3-position Substituent Contains -cooc- Group Patents (Class 514/195)
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Patent number: 6156745Abstract: Compounds of formula I: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting .beta.-lactamase enzymes, for enhancing the activity of .beta.-lactam antibiotics, and for treating .beta.-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula I, and novel intermediates useful for the synthesis of compounds of formula I.Type: GrantFiled: December 29, 1998Date of Patent: December 5, 2000Assignee: Research Corporation Technologies, Inc.Inventors: John D. Buynak, Akireddy Srinivasa Rao, Venkata Ramana Doppalapudi
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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: 5885981Abstract: Antibiotic penem compounds are represented by the following formula: ##STR1## wherein R represents a group of the general formula: ##STR2## in which R.sub.1 is a hydrogen atom or linear or branched C.sub.1 --C.sub.6 alkyl group, R.sub.2 is a particular substituted or unsubstituted alkyl, aryl or aralkyl group, n is an integer of 1-6, Y is a 5- or 6-membered heterocyclic aliphatic group having 1 or 2 oxygen atoms in the ring thereof, and Z is a specific 5-substituted 2-oxo-1,3-dioxolen-4-yl group. Antibiotic compositions for oral administration are also described.Type: GrantFiled: June 6, 1995Date of Patent: March 23, 1999Assignee: Suntory LimitedInventors: Hiromitsu Iwata, Takashi Nakatsuka, Rie Tanaka, Masaji Ishiguro
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Patent number: 5830889Abstract: Antibiotic penem compounds are represented by the following formula: ##STR1## wherein R represents a group of the general formula: ##STR2## in which R.sub.1 is a linear or branched C.sub.1 -C.sub.6 alkyl group, R.sub.2 is a particular substituted or unsubstituted alkyl, aryl or aralkyl group, n is an integer of 1-6, Y is a 5- or 6-membered heterocyclic aliphatic group having 1 or 2 oxygen atoms in the ring thereof, and Z is a specific 5-substituted 2-oxo-1,3-dioxolen-4-yl group. Antibiotic compositions for oral administration are also described.Type: GrantFiled: February 19, 1993Date of Patent: November 3, 1998Assignee: Suntory LimitedInventors: Hiromitsu Iwata, Takashi Nakatsuka, Rie Tanaka, Masaji Ishiguro
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Patent number: 5747483Abstract: Penem derivatives of general formula (I), below, and pharmaceutically acceptable salts thereof are disclosed. ##STR1## wherein: R.sub.1 is H, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.7 cycloalkyl, or an optionally protected C.sub.1 -C.sub.6 hydroxyalkyl; R.sub.2 is a free or esterified carboxyl group or a carboxylate anion; R.sub.3 is H or C.sub.1 -C.sub.6 alkyl; R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 mercaptoalkyl, C.sub.1 -C.sub.6 aminoalkyl, C.sub.1 -C.sub.6 alkyl substituted by a quaternary ammonium group, C.sub.1 -C.sub.6 carboxyalkyl, cycloalkyl, aryl, arylalkyl, heterocyclyl-alkyl optionally substituted, saturated or unsaturated heterocycle, or R.sub.3 and R.sub.4 are linked together to form a heterocyclic ring having 3-7 atoms; R.sub.5 and R.sub.6 independently are H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 mercaptoalkyl, C.sub. -C.sub.6 aminoalkyl, alkenyl, cycloalkyl, aryl, arylalkyl, alkylaryl, heterocyclyl-alkyl, C.sub.Type: GrantFiled: March 17, 1995Date of Patent: May 5, 1998Assignees: A. Menarini Industrie Farmaceutiche Riunite, Istituto Lusofarmaco D'ItaliaInventors: Maria Altamura, Federico Maria Arcamone, Enzo Perrotta, Vittorio Pestellini, Piero Sbraci, Giuseppe Cascio
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Patent number: 5726170Abstract: The salts are prepared by reacting a benzhydrylamine of the formula I (or a salt thereof) with clavulanic acid (or a salt thereof) in solvent, and isolating the resulting salt. In formula I, each of R.sup.1 and R.sup.2 is hydrogen (preferred) or an acceptable substituent. ##STR1## The clavulanic acid salts can be used in pharmaceutical formulations together with a pharmaceutically acceptable carrier, and, preferably, a beta-lactam antibiotic.Type: GrantFiled: February 22, 1996Date of Patent: March 10, 1998Assignee: Spurcourt LimitedInventor: George Leo Callewaert
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Patent number: 5703068Abstract: Antibiotic penem compounds are represented by the following formula: ##STR1## wherein R represents a group of the following formula: ##STR2## in which R.sub.1 is a linear or branched, C.sub.1 -C.sub.6 alkyl group, R.sub.2 is a particular substituted or unsubstituted alkyl, aryl or aralkyl group, n is an integer of 1 or 2, and R.sub.3 represents a specific substituted or unsubstituted alkyl, aryl or aralkyl group. Antibiotic compositions for oral administration are also described.Type: GrantFiled: February 19, 1993Date of Patent: December 30, 1997Assignee: Suntory LimitedInventors: Hiromitsu Iwata, Takashi Nakatsuka, Rie Tanaka, Masaji Ishiguro
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Patent number: 5686441Abstract: Novel 3-(substituted)-3-methyl-4-thia-1-azabicyclo?3.2.0!heptane-2-carboxylate, 4,4-dioxides which are of value for use in combination with .beta.-lactam antibiotics to increase the effectiveness of the antibiotics.Type: GrantFiled: August 4, 1995Date of Patent: November 11, 1997Assignees: Syphar Laboratories, Inc., Taiho Pharmaceutical Co., Ltd.Inventors: Samarendra Nath Maiti, Oludotun Adebayo Phillips, Andhe Venkat Narender Reddy, Eduardo Luis Setti, Ronald George Micetich, Chieko Kunugita, Fusahiro Higashitani, Akio Hyodo
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Patent number: 5650394Abstract: The present invention provides a method of diagnosing and treating a pregnant female at risk for impending preterm delivery. The method comprises the step of diagnosing imminent preterm delivery by testing with a method that has a sensitivity of at least 80% and a specificity of at least 80%, or by testing for fetal fibronectin in the female's vaginal or cervical secretions. If imminent preterm delivery is indicated by the test, the next step comprises administering to the female a combination of a tocolytic agent, at least one urinastatin-like compound, and at least one antibiotic. Also provided is a pharmaceutical composition of MGMTSRYFYNGTSMA (SEQ ID NO:1), RAFIQLWAFDAVKGK (SEQ ID NO:2) and an antibiotic.Type: GrantFiled: November 4, 1993Date of Patent: July 22, 1997Assignee: Adeza BiomedicalInventors: Toshihiko Terao, Naohiro Kanayama, David Casal
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Patent number: 5637579Abstract: The present invention discloses compounds having the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is --COR.sup.4, --CN, --CH.sub.2 R.sup.5, halogen, --CH.dbd.CHR.sup.6 or Q and the other is hydrogen or lower alkyl or both R.sup.1 and R.sup.2 together form a .gamma.-lactam ring,R.sup.3 is hydrogen, lower alkyl, aryl-alkyl, allyl or a residue which is cleavable in vivo,R.sup.4 is hydrogen, lower alkyl, lower alkoxy, benzyloxy, amino, lower alkylamino or lower alkyl-lower alkoxyamino,R.sup.5 is hydroxy, --OCONHR.sup.7, --OCONH.sub.2 or a five- or six-membered hetero-aromatic ring which contains N,S and/or O and which is linked via a nitrogen atom,R.sup.6 is --CN or CHO,R.sup.7 is --COCH.sub.2 Cl,Q is a five- or six-membered hetero-aromatic ring which contains N, S and/or O andn is 0, 1 or 2,and the pharmaceutically compatible salts thereof.These compounds are good .beta.-lactamase inhibitors. They can be used for the prevention or treatment of bacterial infections, optionally together with a .beta.Type: GrantFiled: August 22, 1994Date of Patent: June 10, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Christian Hubschwerlen, Hans Richter, Jean-Luc Specklin
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Patent number: 5538962Abstract: The present invention provides a compound of the formula (I) ##STR1## wherein: R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl;R.sup.2 is hydrogen or C.sub.1-4 alkyl;Z is carboxy, sufonic acid, tetrazol-5-yl or C .sub.1-4 alkylsulfonylcarbamoyl (--CONHSO.sub.2 C.sub.1-4 alkyl);A is a phenyl or thienyl ring;and A is optionally further substituted by one or two substituents or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.Type: GrantFiled: October 6, 1993Date of Patent: July 23, 1996Assignee: Zeneca LimitedInventor: Patrice J. Siret
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Patent number: 5506225Abstract: Antibiotic penem compounds are represented by the following formula: ##STR1## wherein R represents a physiological-hydrolyzable, ester-forming group. The physiologically hydrolyzable, ester-forming group useful in the penem compound of the present invention means a group which can be removed easily by in vivo hydrolysis, such as an acetyloxymethyl, 1-(acetyloxy)ethyl, pivaloyloxymethyl, 1-(ethoxycarbonyloxy)ethyl, 1-(isopropyloxycarbonyloxy)ethyl, 1-(cyclohexyloxycarbonyloxy)ethyl or 3-phthalidyl group. Antibiotic compositions for oral administration are also described.Type: GrantFiled: February 19, 1993Date of Patent: April 9, 1996Assignee: Suntory LimitedInventors: Hiromitsu Iwata, Takashi Nakatsuka, Rie Tanaka, Masaji Ishiguro
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Patent number: 5492903Abstract: Crystalline acetoxymethyl and pivaloyloxymethyl esters of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0] hept-2-ene-carboxylic acid can be obtained by adding a poor solvent to a solution of acetoxymethyl or pivaloyloxymethyl ester of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0] hept-2-ene-carboxylic acid in a good solvent. The crystalline penem compounds obtained show improved stability and are useful antibacterial agents.Type: GrantFiled: August 26, 1993Date of Patent: February 20, 1996Assignee: Takeda Chemical Industries Ltd.Inventors: Yoshiharu Maeda, Yukio Ishibashi, Tetsuya Tsukamoto, Masahiro Mizuno
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Patent number: 5491139Abstract: Antimicrobial quinolonyl lactam compounds comprising a lactam-containing moiety linked, by a non-ester linking moiety, 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 any of a variety of lactam-containing moieties similar to those known in the art to have antimicrobial activity;(2) A, R.sup.6, R.sup.7, and R.sup.8 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity; and(3) Y, together with R.sup.5, form a variety of non-ester linking moieties between the lactam-containing moiety and the quinolone moiety.Type: GrantFiled: April 6, 1994Date of Patent: February 13, 1996Assignee: The Procter & Gamble CompanyInventors: Thomas P. Demuth, Jr., Ronald E. White
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Patent number: 5464616Abstract: A 6.beta.-substituted penicillanic acid of the formula XII: ##STR1## or a pharmaceutically acceptable salt or ester thereof, whereinA and B are each hydrogen wherein the carbon atoms to which A and B are attached are linked by a single bond, or A and B together form a bond, wherein the carbon atoms to which A and B are attached are linked by a double bond,R1 is selected from the group consisting of a) hydrogen, b) a pharmaceutically acceptable salt and c) a pharmaceutically acceptable group selected from the group consisting of C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkyl, C.sub.Type: GrantFiled: August 4, 1994Date of Patent: November 7, 1995Assignee: Synphar Laboratories, Ind.Inventors: Kazuharu Noguchi, Ronald G. Micetich, Mohsen Daneshtalab
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Patent number: 5416208Abstract: Antibacterial penems of formula (I), where R represents a hydrogen atom or a hydroxy protecting group, are prepared by reacting a .beta.-lactam of formula (II) with an oxalyl halide in an inert solvent in the presence of an organic or inorganic base or an acid scavenger to produce a compound of formula (III), wherein X is a halogen atom, treating the resultant compound of formula (III) with a 1,3-dioxolen-2-one of formula (IV), wherein Y is a hydroxy group, in the presence of molecular sieves or an organic or inorganic base to produce a compound of formula (V), and cyclizing the compound of formula (V) in the presence of a trialkylphosphite to provide the penems of formula (I).Type: GrantFiled: February 22, 1994Date of Patent: May 16, 1995Assignee: Farmitalia Carlo Erba S r lInventors: Ettore Perrone, Marco Alpegiani, Franco Zarini, Giuseppe Mazzini, Giovanni Franceschi
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Patent number: 5200403Abstract: Compounds of the formula I ##STR1## wherein R' is a free or esterified carboxy group or a carboxylate anion and R.sup.2 is an organic group have beta-lactamase inhibition activity. A process for the preparation of the same and pharmaceutical compositions containing these compounds are provided.Type: GrantFiled: July 23, 1991Date of Patent: April 6, 1993Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Marco Alpegiani, Stephen Hanessian, Giuseppe Meinardi, Ettore Perrone
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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: 5126335Abstract: Compounds of formula (I) and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof: ##STR1## wherein X is hydrogen or a group NHR.sup.1, wherein R.sup.1 is hydrogen or an amino protecting group, and R is an optionally substituted 5-membered or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from oxygen, sulphur or nitrogen, are useful in the treatment of bacterial infections in humans and animals.Type: GrantFiled: March 21, 1990Date of Patent: June 30, 1992Assignee: Beecham Group p.l.c.Inventors: Roger J. Ponsford, Andrew V. Stachulski
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Patent number: 5116832Abstract: Novel penem compounds of the formula, ##STR1## wherein R is hydrogen or allyl, and A is an aliphatic 5- or 6-membered heterocyclic group having one or two oxygens in the ring and their pharmaceutically acceptable salts are produced from the compounds of the formula, ##STR2## wherein A is the same as above and respective R.sup.1 and R.sup.2 are protective groups for hydroxyl and carboxyl groups, through several steps. The compounds and their salts are useful as antibacterial agents.Type: GrantFiled: February 5, 1991Date of Patent: May 26, 1992Assignee: Suntory LimitedInventors: Masaji Ishiguro, Hiromitsu Iwata, Rie Tanaka
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Patent number: 5100887Abstract: Cephemcarboxylic acid esters of the general formula ##STR1## pharmaceutical preparations which are active against bacterial infections, which contain such cephem derivatives, a process for the preparation of the cephem derivatives and the pharmaceutical preparations, and also the use of the cephem derivatives for combating bacterial infections.Type: GrantFiled: July 23, 1990Date of Patent: March 31, 1992Assignee: Hoechst AktiengesellschaftInventors: Friedhelm Adam, Jurgen Blumbach, Walter Durckheimer, Gerd Fischer, Burghard Mencke, Dieter Isert, Gerhard Seibert
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Patent number: 5089489Abstract: 6-substituted penem esters of formula (I): ##STR1## wherein R.sub.1 is halogen or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyl, phenoxy, benzyl or sulphonyloxy group; R.sub.2 is a C.sub.1 -C.sub.4 alkyl, benzyl diphenylmethyl ##STR2## group where A is C.sub.1 -C.sub.4 alkyl, benzyl, p-nitrobenzyl or p-methoxybenzyl; and R.sub.3 is an organic radical, are elastase inhibitors and thereby useful antiinflammatory and antidegenerative agents.Type: GrantFiled: April 5, 1990Date of Patent: February 18, 1992Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Marco Alpegiani, Ettore Perrone, Piergiuseppe Orezzi, Paolo Carminati, Giuseppe Cassinelli
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Patent number: 5051416Abstract: A method is provided for treating a warm-blooded animal having a susceptible bacterial infection which comprises administering orally to said animal a non-toxic, antibacterially effective amount of acetoxymethyl ester of (5R,6S)-2(5R,6S)-2-carbamoyloxymethyl-6-[1(R)-hydroxyethyl]-2-penem-3-carb oxylic acid.Type: GrantFiled: April 3, 1989Date of Patent: September 24, 1991Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Maurizio Foglio, Giovanni Franceschi, Aurora Sanfilippo
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Patent number: 5036063Abstract: Penem derivatives of the formula ##STR1## having R.sup.1 equal to 3-oxocyclobutyl and R.sup.2 equal to H or an ester-forming group, pharmaceutical preparations active against bacterial infections and which contain penem derivatives of this type, processes for the preparation of the penem derivatives and the pharmaceutical preparations, and use of the penem derivatives for the control of bacterial infections are described.Type: GrantFiled: November 24, 1989Date of Patent: July 30, 1991Assignee: Hoechst AktiengesellschaftInventors: Rudolf Lattrell, Walter Durckheimer, Gerhard Seibert
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Patent number: 5015473Abstract: Beta-lactamase inhibiting compounds of the formula ##STR1## or a pharmaceutically acceptable acid addition or carboxylate salt thereof; where n is zero, 1 or 2; X.sub.3 is H or Br, R.sup.1 is H, the residue of certain carboxy-protecting groups or the residue of an ester group readily hydrolyzable in vivo; one of R.sup.12 and R.sup.13 is H and the other is vinyl, certain aryl, alkylthio, alkylsulfonyl or certain heterocyclyl, aminomethyl, thiocarboxyamido or amidino groups; one of R.sup.2 and R.sup.3 is H and the other is as disclosed for the other of R.sup.12 and R.sup.13, or is Cl or CH.sub.2 OH, and R.sup.18 is H or certain acyl groups; intermediates useful in their production, methods for their preparation and use, and pharmaceutical compositions containing them.Type: GrantFiled: January 13, 1989Date of Patent: May 14, 1991Assignee: Pfizer Inc.Inventor: Yuhpyng L. Chen
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Patent number: 5013729Abstract: Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(1S-oxo-3R-thiolanylthio)-2-penem-3-carboxylic acid and 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio )-2-penem-3-carboxylic acid, and pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, useful as systemic antibacterial agents; and intermediates and processes which are useful in the said synthesis of said diastereoisomers.Type: GrantFiled: October 18, 1989Date of Patent: May 7, 1991Assignee: Pfizer Inc.Inventor: Robert A. Volkmann
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Patent number: 5004738Abstract: A pharmaceutical compound which comprises reacting the sodium penicillanic acid 1,1-dioxides with chloroiodomethane in the presence of a solvent to produce chloromethylpenicillanate 1,1-dioxides, reacting the chloromethylpenicillanate 1,1-dioxides with a sodium iodide to produce iodomethylpenicillanate 1,1-dioxides, and reacting the iodomethylpenicillanate 1,1-dioxide with sodium methampicillin and is effective in the treatment of bacterial infections in a mammal.Type: GrantFiled: July 24, 1989Date of Patent: April 2, 1991Inventor: Young Sul Kim
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Patent number: 4997829Abstract: A penem compound represented by the general formula: ##STR1## (wherein R denotes hydrogen or allyl group, A denotes oxygen atom or methylene group and B denotes methylene, ethylene or carbonyl group) or a pharmacologically acceptable salt is produced through several processes.The compound exhibits stronger activities against wide variety of gram-positive and gram-negative bacteria as compared with known penem compounds.Type: GrantFiled: March 9, 1990Date of Patent: March 5, 1991Assignee: Suntory LimitedInventors: Masaji Ishiguro, Hiromitsu Iwata, Takashi Nakatsuka
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Patent number: 4996313Abstract: A compound of formula II: ##STR1## wherein R is hydrogen or an alkyl group and R' is an alkoxy group, and salts and esters thereof.Type: GrantFiled: November 17, 1989Date of Patent: February 26, 1991Assignee: National Research Development CorporationInventor: Jack E. Baldwin
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Patent number: 4965260Abstract: Compounds of the formula ##STR1## in which R.sub.1 is lower alkyl substituted by hydroxy or by protected hydroxy, R.sub.2 represents carboxy or functionally modified carboxy, R.sub.3 is hydrogen, amino, mono- or di-substituted amino, carbamoyl, hydroxy, protected hydroxy, carbamoyloxy, lower alkoxy, halogen, lower alkanoyl, sulphamoyl or heteroarylthio, each of R.sub.4 and R.sub.5, independently of the other, represents hydrogen, lower alkyl, hydroxy, protected hydroxy, lower alkoxy, halogen, amino, protected amino, lower alkanoylamino or carbamoyl, or R.sub.4 and R.sub.5 together represent methylenedioxy, Y represents a group of the formula --O--, --S-- or --NR.sub.6 --, R.sub.6 is hydrogen or lower alkyl, A.sub.1 represents lower alkylene or unsubstituted or substituted phenylene and A.sub.2 represents a direct bond or lower alkylene, and salts of such compounds, have antibacterial activity. The compounds of the formula I are manufactured by processes that are known per se.Type: GrantFiled: February 8, 1988Date of Patent: October 23, 1990Assignee: Ciba-Geigy CorporationInventor: Marc Lang
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Patent number: 4958020Abstract: A process for producing the compound [2S-(2.alpha.,3.beta.,5.alpha.)]-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-m ethyl)-4-thia-1-azabicyclo[3 2 0]-heptane-2-carboxylic acid, (4-nitrophenyl)methyl ester, 4,4-dioxide, which comprises reacting a solution of azidopenamsulfone, 4-methoxyphenol and vinylpropionate with a solution of bis(trimethylsilyl)acetamide and 4-methoxyphenol is toluene at 80.degree.-100.degree. C. for 18-30 hours followed by filtering the resulting solution and cooling the filtrate to 0.degree.-10.degree. C.Type: GrantFiled: May 12, 1989Date of Patent: September 18, 1990Assignee: American Cyanamid CompanyInventors: Raghavan Krishnan, Jesse Gamble, David Blum, William V. Curran, Ving J. Lee, Ransom B. Conrow
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Patent number: 4954489Abstract: Compounds of formula (I) and their salts and esters: ##STR1## wherein X is hydrogen or a group NHR.sup.1, wherein R.sup.1 is hydrogen or an amino protecting group, and R is optionally substituted C.sub.5-8 cycloalkyl or cycloalkenyl, are useful in the treatment of bacterial infections.Type: GrantFiled: April 5, 1989Date of Patent: September 4, 1990Assignee: Beecham Group p.l.c.Inventors: Roger J. Ponsford, Andrew V. Stachulski
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Patent number: 4954493Abstract: 6-substituted penem esters of formula (I): ##STR1## wherein R.sub.1 is halogen or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyl, phenoxy, benzyl, or sulphonyloxy group; R.sub.2 is a C.sub.1 -C.sub.4 alkyl, benzyl diphenylmethyl ##STR2## group where A is C.sub.1 -C.sub.4 is C.sub.1 -C.sub.4 alkyl, benzyl, p-nitrobenzyl or p-methoxybenzyl; and R.sub.3 is an organic radical, are elastase inhibitors and thereby useful antiinflammatory and antidegenerative agents.Type: GrantFiled: June 14, 1988Date of Patent: September 4, 1990Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Marco Alpegiani, Ettore Perrone, Piergiuseppe Orezzi, Paolo Carminati, Giuseppe Cassinelli
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Patent number: 4952577Abstract: A substantially (.gtoreq.95%) optically pure (5R,6S,1'R) penem of formula ##STR1## and the pharmaceutically acceptable salts and the ester prodrugs thereof, are endowed with antibacterial activity.Type: GrantFiled: June 6, 1988Date of Patent: August 28, 1990Assignee: Farmitalia Carlo Erba S.r.l.Inventors: Marco Alpegiani, Giovanni Franceschi, Ettore Perrone, Franco Zarini, Constantino Della Bruna
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Patent number: 4933333Abstract: Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.Type: GrantFiled: October 8, 1987Date of Patent: June 12, 1990Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masatomo Fukasawa, Masuhiro Kato
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Patent number: 4931434Abstract: Compounds of the general formula (II): ##STR1## in which N.sup.+ denotes an unsubstituted or substituted nitrogen-containing heterocyclyl ring bonded to the remainder of the molecule through a ring nitrogen atom and carrying a positive charge on said nitrogen atom;and the wavy line denotes either the E- or Z-isomeric position,are novel and are useful in the treatment of antibacterial infection in humans or animals.Type: GrantFiled: December 16, 1988Date of Patent: June 5, 1990Assignee: Beecham Group p.l.c.Inventors: Nigel J. P. Broom, Gerald Brooks, Brian P. Clarke
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Patent number: 4918067Abstract: The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof: ##STR1## wherein R.sup.1 is a 5 or 6 membered sulphur and/or nitrogen containing heterocyclic group substituted by an optionally protected amino group, with the proviso that R.sup.1 is not 2-aminothiazol-4-yl, and R is hydrogen; optionally substituted C.sub.1-12 alkyl; optionally substituted C.sub.2-12 alkenyl or alkynyl; carbocyclyl; aryl or heterocyclyl.These compounds have antibacterial properties, and therefore are of use in the treatment of bacterial infections in humans and animals caused by a wide range of organizations.Type: GrantFiled: July 22, 1987Date of Patent: April 17, 1990Assignee: Beecham Group p.l.c.Inventors: Brian C. Gasson, Michael J. Pearson
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Patent number: 4891369Abstract: Disclosed are 2.beta.-substituted-methylpenicillanic acid compounds of the formula ##STR1## wherein n is 0, 1 or 2; and ##STR2## is monocyclic or bicyclic heterocyclic ring group which has 2 to 4 nitrogen atoms as hetero atom in its ring structure and which may be optionally substituted with alkyl, alkoxycarbonyl, phenyl, formyl or benzyloxycarbonyl optionally having alkyl, nitro or a halogen atom on the benzene ring, with the proviso that said heterocyclic ring group is not 1,2,3-triazol-1-yl; or salts or esters thereof.These compounds are useful as .beta.-lactamase inhibitor.Type: GrantFiled: November 23, 1987Date of Patent: January 2, 1990Assignee: Taiho Pharmaceutical Company, LimitedInventors: Sigeru Torii, Hideo Tanaka, Motoaki Tanaka, Shozo Yamada, Akira Nakai, Hisashi Ohbayashi, Tomoyasu Ohno
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Patent number: 4886793Abstract: There are provided compounds of formula I: ##STR1## wherein R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl group either unsubstituted or substituted by one or more substituents chosen from a free or protected hydroxy or halogen atom;R.sup.2 is a free or esterified carboxy group or carboxylate anion;R.sup.3 and R.sup.4 are each independently hydrogen or organic group,X is --O--, ##STR2## --S--, Q is either(a") free or protected hydroxy, or(b") a C.sub.1 -C.sub.1 acyloxy, or(c") carbamoyloxy OCONH.sub.2, or(d") an optionally substituted heterocyclylthio group, or(e") an optionally substituted imido group, or(f") an optionally substituted quaternary ammonium group or(g") a halogen atom,A and the pharmaceutically or veterinarily acceptable salts thereof. There are provided also methods for preparing compounds of formula I. The compounds of formula I are useful as antibacterial agents.Type: GrantFiled: March 5, 1987Date of Patent: December 12, 1989Assignee: Farmitalia Carlo Erba, S.r.l.Inventors: Ettore Perrone, Marco Alpegiani, Angelo Bedeschi, Franco Zarini, Costantino Della Bruna, Giovanni Franceschi
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Patent number: 4882325Abstract: Crystalline 1,1-dioxopenicillanoyloxymethyl 6-(D-.alpha.-amino-.alpha.-phenylacetamido)penicillanate napsylate. The product may be prepared by reacting 1,1-dioxopenicillanoyloxymethyl 6-(D-.alpha.-amino-.alpha.-phenylacetamido)penicillanate or a salt thereof with 2-naphthalenesulfonic acid or salt thereof.Type: GrantFiled: October 21, 1988Date of Patent: November 21, 1989Assignee: Leo Pharmaceutical Products Ltd. A/SInventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4870170Abstract: Process and intermediates for the conversion of 3R,4R-4-acetoxy-3-[1R-1-(silyloxy)ethyl]-2-acetidinones to antibacterial 5R,6S-6-(1R-1-hydroxyethyl)-2-(1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids, and the pharmaceutically-acceptable salts and pivaloyloxymethyl esters thereof.Type: GrantFiled: September 21, 1988Date of Patent: September 26, 1989Assignee: Pfizer Inc.Inventors: Robert A. Volkmann, David L. Lindner
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Patent number: 4863914Abstract: Compounds of formula ##STR1## wherein R is hydrogen atom or C.sub.1 -C.sub.4 alkyl group optionally substituted from halogen atom or hydroxy group optionally protected, A is a Z, Z--O--C--O-- or Z--C)-- residue, wherein Z is phenylene, naphthylene, heterocyclediyl, C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.4 alkenylene, alkynylene, ##STR2## C.sub.3 -C.sub.8 cycloalkylene, aralkylene radical optionally substituted, and O.sup.(+) represents a group +NR.sub.1 R.sub.2 R.sub.3, wherein R.sub.1, R.sub.2 and R.sub.3 are each either:(i) a optionally substituted alkyl, aralkyl or aryl radical or(ii) R.sub.1 is as defined above under (i) and R.sub.2 and R.sub.3, taken together, represent an optionally substituted or fused heterocyclic radical, or(iii) R.sub.1, R.sub.2 and R.sub.3, taken together, represent an optionally substituted azonia-bicyclo or tricyclo radical, or(iv) R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: April 8, 1986Date of Patent: September 5, 1989Assignee: Farmitalia Carlo ErbaInventors: Ettore Perrone, Marco Alpegiani, Angelo Bedeschi, Franco Zarini, Giovanni Franceschi, Costantino D. Bruna
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Patent number: 4861768Abstract: Disclosed is a penicillin derivative of the formula: ##STR1## wherein n is an integer of 0, 1 or 2; Y is a cyano group, a lower acyl group, a mono- or di-lower alkylthiocarbamoyl group, ##STR2## wherein R.sub.1 is a hydrogen atom, a lower alkyl group, a phenyl group, a group --(CH.sub.2).sub.m --OR.sub.2 or --(CH.sub.2).sub.m COOR.sub.2 (m is an integer of 1 to 6 and R.sub.2 is a hydrogen atom or a penicillin carboxyl ester-forming group which is commonly used for penicillin derivatives) or a phenyl group substituted by at least one member selected from the class consisting of lower alkyl group, halogen atom and lower alkoxy group; and R is a hydrogen atom or a penicillin carboxyl ester-forming group, or a salt thereof. They are useful as .beta.-lactamase inhibitors.Type: GrantFiled: February 18, 1987Date of Patent: August 29, 1989Assignee: Taiho Pharmaceutical Company, LimitedInventors: Sigeru Torii, Hideo Tanaka, Motoaki Tanaka, Shozo Yamada, Akira Nakai, Hisashi Ohbayashi
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Patent number: 4849419Abstract: A compound of formula I ##STR1## with R.sup.1 being an alkyl group substituted by one or more substituents and esters thereof at the 2-carboxy group or at the 8-hydroxy group or both; and salts thereof. Compounds I have antibacterial effect. Various intermediates are described. This compound of the formula I, or an ester at the 2-carboxy group or at the 8-hydroxy group or both or a salt thereof is produced by reacting a compound of formula II or of formula IX ##STR2## in which R represents a hydrogen atom or a carboxy protecting group, R.sup.3 represents an activated carboxylic acid group, R.sup.4 represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may be unsubstituted or substituted, R.sup.15 represents a phenyl group or an alkyl group having from 1 to 4 carbon atoms, and X represents an oxygen or sulphur with an amine of the formula III R.sup.1 NH.sub.Type: GrantFiled: December 1, 1987Date of Patent: July 18, 1989Assignee: Hoechst UK LimitedInventors: Andrew J. Barker, Nicholas I. Carruthers, Michael D. Cooke
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Patent number: 4847266Abstract: The present invention relates to a new and improved method for the preparation of a compound of the formula I ##STR1## in which R stands for halogen, giving rise to high yields of substantially pure 6.beta.-halopenicillanic acids, obtained in one step.Type: GrantFiled: April 28, 1987Date of Patent: July 11, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Erik I. Hansen, Mogens P. Kran-Nielsen, Welf Von Daehne
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Patent number: 4847247Abstract: Derivatives of Penicillin, their sulfoxides and sulfones are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: October 16, 1986Date of Patent: July 11, 1989Assignee: Merck & Co., Inc.Inventors: Kevan R. Thompson, Paul E. Finke, James B. Doherty
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Patent number: 4840944Abstract: The present invention relates to hitherto unknown compounds of the general formula I: ##STR1## in which R.sub.1 stands for a phenyl, 4-hydroxyphenyl, 1,4-cyclohexadienyl or a 3-thienyl group; R.sub.2 represents a primary amino or a carboxy group; R.sub.3 is a hydrogen atom, or a lower alkyl, aryl or aralkyl radical, and A stands for a radical of a .beta.-lactamase inhibitor containing a .beta.-lactam ring as well as a carboxy group, A being connected via the carboxy group.The present invention provides new compounds useful in the treatment of bacterial infections. The new compounds are in particular strongly active against .beta.-lactamase producing bacteria.Type: GrantFiled: January 24, 1980Date of Patent: June 20, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4837215Abstract: Compounds of the following formula I ##STR1## wherein X represents a sulphur or an oxygen atom,R is hydrogen or a C.sub.1 -C.sub.4 alkyl group either unsubstituted or substituted by one or more substituents chosen from a free or protected hydroxy group and halogen atom;A is a Z, Z--O--CO-- or --Z--CO-- residue, whereinZ represents(a) an optionally substituted phenylene or naphthylene group,(b) an optionally substituted heterocyclediyl radical wherein the hetero ring is mono or bicyclic, saturated or unsaturated containing at least one heteroatom selected from the group of oxygen, sulphur and nitrogen;(c) an optionally substituted linear or branched C.sub.1 -C.sub.7 alkylene radical;(d) a C.sub.2 -C.sub.4 alkenylene or alkynylene group or a group of formula ##STR2## (e) an optionally substituted C.sub.3 -C.sub.8 cycloalkylene ring; (f) an aralkylene radical of the formula ##STR3## wherein n is 1, 2 or 3; andQ.sup.(+) represents a +NR.sub.1 R.sub.2 R.sub.3 group, wherein(i) R.sub.1, R.sub.2, R.sub.Type: GrantFiled: April 8, 1986Date of Patent: June 6, 1989Assignee: Farmitalia Carlo ErbaInventors: Ettore Perrone, Marco Alpegiani, Angelo Bedeschi, Franco Zarini, Giovanni Franceschi, Costantino D. Bruna
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Patent number: 4831025Abstract: The present invention relates to a crystalline hydrate of a salt of the antimicrobial agent 1,1-dioxopenicillanoyloxymethyl 6-(D-.alpha.-amino-.alpha.-phenylacetamido)penicillanate with p-toluenesulfonic acid, more particularly the mono- and dihydrate.The hydrates are easily obtained in a crystalline state devoid of organic solvent residues, they show good stability on storage, they are effectively absorbed and hydrolyzed in vivo, and they are thus specifically suitable for medical treatment of patients, in particular for oral administration.Type: GrantFiled: March 13, 1987Date of Patent: May 16, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4829053Abstract: New aminoacid derivatives of the formula IX--Z--NR.sup.2 --CHR.sup.3 --CR.sup.4 --(CHR.sup.5).sub.n --CO--E--NR.sup.6 --(CHR.sup.7).sub.s --D Iwherein X, Z, R.sup.2, R.sup.3, R.sup.4, R.sup.5, E, R.sup.6, R.sup.7, D, n and s have the meanings defined herein and their salts, inhibit the activity of human plasma renin.Type: GrantFiled: July 31, 1987Date of Patent: May 9, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Peter Raddatz, Joachim Gante, Claus J. Schmitges, Klaus Otto Minck, Johannes Sombroek, Gunter Holzemann