3-position Substituent Contains Sulfur Patents (Class 540/226)
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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: 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: 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: 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: 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
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Patent number: 4810702Abstract: Cephalosporin compounds having 2-(2-aminothiazol-4-yl)-2{(1S)-carboxyethoxyimino}acetyl group on the side chain at the 7-position thereof and 1-ethylpyridinium-4-ylthiomethyl group on the side chain at the 3-position thereof or non-toxic salts thereof are excellent antibacterial agents for mammals including human. The cephalosporin derivatives have low toxicity.Type: GrantFiled: December 11, 1987Date of Patent: March 7, 1989Assignee: Meiji Seika Kaisha, Ltd.Inventors: Seiji Shibahara, Tsuneo Okonogi, Yasushi Murai, Toshiaki Kudo, Takashi Yoshida, Ken Nishihata, Shinichi Kondo
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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: 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: 4786633Abstract: A cephalosporin compound of the formula: ##STR1## wherein: R.sup.2 is a group of the formula: ##STR2## R.sup.4 is a lower alkenyl group, a lower alkyl group or a lower alkyl group substituted with a member selected from the group consisting of cyano, lower alkylthio, 2-(lower alkyl)-1,3,4-thiadiazol-5-yl, carbamoyl, thiocarbamoyl, and N-lower alkyl(thiocarbamoyl) andR.sup.5 and R.sup.6 are each a hydrogen atom or a lower alkyl group, or a pharmaceutically acceptable salt thereof, is disclosed. These compounds have antimicrobial activity.Type: GrantFiled: June 3, 1987Date of Patent: November 22, 1988Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Mitsuyoshi Wagatsuma, Toyonari Oine, Totaro Yamaguchi
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Patent number: 4784995Abstract: A cephalosporin compound of the formula: ##STR1## wherein R.sup.1 is a protected or unprotected amino group;either one of R.sup.2 and R.sup.3 is a substituted or unsubstituted lower alkylthio group; sulfamoyl group; a lower alkylsulfonyl group; sulfo group; a substituted or unsubstituted amino group; a lower alkyl group; a lower alkyl group having a substituent selected from a lower alkylthio group, amino group and an acylamino group; a halogen atom; carboxy group or a lower alkoxy group; andthe other one of R.sup.2 and R.sup.3 is hydrogen atom; carbamoyl group; a substituted or unsubstituted amino group; a lower alkyl group or a hydroxy-lower alkyl group; orR.sup.2 and R.sup.3 are combined together to form a lower alkylene group;or a salt thereof and processes for preparing the same are disclosed. The cephalosporin compound (I) is useful as an antimicrobial agent.Type: GrantFiled: June 8, 1987Date of Patent: November 15, 1988Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Toyonari Oine, Mitsuyoshi Wagatsuma, Totaro Yamaguchi
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Patent number: 4774330Abstract: There is presented compounds of the formula ##STR1## wherein X represents the 1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-as-triazin-3-yl group or its corresponding tautomeric form, the 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl group, and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of the compounds and hydrates of the compounds of formula I or of their esters, ethers and salts. Also provided is a method of their manufacture and intermediates therefor as well as corresponding pharmaceutical preparations.Type: GrantFiled: April 1, 1987Date of Patent: September 27, 1988Assignee: Hoffmann-La Roche Inc.Inventor: Roland Reiner
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Patent number: 4761409Abstract: A cephem derivative represented by the general formula ##STR1## wherein R.sup.1 represents hydrogen or methyl, R.sup.2 represents carboxyl or esterified carboxyl, and n represents 0 or 1, or a pharmaceutically acceptable salt thereof; intermediates for the cephem derivative or salt thereof; processes for producing these compounds; and a pharmaceutical composition and method for preventing or treating bacterial infectious diseases, wherein the cephem derivative or the salt thereof is used.Type: GrantFiled: August 5, 1985Date of Patent: August 2, 1988Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Hirotada Yamada, Naruhito Masai, Shinji Ueda, Takao Okuda, Masuhiro Kato, Masatomo Fukasawa, Masataka Fukumura
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Patent number: 4758557Abstract: Cephalosporin compounds represented by the following formula (I) and pharmaceutically acceptable salts thereof have a broad bactericidal spectrum against various pathogenic bacteria including Psuedomonas aeruginosa and are useful as bactericidal remedies for pathogenic diseases of human and animals: ##STR1## wherein A represents an unsubstituted or substituted pyridylthio group of a formula (I-1); ##STR2## or an unsubstituted or substituted pyridiniumthio group of a formula (I-2): ##STR3## or an unsubstituted or substituted pyridinium group of a formula (I-3); ##STR4## or a 5- or 6-membered heterocyclicthio or bicycloheterocyclicthio group of a formula (I-4):--S--Het (I-4).Type: GrantFiled: June 9, 1986Date of Patent: July 19, 1988Assignee: Meiji Seika Kaisha, Ltd.Inventors: Takashi Tsuruoka, Katsuyoshi Iwamatsu, Kiyoaki Katano, Hiroko Ogino, Ryoichi Okamoto, Takashi Yoshida, Masaji Sezaki, Fumio Kai, Shigeharu Inoue, Shinichi Kondo
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Patent number: 4758558Abstract: Disclosed herein are the derivatives of substituted cephalosporanic acid represented by the formula (I): ##STR1## wherein R.sup.1 represents a 4-pyridylthiomethyl group, an alpha-aminobenzyl group, a cyanomethyl group or a 1-tetrazolylmethyl group; R.sup.2 represents a hydrogen atom, an acetoxy group or a (5-methyl-1,3,4-thiadiazol-2-yl)thio group; R.sup.3 represents a hydrogen atom, a hydroxyl group, a carbamoyl group, an alkyl group having 1 to 4 carbon atoms or --(CONH).sub.m (CH.sub.2).sub.n --COOH wherein m is 0 or 1, n is 0, 1 or 2 and the carboxyl group may have been converted to a salt or an ester thereof; p is 0, 1 or 2 and X represents carbon atom or nitrogen atom, and antibiotics comprising the derivatives of substituted cephalosporanic acid represented by the formula (I).Type: GrantFiled: May 19, 1986Date of Patent: July 19, 1988Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Akihiko Kanno, Shigeaki Muto, Koichi Niimura, Takao Ando, Takayoshi Fujii, Masahiko Fujii, Takao Furusho, Chikao Yoshikumi
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Patent number: 4737492Abstract: The hydrabamine and benzathine salts of cefamandole are useful in aqueous ophthalmic compositions which have good stability and shelf life.Type: GrantFiled: December 31, 1986Date of Patent: April 12, 1988Assignee: Alcon Laboratories, Inc.Inventors: Steven H. Gerson, Wesley W. Han
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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: 4699981Abstract: Cephalosporin derivatives represented by the general formula ##STR1## Wherein X represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, an allyl group, a cycloalkyl group having 5 or 6 carbon atoms or a benzyl group, and the non-toxic salts thereof are disclosed. These compounds are useful as antibacterial agents.Type: GrantFiled: August 6, 1986Date of Patent: October 13, 1987Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoshiaki Watanabe, Chihiro Yokoo, Masami Goi, Akira Onodera, Mitsuo Murata, Hiroshi Fukushima, Kaoru Sota
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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: 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: 4684639Abstract: A compound having the partial structure (I) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a group --COR.sup.5 or --CO--OR.sup.5 wherein R.sup.5 represents an optionally substituted hydrocarbon group; R.sup.3 is halogen and R.sup.4 is hydrogen, methoxy, hydroxymethyl or formamido.These compounds are suitably bicyclic .beta.-lactam antibiotics.Type: GrantFiled: July 5, 1984Date of Patent: August 4, 1987Assignee: Beecham GroupInventors: George Burton, Desmond J. Best
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Patent number: 4678781Abstract: 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: June 4, 1984Date of Patent: July 7, 1987Assignee: ICI PharmaInventor: Frederic Jung
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Patent number: 4673738Abstract: This invention relates to novel 7-(substituted or unsubstituted amino)-3-substituted methyl-.DELTA..sup.3 -cephem-4-carboxylic acids in which a substituted or unsubstituted 1,2,4-triazolyl or 2-(1,2,3,4-tetrazolyl) group attaches to the exomethylene group at the 3-position of the cephem ring through a carbon-nitrogen bond. These cephalosporins are useful intermediates for producing various novel cephalosporins. Also, this invention concerns a process for producing a compound represented by the formula: ##STR1## which comprises reacting a compound represented by the formula: ##STR2## with an optionally substituted triazole or tetrazole in the presence of an acid or a complex of the acid in an organic solvent at 0.degree. to 80.degree. C.Type: GrantFiled: September 26, 1984Date of Patent: June 16, 1987Assignee: Handi-Pac Inc.Inventors: Hiroshi Sadaki, Hirokazu Narita, Hiroyuki Imaizumi, Yoshinori Konishi, Takihiro Inaba, Tatsuo Hirakawa, Hideo Taki, Masaru Tai, Yasuo Watanabe, Isamu Saikawa
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Patent number: 4656166Abstract: The compounds according to the invention correspond to the formula: ##STR1## in which: The COOA group at the 4 position is an acid radical, or an alkaline or alkaline-earth salt, or an amino acid or amine salt, for example triethylamine or ethanolamines, or an easily hydrolyzable or metabolically labile and pharmaceutically acceptable ester radical.X denotes an oxygen atom or a sulfur atomn is zero or 1R.sub.1 and R.sub.2 each denote independently hydrogen or a lower alkyl group, preferably a methyl group, orR.sub.1 and R.sub.2 taken together with the carbon atom to which they are linked form a cyclobutyl or cyclopentyl nucleus.B is the residue of a primary or secondary amine.Type: GrantFiled: May 22, 1984Date of Patent: April 7, 1987Assignee: SanofiInventors: Ali Salhi, Dominique Olliero
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Patent number: 4654331Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.Type: GrantFiled: August 23, 1984Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventor: Burton G. Christensen
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Patent number: 4649136Abstract: This invention relates to novel compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is carboxy(lower)alkyl or protected carboxy(lower)alkyl,R.sup.2 is carboxy or protected carboxy,R.sup.3 is hydrogen or lower alkyl, andR.sup.4 is lower alkyl, lower alkoxy, acyloxymethyl, lower alkylthiomethyl, lower alkoxymethyl, halogen, lower alkenyl or hydrogen,and pharmaceutically acceptable salts thereof,and processes for making the same.Type: GrantFiled: January 14, 1985Date of Patent: March 10, 1987Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Hideaki Yamanaka
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Patent number: 4637999Abstract: Substituted cephalosporins are found to be potent elastase inhibitors and thereby useful antiinflammatory/antidegenerative agents.Type: GrantFiled: May 2, 1983Date of Patent: January 20, 1987Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Paul E. Finke, Raymond A. Firestone, Shrenik S. Shah, Kevan R. Thompson
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Patent number: 4623645Abstract: Substituted cephalosporin sulfoxides are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: April 18, 1983Date of Patent: November 18, 1986Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Bonnie M. Ashe, Paul E. Finke, Raymond A. Firestone, Shrenik K. Shah, Morris Zimmerman
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Patent number: 4622394Abstract: In accordance with this invention, it has been found that the oxygen analog of 7-amino-cephalosporanic acid and biologically active derivatives thereof can be formed from esters of 7-amino-cephalosporanic acid. Esters of 7-oxocephalosporanic acid can be formed by diazotization of an ester or 7-amino-cephalosporanic acid and contact of the diazo compound so formed with a hypohalous acid and a base in a water miscible organic solvent. Oxygen analogs of 7-aminocephalosporins isolated as esters are then formed by reducing the aforesaid ester to the corresponding 7.beta.-hydroxy-cephalosporanate and then forming the desired analog by introduction of a side chain via hydroxyl group modification. Oxygen analogs of 7-amino-cephalosporins are then formed by regeneration of the acid via protective group removal.Type: GrantFiled: December 2, 1977Date of Patent: November 11, 1986Assignee: Massachusetts Institute of TechnologyInventors: John C. Sheehan, Young S. Lo
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Patent number: 4622318Abstract: The invention relates to new cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or a group of the formula: ##STR2## in which R.sup.5 is amino or a protected amino group,R.sup.9 is lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkenyl, carboxy(lower)alkyl, protected carboxy(lower)alkyl or saturated 4 to 8-membered heteromonocyclic group containing one sulfur atom, andZ is N or CH,R.sup.2 is cyano, phenyl, pyridyl, lower alkylpyridyl, or tri(lower)alkylsilyl,R.sup.3 is carboxy or protected carboxy, andA is --CH.dbd.CH-- or --C.tbd.C--,and pharmaceutically acceptable salt thereof.Type: GrantFiled: October 19, 1984Date of Patent: November 11, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
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Patent number: 4614797Abstract: An antibacterial cephalosporin hydroxamic acid derivative represented by the following formula (I), processes for its preparation, compositions containing the same as an active ingredient, and a method for killing bacteria by contacting with said compound. ##STR1## (wherein, R is acyl; R.sup.1 is hydrogen or methoxy; R.sup.2 is alkylene; R.sup.3 is hydrogen, aliphatic group or a hydroxy-protecting group; R.sup.4 is hydrogen or amino-protecting group; R.sup.5 is hydrogen, light metal atom or carboxy-protecting group; and X is oxygen, sulfur, or sulfinyl).Type: GrantFiled: February 2, 1984Date of Patent: September 30, 1986Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Tsutomu Aoki, Yasuhiro Nishitani
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Patent number: 4605651Abstract: 1. A cephalosporin derivatives of the general formula ##STR1## wherein R.sup.1 is an .alpha.-, .beta.- or .gamma.-amino acid residue (bonded by the ester linkage), which may optionally be substituted by one or two lower alkyl groups at the amino group thereof, R.sup.2 is an 1-alkanoyloxyalkyl, 1-alkoxycarbonyloxyalkyl, phthalidyl or 5-methyl-1,3-dioxolen-2-on-4-ylmethyl group, R.sup.3 is a carbamoyloxymethyl group, which may optionally be substituted by one or two lower alkyl groups, or a heterocyclothiomethyl group, which may optionally be substituted by one or more appropriate substituents, and R.sup.4 is a hydrogen atom or a hydroxy group, or its non-toxic salt are found to be useful as orally administrable antibiotics having broad antimicrobial activities against both gram-positive and gram-negative bacteria.Type: GrantFiled: October 11, 1983Date of Patent: August 12, 1986Assignee: Kyoto Pharmaceutical Industries, Ltd.Inventors: Nobuharu Kakeya, Susumu Nishizawa, Satoshi Tamaki, Kazuhiko Kitao
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Patent number: 4604386Abstract: 3-(alkynylalkyloxy)cephalosporin antibiotics and the intermediates therefor are disclosed. Pharmaceutical compositions for the antibiotics are also disclosed.Type: GrantFiled: July 9, 1984Date of Patent: August 5, 1986Assignee: Eli Lilly and CompanyInventor: Douglas O. Spry