Additional Hetero Ring Containing Patents (Class 540/222)
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Patent number: 4820833Abstract: There is described a product which is a highly pure substantially amorphous form of cefuroxime axetil (cefuroxime 1-acetoxyethyl ester) which is stable, which has increased absorption via the gastro-intestinal tract and has a correspondingly high level of bioavailability on oral or rectal administration.Methods of preparing the product are also described which involve the recovery of the product from a solution thereof. A preferred method is the use of spray drying techniques, though roller drying, solvent precipitation or freeze-drying are also described.Also disclosed are pharmaceutical compositions containing the product and methods for its use in medicine.Type: GrantFiled: December 4, 1986Date of Patent: April 11, 1989Assignee: Glaxo Group LimitedInventors: Harold A. Crisp, John C. Clayton, Leonard G. Elliott, Edward M. Wilson
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Patent number: 4820832Abstract: A process for preparing 7.beta.-acylamino (or 7.beta.-protected amino)-3-H-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters and the corresponding cephalosporins is provided. 7.beta.-Acylamino (or 7.beta.-protected amino)-3-halo (or 3-sulfonyl ester)-1-carba(dethia)-3-cephem carboxylic acid esters and the corresponding cephalosporins are reduced with Pd(O) and a tetra-C.sub.2 -C.sub.6 alkyl stannane and, when a 3-sulfonyloxy ester is reduced, the process is carried out in the presence of an alkali metal halide. 3-Sulfonyloxy-3-cephem esters such as 3-mesylate, 3-tosylate and 3-triflate are employed.Type: GrantFiled: March 23, 1988Date of Patent: April 11, 1989Assignee: Eli Lilly and CompanyInventors: Gwendolyn K. Cook, John H. McDonald, III
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Patent number: 4814328Abstract: The compound having the formula: ##STR1## wherein R is a straight chain, branched chain or cyclic lower alkyl, a lower alkenyl or a lower alkynyl group which may be substituted by a carboxyl group, and R.sup.1 is hydrogen atom or an acetyl group; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: September 26, 1986Date of Patent: March 21, 1989Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Norikazu Otake, Ryosuke Ushizima
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Patent number: 4812561Abstract: 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 sealed by a band of gelatin to make a stable composition for clinical use after storage for a long time.Type: GrantFiled: July 1, 1987Date of Patent: March 14, 1989Assignee: Shionogi & Co., Ltd.Inventors: Yoshio Hamashima, Kyoji Minami, Kyozo Kawata, Teruo Sakamoto, Toyohiko Takeda, Yusuke Suzuki, Masanori Tujikawa
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Patent number: 4808617Abstract: Amorphous solid formed by lyophilization or cosolvent precipitation of an aqueous solution of 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoximinoacetamido]-3-[(1-m ethyl-1-pyrrolidinio)-methyl[-3-cephem-4-carboxylate zwitterion and a salt or mixture of salts from a selected particular group is a broad spectrum antibiotic composition and has better temperature stability at least up to 45.degree. C. than the zwitterion. The salt is one wherein the cation is selected from the group consisting of sodium, lithium, calcium, and magnesium and the anion is selected from the group consisting of chloride, bromide, and iodide. The molar ratio of zwitterion to salt ranges from about 0.5:1 to about 2:l.Type: GrantFiled: January 9, 1987Date of Patent: February 28, 1989Assignee: Bristol-Myers CompanyInventors: Murray A. Kaplan, Nageswara R. Palepu, Joseph B. Bogardus
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Patent number: 4808712Abstract: A process for preparing cephalosporin compounds represented by the formula ##STR1## wherein R.sup.1 represents an alkyl group, alkenyl group, substituted or unsubstituted aryl group, substituted or unsubstituted arylmethyl group or substituted or unsubstituted phenoxymethyl group, R.sup.2 represents a carboxyl group or protected carboxyl group, and Y represents the residue of a nucleophilic reagent.Type: GrantFiled: October 14, 1986Date of Patent: February 28, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventor: Shigeru Torii
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Patent number: 4808711Abstract: There is disclosed a novel .beta.-lactam antibiotics represented by the formula: ##STR1## wherein A is a group represented by the formulae -NHCO--, --NHCONHCO--, --NHCOCH.dbd.CH-- or ##STR2## where R.sub.6 is a hydrogen atom or a lower alkyl group; R.sub.1 and R.sub.2 are independently a hydrogen atom or a protective group; R.sub.3 is a hydrogen atom or a methoxy group; X is a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a halogen atom, a lower alkoxy group or a nitro group; n is an integer of 1 or 2; Y is a group represented by the formulae: ##STR3## provided that a carbon atom which is bonded by a carboxyl group being bonded to nitrogen atom; M is a hydrogen atom, a protective group or an easily hydrolyzable group in a human body; R.sub.7 is a hydrogen atom, a methyl group a lower alkoxy-methyl group or a group represented by the formula: --CH.sub.Type: GrantFiled: January 17, 1986Date of Patent: February 28, 1989Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Co.Inventors: Shigeo Shimizu, Hiroyuki Takano, Fujio Yagihashi
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Patent number: 4801703Abstract: A novel method of producing a cephalosporin compound of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or an acyl group; R is a hydrogen atom or an ester residue; the dotted line means a double bond in 2- or 3-position of the cephem ring; and R.sup.4 is a nucleophilic compound residue, or a salt thereof, directedly in one step from a compound of the formula ##STR2## wherein R.sup.1, R and the dotted line have the meanings defined above, or a salt thereof, by reacting in the presence of an organic solvent the compound [II] or a salt thereof, a nucleophilic compound or a salt thereof, and (1) a trivalent or pentavalent cyclic phosphorus compound having a partial structure of the formula ##STR3## wherein W is an oxygen atom, a sulfur atom or NR.sup.2 ; W.sup.1 is an oxygen atom, a sulfur atom or NR.sup.3 ; and R.sup.2 and R.sup.Type: GrantFiled: August 18, 1986Date of Patent: January 31, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Masayasu Kato, Kazuo Tsukamura
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Patent number: 4800199Abstract: Cephalosporins active as antibacterial agents, and processes for synthesis of such agents, are disclosed.Type: GrantFiled: October 20, 1986Date of Patent: January 24, 1989Assignee: American Cyanamid CompanyInventors: Robert Babine, Ving J. Lee
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Patent number: 4791196Abstract: A storage stable form of the crystalline sulfate of 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[5-(2-hydroxyeth yl)-4-methylthiazoliomethyl]-3-cephem-4-carboxylate has a specified X-ray diffraction pattern and is prepared by adding aqueous sulfuric acid to an aqueous solution of the compound under controlled conditions.Type: GrantFiled: September 23, 1987Date of Patent: December 13, 1988Assignee: Sankyo Company LimitedInventors: Junya Ide, Koichi Fujimoto
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Patent number: 4788185Abstract: A compound of the formula; ##STR1## wherein R.sup.0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S.fwdarw.O, O or CH.sub.2, R.sup.4 stands for hydrogen atom, methoxy group or formamido group, R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof.This compound is novel and has excellent antibacterial activity.Type: GrantFiled: April 23, 1985Date of Patent: November 29, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4783443Abstract: Antibacterial cephalosporin compounds of the Formula (I): ##STR1## wherein W is a pharmaceutically acceptable salt or a carboxyl-protecting group; n is an integer from 1 to 2; --X-- is --X.sup.1 -- where the X.sup.1 moieties are the same or different and selected from the group consisting of (D) or (L) ##STR2## Y is --O--; wherein R.sup.1 is selected from the group consisting of: ##STR3## R.sup.2 is H, --CH.sub.2 R.sup.4, --CHR.sup.5.sub.2 or --CR.sup.5.sub.3, wherein R.sup.4 is H, F, Cl, Br, --OH, --CN, ##STR4## --CH(CH.sub.3).sub.2, --CH.sub.2 (OH), ##STR5## or --C.tbd.CH, where Q.sup.1, Q.sup.2 and Q.sup.3 are the same or different and selected from the group consisting of H, F, Cl or Br; R.sup.5 is F, Cl or Br; and Z.sup.1 is H or an amino protecting group.Type: GrantFiled: March 3, 1986Date of Patent: November 8, 1988Assignee: The University of ChicagoInventors: Michael A. Johnston, Shahrair Mobashery
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Patent number: 4775750Abstract: There is disclosed a process for preparing sodium cefuroxime in very high purity. The process comprises reacting (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyimino-acetamido]-3-hydroxymethylceph-3- em-4-carboxylic acid with a halosulphonyl isocyanate in an alkyl acetate solvent, hydrolyzing the resulting intermediate product, forming sodium cefuroxime by the addition of the sodium salt of a weak acid and isolating the sodium cefuroxime in high purity. The use of methyl acetate is particularly preferred and reaction can be carried out at from -25.degree. to +25.degree. C. The hydrolysis, generally in situ, may be carried out at from 10.degree. to 30.degree. C. Fewer steps are required than in previous processes and the product is of higher purity.Type: GrantFiled: December 1, 1986Date of Patent: October 4, 1988Assignee: Glaxo Group LimitedInventors: Herbert J. White, David T. Eastlick, John F. Oughton
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Patent number: 4767754Abstract: Antibacterially effective cephalosporins of the formula ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.6 -alkyl, phenyl or halogen-substituted phenyl andA represents a nitrogen-containing, positively charged heterocyclic 5-membered to 7-membered ring which is bonded via N and can contain a total of up to 4 hetero-atoms from the group comprising N, O and S, and onto which up to two further rings can be fused, and which can optionally be substituted, with the proviso that, if the ring is a 6-membered ring, A does not represent an unsubstituted pyridine ring or a pyridine ring which is mono- or di-substituted by identical or different substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, chlorine, bromine, carbamoyl or N-C.sub.1 -C.sub.4 -alkylcarbamoyl, or pharmaceutically acceptable salts thereof or esters thereof which can be split under physiological conditions.Type: GrantFiled: October 30, 1986Date of Patent: August 30, 1988Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4767852Abstract: Process for the production of known 2-oximinoacetamido-3-cephem-4-carboxylic derivatives comprising acylation of 7-amino-3-cephem-4-carboxylic acid derivatives with novel 2-oximinoacetic acid thio esters, as well as such thioesters and their production.Type: GrantFiled: November 19, 1986Date of Patent: August 30, 1988Assignee: BiochemieInventor: Gerd Ascher
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Patent number: 4758556Abstract: Cephem derivatives of the general formula ##STR1## in which the R.sub.2 O group is in the syn-position, a process for their manufacture and pharmaceutical formulations which are active against bacterial infections and contain these compounds.Type: GrantFiled: March 30, 1978Date of Patent: July 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Walter Durckheimer, Dieter Bormann, Eberhard Ehlers, Elmar Schrinner, Rene Heymes
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Patent number: 4757065Abstract: Antibacterially effective cephalosporins of the formula ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.6 -alkyl, phenyl or halogen-substituted phenyl andA represents a nitrogen-containing, positively charged heterocyclic 5-membered to 7-membered ring which is bonded via N and can contain a total of up to 4 hetero-atoms from the group comprising N, O and S, and onto which up to two further rings can be fused, and which can optionally be substituted, with the proviso that, if the ring is a 6-membered ring, A does not represent an unsubstituted pyridine ring or a pyridine ring which is mono- or di-substituted by identical or different substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, chlorine, bromine, carbamoyl or N--C.sub.1 -C.sub.4 -alkylcarbamoyl,or pharmaceutically acceptable salts thereof or esters thereof which can be split under physiological conditions.Type: GrantFiled: November 20, 1984Date of Patent: July 12, 1988Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4754031Abstract: A process for the preparation of a cephalosporin of the formula ##STR1## in which R.sup.1 is an aliphatic or cycloaliphatic radical with up to 6 carbon atoms, andA is a pyridinium radical or a radical of the formula ##STR2## comprising reacting an acid of the formula ##STR3## with methanesulphonyl chloride to form an anhydride of the formula ##STR4## and reacting the anhydride with a 7-aminocephalosporanate of the formula ##STR5## The reaction proceeds smoothly and in high yield.Type: GrantFiled: May 6, 1985Date of Patent: June 28, 1988Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Gunther Kinast
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Patent number: 4751295Abstract: 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(substituted)-iminoacetamido]-3-[3-( quaternaryammonio)-1-propen-1-yl]-3-cephem-4-carboxylates of the formula ##STR1## in which R.sup.1 and R.sup.2 are defined herein and --.sup..sym. N.tbd.Q is a quaternary ammonio group as defined herein, and salts, solvates, hydrates and esters thereof, are potent antibacterial agents. Processes for their preparation and intermediates in such processes are described.Type: GrantFiled: October 17, 1986Date of Patent: June 14, 1988Assignee: Bristol-Myers CompanyInventors: Masahisa Oka, Haruhiro Yamashita, Jun Okumura, Takayuki Naito
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Patent number: 4748171Abstract: Described herein is a cephem derivative represented by the general formula: ##STR1## wherein n stands for 1 or 2, Y stands for CH or nitrogen atoms, R.sub.1 represents a lower hydrocarbon group or a carboxyl-substituted, a carbamoyl-substituted, or a cyclopropyl-substituted lower alkyl group, and R.sub.2 denotes hydroxyl group, a lower alkyl group, a hydroxy-substituted lower alkyl group, or carbamoyl group. The derivative is useful as an antibacterial agent. Also described herein are processes for the production of the derivative, antibacterial composition, intermediate of the derivative and process for the production thereof.Type: GrantFiled: January 14, 1986Date of Patent: May 31, 1988Assignee: Eisai Co., Ltd.Inventors: Hiroshi Yamauchi, Isao Sugiyama, Isao Saito, Seiichiro Nomoto, Takashi Kamiya, Yoshimasa Machida, Shigeto Negi
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Patent number: 4748163Abstract: Antibacterially active and animal growth-promoting novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents the radical ##STR2## Y representing N or CR.sup.9, or Y--R.sup.7 representing >C.dbd.O or >C.dbd.N--R.sup.7,Z representing O, S, or NR.sup.10, andR.sup.2 represents hydrogen or a protective group.Type: GrantFiled: February 21, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4748170Abstract: An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group; R.sup.1 is hydrogen or halogen;R.sup.2 is a single bond, alkylene, or thiaalkylene;R.sup.3 is a hydrogen atom or carboxy modifying group;R.sup.4 is hydrogen or methoxy;R.sup.5 is hydrogen or a 3-substituent of cephalosporins;R.sup.6 is a hydrogen atom or carboxy modifying group; andX is oxygen, sulfur, or sulfinyl)a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.Type: GrantFiled: February 20, 1986Date of Patent: May 31, 1988Assignee: Shionogi & Co., Ltd.Inventor: Yoshio Hamashima
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Patent number: 4748172Abstract: Cephalosporin compounds substituted in the 7-position by a 2-(5- or 6-membered heterocyclic)-2-oximinoacetylamino group and in the 3-position with an imidazolo, oxazolo or thiazolopyridinium-methyl group are broad spectrum antibiotics highly effective in combating bacterial infections of gram-negative and gram-positive microorganisms. The cephalosporins are best prepared by reacting a silylated 7-[2-(heterocyclic)-2-oximinoacetylamino-3-iodomethyl-3-cephem-4-carboxyli c acid with an imidazolopyridine, an oxazolopyridine or a thiazolopyridine. Pharmaceutical formulations comprising a compound of the invention and a method for treating bacterial infections comprising their use are also provided.Type: GrantFiled: January 12, 1987Date of Patent: May 31, 1988Assignee: Eli Lilly and CompanyInventor: Allen S. Katner
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Patent number: 4742053Abstract: The invention relates to an antibiotic comprising a compound having the formula: ##STR1## wherein R.sup.1 is a straight chain, branched chain, or cyclic lower alkyl group which may be substituted by a carboxyl group, and R.sup.2 designates vicinal dihydroxyl groups or diacetoxy groups; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: November 8, 1985Date of Patent: May 3, 1988Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Ryosuke Ushijima, Eiichi Mano, Norikazu Ban, Minoru Sanada
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Patent number: 4735937Abstract: The invention concerns 7-amino-ceph-3-em-4-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1.sup.a represents hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represent hydrogen or an acyl group AC, or R.sub.1.sup.A and R.sub.1.sup.b together denote a bivalent amino protective group, and R.sub.2 represents hydrogen or an organic radical R.sub.2.sup.A which together with the --C(.dbd.O)--O-- grouping forms a protected carboxyl group, or salts such compounds which possess salt-forming groups; these compounds have antibiotic properties.Type: GrantFiled: March 28, 1986Date of Patent: April 5, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Karl Heusler, Hans Bickel, Bruno Fechtig, Heinrich Peter, Riccardo Scartazzini
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Patent number: 4736026Abstract: The invention relates to a process for producing a cephalosporin of the formula ##STR1## by reacting the compound ##STR2## with the compound ##STR3## in the presence of boron trifluoride or a complex thereof.Type: GrantFiled: June 24, 1986Date of Patent: April 5, 1988Assignee: Toyama Chemical Co., Ltd.Inventors: Hiroyuki Imaizumi, Takihiro Inaba, Seishi Morita, Ryuko Takeno, Yoshiharu Murotani, Hirohiko Fukuda, Junichi Yoshida, Kiyoshi Tanaka, Shuntaro Takano, Isamu Saikawa
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Patent number: 4734407Abstract: Antibacterially active and animal growth-regulating novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical of the formula ##STR2## Z represents oxygen, sulphur or --N--R.sup.Type: GrantFiled: March 10, 1986Date of Patent: March 29, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4731361Abstract: An oral antibacterial, 7beta-[(Z)-2-(2-aminothiazol-4-yl)-2-alkenoylamino]-3-cephem-4-carboxylic acid pharmaceutically acceptable ester represented by the following formula: ##STR1## (wherein R is amino or protected amino,R.sup.1 is straight, branched, or cyclic alkyl optionally substituted by alkoxy,R.sup.2 is hydrogen or a 3-substitutent of cephalosporins,R.sup.3 is a pharmaceutically acceptable ester group, andX is sulfur or sulfinyl).Type: GrantFiled: March 27, 1986Date of Patent: March 15, 1988Assignee: Shionogi & Co., Ltd.Inventors: Yoshio Hamashima, Koji Ishikura, Kyoji Minami, Tadatoshi Kubota, Tadashi Yoshida
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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: 4729991Abstract: The invention relates to novel cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or protected amino,R.sup.2 is halogen,R.sup.3 is hydrogen or lower alkyl,R.sup.4 is hydrogen, lower alkyl or lower alkoxy,R.sup.5 is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxymethyl or unsaturated heterocyclicthiomethyl in which the heterocyclic moiety may be substituted with lower alkyl or lower alkenyl, andR.sup.6 is carboxy or functionally modified carboxy, and its pharmaceutically acceptable salt thereof.Type: GrantFiled: September 24, 1982Date of Patent: March 8, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Masakazu Kobayashi, Tadashi Kitaguchi
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Patent number: 4727070Abstract: The antibiotic 7-[D-2-amino-2-(4-hydroxyphenyl)acetamido]-3-[(Z)-1-propenyl]ceph-3-em-4-c arboxylic acid (BMY-28100) forms imidazolidinone derivatives on reaction with ketones. These derivatives are useful in pharmaceutical dosage forms and as intermediates for separation thereof from mixtures containing the [(E)-1-propenyl]isomer of the antibiotic.Type: GrantFiled: November 25, 1985Date of Patent: February 23, 1988Assignee: Bristol-Myers CompanyInventors: Murray A. Kaplan, Michael W. Lovell, Joseph B. Bogardus
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Patent number: 4719206Abstract: The invention relates to novel cephem compounds, of high antimicrobial activity, of the formula: ##STR1## wherein R.sup.1 and R.sup.9 are amino or acylamino; andR.sup.9 is a group of the formula: ##STR2## where R.sup.2 is organic group,X is CH or N,Z is acid residueY is CH or N and n is O; orY is N.sup..sym. --R.sup.2 wherein R.sup.2 is as defined above and n is 1,or a group of the formula:--A--N.sup..sym. (R.sup.10).sub.3whereinR.sup.10 is lower alkyl andA is lower alkylene.Type: GrantFiled: January 31, 1986Date of Patent: January 12, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Takashi Masugi, Takashi Ogino, Hisashi Takasugi, Hideaki Yamanaka
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Patent number: 4717768Abstract: 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: September 7, 1984Date of Patent: January 5, 1988Assignee: Glaxo Group LimitedInventors: Colin Robinson, David T. Eastlick, Audrey J. Bownass
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Patent number: 4717767Abstract: This invention relates to a 7-amino-3-(pyrazinylmethyl)- or (pyridazinylmethyl)-cephalosporins of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a group of the formula: ##STR2## in which R.sup.6 represents a hydrogen atom, a C.sub.1-5 alkyl group or a di-C.sub.1-5 alkylamino group; R.sup.13 represents a C.sub.1-5 alkyl group; and R.sup.28 represents an amino group.Type: GrantFiled: July 22, 1986Date of Patent: January 5, 1988Assignee: Toyama Chemical Co., Ltd.Inventors: Hiroshi Sadaki, Hiroyuki Imaizumi, Takashi Nagai, Kenji Takeda, Isao Myokan, Takihiro Inaba, Yasuo Watanabe, Yoshikazu Fukuoka, Shinzaburo Minami, Isamu Saikawa
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Patent number: 4716158Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 represents a lower alkyl group selected from methyl groups and ethyl groups;R.sup.2 represents a hydrogen atom or a methyl group; andR.sup.3 represents a group selected from C.sub.1 --C.sub.5 alkoxy groups,and pharmaceutically acceptable acid addition salts thereof have valuable antibiotic activity and are suitable for oral administration. They may be prepared by a variety of synthetic routes.Type: GrantFiled: June 10, 1986Date of Patent: December 29, 1987Assignee: Sankyo Company LimitedInventors: Hideo Nakao, Koichi Fujimoto, Sadao Ishihara, Shinichi Sugawara, Isamu Igarashi
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Patent number: 4714760Abstract: 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, and intermediates in, the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.Type: GrantFiled: July 11, 1986Date of Patent: December 22, 1987Assignee: Bristol-Myers CompanyInventors: Steven P. Brundidge, Paul R. Brodfuehrer, Chet Sapino, Jr., Kun M. Shih, Donald G. Walker
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Patent number: 4708955Abstract: This invention provides novel cephalosporanic acids and esters thereof having the general formula ##STR1## wherein R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl or acyl, R.sup.3 is hydrogen, lower alkyl, lower alkoxy, lower alkanoyloxy, andR.sup.4 is hydrogen, pivaloyloxymethyl, acetoxymethyl, 1-acetoxyethyl, 5-methyl-2-oxo-1, 3-dioxolen-4-ylmethyl or 4-glycyloxybenzoyloxymethyl. 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.Type: GrantFiled: June 24, 1985Date of Patent: November 24, 1987Assignee: Bristol-Myers CompanyInventors: Seiji Iimura, Yoshio Abe, Jun Okumura, Takayuki Naito, Hajime Kamachi
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Patent number: 4705784Abstract: A cephem compound represent by the general formula ##STR1## wherein, R.sup.1 represents hydrogen or lower alkyl, R.sup.2 and R.sup.3 are the same or different and each represents hydrogen or lower alkyl, R.sup.4 represents carboxyl or esterified carboxyl, and n represents 0 or 1, a salt of the cephem compound, and a process for producing the cephem compound or a salt thereof. Compounds of the above formula and salts thereof are valuable as antibacterial agents and are especially useful as oral drugs in the prevention or treatment of bacterial infectious diseases.Type: GrantFiled: December 17, 1984Date of Patent: November 10, 1987Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Hirotada Yamada, Naruhito Masai, Sinji Ueda, Takao Okuda, Masatomo Fukasawa, Masuhiro Kato, Masataka Fukumura
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Patent number: 4703046Abstract: This invention concerns antibiotic cephalosporins of the formula ##STR1## wherein R.sup.1 is amino or protected amino; R.sup.2 is halogen; R.sup.3 is alkyl; and R.sup.6 is carboxy or protected carboxy.Type: GrantFiled: September 6, 1979Date of Patent: October 27, 1987Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Masakazu Kobayashi, Tadashi Kitaguchi
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Patent number: 4699904Abstract: Tetrazolyl derivatives of .beta.-lactams are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: July 1, 1985Date of Patent: October 13, 1987Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Paul E. Finke, William K. Hagmann, Shrenik K. Shah
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Patent number: 4699980Abstract: Various 7-amino-3-substituted-methyl-3-cephem-4-carboxylic acids and lower alkylsilyl derivatives such as 7-amino-3-(2,3-cyclopenteno-1-pyridiniomethyl)-3-cephem-4-carboxylic acid iodide and trimethylsilyl 7-trimethyl-silylamino-3-(5,6,7,8-tetrahydro-2-isoquinoliniomethyl)-3-ceph em-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: February 8, 1985Date of Patent: October 13, 1987Assignee: Yamanouchi Pharmacutical Co., Ltd.Inventors: Tadao Shibanuma, Kohji Nakano, Noriaki Nagano, Yukiyasu Murakami, Ryuichiro Hara, Akio Koda, Atsuki Yamazaki
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Patent number: 4698336Abstract: Described herein is 3-(pyrrolidinio)methyl-3-cephem derivative represented by the general formula: ##STR1## wherein Y stands for CH or nitrogen atom, R.sub.1 and R.sub.2 are the same or different, and represent a lower alkyl group, R.sub.3 denotes a hydroxy-substituted lower alkyl group, a lower alkyl group, or a carbamoyl group, and when Y stands for CH, R.sub.3 denotes a hydroxy-substituted lower alkyl group. The derivative is useful as antibacterial composition. Also described herein are process for the production of the derivative and antibacterial composition.Type: GrantFiled: January 23, 1986Date of Patent: October 6, 1987Assignee: Eisai Co., Ltd.Inventors: Isao Saito, Seiichiro Nomoto, Takashi Kamiya, Hiroshi Yamauchi, Isao Sugiyama, Yoshimasa Machida, Shigeto Negi
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Patent number: 4698337Abstract: The invention relates to novel cephem compounds, of high antimicrobial activity, of the formula ##STR1## wherein R.sup.1 is amino or protected amino,R.sup.2 is lower alkyl substituted with 1 to 3 halogen atoms,R.sup.3 is thiadiazolylthiomethyl which may be substituted with lower alkyl, or tetrazolylthiomethyl which may be substituted with lower alkyl or lower alkenyl, andR.sup.4 is carboxy or protected carboxy, and a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 25, 1986Date of Patent: October 6, 1987Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Kiyoshi Tsuji, Toshiyuki Chiba
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Patent number: 4695627Abstract: A process for the preparation of 7.beta.-acylamino-3-substituted-3-cephem-4-carboxylic acid compounds comprising reacting at -70.degree. C. to 0.degree. C. in an inert organic solvent phosphorus pentachloride with a cephalosporin compound in the presence of an olefinic compound having at least one carbon-carbon double bond having not more than three hydrogen atoms attached thereto capable of removing chlorine at least in part by addition to a carbon-carbon double bond.Type: GrantFiled: September 21, 1984Date of Patent: September 22, 1987Assignee: Gist-Brocades N.V.Inventors: Jan Verweij, Herman H. Grootveld, Henri G. J. Hirs, Gerardus J. Van Veen, Jan Kalter, Peter W. Henniger
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Patent number: 4694001Abstract: .beta.-Lactam compounds represented by the general formula: ##STR1## (wherein X represents CH.sub.2, S or O; Y represents a hydroxyl group, a lower alkanoyloxy group or a lower alkoxycarbonyloxy group; W is a group represented by CH.sub.2, NH, ##STR2## A is a phenyl group, a naphthyl group, or a monocyclic or dicyclic heterocyclic group, respectively substituted by (Y).sub.n ; R.sub.4 and R.sub.5 each are a hydrogen atom, a lower alkyl group, or a cycloalkylidene group with a carbon atom combined therewith; l is 0 or an integer of 1, 2 or 3; m is 0 or 1; n is an integer of 1, 2, 3, 4 or 5; and R.sub.1, R.sub.2 and R.sub.3 are groups often used in the conventional .beta.-lactam compounds) have strong antimicrobial activities against a wide range of Gram positive and negative bacteria; particularly Gram negative bacteria including Pseudomonas aeruginosa, Pseudomonas sepatia and various Enterobacters.Type: GrantFiled: November 26, 1984Date of Patent: September 15, 1987Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tadashi Hirata, Kenichi Mochida, Chihiro Shiraki, Kiyoshi Sato
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Patent number: 4692516Abstract: Process for the preparation of cephem compounds of the formula ##STR1## wherein R is optionally substituted aminothiazolyl or amino-1,2,4-thiadiazolyl, A is optionally substituted pyridinium, R.sup.1 is hydrogen or methoxy and R.sup.2 are special aliphatic substituents, by a nucleophilic replacement in the substituent in 3-position in the presence of tri-C.sub.1 C.sub.4 -alkyl iodosilane.Type: GrantFiled: May 7, 1984Date of Patent: September 8, 1987Assignee: Hoechst AktiengesellschaftInventors: Reiner Kirrstetter, Walter Durckheimer, Rudolf Lattrell, Wilfried Schwab
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Patent number: 4692517Abstract: There are disclosed novel antibacterial compounds having the formula ##STR1## wherein R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cyclo lower alkyl, aryl of 6-12 carbon atoms, all the said foregoing groups being optionally substituted with carboxy, lower alkoxycarbonyl, phenoxycarbonyl, amino, mono- or di-lower alkyl substituted amino, hydroxy, lower alkoxy, phenoxy, carbamoyl, lower alkyl carbonyl, benzoyl, cyano, nitro, formamido, lower alkanoylamino or benzamido;R.sup.1 is hydrogen, lower alkyl or an alkali metal cation;A is lower alkoxy, lower alkenoxy, lower alkynoxy, aryloxy of 6-12 carbon atoms, di-lower alkyl substituted amino, di-lower alkenyl substituted amino, di-lower alkynyl substituted amino, di-aryl of 6-12 carbon atoms substituted amino, lower alkyl, lower alkenyl, lower alkynyl, aryl of 6-12 carbon atoms.Type: GrantFiled: March 20, 1986Date of Patent: September 8, 1987Assignee: American Home Products CorporationInventors: Jerauld S. Skotnicki, Thomas J. Commons
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Patent number: 4691014Abstract: A cephalosporin compound having the formula: ##STR1## wherein R.sub.1 is a hydroxy group, a lower alkanoyloxy group or a lower alkoxycarbonyloxy group, R.sub.2 is a hydrogen atom, a hydroxy group, a lower alkanoyloxy group or a lower alkoxycarbonyloxy group, R.sub.3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group or --CH.sub.2 R.sub.7 (wherein R.sub.7 is a hydrogen atom, an azido group, a lower alkanoyloxy group, a carbamoyloxy group, a substituted or unsubstituted pyridinium group or a substituted or unsubstituted heterocyclic thio group), R.sub.4 is a hydrogen atom or a carboxy-protecting group, each of R.sub.5 and R.sub.6 is a hydrogen atom or a lower alkyl group, or R.sub.5 and R.sub.6 form a cycloalkylidene group together with the carbon atom to which they are attached, and m is 0 to 1, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 1, 1985Date of Patent: September 1, 1987Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Takanobu Naito, Masaaki Yokoyama, Kazuya Sasaki, Makoto Yamamoto, Kouji Amemiya
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Patent number: 4687769Abstract: A class of new cephem compounds is now provided, which is useful as antibacterial agent and is represented by the general formula (I) ##STR1## wherein R.sup.1 is methyl group or carboxymethyl group and R.sup.2 is carboxyl group or a protected carboxyl group, and a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: December 16, 1985Date of Patent: August 18, 1987Assignee: Meiji Seika Kaisha, Ltd.Inventors: Yuichi Yamamoto, Takashi Yoshida, Shunzo Fukatsu, Toshiyasu Ishimaru
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Patent number: 4686216Abstract: 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: May 6, 1985Date of Patent: August 11, 1987Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler