Additional Hetero Ring Containing Patents (Class 540/222)
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Patent number: 4943631Abstract: The present invention provides compounds of general formula (III) ##STR1## [wherein R is an amino or protected amino group;R.sup.2a is a straight or branched chain alkyl group containing from 1 to 4 carbon atoms, an allyl, but-2-enyl or but-3-enyl group, or is a group of formula ##STR2## (wherein each of R.sup.3 and R.sup.4 is independently a hydrogen atom or a methyl or ethyl group, or R.sup.3 and R.sup.4 taken together with the carbon atom to which they are attached may be a cycloalkylidene group containing from 3 to 5 carbon atoms, and R.sup.5 is a hydrogen atom or a carboxyl blocking group);Y represents a 1-methyl-1-pyrrolidinium group andR.sup.7 represents the group --COO.sup.- or --COOR.sup.6, where R.sup.6 is a hydrogen atom or a carboxyl blocking group] and salts thereof.Type: GrantFiled: January 6, 1988Date of Patent: July 24, 1990Assignee: Glaxo Group LimitedInventor: Brian E. Looker
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Patent number: 4942159Abstract: Novel cephem compounds of the general formula: ##STR1## wherein R.sup.1 is a lower alkyl group, and salts and esters thereof, showing excellent and balanced antibacterial activity against a broad spectrum of bacteria, especially by rectal administration, and their production and use as antimicrobial agents are described.Type: GrantFiled: August 24, 1988Date of Patent: July 17, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Kiminori Tomimatsu, Akio Miyake
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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: 4935508Abstract: A process for the selective formation of oximino o-protected derivatives of lower alkyl 2-(2-aminothiazol-4-yl)-2-oximinoacetates, and their use in the acylation of 7-amino-cephalosporin compounds is disclosed.Type: GrantFiled: August 23, 1988Date of Patent: June 19, 1990Assignee: Bristol-Myers CompanyInventors: Hajime Kamachi, Takaaki Okita, Satsuki Okuyama, Takayuki Naito
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Patent number: 4935507Abstract: The invention relates to crystalline 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-car boxylic acid (syn isomer) useful as an antimicrobial agent.Type: GrantFiled: August 8, 1988Date of Patent: June 19, 1990Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Fumiyuki Shirai, Hitoshi Nakamura, Yasunobu Inaba
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Patent number: 4933443Abstract: An antibacterial, 7.beta.-[(Z)-2-(2-aminothiazol-4-yl)-4-carboxybut-2-enoylamino]-3-cephem-4 -carboxylic acid is stable in a (di or tri)-hydrate crystal form. A pharmacologically effective amount of this hydrate is filled in a gelatin hard capsule and sealed by a band of gelatin to make a stable composition for clinical use after storage for a long time.Type: GrantFiled: November 21, 1988Date of Patent: June 12, 1990Assignee: Shionogi & Co., Ltd.Inventors: Yoshio Hamashima, Kyoji Minami, Kyozo Kawata, Teruo Sakamoto, Toyohiko Takeda, Yusuke Suzuki, Masanori Tujikawa
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Patent number: 4931555Abstract: A process for producing a 2-cephem or 3-cephem derivative compound of the formula: ##STR1## wherein R.sub.1 represents a substituted or unsubstituted amino radical and R.sub.4 represents hydrogen or a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and the dotted line indicates the alternate bond structure providing 3-cephem or 2-cephem, which comprises:reacting a halogenated derivative selected from the group consisting of a halogenated penam derivative having the formula: ##STR2## a halogenated cepham derivative of the formula: ##STR3## wherein X represents a halogen atom, R.sub.3 represents a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and R.sub.1 is as defined above, or mixtures thereof with a dehydrohalogenoic acid reagent.Type: GrantFiled: January 26, 1981Date of Patent: June 5, 1990Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Takashi Kamiya, Yoshihisa Saito, Tsutomu Teraji, Osamu Nakaguit, Teruo Oku, Hitoshi Nakamura, Masashi Hashimoto
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Patent number: 4929612Abstract: Novel thiadiazolylacetamide cephem derivatives of the following formula are described. ##STR1## wherein A represents a quaternary ammonio group; or a pharmaceutically acceptable salt thereof. These novel compounds are useful as antibacterial agents, because they have a broad antibacterial spectrum ranging from gram-negative bacteria to gram-positive bacteria. Processes for the preparation of these novel compounds are also described.Type: GrantFiled: April 14, 1988Date of Patent: May 29, 1990Assignee: Eisai Co., Ltd.Inventors: Yoshimasa Machida, Shigeto Negi, Takashi Kamiya, Yuuki Komatu, Isao Sugiyama, Yasunobu Kai, Takaharu Nakamura, Toshihiko Naito, Kyosuke Kitoh, Kanemasa Katsu, Hiroshi Yamauchi
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Patent number: 4927818Abstract: 7 .beta.-[2-5 amino-1, 2, 4 thiadiazol-3yl) 2(carboxy lower alkyleneoxyimino) acetamido]-3-(3-amino-2-alkyl-1-pyrazolio) methyl 3 cephem 4 carboxylates are prepared. They are antibiotics.Type: GrantFiled: August 28, 1987Date of Patent: May 22, 1990Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Kazuo Sakane, Kenzi Miyai, Kohji Kawabata
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Patent number: 4921851Abstract: This invention relates to a compound of the formula: ##STR1## wherein Q is nitrogen or CH; R.sup.1 is hydrogen or a lower alkyl group which may be substituted; and ring A is a pyridine or pyridazine ring which is substituted at the ring-constituting carbon atom by a group of the formula:--E--(CH.sub.2).sub.n --R.sup.2in which E is sulfur or NH; R.sup.2 is an amino, carbamoylamino, formylamino, acetylamino, N-formimidoylamino, N-acetimidoylamino, lower alkylamino, hydroxyl or carbamoyloxy group; and n is an integer of 2 to 4, or a pharmaceutically acceptable salt thereof. The compound (I) or a pharmaceutically acceptable sale thereof has excellent antibacterial activity and is used as antibiotics.Type: GrantFiled: August 22, 1989Date of Patent: May 1, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Kiminori Tomimatsu, Akio Miyake, Yoshinobu Yoshimura
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Patent number: 4921850Abstract: A 3-propenylcephem derivative of the following formula: ##STR1## wherein R.sub.1 represents a fluoro-substituted lower alkyl group or a cyano-substituted lower alkyl group, and A represents a cyclic or an acylic ammonio group, or a pharmaceutically acceptable salt thereof, exhibiting excellent anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria; Process for the preparation thereof; Anti-bacterial composition; Intermediate for the 3-propenylcephem derivative; and Process for the preparation of the intermediate.Type: GrantFiled: October 13, 1987Date of Patent: May 1, 1990Assignee: Eisai Co., Ltd.Inventors: Takashi Kamiya, Toshihiko Naito, Shigeto Negi, Yuuki Komatu, Yasunobu Kai, Takaharu Nakamura, Isao Sugiyama, Yoshimasa Machida, Seiichiro Nomoto, Kyosuke Kitoh, Kanemasa Katsu, Hiroshi Yamauchi
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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: 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: 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: 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: 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: 4910301Abstract: Crystalline sulfuric, di-nitric, mono-hydrochloric, di-hydrochloric, and di- and sesqui-orthosphosphoric acid addition salts of 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyiminoacetamido]-3-[(1- methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylate are stable even at elevated temperatures. The crystalline sulfuric acid addition salt is made by forming an admixture of (a) at least one molar equivalent of sulfuric acid with (b) zwitterion in an amount so as to be present in the admixture at a concentration of greater than 25 milligrams/ml, causing crystallization, separating the crystals, washing and drying. The crystalline monohydrochloride, dihydrochloride, and orthophosphate salts are prepared by dissolving the zwitterion in the appropriate amount of acid, causing crystallization by adding acetone and isolating the crystals. Physical admixtures of the salts with certain bases in proportions to give a pH ranging from about 3.Type: GrantFiled: January 19, 1988Date of Patent: March 20, 1990Assignee: Bristol-Myers CompanyInventors: Murray A. Kaplan, Thomas W. Hudyma, Robert A. Lipper, Kun M. Shih, Susan D. Boettger
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Patent number: 4908444Abstract: A method of producing 3-alkanoyloxymethyl-3-cephem-4-carboxylic acids, which are useful as antibiotics or as intermediates in the synthesis of antibiotics, by reacting a 3-hydroxymethyl-3-cephem-4-carboxylic acid with a saturated fatty acid anhydride in an aqueous medium in the presence of an acid-acceptor base and a 4-(tertiary amino)pyridine.Type: GrantFiled: January 14, 1987Date of Patent: March 13, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi
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Patent number: 4906748Abstract: Disclosed herein are 7.beta.-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3- (4-carbamoyl-1-quinuclidinio)methyl-3-cephem-4-carboxylate crystals comprising X-ray diffraction pattern possessing the characteristic diffraction intensity at the spacing d (unit: angstrom) shown in the following (i), (ii) or (iii):(i): 6.2, 5.1 and 5.0;(ii): 10.6, 5.3 and 5.1;(iii): 15.4, 5.0 and 4.6.A process for the preparation of the crystals is also disclosed.Type: GrantFiled: July 11, 1988Date of Patent: March 6, 1990Assignee: Eisai Co., Ltd.Inventors: Kazuhide Ashizawa, Kiyohiko Uchikawa, Tadashi Sato, Yasuo Ishibashi
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Patent number: 4906623Abstract: A cephalosporin compound substituted by imidazolium ring in 3-position of cephem having the following formula (I), and pharmaceutically acceptable salt thereof, ##STR1## wherein R.sup.1 is an organic residue known in .beta.-lactam antibiotics, R.sup.2 is hydrogen atom or methoxy, n is 0 or 1, A is a nitrogen-containing group constituting imidazolium ring, is useful as an agent for preventing and treating bacterial infections.Type: GrantFiled: March 25, 1988Date of Patent: March 6, 1990Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Kiyotoshi Matsumura, Hiroshi Akagi, Daisuke Suzuki, Akihiro Shimabayashi
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Patent number: 4904652Abstract: The compound 7[2-(aminothiazol-4-yl)-2-methyoxyiminoacetamido]-methylthiomethyl-3-cephe m-4-carboxylic acid or carboxylic ester thereof, or a pharmaceutically acceptable salt thereof is disclosed as an antimicrobial agent.Type: GrantFiled: October 9, 1985Date of Patent: February 27, 1990Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Takashi Masugi, Hideaki Yamanaka, Kohji Kawabata
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Patent number: 4902793Abstract: A process for preparing 3-alkoxymethylcephalosporins which are useful as an intermediate for various cephalosporin derivatives having a high antimicrobial activity is disclosed. According to the process of the present invention, the 3-alkoxymethylcephalosporins can be easily obtained in high yield on a commercial scale.Type: GrantFiled: October 1, 1987Date of Patent: February 20, 1990Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Joji Nishikido, Kentaro Fukuzaki
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Patent number: 4894371Abstract: An antibacterial cephalosporin derivative of the formula I: ##STR1## in which X is S,O,CH.sub.2 or S0; R2 is hydrogen, methoxy or formylamino; R3 is carboxy or a biodegradable ester thereof; R1 represents a variety of groups known in the cephalosporin art and R4 represents a group NR42R43 wherein R42 is hydrogen, lower alkyl or benzyl and R43 is one of a group of neutral heterocyclic species defined in the specification. Pharmaceutical compositions, manufacturing processes and intermediates are also described. In a specific embodiment, 3-substituted aminomethyl cephalosporin derivatives in which X is S or SO are disclosed.Type: GrantFiled: December 9, 1986Date of Patent: January 16, 1990Assignee: ICI PharmaInventor: Frederic H. Jung
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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: 4883868Abstract: A compound having the formula: ##STR1## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a hydrogen atom or a protecting group for a hydroxyl group, R.sup.3 represents negative charge, a hydrogen atom or a protecting group for a carboxyl group, and n is 0 or 1, and a salt thereof.Type: GrantFiled: June 22, 1987Date of Patent: November 28, 1989Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Ryosuke Ushijima, Fumio Nakano, Koji Yamada, Eiichi Mano
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Patent number: 4880795Abstract: Novel cephalosporins of the formula ##STR1## in which R.sup.1 is an aliphatic or cycloaliphatic hydrocarbyl radical of up to 6 carbon atoms which is optionally substituted by a carboxyl group, ##STR2## R.sup.2 and R.sup.3 each independently is an optionally substituted aliphatic or cycloaliphatic hydrocarbyl radical of up to 6 carbon atoms, but is not unsubstituted methyl,or pharmaceutically acceptable salts thereof, are effective antibacterially and promote the growth of animals.Type: GrantFiled: March 3, 1987Date of Patent: November 14, 1989Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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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: 4879381Abstract: Novel cephalosporins which has attached to the exomethylene group at the 3-position of the cephem ring a substituted or unsubstituted aryl, acylamino, aromatic heterocyclic, triazolyl or tetrazolyl group, said aromatic heterocyclic group being attached through a carbon-carbon bond and said triazolyl or tetrazolyl group being attached through a carbon-nitrogen bond, and has the following group attached to the amino group at the 7-position: ##STR1## wherein A represents a group of the formula, --CH.sub.2 -- or a group of the formula ##STR2## in which R.sup.5 represents a hydrogen atom or an alkyl group, and the bond represents syn or anti isomer or their mixture; R.sup.3 represents a hydrogen or halogen atom; and R.sup.4 represents a hydrogen atom or an amino group which may be protected or substituted. These cephalosporins have a broad antibacterial spectrum, are stable against .beta.-lactamase produced by bacteria, have a low toxicity, and are well absorbed when administered orally or parenterally.Type: GrantFiled: March 6, 1987Date of Patent: November 7, 1989Assignee: Toyoma Chemical Company, Ltd.Inventors: Hiroshi Sadaki, Narita Hirokazu, Hiroyuki Imaizumi, Yoshinori Konishi, Takihiro Inaba, Tatsuo Hirakawa, Hideo Taki, Masaru Tai, Yasuo Watanabe, Isamu Saikawa
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Patent number: 4877782Abstract: Zinc ceftiofur complexes, e.g., zinc ceftiofur hydrochloride and zinc ceftiofur sodium complexes, have been found to provide the good antibiotic activity of ceftiofur while providing low dissolution rate and long half-life properties enabling the formulation of improved long term therapy forms of ceftiofur, useful in antibiotic therapy of valuable warm-blooded animals. Pharmaceutical compositions of such zinc ceftiofur complexes and a method of using such zinc ceftiofur complexes in veterinary antibiotic applications are also provided.Type: GrantFiled: February 16, 1988Date of Patent: October 31, 1989Assignee: The Upjohn CompanyInventors: Alexander R. Cazers, K. Thomas Koshy
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Patent number: 4876351Abstract: A process for the separation of a mixture of syn and anti oxime isomers one from the other which comprises adsorbing said mixed oxime isomers onto a non-functional macroreticular adsorption resin, and eluting said resin to yield at least one eluate fraction containing one of said isomers while being substantially free of the other of said isomers.The application of this process to the separation of syn and anti isomers of cephalosporin compounds possessing an oxime grouping in a side-chain in the 7.beta.-position, and of acids corresponding to this 7.beta.-side chain, is described.Type: GrantFiled: October 30, 1987Date of Patent: October 24, 1989Assignee: Glaxo Group LimitedInventors: Colin Robinson, David T. Eastlick, Audrey J. Bownass
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Patent number: 4874856Abstract: This invention provides novel cephalosporanic acids and esters thereof having the general formula ##STR1## wherein R.sup.2 is hydrogen, or lower acyl, R.sup.3 is hydrogen, or lower alkanoyloxy, andR.sup.4 is hydrogen, 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl, 1-(ethoxycarbonyloxy)ethyl,1-(pivaloyloxy)ethyl, 1-(cyclohexylacetoxy)ethyl, or 1-(cyclohexyloxycarbonyloxy) ethyl. These compounds, especially esters, are useful as broad spectrum antibiotics in the treatment and prevention of infectious diseases of mammals, and for other purposes known in the art. The acids (R.sup.4 is hydrogen) are useful as intermediates for making the esters.Type: GrantFiled: August 17, 1987Date of Patent: October 17, 1989Assignee: Bristol-Myers CompanyInventors: Seiji Iimura, Yoshio Abe, Jun Okumura, Takayuki Naito, Hajime Kamachi
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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: 4870168Abstract: There is disclosed a process for the production of certain 3-hydrocarbyl-3-cephem derivatives wherein the hydrocarbyl group is selected from 1-alkenyl and conjugated and unconjugated 1-polyalkenyl, 1-alkynl, carbocyclic and heterocyclic aryl, and carbocyclic and heterocyclic arylmethyl and, in the case of the 1-alkenyl and conjugated 1-polyalkenyl derivatives, with substantially complete stereospecificity, by coupling a 3-triflyloxy cephem with a hydrocarbyltributylstannane in the presence of bis(dibenzylideneacetonyl)-palladium, a phosphine, and a metal halide such as, for example, zinc chloride. The 3-unsaturated alkyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.Type: GrantFiled: February 26, 1987Date of Patent: September 26, 1989Assignee: Bristol-Myers CompanyInventors: Stephen R. Baker, Vittorio Farina, Chester Sapino, Jr.
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Patent number: 4868173Abstract: According to the invention there is provided a antibacterial cephalosporin derivative of the formula: ##STR1## in which X is sulphur, oxygen, methylene or sulphinyl; R3 is hydrogen or methoxy; R1 and R2 are known in the cephalosporin art and R4 is an aminomethyl group in which the amino group carries one of various positively charged nitrogen-containing species set out in the specification and optionally a further substituent selected from hydrogen, lower alkyl, benzyl or heteroarylloweralkyl groups.Type: GrantFiled: November 15, 1985Date of Patent: September 19, 1989Assignee: ICI PharmaInventor: Frederic H. Jung
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Patent number: 4868174Abstract: The invention relates to an antimicrobial agent of the formula: ##STR1## wherein R.sup.1 is amino or conventional protected amino, R.sup.2 is hydrogen or tetrahydropyranyl, and ##STR2## wherein R.sup.4 is lower alkyl, and R.sup.5 is hydrogen or lower alkyl substituted with hydroxy or conventional protected hydroxy, and pharmaceutically acceptable salts thereof.Type: GrantFiled: January 29, 1987Date of Patent: September 19, 1989Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Yoshiko Inamoto
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Patent number: 4868294Abstract: Processes for the preparation of stable, crystalline cephalosporin intermediates of the formula ##STR1## wherein X is HI or HCl, and Nu and Nu.sup..sym. are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the .DELTA..sup.2 isomer; processes for intermediates in the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.Type: GrantFiled: March 23, 1987Date of Patent: September 19, 1989Assignee: Bristol-Myers CompanyInventors: Steven P. Brundidge, Paul R. Brodfuehrer, Chet Sapino, Jr., Kun M. Shih, Donald G. Walker
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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: 4855420Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, R1 is (optionally-substituted) imidazol-2-yl or one of the C-7 acyl groups known in the cephalosporin art, R2 is hydrogen or methoxy, R3 is carboxy or a biodegradable ester thereof and -R4 is of the formula XII, XIII or XIV: ##STR2## in which R32-R40 inclusive are as defined in the specification; and the salts thereof. Pharmaceutical compositions, methods of manufacture and intermediates are also described.Type: GrantFiled: April 13, 1987Date of Patent: August 8, 1989Assignee: Ici PharmaInventor: Frederic H. Jung
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Patent number: 4855418Abstract: Cephalosporin and 1-carba(1-dethia)cephalosporin antibiotics substituted in the 3-position with, inter alia, alkyl, alkenyl and alkynyl, are provided via process comprising conversion of a cephalosporin or 1-carba(1-dethia)-3-cephem substituted in the 3-position with halogen or a sulfonyloxy ester with Pd(O) mediated alkylation with organostannanes.Type: GrantFiled: March 23, 1988Date of Patent: August 8, 1989Assignee: Eli Lilly and CompanyInventors: Gwendolyn K. Cook, John H. McDonald, III
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Patent number: 4853468Abstract: This invention provides azetidinone derivatives represented by the formula ##STR1## and processes for preparing the same. The azetidinone derivatives are used as the intermediates for producing cephalosporin compounds useful as antibiotic agents.Type: GrantFiled: March 11, 1988Date of Patent: August 1, 1989Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Kenji Uneyama, Hideo Tanaka, Junzo Nokami, Michio Sasaoka, Norio Saito, Takashi Shiroi
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Patent number: 4847373Abstract: There is disclosed a process for the production of certain 2-allyl- and 3-butenyl-3-cephem derivatives by coupling a 3-chloromethyl-3-cephem with a hydrocarbyltributystannane in the presence of bis(dibenzylideneacetonyl)-palladium and a phosphine. The 3-allyl- and 3-butenyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.Type: GrantFiled: February 26, 1987Date of Patent: July 11, 1989Assignee: Bristol-Myers CompanyInventors: Stephen R. Baker, Vittorio Farina, Chester Sapino, Jr.
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Patent number: 4845211Abstract: Various 7-amino-3-substituted-methyl-3-cephem-4-carboxylic acids and lower alkylsily derivatives such as 7-amino-3-(2,3-cyclopenteno-1-pyridiniomethyl)-3-cephem-4 -carboxylic acid iodide and trimethylsilyl 7-trimethylsilylamino-3 -(5,6,7,8-tetrahydro-2-isoquinoliniomethyl)-3-cephem-4 -carboxylate iodide are valuable intermediates in the preparation of new and novel antibacterial agents. A new process for the preparation of these acids and the derivatives has been devised.Type: GrantFiled: May 4, 1987Date of Patent: July 4, 1989Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Tadao Shibanuma, Kohji Nakano, Noriaki Nagano, Yukiyasu Murakami, Ryuichiro Hara, Akio Koda, Atsuki Yamazaki
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Patent number: 4845088Abstract: Tetrazolyl derivatives of .beta.-lactams are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: June 5, 1987Date of Patent: July 4, 1989Assignee: Merck & Co., Inc.Inventors: James B. Doherty, William K. Hagmann, Paul E. Finke, Shrenik K. Shah
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Patent number: 4845087Abstract: Crystallized cephem-acid addition salts of the general formula ##STR1## pharmaceutical preparations which contain such cephem derivatives and are active against bacterial infections, a process for the preparation of the cephem derivatives and the pharmaceutical preparations, and the use of the cephem derivatives for combating bacterial infections.Type: GrantFiled: February 23, 1988Date of Patent: July 4, 1989Assignee: Hoechst AktiengesellschaftInventors: Rudolf Lattrell, Walter Durckheimer, Reiner Kirrstetter
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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: 4826972Abstract: The invention provides crystalline (6R, 7R)-7-[[2-(2-Amino-4-thiazolyl)-(Z)-2-(1-diphenylmethoxycarbonyl-1-methyle thoxy)imino ]acetamido]-3-(1-pyridiniummethyl)-3-cephem-4-carboxylate and a process for its production.Type: GrantFiled: June 3, 1987Date of Patent: May 2, 1989Assignee: BIOCHEMIE Gesellschaft m.b.H.Inventor: Bernhard C. Prager
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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