Chalcogen Attached Directly By A Single Bond To The Carbon Or To An Acyclic Carbon Chain Which Contains The Carbon Patents (Class 540/349)
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Patent number: 8461327Abstract: The present invention relates to a salt of a carboxylic acid with a diamine such as 2,2?-(ethylenedioxy)diethyl amine, 3,3?-(ethylenedioxy)dipropyl amine and 2,2?-oxybis(ethylamine) and a method of preparing such salts. Preferably the carboxylic acid is a fermentation product such as clavulanic acid, mycophenolic acid or pravastatin.Type: GrantFiled: March 31, 2009Date of Patent: June 11, 2013Assignee: DSM Sinochem Pharmaceuticals Netherlands B.V.Inventors: Robertus Mattheus De Pater, Adrianus Antonius Cornelius Van Wijk, Piotr Wnukowski
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Publication number: 20130090470Abstract: 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: September 13, 2012Publication date: April 11, 2013Applicant: LIFE TECHNOLOGIES CORPORATIONInventors: Schuyler CORRY, William Downey, Brian Filanoski, Kyle Gee, Lawrence Greenfield, James Hirsch, Iain Johnson, Aleksey Rukavishnikov
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Publication number: 20110028712Abstract: The present invention relates to a salt of a carboxylic acid with a diamine such as 2,2?-(ethylenedioxy)diethyl amine, 3,3?-(ethylenedioxy)dipropyl amine and 2,2?-oxybis(ethylamine) and a method of preparing such salts. Preferably the carboxylic acid is a fermentation product such as clavulanic acid, mycophenolic acid or pravastatin.Type: ApplicationFiled: March 31, 2009Publication date: February 3, 2011Inventors: Robertus Mattheus De Pater, Adrianus Antonius Wijk Van, Piotr Wnukowski
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Patent number: 7087748Abstract: A novel process for the removal of impurities from clavulanic acid using a selective adsorption material, in particular a molecularly imprinted polymer. Novel selective adsorption materials suitable for the process, and a process for the preparation of such selective adsorption materials, are also disclosed.Type: GrantFiled: September 17, 2001Date of Patent: August 8, 2006Assignee: SmithKline Beecham P.L.C.Inventors: Klaus Mosbach, Lei Ye, Yihua Yu
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Patent number: 6979735Abstract: The present invention describes novel agglomerates in crystalline form of ?-lactam compounds. Furthermore, a process for the preparation of said agglomerates, wherein a solution or suspension of at least one ?-lactam compound in a solvent is mixed with one or more anti-solvents has been described.Type: GrantFiled: April 3, 2000Date of Patent: December 27, 2005Assignee: DSM N.V.Inventors: Johannes Booij, Ageeth Geertruida Lefferts
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Patent number: 6566106Abstract: A process for the isolation of clavulanic acid and pharmaceutically acceptable salts thereof, such as potassium clavulanate, from the aqueous fermentation broth of a clavulanic acid-producing microorganism comprises the microfiltration of the broth without prior treatment.Type: GrantFiled: January 3, 2001Date of Patent: May 20, 2003Assignee: Lek Pharmaceutical & Chemical Co., d.d.Inventor: Egidij Capuder
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Patent number: 6465491Abstract: The present invention relates to certain 6-phenyl-pyridin-2-ylamine derivatives that exhibit activity as nitric oxide synthase (NOS) inhibitors, to pharmaceutical compositions containing them and to their use in the treatment and prevention of central nervous system disorders.Type: GrantFiled: April 4, 2001Date of Patent: October 15, 2002Assignee: Pfizer Inc.Inventors: John A. Lowe, III, Peter J. Whittle
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Patent number: 6417352Abstract: The invention relates to the process for the isolation of a pharmaceutically acceptable alkali metal salt of clavulanic acid from a fermentation broth containing impure clavulanic acid comprising the steps of filtration of the fermented broth, extraction of the clavulanic acid to a water immiscible or partly water immiscible solvent at pH from 1.2-2, precipitation of an alkali metal salt A of clavulanic acid by addition of a solution of an alkali metal alkylalkanoate, characterized by the following steps: before the filtration the fermented broth containing clavulanic acid is diluted with water, a flocculating agent is added and the pH is adjusted to 3-5 for further purification the alkali metal salt A of clavulanic acid is converted to clavulanic acid by addition of an inorganic acid and is extracted into a water immiscible or partly water immiscible solvent a solution of a different alkali metal B alkyl alkanoate is added and the alkali metal salt B of clavulanic acid is precipitated.Type: GrantFiled: February 10, 2000Date of Patent: July 9, 2002Assignee: CIPAN-Companhia Industrial Produtora de Antibioticos, S.A.Inventor: Joaquim P. Cardoso
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Patent number: 6414142Abstract: A new crystalline form of potassium clavulanate is disclosed. Also disclosed are a process for producing the new crystalline form of potassium clavulanate, pharmaceutical compositions containing it and methods of treating bacterial infections.Type: GrantFiled: December 8, 1997Date of Patent: July 2, 2002Assignee: SmithKline Beecham CorporationInventors: Paul Gerard Butterly, Gilroy John Keohane, Esin Fatma Kosal
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Patent number: 6369219Abstract: Provided is a process for purification of clavulanic acid or a pharmaceutically acceptable salt or ester thereof, including adding an additional solvent to a solution of clavulanic acid in water immiscible solvent; contacting the solution with an amine; isolating the amine salt of the clavulanic acid formed; and converting the amine into clavulanic acid or a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: December 14, 2000Date of Patent: April 9, 2002Assignee: LEK Pharmaceutical & Chemical Co. DDInventor: Egidij Capuder
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Patent number: 6300495Abstract: A process for the preparation of a metal salt of clavulanic acid which comprises the reaction between an organic amine salt of clavulanic acid and a metal salt precursor compound, the reaction taking place in a liquid medium which comprises a liquid florinated and/or chlorinated hydrocarbon.Type: GrantFiled: September 30, 1999Date of Patent: October 9, 2001Assignee: SmithKline Beecham p.l.c.Inventors: Michael Allen Cook, Mazin Nicola
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Patent number: 6235747Abstract: The present invention relates to certain 6-phenyl-pyridin-2-ylamine derivatives that exhibit activity as nitric oxide synthase (NOS) inhibitors, to pharmaceutical compositions containing them and to their use in the treatment and prevention of central nervous system disorders.Type: GrantFiled: March 13, 1997Date of Patent: May 22, 2001Assignee: Pfizer Inc.Inventors: John A. Lowe, III, Peter J. Whittle
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Patent number: 6235506Abstract: Improved methods for the preparation of clavams by fermentation of a clavam-producing organism in a suitable medium wherein the ammonium levels are kept low so as to avoid repression of enzymes, particularly urease, are disclosed.Type: GrantFiled: September 29, 1999Date of Patent: May 22, 2001Assignee: SmithKline Beecham, p.l.c.Inventors: Brian Peter Valentine, Paul Alan Jeffkins, William Henry Holms, David Michael Mousdale
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Patent number: 6218380Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of &bgr; lactam antibiotics against many &bgr;-lactamase producing bacteria.Type: GrantFiled: August 15, 1991Date of Patent: April 17, 2001Assignee: SmithKline Beecham p.l.c.Inventors: Martin Cole, Thomas Trevor Howarth, Christopher Reading
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Patent number: 6207428Abstract: A process for the isolation of clavulanic acid and pharmaceutically acceptable salts thereof, such as potassium clavulanate, from the aqueous fermentation broth of a clavulanic acid-producing microorganism comprises the microfiltration of the broth without prior treatment.Type: GrantFiled: October 8, 1999Date of Patent: March 27, 2001Assignee: Lek Pharmaceutical & Chemical Co. d.d.Inventor: Egidij Capuder
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Patent number: 6172221Abstract: A back extraction process in which beta-lactam antibiotics or clavulanic acid is extracted from an organic solvent phase into an aqeous medium phase, using a mixing region in which the phases are mixed rapidly under high turbulence and shear stress.Type: GrantFiled: August 27, 1997Date of Patent: January 9, 2001Assignee: SmithKline Beecham p.l.c.Inventor: Simon Ruddick
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Patent number: 6133441Abstract: Process for the production of alkali salts of clavulanic acid of formula ##STR1## by conversion of clavulanic acid into a pharmaceutically acceptable salt of clavulanic acid which is characterised in that the conversion is carried out in n-butanol or iso-butanol (2-methyl-1-propanol) as a solvent; and a potassium salt of clavulanic acid containing n-butanol or iso-butanol.Type: GrantFiled: May 11, 1998Date of Patent: October 17, 2000Assignee: Biochemie Gesellschaft m.b.H.Inventor: Helmut Wagner
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Patent number: 6051703Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: April 6, 1995Date of Patent: April 18, 2000Assignee: SmithKline Beecham p.l.c.Inventors: Martin Cole, Thomas Trevor Howarth, Christopher Reading
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Patent number: 6048977Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: April 6, 1995Date of Patent: April 11, 2000Assignee: SmithKline Beecham p.l.c.Inventors: Martin Cole, Thomas T Howarth, Christopher Reading
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Patent number: 6031093Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: April 6, 1995Date of Patent: February 29, 2000Assignee: SmithKline Beecham p.l.c.Inventors: Martin Cole, Thomas T Howarth, Christopher Reading
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Patent number: 5994534Abstract: Provided is a process for preparation of pharmaceutically acceptable metal salts of clavulanic acid which avoids the use of toxic amines or other intermediates. The process involves removing solids from a clavulanic acid containing fermentation broth by microfiltration; acidifying the microfiltrate to a pH of between 1 and 3; extracting the acidified microfiltrate with a water immiscible solvent and separating the clavulanic acid containing extract; without converting the clavulanic acid containing extract to an intermediate clavulanate salt, mixing the extract with a metal donor and at least one additional non-aqueous solvent; and separating a pharmaceutically acceptable metal clavulanate salt from the solution.Type: GrantFiled: November 24, 1997Date of Patent: November 30, 1999Assignee: Lek Pharmaceutical and Chemical Co. D.DInventor: Egidij Capuder
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Patent number: 5985624Abstract: Improved methods for the preparation of clavams by fermentation of a clavam-producing organism in a suitable medium wherein the ammonium levels are kept low so as to avoid repression of enzymes, particularly urease, are disclosed.Type: GrantFiled: August 26, 1997Date of Patent: November 16, 1999Assignee: SmithKline Beecham p.l.c.Inventors: Brian Peter Valentine, Paul Alan Jeffkins, William Henry Holms, David Michael Mousdale
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Patent number: 5985625Abstract: A process for the isolation of clavulanic acid pharmaceutically acceptable salts thereof, such as potassium clavulanate, from the aqueous fermentation broth of a clavulanic acid-producing microogranism comprises the microfiltration of the broth without prior treatment.Type: GrantFiled: July 10, 1998Date of Patent: November 16, 1999Assignee: Lek Pharmaceutical & Chemical Co. ddInventor: Egidij Capuder
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Patent number: 5965728Abstract: A process for the preparation of a salt of clavulanic acid, wherein clavulanic acid in solution in a wholly or partly water-imiscible organic solvent is contacted in a region of high turbulence and/or shear stress, with a salt precursor compound to form a solution of the salt of clavulanic acid in an aqueous phase, then the organic solvent and aqueous phases are physically separated during a separation step, followed by a further processing step in which the said salt of clavulanic acid is isolated from solution as a solid.Type: GrantFiled: August 21, 1996Date of Patent: October 12, 1999Assignee: SmithKline Beecham PLCInventors: Michael Alan Cook, Geoffrey Clive Webb
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Patent number: 5859238Abstract: A process for purification of crude clavulanic acid and its subsequent conversion to its potassium salt. A crude clavulanic acid extract is contacted in an organic solvent with an alkylenediamine of the formula II ##STR1## wherein the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each individually denote a hydrogen atom, or a straight chain or a branched chain alkyl group having 1 to 8 carbon atoms, R.sub.5 denotes a hydrogen atom, and n denotes an integer 1. The thus obtained alkylenediammonium diclavulanates of the formula I are isolated ##STR2## wherein the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 and n have the meanings as defined at formula II. Salts of the alkylenediammonium diclavulanate of the formula I are converted with potassium 2-ethyl-hexanoate in isopropanol into potassium salt of clavulanic acid.Type: GrantFiled: January 27, 1997Date of Patent: January 12, 1999Assignee: LEK, Tovarna FarmacevtskihInventor: Anton Copar
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Patent number: 5821364Abstract: New diamine salts of clavulanic acid, pharmaceutical compositions comprising the same, and a new process using these diamine salts in the preparation of clavulanic acid and salts and esters thereof have been provided.Type: GrantFiled: November 14, 1994Date of Patent: October 13, 1998Assignee: Gist-Brocades N.V.Inventor: Pieter Gijsbert Weber
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Patent number: 5786351Abstract: A di-clavulanate salt derived from clavulanic acid and a diamino ether of the formula ##STR1## wherein R.sup.1 is an alkylene group, optionally having one or more inert substituents: and each of R.sup.2 and R.sup.3 is a hydrogen atom or an alkyl group, optionally having one or more inert substituents, or R.sup.2 and R.sup.3 together complete a heterocyclic ring having four to seven carbon atoms, again optionally having one or more inert substituents. A process for preparing the clavulanic acid salt includes the steps of preparing a substantially water free solution of clavulanic acid, or a salt thereof, in an organic solvent which solution is at a maintained temperature of 0.degree. to 15.degree. C. and then reacting the clavulanic acid, or salt thereof, with diamino ether in the organic solvent.Type: GrantFiled: December 3, 1996Date of Patent: July 28, 1998Assignee: Spurcourt LimitedInventor: George Leo Callewaert
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Patent number: 5760218Abstract: New diamine salts of clavulanic acid, pharmaceutical compositions comprising the same, and a new process using these diamine salts in the preparation of clavulanic acid and salts and esters thereof have been provided.Type: GrantFiled: May 31, 1995Date of Patent: June 2, 1998Assignee: Gist-Brocades N.V.Inventor: Pieter Gijsbert Weber
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Patent number: 5750685Abstract: A process is disclosed for preparing potassium clavulanate in the form of crystalline rosettes by addition of a solution of clavulanate ions to a solution of potassium ions in a non-solvent for potassium clavulanate.Type: GrantFiled: June 7, 1995Date of Patent: May 12, 1998Assignee: SmithKline Beecham, p.l.c.Inventors: Dennis Edward Clark, Shaukat Hussain Malik, Paul Gerard Butterly, Clive Elton Badman, Jeffrey David Haseler
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Patent number: 5741903Abstract: A process for the purification of clavulanic acid comprising reacting in an organic solvent impure clavulanic acid with a diamine of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are individually selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and cycloalkyl alkyl of 3 to 8 cycloalkyl carbon atoms and alkyl of 1 to 8 carbon atoms, all optionally substituted with 1 to 3 members of the group consisting of halogen, --OH, lower alkoxy and carboxy esterified with lower alkyl or R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 taken with the nitrogen to which they are attached form piperidino and n is an integer from 1 to 10 to form an amine salt selected from the group consisting of ##STR2## recovering the amine salts and acidifying the amine salt to recover purified clavulanic acid.Type: GrantFiled: March 26, 1993Date of Patent: April 21, 1998Assignee: Gist-Brocades N.V.Inventor: P. G. Weber
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Patent number: 5734048Abstract: According to the present invention, a process for manufacturing alkali metal salt of clavulanic acid wherein impure clavulanic acid in aqueous solution is extracted by a solvent mixture of ketone and alkyl acetate under acidic condition, treated in a conventional manner, and a solution of alkali metal salt of alkanoic acid dissolved in ketone or alkanol solvent is added to obtain pure alkali metal salt of clavulanic acid is provided.Since the process according to the present invention omits a step of formation of amine salt, an economic and simple method for manufacturing alkali metal salt of clavulanic acid in a high yield without excessive use of solvent is provided.Type: GrantFiled: November 7, 1995Date of Patent: March 31, 1998Assignee: Chong Kun Dang Corp.Inventors: Jung Woo Kim, Nam Hee Choi, Gang Sun Choi, Don Wha Lee
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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: 5719277Abstract: New diamine mono and diamine di salts of clavulanic acid, pharmaceutical compositions comprising the same, and a new process using these diamine salts in the preparation of clavulanic acid and salts and esters thereof have been provided.Type: GrantFiled: June 1, 1995Date of Patent: February 17, 1998Assignee: Gist-Brocades N.V.Inventor: Pieter G. Weber
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Patent number: 5679789Abstract: Potassium clavulanate exists in a novel crystalline habit, namely in the form of rosettes, having improved processing properties. The novel form may, for example, be obtained by crystallization or recrystallization using inverse precipitation, preferably at 8.degree.-15.degree. C.Type: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: Beecham Group, p.l.c.Inventors: Dennis Edward Clark, Shaukat Hussain Malik, Paul Gerard Butterly, Clive Elton Badman, Jeffrey David Haseler
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Patent number: 5670638Abstract: The azetidines of the present invention have the formula I ##STR1## wherein R.sup.1 is hydrogen or bromine,R.sup.2 is hydrogen or bromine, wherein at least one of R.sup.1 or R.sup.2 is bromine,R.sup.3 is hydrogen; Me.sub.2 --C.dbd.C--COOR.sup.4 wherein R.sup.4 is hydrogen, methyl, benzyl or some other carboxy-protective group, andX is bromine or nitroxy group (--ONO.sub.2).According to the invention 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3-dibromo-4-oxo-azetidines are prepared by reacting derivatives of protected penicillanic acid 1,1-dioxides with DBN reactant (1,5-diazabicyclo/3.4.Type: GrantFiled: July 8, 1994Date of Patent: September 23, 1997Assignee: PLIVA farmaceutskaInventor: Irena Lukic
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Patent number: 5608052Abstract: Described is a new process for the preparation of alkali clavulanate from an aqueous solution of crude clavulanic acid, which is obtained in a conventional manner after the fermentation with a clavulanic-acid-producing microorganism, extracted with an ethyl acetate solution of a hydrophobic .beta.-cyclodextrin derivative such as heptakis-(2,3,6-tri-O-acetyl)-.beta.-cyclodextrin in at least equimolar ratio with regard to clavulanic acid. The resulting novel inclusion complexes of clavulanic acid and hydrophobic .beta.-cyclodextrin derivative in a molar ratio about 1:1 are isolated, purified and then converted with an alkali base or alkali alkanoate to the desired alkali clavulanate, which is isolated. Furthermore, there are described new inclusion complexes of clavulanic acid and of its pharmaceutically acceptable alkali salts both with hydrophilic .beta.-cyclodextrin derivatives and with hydrophobic .beta.Type: GrantFiled: June 6, 1995Date of Patent: March 4, 1997Assignee: LEK, tovarna farmacevtskih in kemicnihInventors: Janko Zmitek, Darja Fer cej-Temeljotov, Katarina Verhnjak, Sonja Kotnik, Mateja Kova ci c
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Patent number: 5585373Abstract: A derivative of 3-(7'-oxo-1'-aza-4'-oxabicyclo[3.2.0 ]hept-3'-yl)propionic acid represented by the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group optionally having one or more cycloalkyl groups, a lower acyl group, a benzoyl group optionally having one or more substituents or a benzyl group optionally having one or more substituents, R.sub.2 is a hydrogen atom or a carboxyl-protecting group, R.sub.3 is a hydroxyl group, an azido group, a benzenesulfonyloxy group optionally having one or more substituents, a lower alkylsulfonyloxy group optionally having one or more substituents, a tri-substituted silyloxy group or an amino group optionally having one or more substituents, provided that when R.sub.1 and R.sub.2 are hydrogen atoms, R.sub.3 is not an amino group, and a salt thereof.Type: GrantFiled: November 18, 1994Date of Patent: December 17, 1996Assignee: Taiho Pharmaceutical Co., LtdInventors: Zhang Z. Ping, Zhen J. Sheng, Zhang Q. Rong, Zhang J. Liang, Singh Rajeshwar, Tomohiro Yamashita, Toshiyuki Toko, Hiroshi Matsumoto
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Patent number: 5498788Abstract: Described is a new process for the preparation of alkali clavulanate from an aqueous solution of pure clavulanic acid and of pharmaceutically acceptable potassium crude clavulanic acid, which is obtained in a conventional manner after the fermentation with a clavulanic-acid-producing microorganism, extracted with an ethyl acetate solution of a hydrophobic .beta.-CD derivative such as heptakis-(2,3,6-tri-O-acetyl)-.beta.-CD in equimolar amount or up to 10% excess with regard to clavulanic acid. The resulting novel inclusion complexes of clavulanic acid and hydrophobic .beta.-CD derivative in a molar ratio about 1:1 are isolated, purified with water and then converted with potassium 2-ethyl hexanate to the potassium clavulanate, which is isolated. Furthermore, there are described new inclusion complexes of clavulanic acid and of its pharmaceutically acceptable potassium salt both with hydrophilic .beta.-CD derivatives and with hydrophobic .beta.Type: GrantFiled: January 6, 1995Date of Patent: March 12, 1996Assignee: LEK, tovarna farmacevtskihInventors: Janko Zmitek, Darja Fercej-Temeljotov, Katarina Verhnjak, Sonja Kotnik, Mateja Kovacic
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Patent number: 5310898Abstract: A novel process for the preparation of calvulanic acid and pharmaceutically acceptable salt thereof, such as potassium clavulanate, is described. According to the novel process, crude clavulanic acid, which is present in the form of an extract in an organic solvent, such as ethyl acetate, the extract having been obtained in known manner upon fermentation with a calvulanic acid producing microorganism, is reacted with substituted alkylenediamines of the formula II ##STR1## wherein the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 and n have the meanings as defined in claim 1, e.g. with N,N'-diisopropylethylenediamine, to the novel alkylenediammonium diclavulanates of the formula I ##STR2## wherein the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 and n have the meanings as defined in claim 1, e.g. to N,N'-diisopropylethylenediammonium diclavulanate.Type: GrantFiled: March 25, 1993Date of Patent: May 10, 1994Assignee: LEK, torvarna farmacevtskihInventor: Anton Copar
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Patent number: 4797396Abstract: .beta.-Lactam derivatives and analogs are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: July 16, 1987Date of Patent: January 10, 1989Assignee: Merck & Co., Inc.Inventors: Paul E. Finke, Morris Zimmerman, James B. Doherty, Bonnie M. Ashe, Conrad P. Dorn
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Patent number: 4711886Abstract: .beta.-Lactam derivatives and analogs are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: July 2, 1984Date of Patent: December 8, 1987Assignee: Merck & Co., Inc.Inventors: Paul E. Finke, James B. Doherty, Morris Zimmerman, Bonnie M. Ashe, Conrad P. Dorn
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Patent number: 4650795Abstract: The present invention provides the salts of the formula (II): ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl, aralkyl, phenyl or inertly substituted lower alkyl, aralkyl or phenyl group; R.sup.2 is a hydrogen atom or a lower alkyl, aralkyl, phenyl or inertly substituted lower alkyl, aralkyl or phenyl group; and R.sup.3 is lower alkyl, aralkyl, phenyl or inertly substituted lower alkyl, aralkyl or phenyl group; any of said groups R.sup.1, R.sup.2 and R.sup.3 being optionally interlinked to form a ring of 5-7 ring atoms. The compounds are antibacterials.Type: GrantFiled: October 28, 1985Date of Patent: March 17, 1987Assignee: Beecham Group p.l.c.Inventors: Michael Liberman, Kenneth T. Veal
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Patent number: 4647659Abstract: This invention provides a novel process for the preparation of clavulanic acid and pharmaceutically acceptable salts and esters thereof which process utilizes the preparation of the tertiary-butylamine salt of clavulanic acid optionally in the form of an acetone solvate and subsequently converting said salt into the desired product.Type: GrantFiled: January 22, 1985Date of Patent: March 3, 1987Assignee: Beecham Group p.l.c.Inventors: Michael A. Cook, Alan D. Curzons, Robert B. Wilkins
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Patent number: 4609495Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R is an inert organic group of up to 18 carbon atoms and are able to inhibit the action of various bacterial .beta.-lactamases. Thus when a compound of the formula (II) or its salt or ester is used together with a penicillin or cephalosporin, the effectiveness of that penicillin or cephalosporin can be considerably enhanced. These novel synergysts can be prepared by etherification of an ester of clavulanic acid followed if desired by deesterification. The novel synergysts also possess antibacterial activity.Type: GrantFiled: June 29, 1981Date of Patent: September 2, 1986Assignee: Beecham Group p.l.c.Inventors: Roger J. Ponsford, Thomas T. Howarth
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Patent number: H2158Abstract: Use of the 2-amino-2,4,4-trimethylpentane salt of clavulanic acid as an intermediate in the production of pharmaceutically acceptable salts of clavulanic acid.Type: GrantFiled: May 13, 2003Date of Patent: June 6, 2006Assignee: Sandoz AGInventors: Franz Krenmüller, Harald Summer