Patents Assigned to Leo Pharmaceutical Products Ltd.
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Patent number: 5716945Abstract: The present invention relates to compounds of formula in which formula X is hydrogen or hydroxy; R.sup.1 and R.sup.2, which may be the same or different, stand for hydrogen or C.sub.1 -C.sub.4 hydrocarbyl; or R.sup.1 and R.sup.2, taken together with the carbon atom bearing the group X, can form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a single bond or a C.sub.1 -C.sub.4 hydrocarbylene diradical; R.sup.1, R.sup.2 and/or Q may be optionally substituted with one or more fluorine atoms; and prodrugs of formula in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups in vivo. The compounds show antiinflammatory and immunomodulating effects as well as stong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.Type: GrantFiled: November 7, 1995Date of Patent: February 10, 1998Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventor: Gunnar Grue-S.o slashed.rensen
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Patent number: 5710142Abstract: The invention relates to 20(S)-vitamin D compounds having the following formula ##STR1## where U and R' are as defined in the specification. The compounds have strong antiinflammatory and immunomodulating activity. There are also useful in the inhibition of proliferation of undesirable cells.Type: GrantFiled: May 2, 1995Date of Patent: January 20, 1998Assignee: Leo Pharmaceutical Products Ltd. A/S (Bovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Martin John Calverley, Henrik Pedersen
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Patent number: 5696140Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for ##STR1## where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice for treating asthma, allergy, CNS disorders, or cancer.Type: GrantFiled: October 3, 1996Date of Patent: December 9, 1997Assignee: Leo Pharmaceutical Products Ltd.Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5612325Abstract: A compound of formula I ##STR1## wherein R stands for a straight or branched, saturated or unsaturated alkyl group containing from 4 to 12 carbon atoms optionally substituted with a hydroxy group, and possibly containing a ring structure, and in which at least one of the carbon atoms not bearing hydroxyl group is substituted with one or more halogen atoms or an azido group; and prodrugs of I in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups in vivo, in pure form or in mixtures. The compounds show antiinflammatory and immunomodulating effects as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells. The compounds are prepared by oxidizing 1(S),3(R)-bis-(tert-butyldimethylsilyloxy)-20(S)formyl-9,10-seco-pregna-5( E),7(E),10(19)-triene, reducing the resulting product; alkylating the reduction product and then subjecting the alkylated product to triplet-sensitized photoisomerization.Type: GrantFiled: January 3, 1995Date of Patent: March 18, 1997Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventors: Kai Hansen, Henrik Pedersen
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Patent number: 5589471Abstract: Compounds of formula ##STR1## wherein Q is a --CH.sub.2 --, --CH.dbd.CH-- or --C.dbd.C--; U is a C.sub.1 -C.sub.6 alkylene; R.sup.1 is hydrogen, a C.sub.1 -C.sub.4 alkyl or YR' in which Y stands for the radicals --SO-- or --SO.sub.2 -- and R' stands for a C.sub.1 -C.sub.4 alkyl; R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1 -C.sub.4 alkyl, and additionally R.sup.2 and R.sup.3, when taken together with the starred carbon atom, may form a C.sub.3 -C.sub.6 carbocyclic ring; Z is hydrogen or hydroxy; and derivatives thereof. The compounds show antiinflammatory and immunomodulating effects as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells. The compounds are prepared by adding an anion R.sup.- to 1(S),1(R)-bis-(tert-butyldimethylsilyl-oxy)-9,10-secopregna-5(E),7(E),10(1 9)-triene-20-one and the resulting compound is alkylated or acylated with R.sup.1 X.sup.1 where X.sup.Type: GrantFiled: January 3, 1995Date of Patent: December 31, 1996Assignee: Fabrik Produktionsaktieselskab Leo Pharmaceutical Products Ltd.Inventors: Kai Hansen, Claus Aage S. Bretting
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Patent number: 5576438Abstract: The present invention relates to hitherto unknown compounds of formula; Y stands for --CH.dbd.CH--; R.sub.1 is hydrogen or halogen, preferably fluorine, chlorine or bromine; R.sub.2 is halogen, preferably fluorine, chlorine or bromine, CH.sub.3, OCH.sub.3, NO.sub.2 or CF.sub.3, and n=0-3, preferably 0, 1 or 2; A stands for an acidic group, e.g. carboxy, 1-H-tetrazolyl or a hydroxamic acid group. The present compounds are of value in the human and veterinary practice as lipoxygenase inhibitors and/or leukotriene antagonists.Type: GrantFiled: January 13, 1995Date of Patent: November 19, 1996Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktiesel Skab)Inventors: Dorte Kirstein, Schneur Rachlin
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Patent number: 5563160Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for .dbd.N--R.sub.1 where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice as selective serotonin receptor antagonists.Type: GrantFiled: March 15, 1995Date of Patent: October 8, 1996Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5554599Abstract: The present invention relates to compounds of the following formula ##STR1## in which Y is sulfur, S(O), or S(O).sub.2 ; R stands for C.sub.1 -C.sub.3 alkyl, or can form a C.sub.3 -C.sub.8 carbocyclic ring. Q is a C.sub.1 -C.sub.8 hydrocarbylene diradical; and derivatives thereof. The compounds can be made by reacting a 20(S)-formyl vitamin D derivative with tert-butyl hypochlorite to form the corresponding acid chloride which is then reacted with potassium O-ethyl dithiocarbonate followed by photochemical reaction and decarbonylation, treatment with aminoethanol, and conversion to the 22-thiol. The 22-thiol is then alkylated to form the desired sidechain. The compounds show antiinflammatory and immunomodulating effects. They also exhibit strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.Type: GrantFiled: April 11, 1995Date of Patent: September 10, 1996Assignee: Leo Pharmaceutical Products Ltd.Inventors: Gunnar Grue-S.o slashed.rensen, Erik R. Uttosen
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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: 5447924Abstract: Vitamin D analogues of the formula: ##STR1## wherein X is hydrogen or hydroxy; R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.6 hydrocarbyl or R.sup.1 and R.sup.2 together with the starred carbon form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a single bond or a C.sub.1 -C.sub.8 hydrocarbylene diradical; and m is 0, 1 or 2. One of the m carbons designated by .degree. may be optionally substituted with deuterium, fluorine or C.sub.1 -C.sub.2 alkyl. R.sup.1, R.sup.2 and/or Q may also be substituted with deuterium or fluorine. The analogues show, for example, anti-inflammatory and immunomodulating effects.Type: GrantFiled: September 22, 1992Date of Patent: September 5, 1995Assignee: Leo Pharmaceutical Products Ltd.Inventor: Claus Aage S. Bretting
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Patent number: 5401868Abstract: The present invention relates to hitherto unknown intermediate of formula, in which R.sub.1 stands for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.20 carbon chain or an aryl or aralkyl group, aryl and "ar" meaning an aromatic or heterocyclic, 5- or 6-membered ring substituent containing 1 or 2 hetero atoms selected among O, S and N, R.sup.1 optionally being further substituted, and its chain being interrupted by hetero atoms like oxygen, or by carbonyl group(s); and R.sup.3 stands for hydrogen or C.sub.1 -C.sub.3 alkyl. The present intermediates can be used in a one step method for producing prodrugs of formula, where D-H =drug itself.Type: GrantFiled: February 26, 1992Date of Patent: March 28, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)Inventor: Frantz J. Lund
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Patent number: 5401731Type: GrantFiled: August 30, 1993Date of Patent: March 28, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)Inventors: Martin J. Calverley, Ernst T. Binderup
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Patent number: 5401732Type: GrantFiled: February 11, 1993Date of Patent: March 28, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S Kemiske Fabrik Produkionsaktiese SKABInventors: Martin J. Calverley, Kai Hansen, Lise Binderup
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Patent number: 5387582Abstract: The present invention relates to compounds of formula (I) ##STR1## in which R.sup.1 and R.sup.2 may be the same or different and stand for hydrogen, lower alkyl, lower cycloalkyl, or, taken together with the carbon atom (starred in formula I), bearing the groups X, R.sup.1 and R.sup.2, can form a C.sub.3 -C.sub.8 carbocyclic ring; X stands for hydrogen or hydroxy, R.sup.3 and R.sup.4, which may be the same or different stand for hydrogen, lower alkyl or halogen, n is 0, 1 or 2 and m is 0, 1 or 2. The present compounds, which find use both in the human and veterinary practice, show an immunomodulating effect as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells, including cancer cells and skin cells.Type: GrantFiled: March 17, 1992Date of Patent: February 7, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktiesel SKAB)Inventor: Kai Hansen
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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: 5376651Abstract: The present invention relates to the use of 20(R)-22-oxavitamin D analogues for treatment or prevention of skin ageing, and to the use of such compounds for preparation of pharmaceutical compositions for teatment and/or prevention of skin ageing.Type: GrantFiled: January 8, 1993Date of Patent: December 27, 1994Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktiesel SKAB)Inventor: 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: 5292727Abstract: The present invention relates to the use of certain vitamin D analogues in the preparation of a pharmaceutical preparation for the treatment of acne. The preparation contains a vitamin D analogue (calcipotriol) which has only moderate activity on the calcium metabolism when compared to 1,25-(OH).sub.2 D.sub.3, but has retained 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: June 11, 1992Date of Patent: March 8, 1994Assignee: Leo Pharmaceutical Products Ltd.Inventor: Wagn Ole Godtfredsen
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Patent number: 5244664Abstract: This invention relates to pharmaceutical compositions for treatment of alopecia comprising a compound of formula, in the form of the free base or acid addition salts thereof, in association with a pharmaceutical carrier adapted for topical application to mammalian skin. The compounds used have general formula ##STR1## in which the R.sub.1 -substituted cyanoguanidyl radical is placed in the 3- or 4-position of the pyridine ring, and in which R.sub.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, or an aryl or an aralkyl radical. R.sub.2 stands for hydrogen, halogen, hydroxy, lower alkyl or alkoxy radicals. The present compositions find applications both in the human and veterinary use.Type: GrantFiled: January 8, 1992Date of Patent: September 14, 1993Assignee: Leo Pharmaceutical Products Ltd.Inventor: Wagn O. Godtfredsen