The Six-membered Ring Contains Oxygen Patents (Class 540/300)
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Patent number: 8603947Abstract: A description is given of (4-haloalkyl-3-thiobenzoyl)cyclohexanediones of the formula (I) and of their use as herbicides. In this formula (I), X, Y, R1, R2, R3, and R4 are radicals such as hydrogen and organic radicals such as alkyl. A and Z are oxygen or alkylene.Type: GrantFiled: July 20, 2011Date of Patent: December 10, 2013Assignee: Bayer Cropscience AGInventors: Hartmut Ahrens, Dieter Feucht, Elmar Gatzweiler, Isolde Haeuser-Hahn, Christopher Hugh Rosinger
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Patent number: 8563779Abstract: A description is given of (4-trifluoromethyl-3-thiobenzoyl)cyclohexanediones of the formula (I) and of their use as herbicides. In this formula (I), X, R1, R2, R3, and R4 are radicals such as hydrogen and organic radicals such as alkyl. A and Z are oxygen or alkylene.Type: GrantFiled: July 19, 2011Date of Patent: October 22, 2013Assignee: Bayer CropScience AGInventors: Hartmut Ahrens, Andreas Van Almsick, Elmar Gatzweiler, Dieter Feucht, Isolde Haeuser-Hahn, Stefan Lehr, Christopher Hugh Rosinger
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Publication number: 20090047692Abstract: The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a ?-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a ?-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a ?-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a ?-lactmase or instructions for using the components in an assay.Type: ApplicationFiled: April 7, 2008Publication date: February 19, 2009Applicant: INVITROGEN CORPORATIONInventors: Schuyler Boon CORRY, William Louis Downey, Brian Filanoski, Kyle Richard Gee, I. Lawrence Greenfield, James David Hirsch, Iain Johnson, Aleksey Rukavishnikov
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Patent number: 6124278Abstract: Compounds based on the benzoxazine ring system that are remarkably more potent than corresponding benzoyl piperidines for enhancing synaptic responses mediated by AMPA receptors are disclosed, as are methods for the preparation thereof, and methods for their use for treatment of subjects suffering from impaired nervous or intellectual functioning due to deficiencies in the number of excitatory synapses or in the number of AMPA receptors. The invention compounds can also be used for the treatment of non-impaired subjects for enhancing performance in sensory-motor and cognitive tasks which depend on brain networks utilizing AMPA receptors and for improving memory encoding.Type: GrantFiled: April 3, 1998Date of Patent: September 26, 2000Assignee: The Regents of the University of CaliforniaInventors: Gary A. Rogers, Peter Johnstrom
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Patent number: 6080855Abstract: Compounds of formula (I) or salts thereof: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a carboxy protecting group, pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents; X is O, S, SO or SO.sub.2 ; Y is O, S, SO or SO.sub.2 ; n is 0 or 1; and m is 1 or 2. The compounds have antibacterial activity. Methods of synthesis of, and pharmaceutical formulations containing, compounds (I) are also described.Type: GrantFiled: January 8, 1999Date of Patent: June 27, 2000Assignee: Pfizer Inc.Inventors: George Burton, Brian Charles Gasson, Stephen Christopher Martin Fell
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Patent number: 6077952Abstract: A compound of formula (II) or a salt: ##STR1##Type: GrantFiled: June 8, 1999Date of Patent: June 20, 2000Assignee: Pfizer Inc.Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 6063918Abstract: A process for preparing a 2-isocephem derivative characterized in that a thioacetic acid derivative which itself is basic or a mixture of a base and a thioacetic acid derivative is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-isocephem derivative represented by the general formula (2), and a process for preparing a 2-oxaisocephem derivative characterized in that a base is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-oxaisocephem derivative represented by the general formula (3) ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.1 and R.sup.2, when taken together, form a cyclic amino protecting group, R.sup.Type: GrantFiled: July 7, 1997Date of Patent: May 16, 2000Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Daisuke Suzuki, Delsoo Suh, Yoshihisa Tokumaru
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Patent number: 6020329Abstract: .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acy group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.Type: GrantFiled: October 20, 1997Date of Patent: February 1, 2000Assignee: Pzifer Inc.Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 6001997Abstract: .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.2 ; m is 1 or 2; and n is 0, useful in the treatment of bacterial infections.Type: GrantFiled: January 11, 1999Date of Patent: December 14, 1999Inventors: John Hargreaves Bateson, George Burton, Stephen Christopher Martin Fell
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Patent number: 5919925Abstract: Compounds of formula (I) or salts thereof: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a carboxy protecting group, pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents; X is O, S, SO or SO.sub.2 ; Y is O, S, SO or SO.sub.2 ; n is 0 or 1; and m is 1 or 2. The compounds have antibacterial activity. Methods of synthesis of, and pharmaceutical formulations containing, compounds (I) are also described.Type: GrantFiled: October 14, 1997Date of Patent: July 6, 1999Assignee: Pfizer Inc.Inventors: George Burton, Brian Charles Gasson, Stephen Christopher Martin Fell
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Patent number: 5883247Abstract: The invention is concerned with a new process for the preparation of compounds of formula ##STR1## wherein R.sup.1 is trityl, acetyl, tetrahydropyranyl or cyclopentyl;R.sup.2 is hydrogen, hydroxy, lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, lower alkynyl, aryl, aryloxy, aryl-lower alkyl, aryl-lower alkoxy or heterocyclyl or heterocyclyl-lower alkyl; the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aryl-lower alkyl, aryl, aryloxy, aryl-lower alkoxy, the heterocyclyl moieties being unsubstituted or substituted with at least one group selected from carboxy, amino, nitro, cyano, lower alkyl, lower alkoxy, hydroxy, halogen, --CONR.sup.21 R.sup.22, --N(R.sup.22)COOR.sup.23, R.sup.22 CO--, R.sup.22 OCO-- or R.sup.22 COO--, wherein R.sup.21 is hydrogen, lower alkyl, or cycloalkyl; R.sup.22 is hydrogen or lower alkyl; R.sup.23 is lower alkyl, lower alkenyl or a carboxylic acid protecting group;Y is --S-- and Z is --CH.sub.2 -- orY is --CH.sub.Type: GrantFiled: May 14, 1997Date of Patent: March 16, 1999Assignee: Hoffmann-La Roche Inc.Inventor: Thomas Oberhauser
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Patent number: 5880111Abstract: Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, and infectious urinary tract stones, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.Type: GrantFiled: June 7, 1995Date of Patent: March 9, 1999Inventors: Dan Farcasiu, John F. Hartmann, Pal Herczegh, Ferenc J. Sztaricskai
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Patent number: 5854227Abstract: Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, infectious urinary tract stones, and bone cancer, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.Type: GrantFiled: June 7, 1995Date of Patent: December 29, 1998Inventors: John F. Hartmann, Dan Farcasiu
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Patent number: 5811419Abstract: Compounds of formula I ##STR1## wherein R.sup.1 is hydrogen or an acyl group derived from a carboxylic acid;R.sup.2 is hydrogen, hydroxy, lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aryl-lower alkyl, aryl, aryloxy, aryl-lower alkoxy or a heterocyclic ring; the lower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, lower alkynyl, aryl-lower alkyl, aryl, aryloxy, aryl-lower alkoxy and the heterocyclic ring being unsubstituted or substituted with at least one group selected from carboxy, amino, nitro, cyano, lower alkyl, lower alkoxy, hydroxy, halogen, --CONR.sup.21 R.sup.22, --N(R.sup.22)COOR.sup.23, R.sup.22 CO--, R.sup.22 OCO-- or R.sup.22 COO--, wherein R.sup.21 is hydrogen, lower alkyl, or cycloalkyl; R.sup.22 is hydrogen or lower alkyl; R.sup.Type: GrantFiled: December 17, 1996Date of Patent: September 22, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Christian Hubschwerlen, Jean-Luc Specklin
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Patent number: 5703231Abstract: The present invention provides a process for making a compound having a structure according to Formula (I) ##STR1## wherein A.sup.1, A.sup.2 and A.sup.3 are independently carbon or nitrogen and R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are known quinolone substituents; and wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety;or a protected form, salt, pharmaceutically-acceptable salt, biohydrolyzable ester, or solvate thereof;the process comprising reacting one or more organosilicon compounds with a compound having a structure according to Formula (II) ##STR2## wherein A.sup.1, A.sup.2 and A.sup.3, R.sup.1, R.sup.3, R.sup.4 and R.sup.6 as described above; wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety; and X is a leaving group;or a protected form, salt, biohydrolyzable ester, or solvate thereof.Type: GrantFiled: November 14, 1996Date of Patent: December 30, 1997Assignee: The Procter & Gamble CompanyInventors: Jared Lynn Randall, Jane Ellen Godlewski
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Patent number: 5688942Abstract: A process for preparing a 2-isocephem derivative characterized in that a thioacetic acid derivative which itself is basic or a mixture of a base and a thioacetic acid derivative is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-isocephem derivative represented by the general formula (2), and a process for preparing a 2-oxaisocephem derivative characterized in that a base is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-oxaisocephem derivative represented by the general formula (3) ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.1 and R.sup.2, when taken together, form a cyclic amino protecting group, R.sup.Type: GrantFiled: November 6, 1996Date of Patent: November 18, 1997Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Daisuke Suzuki, Delsoo Suh, Yoshihisa Tokumaru
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Patent number: 5580976Abstract: A process for preparing a .beta.-lactam compound of the formula (I): ##STR1## which comprises cyclization of an azetidinone derivative of the formula: ##STR2## is provided in which R.sup.1 is hydrogen, alkyl which is optionally substituted, or amino which is optionally substituted; R.sup.2 is a carboxy-protecting group; and X is alkylene which is optionally intervened by --O-- or --S--, and/or which is optionally substituted; and R.sup.3 is aryl which is optionally substituted.Type: GrantFiled: April 18, 1995Date of Patent: December 3, 1996Assignee: Shionogi & Co., Ltd.Inventors: Masaharu Kume, Tadatoshi Kubota
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Patent number: 5563264Abstract: A process for preparing a .beta.-lactam compound of the formula (I): ##STR1## which comprises cyclization, in the presence of a catalyst, of an azetidinone derivative of the formula: ##STR2## is provided in which R.sup.1 is hydrogen, alkyl which is optionally substituted, or amino which is optionally substituted; R.sup.2 is a carboxy-protecting group; and X is alkylene which is optionally intervened by --O-- or --S--, and/or which is optionally substituted; and R.sup.3 is aryl which is optionally substituted. The catalyst is preferably a transition metal salt (especially rhodium) or is an acid.Type: GrantFiled: April 18, 1995Date of Patent: October 8, 1996Assignee: Shionogi & Co., Ltd.Inventors: Masaharu Kume, Tadatoshi Kubota
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Patent number: 5395931Abstract: New antibacterial 6-amido-1-methyl-2-(substituted-thio)-carbapenems and process for their synthesis involving new azetidinone intermediates.Type: GrantFiled: May 20, 1992Date of Patent: March 7, 1995Assignee: Merck & Co., Inc.Inventors: Mark L. Greenlee, Frank P. DiNinno, Thomas N. Salzmann
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Patent number: 5196529Abstract: Carbapenems of the formula ##STR1## are useful as intermediates to antibacterial agents.Type: GrantFiled: October 9, 1990Date of Patent: March 23, 1993Assignee: Merck & Co., Inc.Inventors: Frank P. Dininno, Thomas N. Salzmann, Mark L. Greenlee
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Patent number: 5180719Abstract: Antimicrobial quinolonyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: ##STR1## wherein (1) R.sup.3, R.sup.4, and R.sup.5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and(2) A.sup.2, A.sup.2, A.sup.3, R.sup.7, R.sup.8, and R.sup.9 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity.Type: GrantFiled: April 29, 1991Date of Patent: January 19, 1993Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventors: Ronald E. White, Thomas P. Demuth, Jr.
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Patent number: 5112966Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.Type: GrantFiled: October 31, 1985Date of Patent: May 12, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 5075435Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.Type: GrantFiled: June 12, 1990Date of Patent: December 24, 1991Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 5070194Abstract: This invention provides a method of producing a .beta.-lactam derivative represented by the formula (I): ##STR1## said method consisting essentially of the step of reacting a .beta.-lactam derivative represented by the formula (II): ##STR2## with a phenol in a reaction system which consists essentially of said .beta.-lactam derivative of formula (II) and said phenol.Type: GrantFiled: April 5, 1989Date of Patent: December 3, 1991Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Nori Saito, Takashi Shiroi, Shigemitsu Nagao, Ryo Kikuchi, Yutaka Kameyama
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Patent number: 5037976Abstract: A 2-oxa-isocephem compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined, pharmaceutically acceptable salts thereof, composition containing the same and processes for preparing the same are disclosed. The compound is useful as an antimicrobial agent.Type: GrantFiled: November 1, 1989Date of Patent: August 6, 1991Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Setsuro Fujii, Hiroshi Ishikawa, Koichi Yasumura, Koichiro Jitsukawa, Sachio Toyama, Hidetsugu Tsubouchi, Kimio Sudo, Kouichi Tsuji
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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: 4898859Abstract: A 2-oxa-isocephem compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined, pharmaceutically acceptable salts thereof, composition containing the same and processes for preparing the same are disclosed. The compound is useful as an antimicrobial agent.Type: GrantFiled: March 9, 1988Date of Patent: February 6, 1990Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Setsuro Fujii, Hiroshi Ishikawa, Koichi Yasumura, Koichiro Jitsukawa, Sachio Toyama, Hidetsugu Tsubouchi, Kimio Sudo, Kouichi Tsuji
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Patent number: 4873324Abstract: Compounds are disclosed of the structural formula: ##STR1## wherein R.sup.2 is independently selected from hydrogen, linear or branched C.sub.1 -C.sub.3 alkyl, which can be substituted with fluoro, hydroxy, or protected hydroxy, R.sup.3 is hydrogen or a protecting group, X is sulfur or selenium, Q is hydroxymethyl, carboxy or C.sub.1 -C.sub.4 alkoxycarbonyl, and R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.6 -C.sub.10 aryl, or pyridyl which can be substituted with C.sub.1 -C.sub.4 alkyl, alkoxy and nitro; such compound are useful for selectively obtaining 1-.beta.-methylcarbapenem intermediates.Type: GrantFiled: February 6, 1989Date of Patent: October 10, 1989Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Lovji D. Cama, Susan M. Schmitt
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Patent number: 4849516Abstract: Compounds of the formula (V): ##STR1## wherein R.sup.1 is certain optionally substituted alkyl groups, R.sup.2 is hydrogen, alkyl or optionally substituted phenyl and R.sup.3 and R.sup.4 are independently alkyl or optionally substituted phenyl, or together form a C.sub.4-7 cycloalkyl ring; are described as useful intermediates in the preparation of carbapenem and penem antibiotics. Processes for their preparation are described as are certain oxadiazine intermediates.Type: GrantFiled: October 14, 1987Date of Patent: July 18, 1989Assignee: Imperial Chemical Industries PLCInventor: Michael B. Gravestock
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Patent number: 4831026Abstract: A 2-oxa-isocephem compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined, pharmaceutically acceptable salts thereof, esters of the carboxy group in the 4-position thereof and quaternary ammonium salts thereof, composition containing the same and processes for preparing the same are disclosed. The compound is useful as an antimicrobial compound.Type: GrantFiled: March 9, 1987Date of Patent: May 16, 1989Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Setsuro Fujii, Hiroshi Ishikawa, Koichi Yasumura, Koichiro Jitsukawa, Sachio Toyama, Hidetsugu Tsubouchi, Kimio Sudo, Kouichi Tsuji
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Patent number: 4816578Abstract: A stereospecific process for preparing 3-trans-R-trisubstituted silyloxyethyl substituted azetidinones useful as intermediates for preparing penems and carbapenems is provided wherein a 3-unsubstituted azetidinone is treated with a strong base and a trisubstituted silylmethyl ketone to form 3-trans-S-[1-trisubstituted silyl-1-hydroxy]ethylazetidinone followed by rearrangement of this resulting carbinol by treatment with an alkali metal alkoxide and a proton source.Type: GrantFiled: February 26, 1988Date of Patent: March 28, 1989Assignee: Merck & Co., Inc.Inventors: F. Aileen Bouffard, Thomas N. Salzmann
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Patent number: 4705852Abstract: 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: June 20, 1986Date of Patent: November 10, 1987Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Tsutomu Aoki, Yasuhiro Nishitani
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Patent number: 4640915Abstract: Compounds of the formula [I] ##STR1## in which R.sup.1 is hydroxy, a protected hydroxy or lower alkoxy group, R.sup.2 is carboxy or an easily eliminable esterified carboxy group and R.sup.3 is pyridyl, and pharmaceutically acceptable salts thereof, having antimicrobial and .beta.-lactamase inhibiting properties, and pharmaceutical compositions containing the same.Type: GrantFiled: March 18, 1983Date of Patent: February 3, 1987Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masashi Hashimoto, Matsuhiko Aratani, Kozo Sawada
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Patent number: 4617152Abstract: A process is described for selectively obtaining 1-.beta.-methylcarbapenem intermediates. The desired chirality is obtained through the hydrogenation of certain bicyclic .beta.-lactam ring structures containing an exocyclic methylene double bond alpha to the .beta.-lactam ring, in the presence of a Group VIII metal hydrogenation catalyst. The hydrogenation results in a mixture of .alpha.- and .beta.-methyl epimers having a high .beta./.alpha. epimeric ratio. New 1-.beta.-methylcarbapenem intermediates made by the process are also described.Type: GrantFiled: February 19, 1985Date of Patent: October 14, 1986Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Lovji D. Cama, Susan M. Schmitt