1988Assignee: Shionogi & Co., Ltd.Inventors: Yoshio Hamashima, Teruji Tsuji, Tetsuo Okada, Kyoji Minami, Hiroyuki Ishitobi, Koji Ishikura
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Patent number: 4604460Abstract: Intermediates for preparaing an antibacterial 1-dethia-1-oxacephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving groupare prepared from a compound of the following formula: ##STR3## wherein R and Y.sup.1 are as defined aboveby the action of an acid.The new compounds of this invention shown by the following formula: ##STR4## wherein A is amino or substituted amino;E is hydrogen or methoxy; andY is a divalent group of the following formula: ##STR5## in which COB, X, and Z are as defined above are convertible into other compounds of the same formula by applying conventional methods in .beta.-lactam chemistry.Type: GrantFiled: October 17, 1983Date of Patent: August 5, 1986Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Uyeo Shoichiro, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4592865Abstract: Intermediates of the following formula are useful for the synthesis of 1-oxacephalosporins. Their preparation from penicillins and the transformation process to make 1-oxacephalosporins are disclosed. The compounds are of the formula: ##STR1## wherein A is amino or a selected acylamino;COB is carboxy or a selected protected-carboxy;X is halogen or the group ORin which R is a group represented by following formulas: ##STR2## wherein Nu is a selected nucleophilic group; R.sup.1 is a group of the following formula: ##STR3## in which Hal is halogen or alkylsulfonyloxy and R.sup.2 is alkyl or aryl; andY is hydrogen or methoxy; with the proviso that when R is propargyl or 2-oxopropyl andR.sup.1 is ##STR4## A is in the 3.alpha.-configuration and Y is 3.beta.-hydrogen or A is in the 3.beta.-configuration and Y is 3.alpha.-methoxy.Type: GrantFiled: March 13, 1984Date of Patent: June 3, 1986Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Hiroshi Onoue, Teruji Tsuji, Yasuhiro Nishitani, Mitsuru Yoshioka, Yoshio Hamashima, Wataru Nagata
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Patent number: 4581173Abstract: A useful industrial chemical, oxazolinoazetidinylhydroxymethylbutenoic acid derivative (II) can be produced by oxidizing the corresponding oxazolinoazetidinylhalomethylbutenoic acid derivative(I). ##STR1## wherein R is an alkyl, aralkyl or aryl group, R.sup.1 is a hydrogen atom or a carboxy protecting group and Hal is a halogen atom.Type: GrantFiled: April 7, 1983Date of Patent: April 8, 1986Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Kanji Tokuyama, Mamoru Tanaka, Hiroyuki Ishitobi
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Patent number: 4570018Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).Type: GrantFiled: May 16, 1984Date of Patent: February 11, 1986Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
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Patent number: 4539148Abstract: Useful intermediates, 7.alpha.-acylamino-3-(oxo or exomethylene)-1-dethia-1-oxacepham-4.alpha.-carboxylates, are produced by the intramolecular carbenoid insertion of a 2-diazo-3-(oxo or exomethylene)-4-(3.alpha.-acylamino-2-oxoazetidin-4.beta.-yl)oxybutyrate prepared in several steps from the corresponding oxazolinoazetidinone and diketone.Type: GrantFiled: August 16, 1983Date of Patent: September 3, 1985Assignee: Shionogi & Co., Ltd.Inventors: Sadao Yamamoto, Hikaru Itani, Hiromi Takahashi, Teruji Tsuji, Wataru Nagata
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Patent number: 4533730Abstract: Intermediates for preparing an antibacterial 1-dethia-1-oxacephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving groupare prepared from a compound of the following formula; ##STR3## wherein R and Y.sup.1 are as defined above by the action of an acid. The new compounds of this invention shown by the following formula: ##STR4## wherein A is amino or substituted amino;E is hydrogen or methoxy; andY is a divalent group of the following formula: ##STR5## in which COB, X, and Z are as defined above are convertible into other compounds of the same formula by applying conventional methods in .beta.-lactam chemistry.Type: GrantFiled: October 19, 1983Date of Patent: August 6, 1985Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Uyeo Shoichiro, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4532233Abstract: An antibacterial 7.beta.-(fluorinated methylthioacetamido)-7.alpha.-methoxy-3-(1-hydroxyalkyl-5-tetrazolyl)thiom ethyl-1-dethia-1-oxa-3-cephem-4-carboxylic acid and its derivatives at the carboxy or hydroxyalkyl represented by the following formula: ##STR1## wherein, R is FCH.sub.2 -- or F.sub.2 CH--; R.sup.1 is R.sup.3 O-substituted-alkyl in which R.sup.3 is hydrogen or a hydroxy-protecting group; and R.sup.2 is a hydrogen or light metal atom or a carboxy-protecting group, antibacterial drugs containing it, its use and production.Type: GrantFiled: December 22, 1983Date of Patent: July 30, 1985Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Hisao Sato, Yoshio Hamashima
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Patent number: 4504659Abstract: Intermediates for preparing an antibacterial 1-dethia-1-oxacephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving groupare prepared from a compound of the following formula: ##STR3## wherein R and Y.sup.1 are as defined above by the action of an acid.Type: GrantFiled: October 19, 1983Date of Patent: March 12, 1985Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Uyeo Shoichiro, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4491547Abstract: Monofluoromethylthioacetic acid (FCH.sub.2 SCH.sub.2 COOH) or difluoromethylthioacetic acid (F.sub.2 CHSCH.sub.2 COOH), or its derivative at the carboxy group can be prepared e.g. by treating a thioglycolic acid ester with monolfuorohalomethane or difluorohalomethane in the presence of a base if required followed by a conventional modification of the produced ester e.g. to make an acid by hydrolysis, a salt by neutralization, a halide with a halogenating agent, and from acid halide or anhydride an ester with an alcohol, or an amide with an amine. These compounds are useful intermediates in the production of medicinal and agricultural chemicals.Type: GrantFiled: December 23, 1981Date of Patent: January 1, 1985Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Hisao Sato, Yoshio Hamashima
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Patent number: 4478997Abstract: Intermediates for preparing an antibacterial 1-dethia-1-oxa-cephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving groupare prepared from a compound of the following formula: ##STR3## wherein R and Y.sup.1 are as defined above by the action of an acid.Type: GrantFiled: October 19, 1983Date of Patent: October 23, 1984Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4443598Abstract: Intermediates for preparing an antibacterial 1-dethia-1-oxacephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving groupare prepared from a compound of the following formula: ##STR3## wherein R and Y.sup.1 are as defined above by the action of an acid. The new compounds of this invention shown by the following formula: ##STR4## wherein A is amino or substituted amino;E is hydrogen or methoxy; andY is a divalent group of the following formula: ##STR5## in which COB, X, and Z are as defined above are convertible into other compounds of the same formula by applying conventional methods in .beta.-lactam chemistry.Type: GrantFiled: May 4, 1982Date of Patent: April 17, 1984Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Uyeo Shoichiro, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4440683Abstract: An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds. ##STR1## wherein A and B each is a hydrogen or amine substituent; R is a hydrogen or thiol substituent; Nal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidimethiazoline bicyclic ring; and the enamine derivatives thereof.Type: GrantFiled: January 11, 1982Date of Patent: April 3, 1984Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Yoshio Hahashima, Mitsuru Yoshioka, Masayuki Narisada, Hiroshi Tanida, Taichiro Komeno, Wataru Nagata
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Patent number: 4366316Abstract: Intermediates for preparing an antibacterial 1-dethia-1-oxacephalosporins which are represented by the following formula: ##STR1## wherein R is a monovalent group (minus the carbonyl) from an acyl group derived from a carboxylic or carbonic acid;Y.sup.1 is a divalent group of the following formula: ##STR2## wherein COB is carboxy or protected carboxy;X is hydrogen or a nucleophilic group; andZ is a leaving group are prepared from a compound of the following formula: ##STR3## wherein R and Y.sup.1 are as defined above by the action of an acid. The new compounds of this invention shown by the following formula: ##STR4## wherein A is amino or substituted amino;E is hydrogen or methoxy; andY is a divalent group of the following formula: ##STR5## in which COB, X, and Z are as defined above are convertible into other compounds of the same formula by applying conventional methods in .beta.-lactam chemistry.Type: GrantFiled: November 18, 1981Date of Patent: December 28, 1982Assignee: Shionogi & Co., Ltd.Inventors: Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Teruji Tsuji, Wataru Nagata
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Patent number: 4346218Abstract: An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof.Type: GrantFiled: February 27, 1980Date of Patent: August 24, 1982Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Yoshio Hamashima, Mitsuru Yoshioka, Masayuki Narisada, Hiroshi Tanida, Taichiro Komeno, Wataru Nagata
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Patent number: 4332722Abstract: An intermediate represented by the following formula, for synthesizing --3-hydroxy-3-cephem compounds. ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof.Type: GrantFiled: February 27, 1980Date of Patent: June 1, 1982Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Yoshio Hamashima, Mitsuru Yoshioka, Masayuki Narisada, Hiroshi Tanida, Taichiro Komeno, Wataru Nagata
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Patent number: 4271296Abstract: Useful intermediates for preparing a 1-dethia-1-oxacephalosporin and represented by the following formula: ##STR1## (wherein R is a monovalent group resulting from the elimination of the carbonyl function of an acyl group derived from a carboxylic or carbonic acid;COB is carboxy or protected carboxy; andX is hydrogen or a nucleophilic group)are prepared from the corresponding penicillin 1-oxides of the following formula: ##STR2## (wherein R, COB, and X are as defined above) by heating, if required in the presence of a desulfurizing reagent, or by exchanging the X group with another one under the condition of an appropriate nucleophilic substitution.Type: GrantFiled: January 14, 1980Date of Patent: June 2, 1981Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Wataru Nagata
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Patent number: 4271295Abstract: Useful intermediates for preparing a 1-dethia-1-oxacephalosporin and represented by the following formula: ##STR1## (wherein R is a monovalent group resulting from the elimination of the carbonyl function of an acyl group derived from a carboxylic or carbonic acid;COB is carboxy or protected carboxy; andX is hydrogen or a nucleophilic group)are prepared from the corresponding penicillin 1-oxides of the following formula: ##STR2## (wherein R, COB, and X are as defined above) by heating, if required in the presence of a desulfurizing reagent, or by exchanging the X group with another one under the condition of an appropriate nucleophilic substitution.Type: GrantFiled: January 14, 1980Date of Patent: June 2, 1981Assignee: Shionogi & Co., Ltd.Inventors: Teruji Tsuji, Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Wataru Nagata
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Patent number: 4233216Abstract: .alpha.-[3(R)-Substituted amino-4(R)-substituted alkoxy-2-oxo-azetidin-1-yl]-.alpha.-isopropenylacetate (Ia) and .alpha.-[3(R)-substituted amino-4(R)-substituted alkoxy-2-oxo-azetidin-1-yl]-.alpha.-isopropylideneacetate (Ib) prepared from (1R,5S)-.alpha.-(3-substituted-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-e n-6-yl)-.alpha.-isopropenylacetate or (1R,5S)-.alpha.-(3-substituted-7-oxo-4-oxa-2,6-diazabicyclo-[3.2.0]hept-2- en-6-yl)-.alpha.-isopropylideneacetate with a primary alcohol in the presence of an acid. The products are useful intermediates for preparing oxadethiacephalosporins.Type: GrantFiled: December 6, 1978Date of Patent: November 11, 1980Assignee: Shionogi & Co., Ltd.Inventors: Shoichiro Uyeo, Mitsuru Yoshioka, Teruji Tsuji, Ikuo Kikkawa, Wataru Nagata