3-position Substituent Contains Sulfur Patents (Class 540/226)
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Patent number: 5258377Abstract: Derivatives of 2-spirocyclopropyl 4-acylcephem sulfones of the formula (I) ##STR1## are provided which are useful as potent elastase inhibitors and hence are useful in the prevention, control and treatment of inflammatory conditions, especially arthritis and emphysema.Type: GrantFiled: April 8, 1991Date of Patent: November 2, 1993Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Samarendra N. Maiti, Narender A. V. Reddy, David Czajkowski, Paul Spevak, Charles Fiakpui, Ronald G. Micetich
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Patent number: 5247073Abstract: The present invention provides compounds of the formula ##STR1## wherein R.sup.0 is amino or protected amino; A and A' are taken together form a group of the formulae ##STR2## wherein X is hydrogen, halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, nitro, carboxy; and Y is nitrogen; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: July 2, 1992Date of Patent: September 21, 1993Assignee: Eli Lilly and CompanyInventor: Robert J. Ternansky
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Patent number: 5244892Abstract: Novel cephem compounds represented by a formula [I] and pharmacologically admissible salts or capable of physiologically hydrolyzable nontoxic esters thereof are disclosed. ##STR1## [wherein R.sup.1 indicates a straight-chain or branched lower alkyl group, which may be substituted by carboxyl group which may be protected, trityl group, hydrogen atom or fluorine-substituted lower alkyl group, R.sup.2 indicates a hydrogen atom, metal atom, protective group for carboxyl group or ester residue producible hydrolyzable ester in vivo, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be identical or different, indicate hydrogen atoms, halogen atoms, straight-chain or branched lower alkyl groups, which may be substituted, mercapto groups, which may be substituted, lower alkylamino groups, hydroxyl groups, which may be protected, lower alkoxy groups, lower alkanoyl groups, lower alkoxycarbonyl groups, or lower alkylenedioxy groups, which may be substituted, being maybe formed with R.sup.3 and R.sup.4, R.sup.Type: GrantFiled: October 11, 1991Date of Patent: September 14, 1993Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Seigo Suzue, Kikoh Obi, Tatsuhiro Saito, Keiji Hirai, Hideyuki Fukuda
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Patent number: 5245027Abstract: 3-Fluorosulfonyloxyceph-3-ems having a protected amino or acylamino group in the 7-position are subject to carbon-carbon bond formation at the 3-position by means of a palladium catalyzed coupling reaction with substituted organostannanes. A process for preparing cefprozil is disclosed.Type: GrantFiled: October 31, 1990Date of Patent: September 14, 1993Assignee: Bristol-Myers Squibb CompanyInventors: Stephen R. Baker, Chester Sapino, Jr., Gregory P. Roth
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Patent number: 5243043Abstract: Novel syn isomers of 3-alkoxymethyl or 3-alkylthio-methyl-7-[2-(2-amino-4-thiazolyl)-2-oximino-acetamido]-cephalo sporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, acyl of an organic carboxylic acid of 1 to 18 carbon atoms and alkoxy carbonyl of 2 to 6 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, --NH.sub.Type: GrantFiled: October 31, 1990Date of Patent: September 7, 1993Assignee: Roussel UclafInventor: Rene Heymes
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Patent number: 5242913Abstract: Certain 7-beta-[2-(2-amino-4-thiazolyl)-(Z)-2-(chloromethylene)acetamido]-3-[(subs tituted)methyl]-ceph-3-em-4-carboxylic acids, pharmaceutically-acceptable salts thereof and conventional in vivo hydrolyzable esters thereof are valuable as broad spectrum antibacterial agents, particularly useful for the treatment of bacterial infections in man and other mammals.Type: GrantFiled: October 11, 1991Date of Patent: September 7, 1993Assignee: Pfizer Inc.Inventor: Susumu Nakanishi
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Patent number: 5239068Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with a more desirable protecting group.Type: GrantFiled: April 20, 1992Date of Patent: August 24, 1993Assignee: Eli Lilly and CompanyInventors: Larry C. Blaszczak, John E. Munroe, Douglas O. Spry
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Patent number: 5233035Abstract: A cephalosporin compound represented by the general formula: ##STR1## This compound exhibits a high antimicrobial activity.Type: GrantFiled: March 27, 1992Date of Patent: August 3, 1993Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Ryuichiro Hara, Noriaki Nagano, Hideki Anan, Tokuo Koide, Ei-ichi Nakai, Masaki Yokota, Katsuhiko Hamaguchi, Masato Sato, Toru Yoden, Tetsuya Maeda
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Patent number: 5223496Abstract: Cephalosporin compounds of Formulas II ##STR1## where R is hydrogen or a pharmaceutical cation, in which case R.sub.1 is not present, orR is hydrogen or a chemical bond when R.sub.1 is an acid addition salt anion, and R.sub.2 is (a) hydrogen, (b) a duplicate of the formula I compound to form a dimer, (c) an aminocarbonylmethyl, or (d) an --SR.sub.3 group where R.sub.3 is alkyl, cyclohexyl, phenyl, chloro-substituted phenyl, nitro-substituted phenyl, benzyl or furfuryl, have been found to be valuable as antibiotics for treating warm-blooded animals to combat pathogenic bacterial infections which cause diseases such as the commonly known "shipping fever".Type: GrantFiled: April 23, 1992Date of Patent: June 29, 1993Assignee: The Upjohn CompanyInventors: Alexander R. Cazers, K. Thomas Koshy, Prem S. Jaglan, Robert J. Yancey, Jr., Terry J. Gilbertson, Thomas S. Arnold, David B. Johnson, Catherine L. Gatchell
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Patent number: 5202315Abstract: The present invention relates to new cephalosporin compounds of the formula(I), pharmaceutically acceptable non-toxic salts thereof, and physiologically hydrolyzable esters and solvates thereof, which have potent and broad antibacterial activities ##STR1## wherein R.sup.1 is a C.sub.1.about.4 alkyl, C.sub.3.about.4 alkenyl, C.sub.3.about.4 alkynyl group, or --C(R.sup.a)(R.sup.b)CO.sub.2 H.sub.1 wherein R.sup.a and R.sup.b are the same or different, and each is a hydrogen atom or a C.sub.1.about.4 alkyl group, or R.sup.a and R.sup.b form a C.sub.3.about.7 cycloalkyl group with the carbon atom to which they are linked;R.sup.2 is a C.sub.1.about.4 alkyl, C.sub.3.about.4 alkenyl or C.sub.3.about.4 cycloalkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted phenyl group;R.sup.3 is hydrogen or a C.sub.1.about.4 alkyl group; andQ is N or CH.The invention further relates to a process for preparing said compounds, and to pharamaceutical compositions containing said compounds.Type: GrantFiled: March 15, 1990Date of Patent: April 13, 1993Assignee: Lucky, Ltd.Inventors: Yong Z. Kim, Hun S. Oh, Jae H. Yeo, Jong C. Lim, Won S. Kim, Chan S. Bang, Hyeon J. Yim
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Patent number: 5196414Abstract: The present invention provides compounds of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.6 haloalkyl;A and A' are independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, amino, a 5-6 membered organic heterocycle containing 1, 2, or 3 hetero atoms selected from nitrogen or sulfur, C.sub.1 -C.sub.6 alkoxy, or phenyl; or A and A' taken together form a group of the formulae ##STR2## wherein X is hydrogen, halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, nitro, or carboxy; and Y is nitrogen or carbon; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions and methods or treatment using the above compounds.Type: GrantFiled: January 18, 1991Date of Patent: March 23, 1993Assignee: Eli Lilly and CompanyInventor: Robert J. Ternansky
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Patent number: 5169945Abstract: The present invention provides a process for protecting an amino group in a compound exposed to nucleophilic reaction conditions in which the imido group used for protection is reacted with a secondary amine to form an acyl group which protects the amino group during exposure to the nucleophilic reaction conditions, after which the acylamino group may be reacted with an acid to reform the imido group so that the compound may then undergo non-nucleophilic manipulations. Also provided is a resolution method in which diasteriometric compounds having the acylamino group as described above are reacted with acid, and as these diasteriomers react at different rates to form the imido group, the reaction may be monitored so as to isolate the desired product at the appropriate point to maximize optical purity.Type: GrantFiled: August 19, 1991Date of Patent: December 8, 1992Assignee: Eli Lilly and CompanyInventor: Leland O. Weigel
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Patent number: 5162521Abstract: This invention relates to a novel process for making a cephem of formula II from 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate of formula I. In another aspect, this invention is concerned with a process of further converting a compound of formula II into an antibacterial cephem of formula III. ##STR1## In formulae I, II and III, R.sup.1 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.2 is an aromatic heterocyclic or aryl group; R.sup.3 is a conventional carboxy protecting group or --CO.sub.2 R.sup.3 taken together forms a physiologically hydrolyzable ester; and R.sup.4 is a group selected from the group consisting of C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, cyclic C.sub.3-6 alkyl, and aryl; and n is 0 or 2.Type: GrantFiled: June 6, 1991Date of Patent: November 10, 1992Assignee: Bristol-Myers Squibb CompanyInventors: Vittorio Farina, Stephen R. Baker
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Patent number: 5162523Abstract: Antibacterial compounds of the formula ##STR1## in which R.sub.1 is a cyclic or secondary acyclic amino group which independently has antibacterial activity;R.sub.2 is hydrogen, lower alkoxy, lower alkylthio or formamido;R.sub.3 is hydrogen or an organic group bonded through carbon, oxygen, sulfur or nitrogen;R.sub.4 is an electronegative acidic group; or R.sub.3 and R.sub.4 together form a heterocycle; andR.sub.5 is hydrogen or lower alkyl, except when R.sub.3 and R.sub.4 form a heterocycle, in which case R.sub.5 is hydrogen only; and methods of using same.Type: GrantFiled: June 20, 1990Date of Patent: November 10, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Dennis D. Keith, John L. Roberts, Chung-Chen Wei
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Patent number: 5147871Abstract: There are presented anti-bacterial cephalosporins having broad antimicrobial activity of the formula ##STR1## wherein R.sub.1 is an antibiotically active quinolonyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkoxy, amino, lower alkylthio and amido; R.sub.3 is selected from the group consisting of hydrogen, and acyl group, and m is 0, 1 or 2 and the readily hydrolysable esters or salts of these compounds and hydrates of the compounds of formula I or of their esters or salts.Type: GrantFiled: December 5, 1991Date of Patent: September 15, 1992Assignee: Hoffmann La-Roche, Inc.Inventors: Harry A. Albrecht, Ka-Kong Chan, Dennis D. Keith, Rudolf L. Then, Manfred Weigele
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Patent number: 5142039Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with a more desirable protecting group.Type: GrantFiled: September 26, 1990Date of Patent: August 25, 1992Assignee: Eli Lilly and CompanyInventors: Larry C. Blaszczak, John E. Munroe, Douglas O. Spry
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Patent number: 5142041Abstract: The present invention provides certain novel cephalosporin derivatives represented by following formula(I), which are especially useful as intermediates for the preparation of cephalosporin compounds possessed with potent and broad antibacterial activities. ##STR1## wherein: R.sup.1 is a C.sub.1-4 alkyl, C.sub.3-4 alkenyl, C.sub.3-4 cycloalkyl, amino optionally substituted with a C.sub.1-4 alkyl radical, or phenyl group optionally substituted on its 2-, 4-and/or 6-position with a halogen, C.sub.1-4 alkyl, C.sub.1-3 alkoxy or hydroxy radical;R.sup.2 is hydrogen or a C.sub.1-4 alkyl group; andn is either 0 or 1.The invention also relates to processes for preparing these intermediates and their pharmacologically active cephalosporin antibiotics.Type: GrantFiled: March 22, 1991Date of Patent: August 25, 1992Assignee: Lucky, Ltd.Inventors: Yong Z. Kim, Jae H. Yeo, Jong C. Lim, Won S. Kim, Chan S. Bang
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Patent number: 5134137Abstract: Cephalosporin compounds of Formulas II ##STR1## where R is hydrogen or a pharmaceutical cation, in which case R.sub.1 is not present, orR is hydrogen or a chemical bond when R.sub.1 is an acid addition salt anion, and R.sub.2 is (a) hydrogen, (b) a duplicate of the formula I compound to form a dimer, (c) an aminocarbonylmethyl, or (d) an --SR.sub.3 group where R.sub.3 is alkyl, cyclohexyl, phenyl, chloro-substituted phenyl, nitro-substituted phenyl, benzyl or furfuryl, have been found to be valuable as antibiotics for treating warm-blooded animals to combat pathogenic bacterial infections which cause diseases such as the commonly known "shipping fever".Type: GrantFiled: May 9, 1990Date of Patent: July 28, 1992Assignee: The Upjohn CompanyInventors: Alexander R. Cazers, K. Thomas Koshy, Prem S. Jaglan, Robert J. Yancey, Jr., Terry J. Gilbertson, Thomas S. Arnold, David B. Johnson, Catherine L. Gatchell
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Patent number: 5126445Abstract: A process for the preparation of cefodizime sodium, which comprises bringing cefodizime into solution in ethanol having a water content of 4-15% by means of 1.5-2.5 moles of an organic amine base and allowing the disodium salt of the cefodizime to crystallize by adding a sodium donor.Type: GrantFiled: April 5, 1990Date of Patent: June 30, 1992Assignee: Hoechst AktiengesellschaftInventor: Wolfgang Martin
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Patent number: 5089491Abstract: 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: January 11, 1990Date of Patent: February 18, 1992Assignee: 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: 5081116Abstract: A 7-[2-(2-amino-4-thiazolyl)-2-(hydroxyimino)-acetamido]-3-(1,3-dithiolan-2- yl)-3-cephem-4-carboxylic acid derivative is provided which can be represented by the general formula: ##STR1## wherein A represents a hydrogen atom, a 1-acetoxyethyl group, a 1-cyclohexylacetoxyethyl group or a pivaloyloxy-methyl group.Type: GrantFiled: April 5, 1990Date of Patent: January 14, 1992Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Noriaki Nagano, Masato Satoh, Masauki Komiya, Toshio Okazaki, Tetsuya Maeda, Tadao Shibanuma
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Patent number: 5079242Abstract: Certain 7-beta-[2-(2-amino-4-thiazolyl)-(Z)-2-(chloromethylene acetamido]-3-[(substituted)methyl]-ceph-3-em-4-carboxylic acids, pharmaceutically-acceptable salts thereof and conventional in vivo hydrolyzable esters thereof are valuable as broad spectrum antibacterial agents, particularly useful for the treatment of bacterial infections in man and other mammals.Type: GrantFiled: July 21, 1989Date of Patent: January 7, 1992Assignee: Pfizer Inc.Inventor: Susumu Nakanishi
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Patent number: 5073551Abstract: Cephalosporin compounds represented by the general formula ##STR1## in which R.sup.1 is a hydrogen atom or a protective group for the amino group,R.sup.2 is a hydrogen atom or a protective group for the hydroxyl group,R.sup.3 is a hydrogen atom, a salt-forming cation or a protective group for the carboxyl group, andR.sup.4 is a hydrogen atom, a halogen atom or a lower alkyl group,and their pharmacologically acceptable salts, process for their production and use of the same compounds as medicaments, particularly as antibiotic agents.Type: GrantFiled: March 24, 1989Date of Patent: December 17, 1991Assignee: Sagami Chemical Research CenterInventors: Takeo Kobori, Daiei Tunemoto
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Patent number: 5066799Abstract: Intermediates useful in synthesis of aminothiazoloximino cephalosporins are disclosed, which intermediates can be radio-labelled for pharmacological evaluation.Type: GrantFiled: June 29, 1990Date of Patent: November 19, 1991Assignee: American Cyanamid CompanyInventor: William V. Curran
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Patent number: 5064953Abstract: 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: September 26, 1989Date of Patent: November 12, 1991Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 5055572Abstract: Acyl derivatives of the formula ##STR1## in which R is an acyl group, excluding those acyl groups of the formula ##STR2## in which A is a group of the formulae --NHCO--, --NHCONHCO--, --NHCOCH.dbd.CH--, ##STR3## wherein R.sup.6 is hydrogen or lower alkyl; R.sup.1 and R.sup.2 are hydrogen or a protecting group, X is hydrogen, halogen, lower alkoxy, nitro or --OR.sup.2, n is 1 or 2, R.sup.4 and R.sup.5 are hydrogen or together represent an additional bond and Z is a direct bond or carbonyl (where R.sup.4 and R.sup.5 both represent hydrogen) or a group of the formula --O--B-- (where R.sup.4 and R.sup.5 together represent an additional bond) in which B is a straight-chain, branched or cyclic lower alkylene;and wherein R.sup.3 is a substituted bicyclic group of the formulae ##STR4## wherein R.sup.7 and R.sup.Type: GrantFiled: April 8, 1988Date of Patent: October 8, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Andre Furlenmeier, Erwin Gotschi, Paul Hebeisen, Werner Hofheinz, Helmut Link
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Patent number: 5037975Abstract: The invention provides a free radical process for preparing 1-carba(1-dethia)cephalosporin antibiotics with 2-substituted methylcephalosporin 1,1-dioxides wherein the substituent on the 2-methylene group is a free radical precursor group such as a phenyl or alkylseleno group. The latter dioxides are treated with a free radical initiator, e.g., a trialkyltin hydride or actinic radiation at 40.degree. C. to 150.degree. C. to provide the 1-carba-3-cephem and 1-carba-2-cephem products. The invention also provides free radical compounds formed as intermediates in the process.Type: GrantFiled: March 28, 1990Date of Patent: August 6, 1991Assignee: Eli Lilly and CompanyInventor: Larry C. Blaszczak
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Patent number: 5013731Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, ##STR2## represents one of the C-7 acyl groups known in the cephalosporin art, R3 is hydrogen or methoxy, R4 is hydrogen, optionally substituted alkyl, allyl, furfuryl or benzyl, and R5 is an aromatic heterocyclic ring system which is linked via carbon, and which contains a quaternized nitrogen atom.Type: GrantFiled: April 19, 1990Date of Patent: May 7, 1991Assignee: ICI PharmaInventors: Jean C. Arnould, Jean J. Lohmann, Georges Pasquet
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Patent number: 4988687Abstract: A compound having the formula: ##STR1## wherein R is a vinyl, phenyl or aralkyl group which may be substituted; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: September 1, 1989Date of Patent: January 29, 1991Assignee: Banyu Pharmaceutical Company, Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima
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Patent number: 4985555Abstract: The invention relates to a cephem compound of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino, R.sup.2 is hydrogen, phenyl, pyridyl which may have a lower alkyl group, or cyano, and R.sup.3 is carboxy or protected carboxy, or a salt thereof.Type: GrantFiled: July 27, 1989Date of Patent: January 15, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
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Patent number: 4983732Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with allyloxycarbonyl, t-butoxycarbonyl, naphthyloxycarbonyl, trichloroethyloxycarbonyl, p-nitrobenzyloxycarbonyl, benzhydryloxycarbonyl, p-methoxybenzyloxycarbonyl, or o-nitrobenzyloxycarbonyl.Type: GrantFiled: September 21, 1989Date of Patent: January 8, 1991Assignee: Eli Lilly and CompanyInventors: Larry C. Blaszczak, John E. Munroe, Douglas O. Spry
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Patent number: 4980464Abstract: A method for producing a compound of the formula; ##STR1## wherein R stands for a hydrogen atom, an acyl group or a protective group other than acyl groups, Q stands for a hydrogen atom or an ester residue, Y stands for the residue of a nucleophilic compound and the dotted line shows the double bond at 2- or 3- position of the cephem ring or a salt thereof, characterized by allowing a compound of the formula; ##STR2## [R, Q and the dotted line are of the same meaning as above] or a salt thereof to react with a nucleophilic compound or a salt thereof and a compound of the formula; ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 independently stand for a hydrocarbon group having not more than 8 carbon atoms, or R.sup.1 and R.sup.2, R.sup.1 and R.sup.3 or R.sup.2 and R.sup.Type: GrantFiled: June 30, 1989Date of Patent: December 25, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi
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Patent number: 4973684Abstract: Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein R.sup.4 is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl; or a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: June 7, 1988Date of Patent: November 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michihiko Ochiai, Taiiti Okada, Osamu Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
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Patent number: 4971961Abstract: This invention provides cephalosporin compounds represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 are same or different hydrogen atom or a lower alkyl group of 1 to 5 carbon atoms; R.sup.3 is a lower alkyl group which may optionally be substituted with a halogen atome (or atoms), an alkenyl group, or a cycloalkylmethyl group of 3 to 6 carbon atoms; and A is hydrogen atom or residue of a nucleophilic compound and pharmacologically acceptable salts thereof. These compounds have broad-spectrum antibacterial activity against Gram-positive and -negative bacteria including Pseudomonas aeruginosa, as well as against a great variety of .beta.-lactamase-producing strains.Type: GrantFiled: November 2, 1988Date of Patent: November 20, 1990Assignee: Meiji Seika Kaisha, Ltd.Inventors: Kaysuyoshi Iwamatsu, Kenji Sakagami, Kunio Atsumi, Takashi Yoshida, Seiji Shibahara, Takashi Tsuruoka, Shinichi Kondo
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Patent number: 4966900Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a lower alkyl group; M is a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; R' and R" are independently a hydrogen atom or a protective group; A is a mercapto group substituted by a substituted or unsubstituted polycyclic nitrogen-containing heterocyclic ring or a group represented by the following formula (a):--OOCNR.sub.3 R.sub.4 (a)where R.sub.3 and R.sub.4 are independently a hydrogen atom or a lower alkyl group, provided that R.sub.1 and R.sub.2 are both hydrogen atoms, both R.sub.3 and R.sub.4 being hydrogen atoms are excluded,or its pharmaceutically acceptable salt, and a method for preparing the same , medicinal composition for microbism therapy containing the same and intermediates for synthesis of the same.Type: GrantFiled: July 20, 1987Date of Patent: October 30, 1990Assignees: Sankei Pharmaceutical Company Ltd., Nippon Pharmaceutical Development Institute Co., Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4965355Abstract: Cefatrizine 1,2-propylene glycolate is prepared by reacting p-hydroxyphenylglycine chloride hydrochloride with 7-amino-3-iodomethyl-3-cephem-4-carboxylic acid, and then reacting the thus obtained novel intermediate, 7-[D(-)-.alpha.-amino-.alpha.-(p-hydroxyphenyl)-acetamido]-3-iodomethyl-3- cephem-4-carboxylic acid, with the sodium salt of 1,2,3-triazol-4(5)-thiol in 1,2-propylene glycol. The addition of water to the reaction mixture causes the cefatrizine, 1,2-propylene glycolate to precipate.Type: GrantFiled: February 23, 1989Date of Patent: October 23, 1990Assignee: Biochimica OPOS SpAInventors: Luigi Ratti, Leone Dall'Asta
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Patent number: 4958019Abstract: There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: --A--OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branced alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is --A--OR.sub.4, R.sub.2 and R.sub.Type: GrantFiled: May 26, 1989Date of Patent: September 18, 1990Assignees: Sankei Pharmaceutical Co., Ltd., Nippon Pharmaceutical Development Institute Company, Ltd.Inventors: Shigeo Shimizu, Hiroyuki Takano
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Patent number: 4950661Abstract: The present invention relates to derivatives of the cephalosporin family, of formula: ##STR1## in which: X is an oxygen atom or a sulfur atomn is zero, 1 or 2.R.sub.1, R.sub.2 and R.sub.3 each designate, a hydrogen atom or else R.sub.1 and R.sub.2 designate a hydrogen atom or a methyl group, and R.sub.3 designates a carboxyl or cyclopropyl group, or elseR.sub.1 and R.sub.2 taken together with the carbon atom to which they are linked form a cyclobutyl or cyclopentyl group and R.sub.3 is a carboxyl group.B is the residue of a primary or secondary amine;their preparation process and application in therapeutics.Type: GrantFiled: April 28, 1988Date of Patent: August 21, 1990Assignee: SANOFIInventors: Dominique Olliero, Ali Salhi
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Patent number: 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: 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: 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: 4921953Abstract: A cephalosporin derivative represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a protecting group of the amino group, R.sup.2 is a hydrogen atom or a protecting group of the hydroxyl group, R.sup.3 is a hydrogen atom or a protecting group of the carboxyl group, X is a halogen atom, a cyano group, a vinyl group, a lower alkoxy group having 1 to 4 carbon atoms or a lower alkylthio group having 1 to 4 carbon atoms and n is an integer of 1 to 3, and a non-toxic salt thereof are useful as antibacterial agents for oral administration.Type: GrantFiled: February 13, 1989Date of Patent: May 1, 1990Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Chihiro Yokoo, Akira Onodera, Hiroshi Fukushima, Yoshiaki Watanabe, Kaoru Sota
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Patent number: 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: 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: 4880797Abstract: A compound having the formula: ##STR1## wherein R is a vinyl, phenyl or aralkyl group which may be substituted; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.Type: GrantFiled: March 20, 1987Date of Patent: November 14, 1989Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Ryuji Mitomo, Ryosuke Ushijima
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Patent number: 4866055Abstract: The present invention relates to novel cephalosporin derivatives and their crystalline form, processes for preparing thereof, compositions for treating and/or preventing infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of a triazolopyrimidine ring as substituent at the 3-position of the cephem skeleton, and a 2-carboxy-4,5-dihydroxyphenylmethyloxyimino moiety as substituent at the 7-position of the cephem skeleton.The compounds of the present invention containing these substituents have a wide antibacterial spectrum against Gram-negative bacteria including Pseudomonas aeruginosa and Gram-positive bacteria including methicillin-resistant Staphylococcus aureus. These compounds are extremely useful for the treatment of infectious diseases.Type: GrantFiled: November 16, 1987Date of Patent: September 12, 1989Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Kazuo Kato, Kimihiro Murakami, Hidenori Mochizuki, Ei Mochida
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Patent number: 4866169Abstract: Diphenylmethyl esters of cephalosporins, and processes for synthesizing such, are described and disclosed.Type: GrantFiled: October 20, 1986Date of Patent: September 12, 1989Assignee: American Cyanamid CompanyInventors: Robert Babine, William V. Curran, Ving J. Lee
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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