Patents by Inventor Laszlo Czibula
Laszlo Czibula has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20150284338Abstract: Our invention relates to trans-(4-{4-[2-(4-amino-cyclohexyl)-ethyl]-piperazin-1-yl}-5,6-dichloro-pyrimidin-2-yl)-methylamine dihydrochloride monohydrate, the process for the synthesis of this compound, the new (4,5-dichloro-6-piperazin-1-yl-pyirimidin-2-yl)-methylamine monohydrochlorid used as starting material in this synthesis, as well as the industrial process for the synthesis of trans-N-(4- {2-[4-(5,6-dichloro-2-methyl-amino-pyirimidin-4-yl-)piperazin-1-yl]-ethly}cyclohexyl-propionamide starting from trans-(4-{4-[2-(4-amino-cyclohexyl)-ethyl]-piperazin-1-yl}-5,6-dichloro-pyrimidin-2-yl)-methylamine dihydrochloride monohydrate.Type: ApplicationFiled: November 20, 2013Publication date: October 8, 2015Applicant: Richter Gedeon Nyrt.Inventors: Krisztina Szavicskó, György Domány, László Czibula, Gizella Bartáné Szalai, László Dobay, Éva Werkné Pap
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Patent number: 8802888Abstract: The invention relates to a process for the preparation of trans 4-amino-cyclohexil ethyl acetate HCl wherein d) hydrogenating 4-nitrophenyl acetic acid in a protic solvent at a temperature between 40-50° C. in the presence of Pd/C under 0.1-0.6 bar overpressure, and e) further hydrogenating the 4-aminophenyl acetic acid obtained in situ in step a) at a temperature between 50-60° C. under 1-4 bar overpressures, then f) heating to reflux the 4-aminocyclohexil acetic acid obtained in step b) for 1-3 hours in hydrochloric ethanol, and if desired after removing the solvent acetonitrile was added to the residue obtained and distilled off.Type: GrantFiled: December 17, 2009Date of Patent: August 12, 2014Assignee: Richter Gedeon Nyrt.Inventors: Laszlo Hegedus, Laszlo Czibula, Balint Juhasz, Judit Nagyne Bagdy, Denes Markos, Olga Marianna Mathe, Julia Mathe
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Patent number: 8569496Abstract: The invention relates to novel trans N-{4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine dihydrochloride monohydrate and a process for the preparation of the trans N-{4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine dihydrochloride monohydrate, said process comprising the steps a) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl)amino]-cyclohexyl}-acetic acid ester with sodium borohydride and aluminum trichloride to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethanol; b) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]cyclohexyl}-ethanol obtained with methanesulfonic acid chloride in the presence of an acid binding agent to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethyl methanesulfonate; c) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethyl methanesulfonate obtained with 2,3-dichlorophenyl-piperazine in the presence of an acid binding agent to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-carbType: GrantFiled: December 17, 2009Date of Patent: October 29, 2013Assignee: Richter Gedeon Nyrt.Inventors: Laszlo Czibula, Eva Againe Csongor, Katalin Nogradi, Balint Juhasz, Ferenc Sebok, Janos Galambos, Istvan Vago
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Patent number: 8569498Abstract: The invention relates to a new process for the preparation of compounds of general formula (I) wherein R1 and R2 represent independently hydrogen or C1-6 alkyl with straight or branched chain optionally substituted with aryl group, or C2-7 alkenyl containing 1-3 double bonds, or monocyclic, bicyclic or tricyclic aryl optionally substituted with one or more C1-6 alkoxy, trifluoro-C1-6 alkoxy, C1-6-alkoxycarbonil, C1-6alkanoyl, aryl, C1-6 alkylthio, halogen or cyano, or optionally substituted monocyclic, bicyclic or tricyclic C3-14 cycloalkyl group, R1 and R2 together with the adjacent nitrogen form a saturated or unsaturated optionally substituted monocyclic or bicyclic heterocyclic ring which may contain further heteroatoms selected from oxygen, nitrogen, or sulphur atoms and hydrochloric acid alts and/or hydrates and/or solvates thereof, by dissolving or suspending trans 4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine of formula (III) or a salt or a hydrate or a solvate thereof in aType: GrantFiled: December 18, 2009Date of Patent: October 29, 2013Assignee: Richter Gedeon Nyrt.Inventors: Laszlo Czibula, Balint Juhasz, Eva Againe Csongor, Ferenc Sebok, Janos Galambos, Katalin Nogradi
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Patent number: 8569497Abstract: The invention relates to a process for the preparation of the trans N-{4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-yl]-ethyl}-cyclohexyl}-carbamide derivatives of general formula (I) by reacting the compound of formula (III) with a carbamoylchloride of general formula (II) which comprises carrying out the reaction in a mixture of a solvent and concentrated aqueous solution of an alkali hydroxide at a temperature between 40-100° C. in the presence of a phase transfer catalyst, separating the phases and washing the organic layer then removing the solvent and drying the compound of formula (I) obtained until its weight is constant.Type: GrantFiled: December 18, 2009Date of Patent: October 29, 2013Assignee: Richter Gedeon Nyrt.Inventors: Eva Againe Csongor, Laszlo Czibula, Ferenc Sebok, Balint Juhasz, Janos Galambos, Katalin Nogradi
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Publication number: 20120059034Abstract: The invention relates to novel crystalline hydrate, amorphous and crystalline polymorphic forms of 2-[4-(4-Fluoro-benzyl)-piperidine-1-yl]-2-oxo-N-(2-oxo-2,3-dihydro-benzoxazole-6-yl)-acetamide (I) (radiprodil). Processes for the preparation of these forms, compositions containing these forms, and methods of use thereof are also described.Type: ApplicationFiled: March 1, 2010Publication date: March 8, 2012Inventors: Ádám Demeter, Zoltán Német, András Nemes, Ferenc Sebok, Gizella Bartáné Szalai, László Czibula
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Publication number: 20110288329Abstract: The invention relates to a process for the preparation of trans 4-amino-cyclohexil ethyl acetate HCl wherein d) hydrogenating 4-nitrophenyl acetic acid in a protic solvent at a temperature between 40-50° C. in the presence of Pd/C under 0.1-0.6 bar overpressure, and e) further hydrogenating the 4-aminophenyl acetic acid obtained in situ in step a) at a temperature between 50-60° C. under 1-4 bar overpressures, then f) heating to reflux the 4-aminocyclohexil acetic acid obtained in step b) for 1-3 hours in hydrochloric ethanol, and if desired after removing the solvent acetonitrile was added to the residue obtained and distilled off.Type: ApplicationFiled: December 17, 2009Publication date: November 24, 2011Inventors: Tibor Bence Mathe, Olga Marianna Mathe, Julia Mathe Heiress, Laszlo Hegedus, Laszlo Czibula, Balint Juhasz, Judit Nagyne Bagdy, Denes Markos
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Publication number: 20110275816Abstract: The invention relates to novel trans N-{4-{2-[4-(2, 3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine dihydrochloride monohydrate and a process for the preparation of the trans N-{4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine dihydrochloride monohydrate, said process comprising the steps a) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl) amino]-cyclohexyl}-acetic acid ester with sodium borohydride and aluminium trichloride to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethanol; b) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]cyclohexyl}-ethanol obtained with methanesulfonic acid chloride in the presence of an acid binding agent to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethyl methanesulfonate; c) reacting trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexyl}-ethyl methanesulfonate obtained with 2,3-dichlorophenyl-piperazine in the presence of an acid binding agent to give trans 2-{1-[4-(N-tert-butoxycarbonyl)-amino]-cyclohexylType: ApplicationFiled: December 17, 2009Publication date: November 10, 2011Inventors: Laszlo Czibula, Eva Againe Csongor, Katalin Nogradi, Balint Juhasz, Ferenc Sebok, Janos Galambos, Istvan Vago
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Publication number: 20110275804Abstract: The invention relates to a new process for the preparation of compounds of general formula (I) wherein R1 and R2 represent independently hydrogen or C1-6 alkyl with straight or branched chain optionally substituted with aryl group, or C2-7 alkenyl containing 1-3 double bonds, or monocyclic, bicyclic or tricyclic aryl optionally substituted with one or more C1-6 alkoxy, trifluoro-C1-6 alkoxy, C1-6-alkoxycarbonil, C1-6alkanoyl, aryl, C1-6 alkylthio, halogen or cyano, or optionally substituted monocyclic, bicyclic or tricyclic C3-14 cycloalkyl group, R1 and R2 together with the adjacent nitrogen form a saturated or unsaturated optionally substituted monocyclic or bicyclic heterocyclic ring which may contain further heteroatoms selected from oxygen, nitrogen, or sulphur atoms and hydrochloric acid alts and/or hydrates and/or solvates thereof, by dissolving or suspending trans 4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-il]-ethyl}-cyclohexylamine of formula (III) or a salt or a hydrate or a solvate thereof in anType: ApplicationFiled: December 18, 2009Publication date: November 10, 2011Inventors: Laszlo Czibula, Balint Juhasz, Eva Againe Csongor, Ferenc Sebok, Janos Galambos, Katalin Nogradi
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Publication number: 20110269959Abstract: The invention relates to a process for the preparation of the trans N-{4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-yl]-ethyl}-cyclohexyl}-carbamide derivatives of general formula (I) by reacting the compound of formula (III) with a carbamoylchloride of general formula (II) which comprises carrying out the reaction in a mixture of a solvent and concentrated aqueous solution of an alkali hydroxide at a temperature between 40-100° C. in the presence of a phase transfer catalyst, separating the phases and washing the organic layer then removing the solvent and drying the compound of formula (I) obtained until its weight is constant.Type: ApplicationFiled: December 18, 2009Publication date: November 3, 2011Inventors: Eva Againe Csongor, Laszlo Czibula, Ferenc Sebok, Balint Juhasz, Janos Galambos, Katalin Nogradi
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Patent number: 7943621Abstract: The present invention relates to novel monohydrochloride, dihydrochloride, monohydrobromide, maleate and methanesulphonate salts of trans 4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-yl]-ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine and/or their hydrates and/or solvates. Moreover, the invention relates to the process for preparing the salts and their hydrates and/or solvates, to their use in the treatment and/or prevention of conditions which require modulation of dopamine receptor and to pharmaceutical compositions containing them.Type: GrantFiled: May 9, 2008Date of Patent: May 17, 2011Assignee: Richter Gedeon Nyrt.Inventors: Laszlo Czibula, Ferenc Sebok, Istvan Greiner, Gyorgy Domany, Eva Againe Csongor
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Patent number: 7858791Abstract: A process for preparing cabergoline (I) from ergoline-8?-carboxylic acid ester (XIII) comprising the following steps. (XIII), (XVI), (XVII), (XVIII), (XIX), (I). The present case also relates to the intermediates (XVI), (XVII), (XVIII) and (XIX) as well as the polymorphic amorphous form of Cabergoline (I) and the production thereof.Type: GrantFiled: March 2, 2005Date of Patent: December 28, 2010Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Janos Galambos, Laszlo Czibula, Ferenc Sebök, Sandorné Balint, Ferencné Kassai, Gyorgyi Ignaczné Szendrei, Adam Demeter
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Patent number: 7625935Abstract: One object of the invention is high purity butoconazole nitrate of the formula (I) (I) containing maximum 0.1 wt % of chemical impurities, wherein at least 95% of the particles of the substance are below 75 ?m by diameter, whereas at least 99% of the particles are below 250 ?m by diameter, and process for its preparation. A pharmaceutical composition comprising as active ingredient, high purity butoconazole nitrate of specified particle size in admixture with known auxiliaries is also within the scope of the invention.Type: GrantFiled: January 25, 2005Date of Patent: December 1, 2009Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Laszlo Czibula, Laszlo Dobay, Eva Werkne Papp, Judit Nagyne Bagdy, Ferenc Sebok
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Publication number: 20090270630Abstract: Process for the synthesis of 5-{4-[N-methyl-N-(2-pyridyl)-amino-ethoxy]-benzylidene}-thiazolidine-2,4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained compound of formula (III) with 4-fluorobenzaldehyde Step c) reaction of the obtained compound of formula (IV) with thiazolidine-2,4-dione characterized by dissolving 4-{2-[N-methyl-N-(2-pyridyl)amino]-ethanol of formula (III) obtained in Step a) in toluene and using it in Step b) without isolation; reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50° C.; reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product.Type: ApplicationFiled: June 21, 2007Publication date: October 29, 2009Inventors: Laszlo Czibula, Ferenc Sebok, Laszlo Dobay, Eva Werkne Papp, Ida Deutschne Juhasz, Judit Nagyne Bagdy, Tamasne Uberhardt
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Publication number: 20090023750Abstract: The present invention relates to novel monohydrochloride, dihydrochloride, monohydrobromide, maleate and methanesulphonate salts of trans 4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-yl]-ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine and/or their hydrates and/or solvates. Moreover, the invention relates to the process for preparing the salts and their hydrates and/or solvates, to their use in the treatment and/or prevention of conditions which require modulation of dopamine receptor and to pharmaceutical compositions containing them.Type: ApplicationFiled: May 9, 2008Publication date: January 22, 2009Applicant: RICHTER GEDEON NYRT.Inventors: Laszlo Czibula, Ferenc Sebok, Istvan Greiner, Gyorgy Domany
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Publication number: 20080221190Abstract: One object of the invention is high purity butoconazole nitrate of the formula (I) (I) containing maximum 0.1 wt % of chemical impurities, wherein at least 95% of the particles of the substance are below 75pm by diameter, whereas at least 99% of the particles are below 250 ?m by diameter, and process for its preparation.Type: ApplicationFiled: January 25, 2005Publication date: September 11, 2008Inventors: Laszlo Czibula, Laszlo Dobay, Eva Werkne Papp, Judit Nagyne Bagdy, Ferenc Sebok
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Publication number: 20070293671Abstract: The invention relates to a process for the preparation of risperidone (chemical name: 3-[2-[4-(6-fluoro-1,2-benzisoxazole-3-yl)-1piperidmyl]ethyl-2-methyl-6,7,8,9-terahydro-4H-pyrido[1,2-a]pyrimidine-4-one) of the formula (I) by reacting 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-4-one of the formula (II) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole of the formula (III), in which the reaction is carried out in dry methanol solvent under pressure, at a temperature between 65 and 90° C., the product is recovered by using a methanol/water mixture of specified ratio and if desired is recrystallized from an alcohol.Type: ApplicationFiled: July 6, 2005Publication date: December 20, 2007Inventors: Laszlo Czibula, Peter Turcsanyi, Krisztina Feher, Ferenc Sebok, Gyorgy Szabo, Eva Papp
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Publication number: 20070066835Abstract: The invention relates to a new process for the synthesis of amorphous atorvastatin calcium, which consists of dissolving the salt of the formula (I) of atorvastatin acid formed with a basic amino acid (I); in a mixture of water and a water miscible organic solvent, adding an aqueous solution of a water soluble calcium salt to the solution and isolating the so obtained entirely amorphous atorvastatin calcium of high purity by filtration.Type: ApplicationFiled: March 23, 2004Publication date: March 22, 2007Inventors: Laszlo Czibula, Laszlo Dobay, Eva Papp, Ida Juhasz, Sandorne Balint
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Patent number: 7094904Abstract: A new process is disclosed for the synthesis of fluconazole monohydrate and for crystal modifications of fluconazole which comprises the step of hydrolyzing a silyl ether of the formula (II) ?wherein R2 is hydrogen, or a C1 to C10 alkyl or phenyl group, R3 and R4 independently of each other are a C1 to C10 alkyl or phenyl group in an aqueous solution, preferably at a pH below 3 or above 8.Type: GrantFiled: September 22, 2003Date of Patent: August 22, 2006Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Jánosné´ Kreidl née Regina Hegedus, legal representative, Laszlo Czibula, Csaba Szantay, Jenone Farkas, Ida Deutschne Juhasz, Istvan Hegedus, Eva Werkne Papp, Judit Nagyne Bagdy, Agnes Piller, Janos Kreidl, deceased
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Publication number: 20040106804Abstract: A new process is disclosed for the synthesis of fluconazole monohydrate and for crystal modifications of fluconazole which comprises the step of hydrolyzing a silyl ether of the formula (II) 1Type: ApplicationFiled: September 22, 2003Publication date: June 3, 2004Applicant: RICHTER GEDEON VEGYESZETI GYAR RT.Inventors: Janos Kreidl, Laszlo Czibula, Csaba Szantay, Jenone Farkas, Ida Deutschne Juhasz, Istvan Hegedus, Eva Werkne Papp, Judit Nagyne Bagdy, Agnes Piller, Janosne Kreidl nee Regina Hegedus