Patents Assigned to LEK
  • Patent number: 5069910
    Abstract: There are described novel dispersible cimetidine tablets containing 30 to 90% by weight of one of the polymorphous modifications of cimetidine A, B or C, 5 to 55% by weight of one or more disintegrationg agents, 0.05 to 5.0% by weight of a surfactant, such as sodium lauryl sulphate together with other common adjuvants. The process for the manufacture of dispersible cimetidine tablets is effected on the basis of known methods by granulating the ingredients and by compressing the granulate to tablets. Dispersible tablets disintegrate when brought in contact with water at room temperature within less than 1 minute to yield a fine dispersion, which facilitates the oral application. Therefore such tablets are particularly suitable for certain groups of patients, especially for the aged and children. Dispersible tablets containing cimetidine excell by their improved rate of dissolution and good bioavailability.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: December 3, 1991
    Assignee: Lek
    Inventors: Mateja Kovacic, Jenny Milovac, Polona Cvelbar, Anton Stalc, Zvezdana Trost, Zdravko Kopitar, Bojan Kofler, Vida Nikolic, Marija Lampret, Marija Lippai
  • Patent number: 5047247
    Abstract: There are described novel dispersible tablets of dihydroergotoxine or of acid addition salts thereof, containing 0.1 to 4% by weight of dihydroergotoxine or its acid addition salts, 4 to 60% by weight of one or more disintegrating agents, 0.8 to 10% by weight of an organic acid and, optionally, 0.2 to 2% by weight of an antioxidizing agent together with other common adjuvants. The process for the manufacture of dispersible tablets of dihydroergotoxine and of acid addition salts thereof is carried out on the basis of known methods by granulating the ingredients and by compressing the granulate to tablets. Dispersible tablets disintegrate within less than 1 minute when brought in contact with water at room temperature to yield a fine dispersion, which facilitates the oral application. Therefore such tablets are particularly suitable for the aged. Dispersible tablets containing dihydroergotoxine or acid addition salts thereof excell by their improved rate of dissolution and good bioavailability.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: September 10, 1991
    Assignee: LEK
    Inventors: Jenny Milovac, Mateja Kovacic, Zdravko Kopitar, Janja Urbancic-Smerkolj, Andrej Lenardic, Mirjan Zorz, Bojan Kofler, Angela Vene-Mozina, Vida Nikolic, Marija Lampret, Breda Meden
  • Patent number: 4855439
    Abstract: A new and simple process for the preparation of crystalline cimetidine (N-cyano-N'-methyl-N"-{2/(5-methyl-1H-imidazole-4-yl)methylthio/ethyl}guan idine) is described, wherein cimetidine is obtained by reacting O-ethyl-S-(4-methylimidazolyl-5-methyl)dithiocarbonate hydrobromide with N-cyano-N'-methyl-N"-(2-chloroethyl)guanidine in an aqueous methylamine solution at a temperature between room temperature and the reflux temperature of the reaction mixture, whereupon the desired compound is separated.Cimetidine is a valuable drug in the therapy of the ulcer disease.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: August 8, 1989
    Assignee: LEK
    Inventor: Teofil Zizek
  • Patent number: 4769465
    Abstract: A new, technologically easily feasible process for the preparation of 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, comprising a partrial hydrolysis of dimethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in an inert organic solvent at a temperature between room temperature and the reflux temperature of the reaction mixture with an aqueous solution of alkali hydroxide and the reaction of the obtained 3-methoxycarbonyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-5-car boxylic acid either with N-(2-hydroxyethyl)-N-benzyl-methylamine in the presence or absence of an organic solvent in the presence of N,N'-dicyclohexylcarbodiimide at a temperature of between 25.degree. and 120.degree. C. or with N-(2-haloethyl)-N-benzyl-methylamine in the presence of an inert organic solvent and of a proton acceptor at a temperature of between 25.degree. and 140.degree. C.
    Type: Grant
    Filed: May 14, 1986
    Date of Patent: September 6, 1988
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Ljubo Antoncic, Iztok Jazbec, Darko Kocjan, Ivana Krivec
  • Patent number: 4720552
    Abstract: A new, technologically easily feasible process for the preparation of 4(5)-methyl-5(4)-thiomethyl imidazole of the formula ##STR1## and of acid addition salts thereof is described, wherein 4(5)-methyl-5(4)-bromomethyl imidazole hydrobromide is reacted in an aqueous medium at room temperature with potassium O-ethyl dithiocarbonate to the intermediate O-ethyl-S-(4-methylimidazolyl-5-methyl) dithiocarbonate, which is hydrolyzed at the reflux temperature under nitrogen atmosphere with an aqueous HBr or HCl solution to 4(5)-methyl-5(4)-thiomethyl imidazole hydrobromide or hydrochloride resp.The compound is a valuable starting material in the synthesis of cimetidine, a well-known drug in the therapy of the ulcer disease.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: January 19, 1988
    Assignee: LEK, tovarna facmacevtskih in kemicnih izdelkov, n.sol.o
    Inventors: Teofil Zizek, Janko Zmitek
  • Patent number: 4467093
    Abstract: In the process for preparing 4-(2'-nitrophenyl-2,6-dimethyl)-3,5-dicarbmethoxy-1,4-dihydropyridine of the formula ##STR1## 2-nitrobenzaldehyd-diacetate, methyl acetoacetate and ammonia are reacted in the presence of an inert organic solvent, such as methanol, and in the presence or absence of an organic base, such as pyridine, at a temperature of between 20.degree. and 150.degree. C. The compound is a valuable medicine for the treatment of angina pectoris.
    Type: Grant
    Filed: July 27, 1982
    Date of Patent: August 21, 1984
    Assignee: LEK, Tovarna Farmacevtskih in Kemicnih Izdelkov, N.Sol.O.
    Inventors: Branko Jenko, Igor Langof
  • Patent number: 4440772
    Abstract: Medicine containing salts of ergotaminine, ergosinine, ergocryptinine, ergocristinine, and ergocorninine and use for treating arterial hypertension, heart insufficiency, heart arrhythmia or cephalalgia.
    Type: Grant
    Filed: June 2, 1981
    Date of Patent: April 3, 1984
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Nebojsa Djordjevic, Rudolf Rucman, Suncica Jovanovic, Breda Bole-Vunduk, Tone Lavric, Boza Lavric, Cvetka Gruskovnjak, Ana Kocjan, Hermina Krmelj
  • Patent number: 4354940
    Abstract: Sodium alumoglucoheptonate, process of preparing from sodium glucoheptonate and sodium aluminate, and use of sodium alumoglucoheptonate as a sequestering agent.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: October 19, 1982
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Peter Suhac, Natasa Hafner-Milac, Bozidar Dolenc
  • Patent number: 4304929
    Abstract: Preparation of 4-(n-hexadecylamino)-benzoic acid or salt thereof employing as catalyst quaternary ammonium or phosphonium salt.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: December 8, 1981
    Assignee: LEK tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Branko Jenko, Natasa Hafner-Milac, Joza Habjan, Anton Prosen, Igor Langof
  • Patent number: 4297293
    Abstract: Sodium alumoglucoheptonate, process of preparing from sodium glucoheptonate and sodium aluminate, and use of sodium alumoglucoheptonate as a sequestering agent.
    Type: Grant
    Filed: February 6, 1980
    Date of Patent: October 27, 1981
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov. n.sol.o.
    Inventors: Peter Suhac, Natasa Hafner-Milac, Bozidar Dolenc
  • Patent number: 4230884
    Abstract: Process for preparing 2-(3-benzoylphenyl)-propionic acid or salt thereof which includes methylating 3-benzoyl-phenyl acetonitrile or an alkoxide thereof in the presence of neutral non-cyclic ligands with an open polyether chain.
    Type: Grant
    Filed: April 10, 1979
    Date of Patent: October 28, 1980
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Boris Zupancic, Mirko Sopoic
  • Patent number: 4230859
    Abstract: A process for the preparation of N-substituted esters of 9,10-dihydrolysergic acids of the formula: ##STR1## wherein R.sub.1 is an alkyl group of 1-5 carbon atoms, an alkenyl group of 2-5 carbon atoms or a cycloalkyl group of 3-5 carbon atoms,R.sub.2 is hydrogen or an alkoxy group of 1-3 carbon atoms andX' is hydrogen or halogen,characterized in that esterified 9,10-dihydrolysergic acids of the formula: ##STR2## wherein R is hydrogen or a hydrolyzable organic group,X' is hydrogen or halogen, andR.sub.2 has the meaning as stated above,are reacted with a compound of the formula:R.sub.1 Y (III)whereinR.sub.1 has the meaning as stated above,Y is halogen or sulphate,in the presence of a catalyst for phase transition in the presence of aqueous alkali medium in an inert organic solvent immiscible with water, and certain novel esters obtained thereby.
    Type: Grant
    Filed: July 7, 1978
    Date of Patent: October 28, 1980
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventor: Rudolf Rucman
  • Patent number: 4219555
    Abstract: 2-Bromoergosine of the formula: ##STR1## and acid addition salts thereof. The acid addition salts are employed in the treatment of arterial hypertension and of heart arrythmias.
    Type: Grant
    Filed: August 9, 1978
    Date of Patent: August 26, 1980
    Assignee: LEK, Tovarna farmacevtskik in kemicnik izdelkov, N.sol.o.
    Inventors: Rudolf Rucman, Nebojsa Djordjevic
  • Patent number: 4201870
    Abstract: A process for the preparation of 2-(3-benzoylphenyl)propionic acid or salt thereof wherein 3-benzoylphenyl acetonitrile or an alkoxide thereof is reacted with a methylating agent and wherein the mixture obtained is hydrolized to thereby provide the desired acid.
    Type: Grant
    Filed: October 17, 1977
    Date of Patent: May 6, 1980
    Assignee: LEK Tovarna Farmacevtskih in Kemicnih Izdelkov, n.sol.o.
    Inventor: Boris Zupancic
  • Patent number: 4200761
    Abstract: A process of preparing ##STR1## by reacting 4-thiomethyl-5-methyl imidazole with N-cyano-N'-methyl-N"-(2-chloroethyl) guanidine in a two-phase system under the conditions of phase transfer catalysis.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: April 29, 1980
    Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Branko Jenko, Igor Langof, Joza Habjan
  • Patent number: 4162364
    Abstract: A process for preparing 2-(3-benzoylphenyl)-propionic acid which includes treating 1-(3-benzoylphenyl)-propine with a thallium (III) salt in a lower alkanol to obtain 2-(3-benzoylphenyl)-propionic ester, and hydrolyzing the ester.
    Type: Grant
    Filed: October 17, 1977
    Date of Patent: July 24, 1979
    Assignee: LEK Tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Boris Zupancic, Branko Jenko
  • Patent number: 4147729
    Abstract: 1-(3-Benzoylphenyl)-propine represented by the formula: ##STR1## useful as an intermediate is provided.
    Type: Grant
    Filed: April 3, 1979
    Date of Patent: April 3, 1979
    Assignee: LEK tovarna farmacevtskih in kemicnih izdelkov, n.sol.o
    Inventors: Boris Zupancic, Branko Jenko
  • Patent number: 4145528
    Abstract: Preparation of .beta.-methyldigoxin in the presence of dimethyl formamide, an inert solvent, methyl ester of a sulphuric acid, and strontium hydroxide.
    Type: Grant
    Filed: August 10, 1977
    Date of Patent: March 20, 1979
    Assignee: LEK tovarna farmacevtskih in kemicnih izdelkov, n.sol.o.
    Inventors: Borut Pelan, Marija Milohnoja, Magda Pezdirc
  • Patent number: PP5394
    Abstract: A new variety of carnation plant distinguished by a continuous and profuse production of medium sized flowers having a generally orange coloration borne on long, strong flower stems growing raceme on strong main stems of about one meter in length, the plant being of the spray type with a vigorous and rapid growth rate with strong stem character and with abundant foliage.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: January 22, 1985
    Assignee: M. Lek en Zonen, B.V.
    Inventor: J. F. Sarneel
  • Patent number: PP5395
    Abstract: A new carnation cultivar distinguished by its continuous and profuse production of very pleasing, bright pink blossoms of medium size, borne raceme with more than three per stem on medium strong peduncles of medium length, the plant being a tall, spray type with a vigorous, rapid and sturdy growth habit and an average height of about one meter.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: January 22, 1985
    Assignee: M. Lek en Zonen, B.V.
    Inventor: J. F. Sarneel