Patents Assigned to Leo Pharmaceutical Products Ltd. A/S Lovens Kemiske Fabrik Produktionsaktieselskab
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Patent number: 6566554Abstract: The present invention relates to a compound of general formula (I) wherein R1, R2, and R3 represents one or more, same or different substituents selected from the group consisting of halogen, hydroxy, mercapto, trifluoromethyl, amino, (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)akylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, cyano, —CONH2, phenyl, or nitro; further R2 can be hydrogen, and R3 can be carboxy and carbamoyl; R4 represents hydrogen, (C1-C3)alkyl, or allyl; X represents oxygen or sulphur; Q represents —(CO)—, —(CS)—, or a bond; Y represents (C5-C15)alkyl; (C2-C15)olefinic group; (C3-C10)monocyclic hydrocarbon group; or phenyl; any of which may be optionally substituted by one or more, same or different substituents selected from the group consisting of the formula R5 defined below; (C1-C4)alkyl substituted by one or more substituents selected for the group R5; or a group of the formula —(Z—O)n—Z, wherein Z is a (C1-C3)alkyl, n is anType: GrantFiled: February 22, 2002Date of Patent: May 20, 2003Assignee: Leo Pharmaceutical Products Ltd. a/s (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventor: Erik Rytter Ottosen
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Patent number: 6555710Abstract: The present invention relates to compounds of formula (I) wherein R1 and R2 independently represent one or more, same or different substituents selected from the group consisting of halogen, hydroxy, mercapto, trifluoromethyl, amino (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)alkylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, cyano, carbamoyl, phenyl, or nitro; R2 further being represented by hydrogen; R3 represents hydrogen, halogen, hydroxy, mercapto, trifluoromethyl, amino, (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)alkylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, phenyl, cyano, carboxy or carbomoyl; R4 represents hydrogen, (C1-C3)alkyl, or allyl; X represents oxygen or sulpher; with the proviso that formula (I) does not comprise the compound 2,2,2-trifluoro-N-[2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]-phenyl]acetamide wherein R1 is a 2-methyl, R2 is 2-chloro, R3 and R4 is hydrogen, and X is oxygen; and a salt thereof with a pharmaceutically accepType: GrantFiled: March 15, 2002Date of Patent: April 29, 2003Assignee: Leo Pharmaceutical Products Ltd a/s Lovens Kemiske Fabrik ProduktionsaktieselskabInventor: Erik Rytter Ottosen
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Patent number: 6313174Abstract: The compounds of the present invention are represented by general formula (I) in which formula R1 and R2 stand independently for one or more, similar or different substituents selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, trifluoromethyl, amino, alkyl, alkoxy, alkylthio, alkylamino, or alkoxycarbonyl, the C-content of which can be from 1 to 5, cyano, carboxy, carbamoyl, phenyl, or nitro; R3 stands for hydrogen, halogen, hydroxy, mercapto, trifluoromethyl, amino, alkyl, alkoxy, alkylthio, alkylamino, or alkoxycarbonyl, the C-content of which can be from 1 to 5, phenyl, cyano, carboxy, or carbamoyl; R4, R5 and R6 stand independently for hydrogen, trifluoromethyl, alkyl, carbamoyl, alkoxycarbonyl, or alkyloxo, the C-content of which can be from 1 to 5; X stands for oxygen, N—OH, N—O-alkyl, dialkoxy, cyclic dialkoxy, dialkylthio, or cyclic dialkylthio, the C-content of which can be from 1 to 5.Type: GrantFiled: July 21, 1999Date of Patent: November 6, 2001Assignee: Leo Pharmaceutical Products Ltd.A/S/ (Løvens kemiske Fabrik Produktionsaktieselskab)Inventors: Erik Rytter Ottosen, Schneur Rachlin
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Patent number: 6197797Abstract: The present invention relates to hitherto unknown compounds of formula (I) or their tautomeric forms, the attachment to the pyridine being in the 3- or 4-position, in which formula R1 stands for one or more substituents which can be the same or different and are selected from the group consisting of: hydrogen, halogen, trifluoromethyl nitro, amino, cyano, carboxy, or alkyl, alkoxy, or alkoxycarbonyl, the C-content of which can be from 1 to 4; X stands for a straight or branched C9-C20 carbon chain, saturated or unsaturated or Q—Ar—R; in which formula Ar stands for phenyl, Q stands for a C5-C20 divalent hydrocarbon radical which can be straight, branched, saturated or unsaturated and R stands for hydrogen or for one or more substituents which can be the same or different and are selected from the group consisting of: hydroxy, amino, halogen, trifluoromethyl, cyano, nitro, carboxy, carbamoyl, or alkyl, alkoxy, alkylthio, alkylamino, or alkoxycarbonyl, the C-content of which can be from 1 to 4; and pType: GrantFiled: November 26, 1999Date of Patent: March 6, 2001Assignee: Leo Pharmaceutical Products Ltd. A/S (Løvens kemiske Fabrik Produktionsaktieselskab)Inventors: Charlotte Schou, Erik Rytter Ottosen
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Patent number: 5545633Abstract: The invention relates to vitamin D compounds of formula (I) ##STR1## in which X is hydrogen or hydroxy; R.sup.1 and R.sup.2 stand for hydrogen or a C.sub.1-6 hydrocarbyl radical which is optionally substituted with one or more deuterium or fluorine atoms, or taken together with the carbon atom bearing the group X can form a C.sub.3-8 carbocyclic ring; Q is a single bond or a C.sub.1-8 hydrocarbylene diradical which is optionally substituted with one or more deuterium or fluorine atoms; and derivatives of formula I. The compounds show anti-inflammatory and immunomodulating effects as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.Type: GrantFiled: September 1, 1994Date of Patent: August 13, 1996Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske / Fabrik Produktionsaktieselskab)Inventor: Claus A. S. Bretting
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Patent number: 5378695Type: GrantFiled: May 17, 1993Date of Patent: January 3, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Martin J. Calverley, Kai Hansen, Lise Binderup
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Patent number: 5374629Abstract: The invention relates to compounds of formula I ##STR1## in which formula X is hydrogen or hydroxy; Y is oxygen, sulphur, or oxidized sulfur (S(O) or S(O.sub.2)); R.sup.1 and R.sup.2, which may be the same or different, stand for hydrogen or C.sub.1 -C.sub.6 hydrocarbyl, or R.sup.1 and R.sup.2, taken together with the carbon atom (starred in formula I) bearing the group X, form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a C.sub.1 -C.sub.8 hydrocarbylene diradical. R.sup.3 is hydrogen or C.sub.1 -C.sub.6 hydrocarbyl. R.sup.1, R.sup.2 and/or Q, may be optionally substituted with one or more deuterium or fluorine atoms; n is 0 or 1. The present compounds show antiinflammatory and immunomodulating effects as well as a strong activity in inducing cell differentiation and inhibiting undesirable proliferation of certain cancer and skin cells.Type: GrantFiled: July 23, 1992Date of Patent: December 20, 1994Assignee: Leo Pharmaceutical Products Ltd. A/S Lovens Kemiske Fabrik ProduktionsaktieselskabInventors: Martin J. Calverley, Gunnar Grue-Sorensen, Ernst T. Binderup
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Patent number: 5362719Abstract: The invention relates to the use of certain vitamin D analogues for the treatment of acne. The analogues have only moderate activity on the calcium metabolism when compared to 1,25-(OH).sub.2 D.sub.3, but retain the ability to activate receptors for 1,25-(OH).sub.2 D.sub.3 not associated with calcium absorption or bone calcium mobilization.Type: GrantFiled: November 24, 1993Date of Patent: November 8, 1994Assignee: Leo Pharmaceutical Products, Ltd. a/s Lovens Kemiske Fabrik Produktionsaktieselskab)Inventor: Wagn Ole Godtfredsen
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Patent number: 4945098Abstract: A derivative of 2-methylenepropane-1,3-diol of the general formula I ##STR1## where O--A.sup.1 and O--A.sup.2, which can be the same or different, each represents O, O--C(O), O--C(O)NH, O--C(S)NH or O--C(O)O, R.sup.1 represents an alkyl or alkenyl group of 10-22 carbon atoms, n is an integer from 1 to 11, B.sup.+ represents a quaternary ammonium group, either N.sup.+ R.sup.4 R.sup.5 R.sup.6, or N.sup.+ (Het), where R.sup.4, R.sup.5 and R.sup.6 are similar or different alkyl groups of 1-4 carbon atoms, or two or all of R.sup.4, R.sup.5 and R.sup.6 may be incorporated into a cyclic or bicyclic structure, which may contain additional hetero atoms; X.sup.- means the anion of a pharmceutically acceptable inorganic or organic acid; and R.sup.2 and R.sup.3 are the same or different, and represent hydrogen or alkl groups of 1-4 carbon atoms.Type: GrantFiled: July 10, 1987Date of Patent: July 31, 1990Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Gunnar Grue-Sorensen, Christian K. Nielsen
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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: 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: 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: 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: 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: 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