Patents Assigned to Leo Pharmaceutical Products Ltd.
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Patent number: 5234932Abstract: The present invention relates to hitherto unknown compounds of formula, in which m and n stand for an integer from 0-5, p stands for 0 or 1, and q stands for an integer from 0-4, R.sub.1 and R.sub.2 are the same or different and stand for hydrogen, halogen, nitro, amino, alkyl or alkoxy; R.sub.3 is hydroxy, hydrogen, straight or branched, saturated or unsaturated C.sub.1 -C.sub.6 alkyl; R.sub.5 stands for an acidic group, e.g. carboxy, 1-H tetrazolyl, a sulphonic acid group, a sulfamyl group, a sulphinic acid group, or a hydroxamic acid group; R.sub.4 and R.sub.6 are the same or different and stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.6 alkyl groups or unsubstituted or substituted aralkyl groups. R.sub.7 has the same meaning as R.sub.5 or represents a hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group.Type: GrantFiled: January 29, 1992Date of Patent: August 10, 1993Assignee: Leo Pharmaceutical Products ltd.Inventors: Schneur Rachlin, Erik T. Hansen
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Patent number: 5206229Type: GrantFiled: October 10, 1990Date of Patent: April 27, 1993Assignee: Leo Pharmaceutical Products LTDInventors: Martin J. Calverley, Lise Binderup, Ernst T. Binderup
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Patent number: 5190935Type: GrantFiled: November 19, 1991Date of Patent: March 2, 1993Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ernst T. Binderup, Martin J. Calverley
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Patent number: 5157039Abstract: The present invention relates to compounds of formula ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1- C.sub.8 -alkyl, aryl or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.Type: GrantFiled: December 31, 1990Date of Patent: October 20, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent T. Nielsen, Ian Ahnfelt-Ronne
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Patent number: 5130304Abstract: The present invention relates to compounds of formula in which R.sub.1 -R.sub.8 can be the same or different and stand for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.10 hydrocarbon radical. In addition, R.sub.3 when taken together with either R.sub.1 or R.sub.5 can form a saturated aliphatic 5-, 6-or 7-membered ring, which may be substituted with one or more C.sub.1 -C.sub.4 -alkyl radicals. The present compounds are effective e.g. in drugs influencing calcium metabolism.Type: GrantFiled: October 9, 1990Date of Patent: July 14, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ernst T. Binderup, Sven Liisberg
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Patent number: 5110819Abstract: The present invention relates to hitherto unknown compounds of formula, in which formula R.sub.1 stands for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 --C.sub.8 --alkyl, aryl or for ar--C.sub.1 --C.sub.4 --alkyl, aryl or an being unsubstituted or substituted phenyl, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, carbalkoxy, carbamyl, hydroxy, alkyl, alkoxy; n and m are the same or different and stand for an integer from 0-6; provided that n cannot be zero when A stands for carboxy and X and Q both stand for a bond; X stands for a bond or for O, S, S(O), S(O).sub.2 or for NR.sub.8 where R.sub.8 is defined as R.sub.1 above; Q stands for a bond of for straight or branched, C.sub.1 --C.sub.6 --alkylene; A stands for an acidic group, e.g.Type: GrantFiled: June 1, 1990Date of Patent: May 5, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ian Ahnfelt-Ronne, Erik T. Hansen, Dorte Kirstein, Ole Bent I. Nielsen, Schneur Rachlin
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Patent number: 5109009Abstract: The present invention relates to compounds of formula ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, aryl or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.Type: GrantFiled: September 10, 1990Date of Patent: April 28, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent T. Nielsen, Ian Ahnfelt-Ronne
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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: 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: 4870063Abstract: Novel compounds of the formula I ##STR1## in which R.sub.1 -R.sub.11 can be the same or different and stand for hydrogen, a straight or branced aliphatic or alicyclic C.sub.1 -C.sub.10 hydrocarbon radical, an aryl or an aryl-C.sub.1 -C.sub.4 -alkyl radical; n is zero or one, and m is zero, one or two; or R.sub.2 and R.sub.4 when taken together form a saturated aliphatic 5-, 6- or 7-membered ring which may be substituted with one or more C.sub.1 -C.sub.4 alkyl radicals; and pharmaceutically acceptable salts and easily hydroyzable esters thereof, methods for producing said new compounds, pharmaceutical compositions containing the new compounds, dosage units of the compositions, and methods of treating patients using said compositions and dosage units.The present compounds are valuable in the human and veterinary practice by reducing bone resorption and surprisingly also stimulating bone alkaline phosphatase. A substantial increase in bone mass is actually observed during treatment with the present compounds.Type: GrantFiled: August 10, 1987Date of Patent: September 26, 1989Assignee: Leo Pharmaceutical Products Ltd. A/SInventors: Ernst T. Binderup, Sven Liisberg
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Patent number: 4866048Abstract: This invention relates to vitamin D analogues represented by the general formula I ##STR1## in which formula X stands for hydrogen, lower alkyl, halogen or hydroxy; Y stands for hydrogen or hydroxy; R.sup.1 and R.sup.2, which may be the same or different, stand for lower alkyl, optionally substituted with halogen or hydroxy with the proviso that R.sup.1 and R.sup.2 cannot both be methyl when X is other than lower alkyl, or, taken together with the carbon atom numbered 25, R.sup.1 and R.sup.2 can form a saturated or unsaturated C.sub.3 -C.sub.9 carbocyclic ring which may optionally be substituted at any possible position(s) with lower alkyl, halogen or hydroxy; R.sup.3 stands for hydrogen or lower alkyl; R.sup.4 and R.sup.5 represent either each hydrogen, or when taken together constitute a bond, with the result that a double bond connects carbon atoms numbered 22 and 23; and bioreversible derivatives thereof.Type: GrantFiled: March 18, 1987Date of Patent: September 12, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Martin J. Calverley, Ernst T. Binderup
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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: 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: 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: 4826987Abstract: The present invention relates to compounds of formula I ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.Type: GrantFiled: February 28, 1986Date of Patent: May 2, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
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Patent number: 4816580Abstract: The present invention relates to a new process for the debromination and/or deiodination of 6,6-dihalo- and 6-monohalopenicillanic acids or derivatives thereof by treatment with dialkyl, trialkyl or diaralkyl phosphite, the desired compounds being obtained in good to excellent yield and in a high state of purity.Type: GrantFiled: November 24, 1987Date of Patent: March 28, 1989Assignee: Leo Pharmaceutical Products Ltd. A/SInventor: Erik T. Hansen
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Patent number: 4732998Abstract: The present invention relates to hitherto unknown compounds of the formula I ##STR1## in which R.sub.1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C.sub.1 -C.sub.10 hydrocarbon radical, an aryl or an aryl-C.sub.1 -C.sub.4 -alkyl radical, R.sub.1 if desired being unsubstituted or substituted with straight or branched C.sub.1 -C.sub.4 -alkyl, amino, C.sub.1 -C.sub.4 -alkamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino, carboxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxy, C.sub.1 -C.sub.4 -alkoxy, phenoxy, mercapto, C.sub.1 -C.sub.4 -alkylthio, phenylthio, halogen, trifluoromethyl; R.sub.2 stands for hydrogen, C.sub.1 -C.sub.8 -alkyl, aryl-C.sub.1 -C.sub.4 -alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the proviso that R.sub.2 cannot be hydrogen or methyl if n=O and R.sub.1 is methyl.The compounds of the invention are valuable in the human and veterinary practice.Type: GrantFiled: March 31, 1986Date of Patent: March 22, 1988Assignee: Leo Pharmaceutical Products, Ltd.Inventor: Ernst T. Binderup
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Patent number: 4600577Abstract: New pharmaceutical preparation containing pinacidil (N"-cyano-N-4-pyridyl-N'-1,2,2-trimethylpropylguanidine) in slow-release form, providing more uniform absorption rates and resulting blood levels when administered to the individual patients.Type: GrantFiled: January 23, 1984Date of Patent: July 15, 1986Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselkab)Inventor: Erik J. Didriksen
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Patent number: 4557932Abstract: The present invention relates to a new compounded composition with synergistic properties, to dosage units thereof, and to the use of the said compounded composition and dosage units.The composition contains as active ingredients the amidinopenicillanic acid mecillinam or a pharmaceutically acceptable, non-toxic salt or pro-drug thereof in combination with another antibiotic compound of the formula ##STR1## or a pharmaceutically acceptable, non-toxic salt or pro-drug thereof, optionally together with pharmaceutically acceptable, non-toxic carriers and/or auxiliary agents.The new composition is valuable in the human and veterinary practice for the treatment of patients suffering from infectious diseases.Type: GrantFiled: December 29, 1982Date of Patent: December 10, 1985Assignee: Leo Pharmaceutical Products Ltd.Inventor: Leif Tybring
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Patent number: D296824Type: GrantFiled: August 16, 1985Date of Patent: July 19, 1988Assignee: Leo Pharmaceutical Products Ltd.Inventor: Howard W. Biddle