3-position Substituent Contains Pyridine Ring Patents (Class 514/203)
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Patent number: 6057312Abstract: The present invention includes novel compounds of formula ##STR1## where G, H, J, L and M are carbon or nitrogen, R.sup.99 is selected from the group consisting of sulfur, SO, SO.sub.2, NH, N-alkyl, oxygen, C.dbd.C (cis or trans), and C.tbd.C, and R.sup.12 is NR.sup.13 R.sup.14, ##STR2## The invention also includes the pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.Type: GrantFiled: October 11, 1996Date of Patent: May 2, 2000Assignee: Microcide Pharmaceuticals, Inc.Inventors: In-Seop Cho, Scott J. Hecker, Tomasz W. Glinka, Ving J. Lee, Zhijia J. Zhang
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Patent number: 6034076Abstract: The cephalosporin compound [6R, 7R]-7-[2-(2-Amino-4-thiazolyl)-2-(Z)-(methoxyimino)acetamido]-3-[1-(methyl amino)pyridinium-4-thiomethyl]-ceph-3-em-4-carboxylic acid chloride hydrochloride is provided as a mono-, di- or tri-hydrate. The hydrates are produced by treating an aqueous solution of the corresponding carboxylate with hydrogen chloride and have been found to possess unexpectedly superior stability properties over other forms of the compound. The hydrates may be used in the treatment and/or prevention of bacterial infections in humans and animals.Type: GrantFiled: August 14, 1997Date of Patent: March 7, 2000Assignee: Pfizer Inc.Inventor: Richard Andrew Bentely Webster
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Patent number: 6025352Abstract: The present invention includes novel compounds of formula ##STR1## where G, H, J, L and M are carbon or nitrogen, R.sup.99 is selected from the group consisting of sulfur, SO, SO.sub.2, NH, N-alkyl, oxygen, C.tbd.C (cis or trans), and C.tbd.C, and R.sup.12 is NR.sup.13 R.sup.14, ##STR2## The invention also includes the pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.Type: GrantFiled: September 29, 1997Date of Patent: February 15, 2000Assignee: Microcide Pharmaceuticals, Inc.Inventors: In-Seop Cho, Scott J. Hecker, Tomasz W. Glinka, Ving J. Lee, Zhijia J. Zhang
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Patent number: 5994340Abstract: New 2-oxo-1-azetidine sulfonic acid derivatives with an aminoalkyl substituted "anti" (E-isomer) oxyimino group in the acylamino substituent at the 3 position of the monobactam ring. These compounds are potent inhibitors of bacterial .beta.-lactamases. These compounds can be used in combination with .beta.-lactam antibiotics to increase the effectiveness of the .beta.-lactam antibiotics in fighting infection caused by .beta.-lactamase producing bacteria.Type: GrantFiled: August 29, 1997Date of Patent: November 30, 1999Assignee: SynPhar Laboratories, Inc.Inventors: Samarendra N. Maiti, Oludotun A. Phillips, Eduardo L. Setti, Andhe V. Narender Reddy, Ronald G. Micetich, Fusahiro Higashitani, Chieko Kunugita, Koichi Nishida, Tatsuya Uji
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Patent number: 5981519Abstract: The present invention relates to compounds having the formula ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are as defined herein as well as readily hydrolyzable esters thereof, pharmaceutically acceptable salts of said compounds and hydrates of the compounds of formula I and of their esters and salts. These compounds have valuable pharmacological activity for the treatment and prophylaxis of infectious diseases, especially those caused by methicillin resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa.Type: GrantFiled: December 8, 1997Date of Patent: November 9, 1999Assignee: Hoffman-La Roche Inc.Inventors: Peter Angehrn, Paul Hebeisen, Ingrid Heinze-Krauss, Malcolm Page, Valerie Runtz
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Patent number: 5948774Abstract: Cephem compounds of the formula: ##STR1## wherein R.sup.1 is an optionally protected amino group; R.sup.2 is a fluoro-lower alkyl group; and the ring A may have further substituent(s), or their esters or salts, show broad and excellent antibacterial activities and are useful as antibacterial agents.Type: GrantFiled: July 29, 1997Date of Patent: September 7, 1999Assignee: Takeda Chemical Industries, Ltd.Inventors: Keiji Kamiyama, Kenji Okonogi, Akio Miyake
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Patent number: 5945414Abstract: Cefazolin, cefazedone, cefoperazone, cefamandole, cefatrizine or ceftriaxone is prepared by reacting glutaryl 7-ACA of the formula: ##STR1## with a compound of formula (II):R--SH (II)wherein R is 5-methyl-1,3,4-thiadiazol-2-yl, 1H-1,2,3-triazol-4-yl, 1-methyl-tetrazol-5-yl or1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl group, and R.sup.1 and R.sup.2 are both hydrogen and the other is an acyl group, in an aqueous solution in an amount of 3-5 mols per mol of glutaryl 7-ACA to about 90.degree. C. and for a time from about 2 to about 10 hours;optionally recovering the excess of the compound of formula (II), thereby preparing a compound of formula (III) in an aqueous solution: ##STR2## wherein R is as above defined and optionally deacylating said compound of formula (III); andconverting the resulting compound of formula (I) ##STR3## wherein R, R.sup.1 and R.sup.2 are as defined above in the presence of a non-chlorinated solvent into one of said cephalosporins.Type: GrantFiled: December 2, 1997Date of Patent: August 31, 1999Assignee: Antibioticos S.p.A.Inventors: Loris Sogli, Daniele Terrassan, Ermanno Bernasconi, Francisco Salto
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Patent number: 5935950Abstract: Compounds of formula I ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, cycloalkyl or acetyl;x is CH or N;n is 0, 1 or 2;m is 0 or 1;R.sup.2 is hydrogen, lower alkyl, .omega.-hydroxy alkyl, benzyl or lower alkyl-heterocyclyl, the benzyl and the heterocyclyl group being unsubstituted or substituted with at least one of the groups amino, cyano, carboxy, halogen, hydroxy, lower alkyl, lower alkoxy or --CONR.sub.2, where R is hydrogen or lower alkyl; or R.sup.2 is --CH.sub.2 CONR.sup.4 R.sup.5 ; whereinR.sup.4, R.sup.5 are each independently hydrogen, .omega.-hydroxy-alkyl, phenyl, benzyl, naphthyl or heterocyclyl, the phenyl, benzyl, naphthyl or heterocyclyl groups being unsubstituted or substituted with at least one of the groups optionally protected hydroxy, halogen, optionally substituted lower alkyl, optionally substituted lower alkoxy, .omega.-hydroxyalkyl or cyano; or R.sup.4 and R.sup.Type: GrantFiled: September 5, 1997Date of Patent: August 10, 1999Assignee: Hoffmann-La Roche Inc.Inventors: Peter Angehrn, Ingrid Heinze-Krauss, Malcolm Page, Urs Weiss
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Patent number: 5834458Abstract: The present invention relates to therapeutically active heterocyclic compounds and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system caused by malfunctioning of the muscarinic cholinergic system.Type: GrantFiled: October 9, 1996Date of Patent: November 10, 1998Assignee: Eli Lilly and CompanyInventor: Charles H. Mitch
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Patent number: 5734047Abstract: Novel cephem derivatives represented by the general formula ##STR1## wherein Ar is an optionally substituted lipophilic phenyl, naphthyl, benzthiazolyl or pyridyl group; R.sup.1 represents a group of the formula ##STR2## in which R.sup.8 and R.sup.9 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or (C.sub.1 -C.sub.6)alkoxycarbonyl, said C.sub.1 -C.sub.6 alkyl group being optionally substituted by 1-5 hydroxy or C.sub.1 -C.sub.6 alkoxy groups; m is either 0 or 1; A is a C.sub.2 -C.sub.10 alkyl group optionally substituted by 1-5 hydroxy groups; and R.sup.2 and R.sup.3 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl. The derivatives are gram-positive antibacterial agents especially useful in the treatment of diseases caused by methicillin-resistant Staphylococcus aureus.Type: GrantFiled: December 5, 1996Date of Patent: March 31, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Choung U. Kim, Muzammil M. Mansuri, Peter F. Misco, John A. Wichtowski
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Patent number: 5728691Abstract: Derivatives of 7-aminoceph-3-em-4-carboxylic acid with 6-fluoroquinolone derivatives in which the cephem and 6-fluoroquinolone moieties are bound to each other through a carboxamido bond as well as the pharmaceutical compositions containing them are described. These compounds possess antibacterial, growth promoting and probiotic activity.Type: GrantFiled: August 22, 1996Date of Patent: March 17, 1998Assignees: Laboratorios Aranda S.A. De C.V., Judith Marcia Arrieta MunguiaInventor: Miguel Angel Corpi Constantino
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Patent number: 5714469Abstract: The invention relates to the method of preventing and treating sepsis using (S)-5-oxo-L-prolyl-L-.alpha.-glutamyl-L-.alpha.-aspartyl-N.sup.8 -(5-amino-1-carboxypentyl)-8-oxo-N.sup.7 -?N-?N-(5-oxo-L-prolyl)-L-.alpha.-glutamyl!-L-.alpha.-aspartyl!-L-threo-2, 7,8 triaminooctanoyl-lysine ?(pGlu-Glu-Asp).sub.2 -Sub-(Lys).sub.2 ! alone or in conjunction with an anti-infective agent.Type: GrantFiled: September 1, 1994Date of Patent: February 3, 1998Assignee: SmithKline Beecham CorporationInventor: Peter Lawrence DeMarsh
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Patent number: 5698544Abstract: The present invention provides a cephem compound having a high antimicrobial activity against various pathogenic bacteria.The cephem compound of the invention is represented by the formula ##STR1## wherein Q represents CH or N, R.sup.1 represents a carboxylate or the like, R.sup.2 represents a hydrogen atom, and R represents ##STR2## wherein R.sup.3 represents a group --(CH.sub.2).sub.m --Y (wherein m is an integer of 1 to 5, and Y represents a quaternary ammonium group) or the like, n is an integer of 0 to 4, B.sup.- represents an anion, f is 0 or 1 when R.sup.1 represents a carboxylate, and 2 when R.sup.1 represents a carboxyl group, and the ring C represents a 5-membered heterocyclic group of not more than 4 nitrogen atoms, which may be substituted by a lower alkyl group.Type: GrantFiled: November 16, 1995Date of Patent: December 16, 1997Assignees: Otsuka Kagaku Kabushiki Kaisha, Taiho Pharmaceutical Co., Ltd.Inventors: Hiroshi Akagi, Masaru Yasui, Takae Yamada, Masahiro Ito, Akio Hyodo, Hideaki Hanaki
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Patent number: 5698547Abstract: The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.Type: GrantFiled: May 31, 1995Date of Patent: December 16, 1997Assignee: Microcide Pharmaceuticals, Inc.Inventors: Burton Christensen, In-Seop Cho, Tomasz Glinka, Scott Hecker, Ving J. Lee, Zhijia J. Zhang
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Patent number: 5635500Abstract: The object of the present invention is to provide a cephem compound having high activity against various pathogenic microorganisms. The cephem compound of this invention is represented by the general formula ##STR1## wherein Q represents CH or N; R.sup.1 represents a carboxylate etc; and R represents ##STR2## or the group ##STR3## where R.sup.2 represents a lower alkyl group etc, n represents an integer of 0 or 1 through 3, B.sup.- represents an anion, f is equal to 0 when R.sup.1 represents a carboxylate and 1 where R.sup.1 represents a carboxyl group, and the ring C represents a 5-membered heterocyclic group of not more than 4 nitrogen atoms, which may be substituted by lower alkyls.Type: GrantFiled: May 16, 1994Date of Patent: June 3, 1997Assignees: Otsuka Kagaku Kabushiki Kaisha, Taiho Pharmaceutical Co., Ltd.Inventors: Hiroshi Akagi, Masaru Yasui, Yoshifumi Hara, Hideaki Hanaki, Akio Hyodo
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Patent number: 5620969Abstract: Novel cephem derivatives represented by the general formula ##STR1## in which the Acyl substituent is a group of the formula ##STR2## wherein Ar is a lipophilic optionally substituted phenyl, naphthyl or pyridyl group; R.sup.1 represents either the residue of a heterocyclic amino acid or a C.sub.2 -C.sub.10 alkyl group substituted by both a carboxyl group and a group of the formula --NR.sup.9 R.sup.10 or ##STR3## in which R.sup.9 and R.sup.10 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl, said C.sub.2 -C.sub.10 alkyl group being optionally interrupted by one or more nitrogen atoms or carbonyl groups, and R.sup.2 and R.sup.3 are each independently hydrogen, alkyl or aminoalkyl are gram-positive antibacterial agents, especially useful in the treatment of diseases caused by methicillin-resistant Staphylococcus aureus (also referred to below as MRSA or methicillin-resistant S. aureus).Type: GrantFiled: April 25, 1995Date of Patent: April 15, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Joanne J. Bronson, Stanley V. D'Andrea, Shelley E. Hoeft, John D. Matiskella, Peter F. Misco, Jr., Bing Y. Luh, Dane M. Springer, Yasutsugu Ueda, John A. Wichtowski
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Patent number: 5607926Abstract: The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.Type: GrantFiled: March 29, 1995Date of Patent: March 4, 1997Assignee: Microcide Pharmaceuticals, Inc.Inventors: Scott J. Hecker, In-Seop Cho, Burton G. Christensen, Tomasz W. Glinka
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Patent number: 5607927Abstract: An aminothiazolyl- or aminothiadiazolyl-cephalosporin derivative represented by the following general formula (I) which has a condensed-ring thio group as a 3-positioned substituent group that contains a thiazolylthio group, an oxazolylthio group or a heterocyclic ring thereof as one of the ring components. The compound according to the present invention has excellent activities to inhibit growth of various bacteria, especially Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), and therefore, the antibacterial agent comprising, as an active ingredient, the inventive compound can be used as a therapeutic drug for the treatment of various bacterial infections.Type: GrantFiled: February 7, 1995Date of Patent: March 4, 1997Assignee: Meiji Seika Kaisha, Ltd.Inventors: Masaki Tsushima, Katsuyoshi Iwamatsu, Atsushi Tamura, Seiji Shibahara
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Patent number: 5604218Abstract: The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.Type: GrantFiled: March 30, 1995Date of Patent: February 18, 1997Assignee: Microcide Pharmaceuticals, Inc.Inventors: Scott Hecker, In-Seop Cho, Burton Christensen, Tomasz Glinka, Ving J. Lee
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Patent number: 5593985Abstract: Novel cephalosporin compounds of formula (I) exhibit potent and broad antibiotic activities against Gram-negative and Gram-positive bacteria and various resistant bacteria: ##STR1##Type: GrantFiled: May 22, 1995Date of Patent: January 14, 1997Assignee: Korea Institute of Science And TechnologyInventors: Joong H. Kim, Sung H. Kim, Ghil S. Nam, Ha Y. Kim, Hyen J. Son, Eun S. Jang
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Patent number: 5587372Abstract: A syn isomer in (R) or (S) form or a mixture thereof of a compound of the formula ##STR1## syn isomer, in the (R) or (S) form or in the form of an (R,S) mixture, in the form of an internal salt or their salts with organic or mineral acids,wherein the variables are herein below defined, having antibacterial properties.Type: GrantFiled: December 13, 1993Date of Patent: December 24, 1996Assignee: Roussel UclafInventors: Jozsef Aszodi, Jean-Francois Chantot, Patrick Fauveau, Solange G. D'Ambrieres, Daniel Hunbert, Christophe Dini
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Patent number: 5571804Abstract: Cephalosporin compounds of formula (I): ##STR1## wherein: R.sup.1 is a hydrogen or an amino protecting group;R.sup.2 and R.sup.3 are, independently, a hydrogen or a hydroxy protecting group, or form together a cyclic diol protecting group;R.sup.4 and R.sup.5 are, independently, a hydrogen or a carboxyl protecting group;X and Y are a nitrogen and a carbon atom, respectively, or a carbon and a nitrogen atom, respectively;R.sup.6 and R.sup.7 are, independently, a hydrogen or an amino, substituted amino, hydroxy, alkoxy, C.sub.1-4 alkyl, carboxyl or alkoxy carbonyl group, or jointly form a C.sub.3-7 cycloalkyl group together with the carbon to which they are attached, when X and Y are a nitrogen and a carbon, respectively, or R.sup.7 is a hydrogen or an amino group when X and Y are a carbon and a nitrogen, respectively; andQ is .dbd.CH-- or .dbd.Type: GrantFiled: September 9, 1994Date of Patent: November 5, 1996Assignee: Lucky LimitedInventors: Chan S. Bang, Jae H. Yeo, Young M. Woo, Jong C. Lim, Deog H. Yang, Se H. Kim, Jae H. Jeon, Mi K. Seo, Sam S. Kim, Tae H. Lee, Yong Z. Kim, Hun S. Oh
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Patent number: 5559108Abstract: Novel cephem derivatives represented by the general formula ##STR1## in which the Acyl substituent is a group of the formula ##STR2## where Ar is a substituted phenyl or optionally substituted naphthyl or benzthiazolyl group and A is a substituted-pyridinium group are gram-positive antibiotics, especially useful in the treatment of diseases caused by methicillin-resistant Staphylococcus aureus.Type: GrantFiled: May 22, 1995Date of Patent: September 24, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Choung U. Kim, Muzammil M. Mansuri, Peter F. Misco, Jr., John A. Wichtowski, Joanne J. Bronson, Stanley V. D'Andrea, Thomas W. Hudyma
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Patent number: 5439904Abstract: 2-spiro (2'-spirocycloalkyl) cyclopropyl cephalosporin sulfone compounds, methods of treating patients for elastase inhibition, and processes for preparing such compounds.Type: GrantFiled: December 7, 1993Date of Patent: August 8, 1995Assignee: Synphar Laboratories, Inc.Inventors: Samarendra N. Maiti, Charles Y. Fiakpui, Andhe V. N. Reddy, David P. Czajkowski, Ronald G. Micetich
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Patent number: 5409917Abstract: A method and composition for topically treating acne and acneiform dermal disorders includes applying an amount of a cephalosporin antibiotic effective to treat the acne and acneiform dermal disorders. The antibiotic is blended with a carrier suitable for topical application to dermal tissues. The carrier is selected from the group consisting of an aqueous liquid, an alcohol base, a water soluble gel, a lotion, an ointment, a nonaqueous liquid base, a mineral oil base, a blend of mineral oil and petrolatum, liposomes, a time-release patch, and a liquid-absorbed wipe. The cephalosporin can also be combined with benzoyl peroxide in a gel carrier.Type: GrantFiled: September 24, 1993Date of Patent: April 25, 1995Assignees: Marvin S. Towsend, Leonard BloomInventors: Howard N. Robinson, Neil F. Martin
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Patent number: 5397779Abstract: A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## in the R or S form or in the form of an R, S mixture wherein R.sub.1, Rc, Rb, A and A' are defined as in the following specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-bacterial activity.Type: GrantFiled: December 7, 1992Date of Patent: March 14, 1995Assignee: Roussel-UclafInventors: Jozsef Aszodi, Jean-Francois Chantot, Solange G. D'Ambrieres
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Patent number: 5373000Abstract: A cephalosporin derivative represented by the formula: ##STR1## wherein R.sub.1 represents a lower alkyl group, and A is selected from: a group of the following formula: ##STR2## where R.sub.2 and R.sub.3 are the same or different lower alkyl group, R.sub.4 represents a substituted lower alkyl or amino group;a group which may be substituted and which is represented by the following formula: ##STR3## where R.sub.5 represents a lower alkyl group; or a group of the following formula: ##STR4## where R.sub.5 is as defined above, R.sub.6 represents a hydroxyl lower alkyl or carboxyl group, or its pharmacologically acceptable salt, and a process for preparing the same, as well as an antibacterial agent containing the same.Type: GrantFiled: April 1, 1992Date of Patent: December 13, 1994Assignee: Eisai Co., Ltd.Inventors: Yoshimasa Machida, Takashi Kamiya, Shigeto Negi, Toshihiko Naito, Yuuki Komatu, Seiichiro Nomoto, Isao Sugiyama, Hiroshi Yamauchi
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Patent number: 5356888Abstract: There are provided compounds I ##STR1## wherein A is a hydrogen atom or an organic group,R.sub.1 is hydrogen or halogen atom or an organic group,R.sub.2 is hydrogen or halogen atom, C.sub.1 -C.sub.4 alkyl or acyloxy group,R.sub.3 is hydrogen atom, C.sub.1 -C.sub.4 alkyl or alkoxy, benzyl group or a methylene andR.sub.4 is chloro, fluoro, hydrogen atom or an organic group.The compounds I are elastase inhibitors. A process for their preparation is also provided, as are pharmaceutical compositions containing them.Type: GrantFiled: October 22, 1991Date of Patent: October 18, 1994Assignee: Farmitalia Carlo ErbaInventors: Marco Alpegiani, Pierluigi Bissolino, Ettore Perrone, Francesco Di Matteo, Piergiuseppe Orezzi, Giuseppe Cassinelli
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Patent number: 5312813Abstract: A method of killing microorganisms which form a biofilm on a tissue or implant surfaces in a patient, and which are refractory to a biocide at a dose which is effective to kill the microorganism in planktonic form. The effect of the biocide is potentiated, to an effective killing level, by applying an electric field across the surface containing the biofilm.Type: GrantFiled: July 22, 1992Date of Patent: May 17, 1994Assignee: University Technologies InternationalInventors: John W. F. Costerton, Antoine E. Khoury, Frank Johnson
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Patent number: 5244890Abstract: Cephem compounds having the following formula are disclosed: ##STR1## R.sup.1 =amino or protected amino R.sup.2 =an organic group ##STR2## R.sup.6 =lower alkyl R.sup.7, R.sup.8 .dbd.OH or protected OHY.dbd.N or CHThe compounds are useful as antimicrobial agents.Type: GrantFiled: May 20, 1992Date of Patent: September 14, 1993Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hideaki Yamanaka, Yoshiki Yoshida, Jiro Goto, Takeshi Terasawa, Shinya Okuda, Kazuo Sakane
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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: 5077286Abstract: Compounds of formulae Ia and Ib ##STR1## wherein A is hydrogen atom or an organic residue, R.sup.1 is halogen atom, or an organic group, R.sup.2 is hydrogen or halogen atom, C.sub.1 -C.sub.4 alkyl or alkoxy group, R.sup.3 is hydrogen atom, C.sub.1 -C.sub.4 alkyl or alkoxy group, benzyl or a methylene group and R.sub.4 is an organic residue are disclosed. Compounds (Ia) and (Ib) are endowed with elastase inhibitory activity. A two-step process for their preparation starting from the corresponding 4-carboxy cephem or 3-carboxy penam is also provided.Type: GrantFiled: April 10, 1989Date of Patent: December 31, 1991Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Pierluigi Bissolino, Marco Alpegiani, Ettore Perrone, Piergiuseppe Orezzi, Giuseppe Cassinelli, Giovanni Franceschi
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Patent number: 5028427Abstract: .beta.-Lactam antibiotics have the formula (Ia) or are pharmaceutically acceptable salts or pharmaceutically acceptable in vivo hydrolysable esters thereof: ##STR1## in which the group CO.sub.2 R.sup.1 is carboxy or a carboxylate anion. The use of the compounds and processes for their preparation are disclosed.Type: GrantFiled: August 22, 1988Date of Patent: July 2, 1991Assignee: Beecham Group p.l.c.Inventor: Stephen C. Finch
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Patent number: 4988686Abstract: Disclosed is a novel cephem compound which is either one of a cis- or trans-isomer or a mixture of the cis-and trans-isomers, represented by the following general formula (I) and a pharmacologically acceptable salt thereof: ##STR1## wherein all of the substituents are as defined hereinbefore. Also disclosed are a process for producing the above compound and its use as an anti-bacterial agent comprising the same.Type: GrantFiled: June 28, 1989Date of Patent: January 29, 1991Assignee: Meiji Seika Kabushiki KaishaInventors: Kunio Atsumi, Katsuyoshi Iwamatsu, Kenji Sakagami, Hiroko Ogino, Takashi Yoshida
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Patent number: 4962100Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is an amino group which may be protected, R.sup.3 is a hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S.fwdarw.O, O or CH.sub.2, R.sup.4 is a hydrogen atom, methoxy group or formamido group, R.sup.13 is a hydrogen atom, methyl group, hydroxyl group or halogen atom and A.sup..sym. is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof is novel and has excellent antibacterial activity.Type: GrantFiled: March 28, 1989Date of Patent: October 9, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4943567Abstract: Cephalosporin compounds represented by the general formula (I): ##STR1## wherein R.sup.1 and R.sup.5 independently represent a hydrogen atom or a protective group for an amino group; R.sup.2 represents an alkyl group or a cycloalkyl group; R.sup.3 represents a hydrogen atom, a lower alkenyl group, an alkanoyloxymethyl group, a carbamoyloxymethyl group, a heterocyclic thiomethyl group or a heterocyclic methyl group; R.sup.4 represents a hydrogen atom or an ester residue; and X represents CH or a nitrogen atom and pharmacologically acceptable addition salts thereof, intermediate compounds used in the synthesis process of these compounds, production methods of these compounds and pharmaceutical compositions containing these compounds.Type: GrantFiled: May 27, 1988Date of Patent: July 24, 1990Assignee: Kyoto Pharmaceutical Industries, Ltd.Inventors: Susumu Nishizawa, Hiroyuki Muro, Masayasu Kasai, Satoru Hatano, Syouzi Kamiya, Nobuharu Kakeya, Kazuhiko Kitao
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Patent number: 4921851Abstract: This invention relates to a compound of the formula: ##STR1## wherein Q is nitrogen or CH; R.sup.1 is hydrogen or a lower alkyl group which may be substituted; and ring A is a pyridine or pyridazine ring which is substituted at the ring-constituting carbon atom by a group of the formula:--E--(CH.sub.2).sub.n --R.sup.2in which E is sulfur or NH; R.sup.2 is an amino, carbamoylamino, formylamino, acetylamino, N-formimidoylamino, N-acetimidoylamino, lower alkylamino, hydroxyl or carbamoyloxy group; and n is an integer of 2 to 4, or a pharmaceutically acceptable salt thereof. The compound (I) or a pharmaceutically acceptable sale thereof has excellent antibacterial activity and is used as antibiotics.Type: GrantFiled: August 22, 1989Date of Patent: May 1, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Kiminori Tomimatsu, Akio Miyake, Yoshinobu Yoshimura
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Patent number: 4921850Abstract: A 3-propenylcephem derivative of the following formula: ##STR1## wherein R.sub.1 represents a fluoro-substituted lower alkyl group or a cyano-substituted lower alkyl group, and A represents a cyclic or an acylic ammonio group, or a pharmaceutically acceptable salt thereof, exhibiting excellent anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria; Process for the preparation thereof; Anti-bacterial composition; Intermediate for the 3-propenylcephem derivative; and Process for the preparation of the intermediate.Type: GrantFiled: October 13, 1987Date of Patent: May 1, 1990Assignee: Eisai Co., Ltd.Inventors: Takashi Kamiya, Toshihiko Naito, Shigeto Negi, Yuuki Komatu, Yasunobu Kai, Takaharu Nakamura, Isao Sugiyama, Yoshimasa Machida, Seiichiro Nomoto, Kyosuke Kitoh, Kanemasa Katsu, Hiroshi Yamauchi
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Patent number: 4919932Abstract: A pharmaceutical formulation having a synergistic anti-bacterial activity and comprising(a) a cephalosporin derivative or a physiologically acceptable salt or ester thereof and(b) a penem antibiotic of the basic structure (B) ##STR1## or a physiologically acceptable salt or ester thereof, a process for preparing such a formulation and its use for the treatment of bacterial infections.Type: GrantFiled: June 2, 1987Date of Patent: April 24, 1990Assignee: Hoechst AktiengesellschaftInventors: Michael Limbert, Elmar Schrinner, Gerhard Seibert
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Patent number: 4918070Abstract: A cephalosporin derivative having the formula: ##STR1## wherein R.sup.1 is a substituted amino group, X is an alkylene group, R.sup.2 is an aryl or heterocyclic group which may be substituted and R.sup.3 is a hydrogen atom, a negative charge or a residue of an ester which can form a pharmaceutically acceptable ester hydrolyzable in a living body; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: February 26, 1988Date of Patent: April 17, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Hiroshi Fukatsu, Yoshiaki Katoh, Satoshi Murase
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Patent number: 4871730Abstract: A cephem compound of the formula: ##STR1## wherein R.sup.1 is a group of the formula: ##STR2## in which R.sup.5 is amino or protected amino, R.sup.6 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, carboxy(lower) alkyl, protected carboxy(lower) alkyl, cyclo(lower) alkyl or cyclo (lower)alkenyl, and Z is CH or N;R.sup.2 is hydrogen, phenyl, pyridyl which may have a lower alkyl group, or cyano; andR.sup.3 is carboxy or protected carboxy; and pharmaceutically acceptable salt thereof.Type: GrantFiled: November 24, 1986Date of Patent: October 3, 1989Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
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Patent number: 4868173Abstract: According to the invention there is provided a antibacterial cephalosporin derivative of the formula: ##STR1## in which X is sulphur, oxygen, methylene or sulphinyl; R3 is hydrogen or methoxy; R1 and R2 are known in the cephalosporin art and R4 is an aminomethyl group in which the amino group carries one of various positively charged nitrogen-containing species set out in the specification and optionally a further substituent selected from hydrogen, lower alkyl, benzyl or heteroarylloweralkyl groups.Type: GrantFiled: November 15, 1985Date of Patent: September 19, 1989Assignee: ICI PharmaInventor: Frederic H. Jung
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Patent number: 4864022Abstract: A compound of the formula; ##STR1## wherein R.sup.1 is an amino group which may be protected, R.sup.3 is a hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S.fwdarw.O, O or CH.sub.2, R.sup.4 is a hydrogen atom, methoxy group or formamido group, R.sup.13 is a hydrogen atom, methyl group, hydroxyl group or halogen atom and A.sym. is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof is novel and has excellent antibacterial activity.Type: GrantFiled: February 28, 1986Date of Patent: September 5, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4861769Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is lower alkyl, lower alkanoyl, aryl, ar(lower)alkyl or a heterocyclic group, each of which may have suitable substituent(s),R.sup.2 is carboxy or protected carboxy,R.sup.3 is hydrogen, halogen, hydroxy, lower alkoxy, acyloxy, lower alkylthio, lower alkenyl, lower alkenylthio, lower alkynyl, heterocyclicthio or a heterocyclic group, in which lower alkylthio, lower alkenyl, lower alkenylthio, heterocyclicthio and a heterocyclic group may have suitable substituent(s),R.sup.4 and R.sup.5 are each hydrogen, halogen or arylthio,A is lower alkylene, andn is an integer of 0 or 1,and a pharmaceutically acceptable salt thereof, processes for preparation thereof and pharmaceutical composition comprising the same.Type: GrantFiled: February 12, 1986Date of Patent: August 29, 1989Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Shintaro Nishimura
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Patent number: 4839351Abstract: A compound of the general formula: ##STR1## wherein R.sup.0 is hydrogen, a nitrogen-containing heterocyclic group, an acyl group or an amino-protective group; A is S, S.fwdarw.O, O or CH.sub.2 ; R.sup.4 is hydrogen, methoxy group or formamido group; R.sup.13 is hydrogen, methyl, hydroxyl or a halogen; and A is an optionally substituted condensed cyclic group formed by combining an imidazole or pyrazole ring with 5- or 6-membered nitrogen-containing aromatic heterocyclic ring to share a C-N bond with each other,or a salt or ester thereof.and a process for preparing the same and a pharmaceutical composition thereof are disclosed.Type: GrantFiled: December 12, 1986Date of Patent: June 13, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Tatsuo Nishimura, Yoshinobu Yoshimura, Akio Miyake, Naoto Hashimoto
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Patent number: 4833242Abstract: Novel cephalosporin derivatives and salts thereof are disclosed. These compounds exhibit excellent antimicrobial activity against a wide variety of Gram-negative and Gram-positive bacteria and also have other excellent characteristics as a medicine such as stability and low toxicity. These compounds can be administered in a form of subcutaneous, intravenous or intramuscular injections.Type: GrantFiled: April 17, 1985Date of Patent: May 23, 1989Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Minoru Furukawa, Hiroaki Tagawa, Takeshi Hayano, Akio Ejima
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Patent number: 4833134Abstract: Cephem compounds of the formula: ##STR1## wherein Q stands for a nitrogen atom or CH, R.sup.1 stands for a hydrogen atom or an optionally substituted lower alkyl group, R.sup.2 stands for a hydrogen atom or a lower alkyl group, A stands for a sulfur atom or NH, and n denotes an integral number ranging from 2 to 4, or salts thereof, and processes for producing them. The compounds (I) or salts thereof show not only excellent antibacterial activities against a wide range of pathogenic bacteria from gram-positive to gram-negative ones, including a variety of strains isolated clinically but also hydrophilic properties, and therefore they are excellent antibiotic substances having desirable water-solubility when used as injections.Type: GrantFiled: August 13, 1987Date of Patent: May 23, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Kiminori Tomimatsu, Michiyuki Sendai
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Patent number: 4822786Abstract: A cephalosporin compound having the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a halogen atom, a methoxy group, a substituted or unsubstituted vinyl group, or --CH.sub.2 --A wherein A is a hydrogen atom, an azido group, an acyloxy group, a carbamoyloxy group, a subsituted or unsubstituted heterocyclic group (wherein the hetrocyclic ring is a 5- or 6-membered heterocyclic ring having from 1 to 4 oxygen, nitrogen or sulfur atoms), or a substituted or unsubstituted heterocyclic thio group (wherein the heterocyclic ring is a monocyclic or bicyclic heterocyclic ring having from 1 to 5 oxygen, nitrogen or sulfur atoms), or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 17, 1987Date of Patent: April 18, 1989Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Yoshiyuki Zama, Nobuo Ishiyama, Tsuneo Saita, Takanobu Naito, Masao Hirose, Masaaki Yokoyama, Taiji Asano, Hisato Senda, Keiji Sekine, Shigeru Sanai
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Patent number: 4803196Abstract: A solid pharmaceutical composition comprising one or more .beta.-lactam antibiotics in acid or amphoteric form in association with at least one physiologically acceptable base in the presence of a gaseous atmosphere containing a stabilizing amount of carbon dioxide at a concentration greater than that of atmospheric air. The compositions exhibit enhanced stability. A preferred antibiotic for the compositions is ceftazidime or a hydrate thereof, and a preferred base is sodium cabonate or a mixture thereof with one or more other bases.Type: GrantFiled: June 4, 1987Date of Patent: February 7, 1989Assignee: Glaxo Group LimitedInventor: Betty L. Richardson
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Patent number: RE33948Abstract: 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 ##STR3## Z representing O, S, or NR.sup.10, and R.sup.2 represents hydrogen or a protective group.Type: GrantFiled: August 29, 1989Date of Patent: June 2, 1992Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger