Patents Assigned to Leo Pharmaceutical Products Ltd.
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Patent number: 4511512Abstract: This invention relates to penicillanic acid derivatives of the formula I ##STR1## in which X stands for chlorine, bromine or iodine, to pharmaceutically acceptable, non-toxic salts of the compounds of formula I, to pharmaceutically acceptable, easily hydrolyzable esters thereof, including salts of such esters, to pharmaceutical compositions containing the compounds of the invention and dosage units thereof, to methods for the preparation of the compounds of the invention, and to methods of using the said new compounds in the human and veterinary therapy.The 6.beta.-halopenicillanic acids of formula I are potent inhibitors of .beta.-lactamases from a variety of gram-positive and gram-negative bacteria, making the 6.beta.-halopenicillanic acids as well as their salts and easily hydrolyzable esters valuable in human and veterinary medicine.Type: GrantFiled: May 1, 1980Date of Patent: April 16, 1985Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Produktionsaktiensel skab)Inventor: Welf von Daehne
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Patent number: 4446144Abstract: This invention relates to penicillanic acid derivatives of the formula I ##STR1## in which X stands for chlorine, bromine or iodine, to pharmaceutically acceptable, non-toxic salts of the compounds of formula I, to pharmaceutically acceptable, easily hydrolyzable esters thereof, including salts of such esters, to pharmaceutical compositions containing the compounds of the invention and dosage units thereof, to methods for the preparation of the compounds of the invention, and to methods of using the said new compounds in the human and veterinary therapy.The 6.beta.-halopenicillanic acids of formula I are potent inhibitors of .beta.-lactamases from a variety of gram-positive and gram-negative bacteria, making the 6.beta.-halopenicillanic acids as well as their salts and easily hydrolyzable esters valuable in human and veterinary medicine.Type: GrantFiled: November 17, 1980Date of Patent: May 1, 1984Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventor: Welf von Daehne
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Patent number: 4409222Abstract: The present invention relates to a pharmaceutical preparation containing as the vasodilator N"-cyano-N-4-pyridyl-N'-1,2,2-trimethylpropylguanidine and as the diuretic active component a compound selected from the group consisting of the thiazide or thiazide-like type diuretics and loop diuretics.The combination is valuable in the treatment of mammals, including man, suffering e.g. from hypertension or congestive heart failure.Type: GrantFiled: March 31, 1982Date of Patent: October 11, 1983Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiski Fabrik Produktionsaktieselskab)Inventor: Edoardo Arrigoni-Martelli
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Patent number: 4407751Abstract: 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: August 7, 1981Date of Patent: October 4, 1983Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4345071Abstract: Novel intermediates useful for the preparation of substituted 6-.beta.-amidinopenicillanic acids.Type: GrantFiled: June 30, 1980Date of Patent: August 17, 1982Assignee: Leo Pharmaceutical Products, Ltd. A/SInventor: Ernst T. Binderup
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Patent number: 4342772Abstract: 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: December 4, 1980Date of Patent: August 3, 1982Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4325960Abstract: The present invention relates to hitherto unknown compounds of the general formula I: ##STR1## in which R.sub.1 stands for a five- to ten-membered azacycloalkyl or azabicycloalkyl residue attached via the nitrogen atom and optionally being substituted by one or two, the same or different, lower alkyl groups; R.sub.2 represents a hydrogen atom or a lower alkyl, aryl, or aralkyl radical; and A represents 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 compounds are useful in the treatment of bacterial infections. The new compounds are in particular strongly active against .beta.-lactamase producing bacteria.Type: GrantFiled: January 29, 1980Date of Patent: April 20, 1982Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Wagn O. Godtfredsen, Welf von Daehne
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Patent number: 4315004Abstract: A method for treating arthritis which comprises administering to a subject in need of such treatment an effective amount of a fusidic acid derivative selected from compounds of the formula I: ##STR1## in which R.sub.1 stands for a straight or branched alkyl radical having from 1 to 12 carbon atoms, and pharmaceutically acceptable, non-toxic salts and easily hydrolyzable esters thereof, and salts of such esters. The pure diastereomers as well as mixtures thereof may be used in carrying out the invention.Type: GrantFiled: May 31, 1979Date of Patent: February 9, 1982Assignee: Leo Pharmaceutical products Ltd. A/SInventors: Welf von Daehne, Poul R. Rasmussen
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Patent number: 4293549Abstract: This invention relates to new compounds, salts, complexes and acylated derivatives thereof, methods of producing said compounds, intermediates used in the method, pharmaceutical compositions containing the present compounds and methods of producing same, and a method of treating patients using the present compounds, having the general formula (I) ##STR1## in which R.sub.1 represents hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or phenyl; R.sub.2 represents hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, or hydroxy; R.sub.3 represents alkyl, cycloalkyl which can be further mono- or disubstituted with methyl or ethyl, phenyl or phenyl-alkyl, optionally being further substituted; and R.sub.Type: GrantFiled: October 27, 1978Date of Patent: October 6, 1981Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktion-saktieselskab)Inventors: Schneur Rachlin, Edoardo Arrigoni-Martelli
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Patent number: 4259333Abstract: Substituted 7.beta.-amidino-.DELTA..sup.3 -cephem-4-carboxylic acids, pharmaceutically acceptable, non-toxic salts and esters thereof, antibacterial compositions containing these compounds and methods and methods of using the same against infection diseases.Type: GrantFiled: October 6, 1978Date of Patent: March 31, 1981Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventor: Ernst T. Binderup
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Patent number: 4247550Abstract: The invention relates to a series of new compounds, salts thereof and to methods for the preparation of the compounds which have the general formula ##STR1## in which R.sub.1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical;R.sub.2 stands for a --YR.sub.2 ' radical, in which Y represents --O--, --S--, or --NH--, and R.sub.2 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or -alkynyl; or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl;R.sub.3 and R.sub.4 which can be the same or different, and unsubstituted or substituted, stand for hydrogen or for a straight or branched C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl or -alkynyl radical, a C.sub.5 -C.sub.7 -cycloalkyl, a phenyl, or a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen, or for a C.sub.1 -C.sub.Type: GrantFiled: December 21, 1977Date of Patent: January 27, 1981Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Peter W. Feit, Ole B. T. Nielsen, Herta Bruun, Claus A. S. Bretting
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Patent number: 4246262Abstract: The present invention relates to new 6.beta.-amidino-penicillanic acids of the formula: ##STR1## in which X is oxygen or sulphur, --A-- is aliphatic hydrocarbon, or a single bond, --B-- is aliphatic hydrocarbon, or a single bond; R.sub.1 and R.sub.2 stand for hydrogen, lower alkyl, phenyl or phenyl-lower alkyl; or R.sub.2 is acyl or guanyl; or R.sub.1 and R.sub.2 together with the nitrogen atom can form a monocyclic, saturated ring or represent ##STR2## in which R.sub.3 and R.sub.4 each stands for hydrogen, lower alkyl, phenyl, or phenyl-lower alkyl, or R.sub.3 and R.sub.Type: GrantFiled: June 8, 1978Date of Patent: January 20, 1981Assignee: Leo Pharmaceutical Products, Ltd. A/SInventor: Ib S. Vangedal
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Patent number: 4229443Abstract: The present invention relates to new substituted 6.beta.-amidinopenicillanic acids; pharmaceuticallyacceptable salts, easily hydrolyzable esters thereof and salts of such esters; to methods of producing the compounds; to intermediates in their preparation, to pharmaceutical compositions containing the compounds; to dosage units thereof; and to their use.Type: GrantFiled: June 14, 1977Date of Patent: October 21, 1980Assignee: Leo Pharmaceutical Products, Ltd. A/SInventor: Ernst T. Binderup
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Patent number: 4181659Abstract: The present invention relates to hitherto unknown esters of the below formula I, to salts of the esters of formula I with pharmaceutically acceptable acids, to methods for producing said new compounds, to pharmaceutical compositions containing said new compounds, and to methods of treating patients suffering from infectious diseases using said new compounds.The compounds of the invention, which are valuable in the human and veterinary practice, have the formula I ##STR1## in which R.sub.1 and R.sub.Type: GrantFiled: April 4, 1977Date of Patent: January 1, 1980Assignee: Leo Pharmaceutical Products Ltd. A/SInventor: Kai Hansen
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Patent number: 4162259Abstract: Fusidic acid derivatives which possess anti-bacterial, antimicrobial and pharmacokinetic properties. These derivatives include, for example, 3.alpha.,11.alpha.-dihydroxy-16.beta.-(2'-methlyphenyl) thiofusida-13(17),24-dien-21-oic acid and pharmaceutically acceptable, non-toxic salts or easily hydrolysable esters thereof.Type: GrantFiled: May 16, 1978Date of Patent: July 24, 1979Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske fabrik Produktionsaktienselskab)Inventors: Welf von Daehne, Poul R. Rasmussen
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Patent number: 4119717Abstract: The present invention relates to a new series of fusidic acid derivatives, to salts and easily hydrolysable esters thereof, to the preparation of these compounds, and to pharmaceutical compositions containing the compounds, the new fusidic acid derivatives having the general formula: ##STR1## in which the dotted line between C-24 and C-25 indicates that the carbon atoms in question are connected by either a double bond or a single bond, and in which Q.sub.1 represents oxygen or one of the groupings ##STR2## Z being a hydroxy group, a halogen atom, an alkylsulfonyloxy or arylsulfonyloxy group, such as methanesulfonyloxy or p-toluenesulfonyloxy, an azido or a nitro group, Q.sub.2 is oxygen or the grouping ##STR3## and R.sub.Type: GrantFiled: June 14, 1977Date of Patent: October 10, 1978Assignee: Leo Pharmaceutical Products Ltd. A/S Lovens Kemiske Fabrik ProduktionsaktieselskabInventors: Welf von Daehne, Poul Rodbroe Rasmussen
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Patent number: 4100276Abstract: The invention relates to a new series of fusidic acid derivatives, to salts and easily hydrolyzable esters thereof, to the preparation of these compounds and to pharmaceutical compositions containing the compounds, the new compounds having the general formula: ##STR1## in which Q.sub.1 and Q.sub.2 stand for the group ##STR2## or oxygen, A represents oxygen or sulphur, and R.sub.1 stands for a straight or branched alkyl radical having from 1 to 12 carbon atoms, R.sub.1 can further be an alkenyl or alkynyl radical having from 3 to 6 carbon atoms, a cycloalkyl radical having from 3 to 7 carbon atoms in the alicyclic ring, an aralkyl or aryl radical, R.sub.1 can also be a heterocyclic radical having 5 or 6 ring atoms and containing oxygen, sulphur and/or nitrogen atoms, R.sub.Type: GrantFiled: November 24, 1976Date of Patent: July 11, 1978Assignee: Leo Pharmaceutical Products Ltd. A/SInventors: Welf von Daehne, Poul Rodbroe Rasmussen
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Patent number: 4082851Abstract: The invention relates to a series of new compounds, salts thereof and to methods for the preparation of the compounds which have the general formula ##STR1## in which R.sub.1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical;R.sub.2 stands for a -YR.sub.2 ' radical, in which Y represents -O-, -S-, or -NH-, and R.sub.2 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or -alkynyl; or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl;R.sub.3 and R.sub.4 which can be the same or different, and unsubstituted or substituted, stand for hydrogen or for a straight or branched C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl or -alkynyl radical, a C.sub.5 -C.sub.7 -cycloalkyl, a phenyl, or a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen, or for a C.sub.1 -C.sub.Type: GrantFiled: June 16, 1976Date of Patent: April 4, 1978Assignee: Leo Pharmaceutical Products Ltd.Inventors: Peter Werner Feit, Ole Bent Tvaermose Nielsen, Herta Bruun, Claus Aage Svensgaard Bretting
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Patent number: 4076816Abstract: The present invention relates to a new pharmaceutical composition with synergistic properties, to dosage units thereof, and to the use of the said composition and dosage units in the human or veterinary practice for the treatment of patients suffering from infectious diseases. The composition contains as active ingredients an amidinopenicillanic acid derivative of the formula ##STR1## in which R is hydrogen or a lower alkanoyloxymethyl radical including the pivaloyloxymethyl radical or atoxic salts thereof in combination with 2,4-diamino-5(3,4,5-trimethoxybenzyl)-pyrimidine, also known under the name trimethoprim, used hereinafter, or atoxic salts thereof.Type: GrantFiled: May 1, 1975Date of Patent: February 28, 1978Assignee: Leo Pharmaceutical Products Ltd. A/SInventor: Leif Tybring
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Patent number: RE31244Abstract: The invention relates to a series of new compounds, to methods for preparing the compounds, to compositions containing said compounds which are useful in the human and veterinary medical practice, and to methods for treating patients suffering from certain illnesses with said compounds, the new compounds having the general formula I ##STR1## or the tautomeric forms thereof in which the R.sup.1 -substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R.sup.1 stands for a straight or branched, saturated or unsaturated, aliphatic hydrocarbon radical having from 1 to 8 carbon atoms, a cycloalkyl or cycloalkenyl radical having from 3 to 7 carbon atoms, an aryl or an aralkyl radical, and R.sup.Type: GrantFiled: October 22, 1981Date of Patent: May 17, 1983Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens kemiske Fabrik Produktionsaktieselskab)Inventor: Hans J. Petersen