7-position Substituent Contains Hetero Ring Patents (Class 540/227)
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Patent number: 5013731Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, ##STR2## represents one of the C-7 acyl groups known in the cephalosporin art, R3 is hydrogen or methoxy, R4 is hydrogen, optionally substituted alkyl, allyl, furfuryl or benzyl, and R5 is an aromatic heterocyclic ring system which is linked via carbon, and which contains a quaternized nitrogen atom.Type: GrantFiled: April 19, 1990Date of Patent: May 7, 1991Assignee: ICI PharmaInventors: Jean C. Arnould, Jean J. Lohmann, Georges Pasquet
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Patent number: 5001121Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: June 20, 1989Date of Patent: March 19, 1991Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 4992431Abstract: Novel syn isomers of 3-alkoxymethyl or 3-alkylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-oximino-acetamido]-cephalos poranic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, acyl of an organic carboxylic acid of 1 to 18 carbon atoms and alkoxy carbonyl of 2 to 6 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, --NH.sub.Type: GrantFiled: June 30, 1982Date of Patent: February 12, 1991Assignee: RousselUclafInventors: Rene Heymes, Didier Pronine
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Patent number: 4988687Abstract: A compound having the formula: ##STR1## wherein R is a vinyl, phenyl or aralkyl group which may be substituted; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: September 1, 1989Date of Patent: January 29, 1991Assignee: Banyu Pharmaceutical Company, Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima
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Patent number: 4987129Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: --A--OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is --A--OR.sub.4, and R.sub.Type: GrantFiled: July 21, 1988Date of Patent: January 22, 1991Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4985555Abstract: The invention relates to a cephem compound of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino, R.sup.2 is hydrogen, phenyl, pyridyl which may have a lower alkyl group, or cyano, and R.sup.3 is carboxy or protected carboxy, or a salt thereof.Type: GrantFiled: July 27, 1989Date of Patent: January 15, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
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Patent number: 4980464Abstract: A method for producing a compound of the formula; ##STR1## wherein R stands for a hydrogen atom, an acyl group or a protective group other than acyl groups, Q stands for a hydrogen atom or an ester residue, Y stands for the residue of a nucleophilic compound and the dotted line shows the double bond at 2- or 3- position of the cephem ring or a salt thereof, characterized by allowing a compound of the formula; ##STR2## [R, Q and the dotted line are of the same meaning as above] or a salt thereof to react with a nucleophilic compound or a salt thereof and a compound of the formula; ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 independently stand for a hydrocarbon group having not more than 8 carbon atoms, or R.sup.1 and R.sup.2, R.sup.1 and R.sup.3 or R.sup.2 and R.sup.Type: GrantFiled: June 30, 1989Date of Patent: December 25, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi
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Patent number: 4977256Abstract: A method of deprotection which comprises reacting a compound having at least one of amino, hydroxyl, mercapto and carboxyl groups protected by a substituted or unsubstituted benzyloxycarbonyl group or by a substituted or unsubstituted benzyl group with zinc in a buffer, thereby splitting off the protective benzyloxycarbonyl or benzyl group.Type: GrantFiled: June 10, 1988Date of Patent: December 11, 1990Assignee: Lederle (Japan), Ltd.Inventors: Sakae Aoyagi, Takaaki Hayashi, Yasuhiro Kuramoto
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Patent number: 4973684Abstract: Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein R.sup.4 is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl; or a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: June 7, 1988Date of Patent: November 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michihiko Ochiai, Taiiti Okada, Osamu Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
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Patent number: 4973685Abstract: Heteroannellated penicillins and cephalosporins of the formula ##STR1## in which R.sup.Type: GrantFiled: September 28, 1988Date of Patent: November 27, 1990Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4971962Abstract: The present invention relates to novel cephalosporin compounds having high antimicrobial activity, which are shown by the formula(I), and to a process for preparing them ##STR1## wherein R.sup.1 is a hydrogen atom or an amino protecting group;R.sup.2 is acetoxy; andR.sup.3 is a hydrogen atom or a carboxyl protecting group (wherein when R.sup.2 contains quaternary ammonium, r.sup.2 and R.sup.3 may form a zwitter ion).The present invention also relates to the non-toxic and pharmaceutically acceptable salts of the cephalosporin compounds of the formula (I). Also described are compositions containing the antibiotics according to the present invention.Type: GrantFiled: May 11, 1989Date of Patent: November 20, 1990Assignee: Lucky, Ltd.Inventors: Hun S. Oh, Yong Z. Kim, Jae H. Yeo, Jong C. Lim, Won S. Kim, Soon H. An, Chan S. Bang, Hyeon J. Yim
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Patent number: 4971961Abstract: This invention provides cephalosporin compounds represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 are same or different hydrogen atom or a lower alkyl group of 1 to 5 carbon atoms; R.sup.3 is a lower alkyl group which may optionally be substituted with a halogen atome (or atoms), an alkenyl group, or a cycloalkylmethyl group of 3 to 6 carbon atoms; and A is hydrogen atom or residue of a nucleophilic compound and pharmacologically acceptable salts thereof. These compounds have broad-spectrum antibacterial activity against Gram-positive and -negative bacteria including Pseudomonas aeruginosa, as well as against a great variety of .beta.-lactamase-producing strains.Type: GrantFiled: November 2, 1988Date of Patent: November 20, 1990Assignee: Meiji Seika Kaisha, Ltd.Inventors: Kaysuyoshi Iwamatsu, Kenji Sakagami, Kunio Atsumi, Takashi Yoshida, Seiji Shibahara, Takashi Tsuruoka, Shinichi Kondo
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Patent number: 4971963Abstract: An antibacterial agent is provided which is a cephem compound of the formula: ##STR1## wherein R.sup.1 is an acyl group; R.sup.2 is a carboxy group which may be esterified; R.sup.3 is a hydrogen atom, a lower alkyl group or cyano group; R.sup.4 is a hydrogen atom or a lower alkyl group, or R.sup.4 together with R.sup.3 is a methylene chain having 2 or 3 carbon atoms; R.sup.5 is a hydrogen atom or a lower alkyl group; A is an optionally substituted bivalent aromatic heterocyclic group which is bonded to a ring-constituting carbon atom with the adjacent sulfur atom; Y is a binding arm, sulfur or oxygen atom, --NH--, --CONH-- or --NHCO--; Z is a binding bond or --NH--; m is an integer of 0 to 4 and n is an integer of 0 to 6, or a pharmacologically acceptable salt thereof.Type: GrantFiled: March 15, 1989Date of Patent: November 20, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michiyuki Sendai, Shoji Kishimoto
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Patent number: 4966900Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a lower alkyl group; M is a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; R' and R" are independently a hydrogen atom or a protective group; A is a mercapto group substituted by a substituted or unsubstituted polycyclic nitrogen-containing heterocyclic ring or a group represented by the following formula (a):--OOCNR.sub.3 R.sub.4 (a)where R.sub.3 and R.sub.4 are independently a hydrogen atom or a lower alkyl group, provided that R.sub.1 and R.sub.2 are both hydrogen atoms, both R.sub.3 and R.sub.4 being hydrogen atoms are excluded,or its pharmaceutically acceptable salt, and a method for preparing the same , medicinal composition for microbism therapy containing the same and intermediates for synthesis of the same.Type: GrantFiled: July 20, 1987Date of Patent: October 30, 1990Assignees: Sankei Pharmaceutical Company Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4965358Abstract: A new compound called N,N'-carbonyl-bis-(4-ethyl-2,3-dioxo)-piperazine of Formula I ##STR1## A process for the preparation thereof based on the reaction of 4-ethyl-2,3-dioxo-piperazine or a trimethylsilyl derivative thereof with carbonyl chloride or a derivative thereof.The use of the compound of Formula I as an intermediate in the preparation of compounds of Formula II ##STR2## where R is a radical, substituted in alpha position, of a molecule of an acid selected from the group formed by phenylacetic acid, p-hydroxy phenylacetic acid, a 6-(phenylacetamido)-penicillanic acid and a 7-(phenylacetamido)-cephalosporanic acid.Type: GrantFiled: November 10, 1988Date of Patent: October 23, 1990Assignee: Gema, S. A.Inventors: Juan Cabre Castellvi, Jose Diago Meseguer, Asuncion Esteve Bianchini, Carlos E. Lenhardt Padro, Esteve Sans Pitarch
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Patent number: 4962202Abstract: New derivatives of penem and pharmaceutically acceptable salt thereof are herein disclosed; these compounds being useful as an antibacterial agent which has an extremely wide antibacterial spectrum, exhibits a high sensitivity to bacteria resistant to conventional penicillins and cephalosporing antibiotics and is excellent in its physico-chemical stability, solubility to water and biological stability, in particular, stability to decomposition by enzyme such as dehydropeptidase I in kidney, .beta.-lactamase; these derivatives of penem being able to be prepared by reacting 2-substituted sulfinyl derivative of penem with a thiol compound and then optionally removing protective group(s) and further alkylating the reaction product or vice versa.Type: GrantFiled: January 11, 1988Date of Patent: October 9, 1990Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Makoto Sato, Makoto Takemura, Kunio Higashi, Tsunehiko Soga, Hiroo Matsumoto, Toshiyuki Nishi
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Patent number: 4962100Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is an amino group which may be protected, R.sup.3 is a hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S.fwdarw.O, O or CH.sub.2, R.sup.4 is a hydrogen atom, methoxy group or formamido group, R.sup.13 is a hydrogen atom, methyl group, hydroxyl group or halogen atom and A.sup..sym. is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof is novel and has excellent antibacterial activity.Type: GrantFiled: March 28, 1989Date of Patent: October 9, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4959495Abstract: A process is disclosed for the preparation of intermediates useful in the synthesis of aminothiazoloximino cephalosporins.Type: GrantFiled: June 30, 1989Date of Patent: September 25, 1990Assignee: American Cyanamid CompanyInventor: William V. Curran
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Patent number: 4958019Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: --A--OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branced alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is --A--OR.sub.4, R.sub.2 and R.sub.Type: GrantFiled: May 26, 1989Date of Patent: September 18, 1990Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Company, Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4956462Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group of an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: -A-OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group of an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is -A-OR.sub.4, R.sub.2 and R.sub.Type: GrantFiled: May 26, 1989Date of Patent: September 11, 1990Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4950661Abstract: The present invention relates to derivatives of the cephalosporin family, of formula: ##STR1## in which: X is an oxygen atom or a sulfur atomn is zero, 1 or 2.R.sub.1, R.sub.2 and R.sub.3 each designate, a hydrogen atom or else R.sub.1 and R.sub.2 designate a hydrogen atom or a methyl group, and R.sub.3 designates a carboxyl or cyclopropyl group, or elseR.sub.1 and R.sub.2 taken together with the carbon atom to which they are linked form a cyclobutyl or cyclopentyl group and R.sub.3 is a carboxyl group.B is the residue of a primary or secondary amine;their preparation process and application in therapeutics.Type: GrantFiled: April 28, 1988Date of Patent: August 21, 1990Assignee: SANOFIInventors: Dominique Olliero, Ali Salhi
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Patent number: 4943568Abstract: Antibacterially active novel cephalosporins of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkoxy, alkylthio, halogen, trifluoromethyl or trifluoromethoxy,R.sup.2 represents hydrogen or an organic radical,R.sup.3 represents hydrogen, alkyl, alkenyl, alkoxy, alkylthio, halogen, hydroxymethyl or ethers or esters thereof, or various organothiomethyl or substituted aminomethyl radicals, andR.sup.4 represents COO.sup.- or COOH, or salts thereof.Type: GrantFiled: November 21, 1986Date of Patent: July 24, 1990Assignee: Bayer AktiengesellschaftInventors: Michael Boberg, Rolf Angerbauer, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4943567Abstract: Cephalosporin compounds represented by the general formula (I): ##STR1## wherein R.sup.1 and R.sup.5 independently represent a hydrogen atom or a protective group for an amino group; R.sup.2 represents an alkyl group or a cycloalkyl group; R.sup.3 represents a hydrogen atom, a lower alkenyl group, an alkanoyloxymethyl group, a carbamoyloxymethyl group, a heterocyclic thiomethyl group or a heterocyclic methyl group; R.sup.4 represents a hydrogen atom or an ester residue; and X represents CH or a nitrogen atom and pharmacologically acceptable addition salts thereof, intermediate compounds used in the synthesis process of these compounds, production methods of these compounds and pharmaceutical compositions containing these compounds.Type: GrantFiled: May 27, 1988Date of Patent: July 24, 1990Assignee: Kyoto Pharmaceutical Industries, Ltd.Inventors: Susumu Nishizawa, Hiroyuki Muro, Masayasu Kasai, Satoru Hatano, Syouzi Kamiya, Nobuharu Kakeya, Kazuhiko Kitao
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Patent number: 4939250Abstract: A process for preparing compounds of the formula I: ##STR1## wherein X is sulphur, oxygen, methylene or sulphinyl (R or S configuration), R.sup.3 is hydrogen or methoxy, R.sup.4 is an optionally substituted (1-4C)alky group, Y is hydrogen or a carboxyl protecting group and Q is an optionally protected amino group or an acylamino group, which comprises reacting a compound of formula (II) ##STR2## with a compound of formula (III) ##STR3## wherein R.sup.4 is as defined above and W and Z represent hydrogen atoms or a group or groups removable to yield the compound of formula (I). The compounds of the formula I are useful intermediates in the preparation of cephalosporin antibiotics.Type: GrantFiled: May 12, 1987Date of Patent: July 3, 1990Assignee: Imperial Chemical Industries PlcInventors: Frank Lotus, Stephen J. Pegg, Evan W. Snape
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Patent number: 4937330Abstract: The present invention relates to processes for the preparation of alkali metal salts of amino acids. Preferably, the present invention relates to solid phase alkali metal salts of cephalosporins of formula III, wherein M is selected from the group consisting of sodium, potassium and lithium, characterized by birefringent lath- and rod-shaped particles, and processes for their manufacture.Type: GrantFiled: April 10, 1987Date of Patent: June 26, 1990Assignee: The Upjohn CompanyInventors: Clifford E. Sacks, Loren H. Dill
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Patent number: 4937332Abstract: A cephalosporin derivative represented by the general formula ##STR1## wherein R.sup.1 is a hydrogen atom or a protecting group of the amino group, R.sup.2 is a hydrogen atom or a protecting group of the hydroxyl group, R.sup.3 is a hydrogen atom or a protecting group of the carboxyl group, and R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the non-toxic salts thereof are useful as antibacterial agents.Type: GrantFiled: December 19, 1988Date of Patent: June 26, 1990Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Chihiro Yokoo, Akira Onodera, Hiroshi Fukushima, Yoshiaki Watanabe, Kaoru Sota
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Patent number: 4927922Abstract: 7.beta.-(Substituted)amino-3-substituted cephalosporanic acids, esters and salts, useful as anti-bacterial agents are described.Type: GrantFiled: July 21, 1988Date of Patent: May 22, 1990Assignee: American Cyanamid CompanyInventors: Ving J. Lee, William V. Curran
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Patent number: 4921954Abstract: Process for the preparation of 7.beta.-amino-3-substituted methyl-3-cephem-4-carboxylic acid derivatives, new intermediates comprising 7.beta.-(cyclo)alkylideneammonio-3-halomethyl-3-cephem-4-carbox ylic acid derivatives and 7.beta.-amino/ammonio-3-bromomethyl-3-cephem-4-carboxylic acid derivatives and the processes for the preparation of these intermediates.Type: GrantFiled: July 8, 1988Date of Patent: May 1, 1990Assignee: Gist-Brocades N.V.Inventors: Hendrik A. Witkamp, Jan Verweij, Jan J. DeKoning, Herman H. Grootveld, Everardus J. A. M. Leenderts
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Patent number: 4921953Abstract: A cephalosporin derivative represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a protecting group of the amino group, R.sup.2 is a hydrogen atom or a protecting group of the hydroxyl group, R.sup.3 is a hydrogen atom or a protecting group of the carboxyl group, X is a halogen atom, a cyano group, a vinyl group, a lower alkoxy group having 1 to 4 carbon atoms or a lower alkylthio group having 1 to 4 carbon atoms and n is an integer of 1 to 3, and a non-toxic salt thereof are useful as antibacterial agents for oral administration.Type: GrantFiled: February 13, 1989Date of Patent: May 1, 1990Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Chihiro Yokoo, Akira Onodera, Hiroshi Fukushima, Yoshiaki Watanabe, Kaoru Sota
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Patent number: 4918068Abstract: There are provided new cephem compounds (synisomers) represented by the following general formula (I): ##STR1## wherein R.sup.1 means a lower group, R.sup.2 denotes an ester-forming group of the carboxyl group, and the 4-methylthiazolyl group and the cephem moiety are cis to each other relative to the carbon-carbon double bond of the substituted vinyl group in the side chain at the 3-position of the cephem nucleus. The cephem compounds exhibit strong antibacterial activities not only against resistant strains of bacteria and gram-negative bacteria but also against gram-positive bacteria and moreover have very low toxicity.Type: GrantFiled: February 26, 1987Date of Patent: April 17, 1990Assignee: Meiji Seika Kaisha, Ltd.Inventors: Yuichi Yamamoto, Kunio Atsumi, Kenji Sakagami, Takashi Yoshida, Ken Nishihata, Sinichi Kondo
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Patent number: 4918070Abstract: A cephalosporin derivative having the formula: ##STR1## wherein R.sup.1 is a substituted amino group, X is an alkylene group, R.sup.2 is an aryl or heterocyclic group which may be substituted and R.sup.3 is a hydrogen atom, a negative charge or a residue of an ester which can form a pharmaceutically acceptable ester hydrolyzable in a living body; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: February 26, 1988Date of Patent: April 17, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Hiroshi Fukatsu, Yoshiaki Katoh, Satoshi Murase
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Patent number: 4912212Abstract: Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein -W-R is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl, or a pharmaceutically acceptable salt or 4-carboxy ester which is the alkoxymethyl, .alpha.-alkoxyethyl, .alpha.-alkoxy-.alpha.-substituted methyl, alkylthiomethyl, acyloxymethyl or .alpha.-acyloxy-.alpha.-substituted methyl ester thereof.Type: GrantFiled: June 7, 1988Date of Patent: March 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michihiko Ochiai, Taiiti Okada, Osamu Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
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Patent number: 4912211Abstract: A process is described for producing pure crystalline products, in particular penicillin and cephalosporin, wherein the desired product, prepared according to a known method, is treated with ethanol in one or two steps, whereby the crystallization of the pure product and impurity separation are achieved.Type: GrantFiled: November 10, 1987Date of Patent: March 27, 1990Inventor: Giovanni Bonfanti
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Patent number: 4902683Abstract: Crystalline hydrohalide salts of the cephalosporin antibiotic ceftiofur, processes for their manufacture, and pharmaceutical compositions containing one of these salts are provided.Type: GrantFiled: February 17, 1989Date of Patent: February 20, 1990Assignee: The Upjohn CompanyInventors: Mahendra I. Amin, Jay A. Campbell
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Patent number: 4898937Abstract: This invention relates to .alpha.-crystals of cefazolin sodium with a water content in the range of 13.0 to 15.8%, useful as an antibiotic of improved thermal and light stability.Type: GrantFiled: February 2, 1989Date of Patent: February 6, 1990Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Toshinobu Uemura, Keiji Kai, Masateru Kodani, Fumiyo Yoshida, Matsuhiko Aratani
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Patent number: 4888332Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The novel cephalosporin derivatives according to the present invention contain condensed heterocyclic groups, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring as substituents at the 3-position of the cephem skeleton, and a hydroxyimino, an alkyloxyimino or an acyloxyimino moiety as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against gram-negative bacteria and also against gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: December 28, 1984Date of Patent: December 19, 1989Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 4880798Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring, as substitutents at the 3-position of the cephem skeleton, and of groups containing a carboxyl and hydroxy substituted phenylmethyloxyimino moiety, particularly a (carboxy substituted catechol)methyloxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: November 20, 1987Date of Patent: November 14, 1989Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Kazuo Kato, Kimihiro Murakami, Hidenori Mochizuki, Ei Mochida
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Patent number: 4871730Abstract: A cephem compound of the formula: ##STR1## wherein R.sup.1 is a group of the formula: ##STR2## in which R.sup.5 is amino or protected amino, R.sup.6 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, carboxy(lower) alkyl, protected carboxy(lower) alkyl, cyclo(lower) alkyl or cyclo (lower)alkenyl, and Z is CH or N;R.sup.2 is hydrogen, phenyl, pyridyl which may have a lower alkyl group, or cyano; andR.sup.3 is carboxy or protected carboxy; and pharmaceutically acceptable salt thereof.Type: GrantFiled: November 24, 1986Date of Patent: October 3, 1989Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
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Patent number: 4868295Abstract: A process for the preparation of cefodizime of the formula ##STR1## wherein (a) a compound of the formula II (ATS) ##STR2## wherein R.sub.1 represents hydrogen or an aminoprotective group and A represents a hydrogen atom or one equivalent of an alkali metal or alkaline earth metal, of ammonium or of an organic nitrogen base, is first reacted with a compound of the formula IIIR--SO.sub.2 Halwherein R represents an optionally substituted alkyl, aryl or aralkyl radical and Hal represents a halogen atom, in an organic solvent and, if appropriate, in the presence of a base,(b) a compound of the formula I (TACS) ##STR3## in which A has the above meaning, is reacted with a silylating agent in an organic solvent and, if appropriate, in the presence of a base, and(c) the two products formed in (a) and (b) are reacted in their reaction solutions, and any protective group R.sub.1 present in the end product of the formula I is eliminated.Type: GrantFiled: December 1, 1986Date of Patent: September 19, 1989Assignee: Hoechst AktiengesellschaftInventors: Ottmar Jaenicke, Hans Wagner, Manfred Worm
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Patent number: 4866055Abstract: The present invention relates to novel cephalosporin derivatives and their crystalline form, processes for preparing thereof, compositions for treating and/or preventing infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of a triazolopyrimidine ring as substituent at the 3-position of the cephem skeleton, and a 2-carboxy-4,5-dihydroxyphenylmethyloxyimino moiety as substituent at the 7-position of the cephem skeleton.The compounds of the present invention containing these substituents have a wide antibacterial spectrum against Gram-negative bacteria including Pseudomonas aeruginosa and Gram-positive bacteria including methicillin-resistant Staphylococcus aureus. These compounds are extremely useful for the treatment of infectious diseases.Type: GrantFiled: November 16, 1987Date of Patent: September 12, 1989Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Kazuo Kato, Kimihiro Murakami, Hidenori Mochizuki, Ei Mochida
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Patent number: 4864022Abstract: A compound of the formula; ##STR1## wherein R.sup.1 is an amino group which may be protected, R.sup.3 is a hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S.fwdarw.O, O or CH.sub.2, R.sup.4 is a hydrogen atom, methoxy group or formamido group, R.sup.13 is a hydrogen atom, methyl group, hydroxyl group or halogen atom and A.sym. is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof is novel and has excellent antibacterial activity.Type: GrantFiled: February 28, 1986Date of Patent: September 5, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4861769Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is lower alkyl, lower alkanoyl, aryl, ar(lower)alkyl or a heterocyclic group, each of which may have suitable substituent(s),R.sup.2 is carboxy or protected carboxy,R.sup.3 is hydrogen, halogen, hydroxy, lower alkoxy, acyloxy, lower alkylthio, lower alkenyl, lower alkenylthio, lower alkynyl, heterocyclicthio or a heterocyclic group, in which lower alkylthio, lower alkenyl, lower alkenylthio, heterocyclicthio and a heterocyclic group may have suitable substituent(s),R.sup.4 and R.sup.5 are each hydrogen, halogen or arylthio,A is lower alkylene, andn is an integer of 0 or 1,and a pharmaceutically acceptable salt thereof, processes for preparation thereof and pharmaceutical composition comprising the same.Type: GrantFiled: February 12, 1986Date of Patent: August 29, 1989Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Shintaro Nishimura
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Patent number: 4841044Abstract: Cephalosporin derivatives represented by the general formula ##STR1## wherein R is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R' is a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms or a benzyl group, or R and R' together with the nitrogen atom to which they are attached form a tetrahydropyridinyl group, a morpholinyl group or pyrroridinyl group, and the non-toxic salts thereof are disclosed. These compounds are useful as antibacterial agents.Type: GrantFiled: December 18, 1986Date of Patent: June 20, 1989Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoshiaki Watanabe, Chihiro Yokoo, Masami Goi, Akira Onodera, Mitsuo Murata, Hiroshi Fukushima, Minoru Taguchi, Kaoru Sota
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Patent number: 4840945Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: March 10, 1986Date of Patent: June 20, 1989Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 4839350Abstract: A class of new caphalosporin compounds (syn-isomer) is now provided, which is useful as antibacterial agent and is represented by the general formula (I) ##STR1## wherein R.sup.1 is an amino group or a protected amino group; R.sup.2 is a lower alkyl group, a carboxymethyl group or a protected carboxymethyl group; R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group; A is an unsubstituted or substituted phenyl group, an unsubstituted or substituted furyl group, an unsubstituted or substituted thiazolyl group or an unsubstituted or substituted 3-lower-alkylthiazolio group, and a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: April 7, 1987Date of Patent: June 13, 1989Assignees: Meiji Seika Kaisha, Ltd., Susumu MitsuhashiInventors: Kunio Atsumi, Kenji Sakagami, Yuichi Yamamoto, Takashi Yoshida, Ken Nishihata, Shinichi Kondo, Shunzo Fukatsu
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Patent number: 4839351Abstract: A compound of the general formula: ##STR1## wherein R.sup.0 is hydrogen, a nitrogen-containing heterocyclic group, an acyl group or an amino-protective group; A is S, S.fwdarw.O, O or CH.sub.2 ; R.sup.4 is hydrogen, methoxy group or formamido group; R.sup.13 is hydrogen, methyl, hydroxyl or a halogen; and A is an optionally substituted condensed cyclic group formed by combining an imidazole or pyrazole ring with 5- or 6-membered nitrogen-containing aromatic heterocyclic ring to share a C-N bond with each other,or a salt or ester thereof.and a process for preparing the same and a pharmaceutical composition thereof are disclosed.Type: GrantFiled: December 12, 1986Date of Patent: June 13, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Tatsuo Nishimura, Yoshinobu Yoshimura, Akio Miyake, Naoto Hashimoto
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Patent number: 4835267Abstract: The present invention relates to an improved process for producing cephalosporin derivatives of formula (I), the 3-position of which being substituted by acetoxymethyl or tetrazolylthiomethyl and the 7-acyl group of which being substituted by D-mandelic acid derivatives, which comprises simultaneously reacting the compound of formula (III) with the compound of formula (IV) in the presence of a compound of formula (II) and anamine in high yield, ##STR1## wherein, R.sup.1 is hydrogen or ##STR2## R.sup.Type: GrantFiled: January 9, 1987Date of Patent: May 30, 1989Assignee: Korea Advanced of Institute of Science and TechnologyInventors: Moon H. Chang, Bong J. Kim, Sung K. Kim, Woan J. Kim
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Patent number: 4826834Abstract: A compound having the general formula ##STR1## wherein, R.sup.0 is a hydrogen atom, a nitrogen-containing heterocyclic group, an acyl group or an amino-protective group; Z is S, S.fwdarw.O,O or CH.sub.2 ; R.sup.4 is a hydrogen atom, a methoxy group, or a formamide group; R.sup.13 is a hydrogen atom, a methyl group, a hydroxyl group, or a halogen atom; A.sym. is a condensed triazolio group which may be substituted, or a pharmaceutically acceptable salt or ester thereof is novel and has an excellent antibacterial activity.Type: GrantFiled: September 22, 1986Date of Patent: May 2, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Yoshinobu Yoshimura, Naoto Hashimoto, Shoji Kishimoto
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Patent number: 4822786Abstract: A cephalosporin compound having the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a halogen atom, a methoxy group, a substituted or unsubstituted vinyl group, or --CH.sub.2 --A wherein A is a hydrogen atom, an azido group, an acyloxy group, a carbamoyloxy group, a subsituted or unsubstituted heterocyclic group (wherein the hetrocyclic ring is a 5- or 6-membered heterocyclic ring having from 1 to 4 oxygen, nitrogen or sulfur atoms), or a substituted or unsubstituted heterocyclic thio group (wherein the heterocyclic ring is a monocyclic or bicyclic heterocyclic ring having from 1 to 5 oxygen, nitrogen or sulfur atoms), or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 17, 1987Date of Patent: April 18, 1989Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Yoshiyuki Zama, Nobuo Ishiyama, Tsuneo Saita, Takanobu Naito, Masao Hirose, Masaaki Yokoyama, Taiji Asano, Hisato Senda, Keiji Sekine, Shigeru Sanai
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Patent number: 4812562Abstract: Cephalosporin derivatives represented by the general formula ##STR1## wherein X represents a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, an amino group, a lower alkylcarbonylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkoxycarbonyl group, a carbamoyl group, a substituted carbamoyl group, a carbamoyloxy group, a lower alkylcarbonyl group, a lower alkenyl group, an ethynyl group, a thiocyanate group, an .alpha.-carboxyaminomethyl group, a phenyl group, a pyridinyl group or an aminothiazolyl group, and n is an integer of 1 to 3, and the non-toxic salts thereof, are disclosed. These compounds are useful as antibacterial agents.Type: GrantFiled: July 22, 1986Date of Patent: March 14, 1989Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoshiaki Watanabe, Chihiro Yokoo, Masami Goi, Akira Onodera, Mitsuo Murata, Hiroshi Fukushima, Kaoru Sota