Patents by Inventor Josef Jirman
Josef Jirman 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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Patent number: 8394962Abstract: Intermediates for the preparation of dabigatran of formulae (VII-2HCl) and (VII-HCl), methods for their preparation and a method for preparation of dabigatran of formula (VIII) using these intermediates.Type: GrantFiled: October 26, 2009Date of Patent: March 12, 2013Assignee: Zentiva k.s.Inventors: Petr Lustig, Josef Jirman
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Patent number: 8394961Abstract: A method for the manufacture of dabigatran of formula VIII, in which the product of a reaction of 4-ethylamino-3-nitrobenzoic acid chloride with ethyl-3-(pyridin-2-ylamino)propanoate, is converted to the hydrochloride using a hydrogen chloride solution producing the compound of formula III-HCl, in which the nitro group is reduced by means of a reaction with sodium dithionite, and the resulting compound of formula IV is subjected to a reaction with [(4-cyanophenyl)amino]acetic acid and oxalic acid, the product of this reaction VI-oxal is then subjected to hydrolysis and a reaction with ammonium carbonate to produce the intermediate of formula VII-HCl, which is then converted to dabigatran by means of a reaction with hexyl chloroformate.Type: GrantFiled: March 10, 2009Date of Patent: March 12, 2013Assignee: Zentiva k.s.Inventors: Josef Jirman, Jindrich Richter, Petr Lustig
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Patent number: 8034942Abstract: A process for the preparation of (1S)-QR)-I-azabicyclo[2.2.2.]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate by reacting (1S)-alkyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinoline carboxylate with 3-(R)-quinuclidol in an inert solvent, where a primary alkyl ester of the carboxylate whose alkyl length is C1-C4 is used and the reaction is catalyzed by a non-nucleophilic base.Type: GrantFiled: June 21, 2007Date of Patent: October 11, 2011Assignee: Zentiva k s.Inventors: Josef Jirman, Richard Junek, Petr Lustig, Jindrich Richter, Lukas Placek
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Patent number: 8034807Abstract: The invention deals with new crystalline salts of bazedoxifene, by means of which a high API quality can be achieved in a high yield.Type: GrantFiled: July 24, 2008Date of Patent: October 11, 2011Assignee: Zentiva k.s.Inventors: Josef Jirman, Jindrich Richter
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Publication number: 20110224441Abstract: Intermediates for the preparation of dabigatran of formulae (VII-2HCl) and (VII-HCl), methods for their preparation and a method for preparation of dabigatran of formula (VIII) using these intermediates.Type: ApplicationFiled: October 26, 2009Publication date: September 15, 2011Inventors: Petr Lustig, Josef Jirman
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Publication number: 20110082299Abstract: A method for the manufacture of dabigatran of formula VIII, in which the product of a reaction of 4-ethylamino-3-nitrobenzoic acid chloride with ethyl-3-(pyridin-2-ylamino)propanoate, is converted to the hydrochloride using a hydrogen chloride solution producing the compound of formula III-HCl, in which the nitro group is reduced by means of a reaction with sodium dithionite, and the resulting compound of formula IV is subjected to a reaction with [(4-cyanophenyl)amino] acetic acid and oxalic acid, the product of this reaction VI-oxal is then subjected to hydrolysis and a reaction with ammonium carbonate to produce the intermediate of formula VII-HCl, which is then converted to dabigatran by means of a reaction with hexyl chloroformate.Type: ApplicationFiled: March 10, 2009Publication date: April 7, 2011Inventors: Josef Jirman, Jindrich Richter, Petr Lustig
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Publication number: 20110034692Abstract: The subject-matter of the invention consists in a method of removing specific impurities of montelukast of formula (I), which occur due to chemical instability of the target substance and also contaminate the substance in the preparation process. Further, methods of isolation of specific impurities of montelukast defined by formulae (V-A), (IV-A), (XIIIa-A), (XIIIb-A) and analytic methods used for the control of the production of montelukast in the pharmaceutical quality.Type: ApplicationFiled: March 11, 2009Publication date: February 10, 2011Applicant: ZENTIVA, K.S.Inventors: Ales Halama, Olga Bouskova, Petr Gibala, Josef Jirman
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Publication number: 20100317871Abstract: A method of preparing (3S)-1-[2-(2,3-dihydro-5-benzofuranyl)ethyl}-?,?-diphenyl-3-pyrrolidine acetamide hydrogen bromide, wherein 3-(S)-(I-carbamoyl-1,1-diphenylmethyl)pyrrolidine or its salt with an organic acid is alkylated in the presence of an inorganic base with 5-(2-bromoethyl)-2,3-dihydrobenzofurane in a heterogeneous system of the solvents water and an organic solvent selected from C6 to C9 aliphatic, alicyclic or aromatic hydrocarbons, after separation of the two phases the crude darifenacin base is isolated, which is converted to the hydrobromide by addition of a C3 to C9 ketone or C3 to C9 alcohol and concentrated hydrobromic acid.Type: ApplicationFiled: January 14, 2009Publication date: December 16, 2010Inventors: Ludmila Hejtmankova, Josef Jirman
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Publication number: 20100267958Abstract: A method of isolation of Montelukast of formula I from reaction mixtures, comprising conversion of the crude sub-stance to well-crystallizing salts with primary amines in the environment of at least one organic solvent and acetonitrile, followed by re-crystallization of these salts with simultaneous removal of chemical impurities and use of the chemically pure salts of Montelukast with primary amines for direct transformation to the pharmaceutically useful amorphous form of Montelukast sodium of formula II.Type: ApplicationFiled: July 8, 2008Publication date: October 21, 2010Inventors: Ales Halama, Josef Jirman, Hana Petrickova
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Publication number: 20100240888Abstract: The invention deals with new crystalline salts of bazedoxifene, by means of which a high API quality can be achieved in a high yield.Type: ApplicationFiled: July 24, 2008Publication date: September 23, 2010Inventors: Josef Jirman, Jindrich Richter
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Publication number: 20100174083Abstract: A method of preparation of Montelukast of formula (I) by reaction of the compound of formula (III) and a compound of formula (IX), characterized in that the reaction is carried out in the presence of a base, an inert solvent and a component increasing selectivity of the process, especially of a polyether of general formula (XIII), wherein R stands for hydrogen or an alkyl and the value of n varies from 1 to 40, polyethyleneglycol of general formula (XIV), wherein n=1 to 40 or a crown-ether of formulae (XV), (XVI) or (XVII).Type: ApplicationFiled: January 8, 2008Publication date: July 8, 2010Inventors: Ales Halama, Josef Jirman
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Publication number: 20100145055Abstract: A method of preparing (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate (solifenacin) or its pharmaceutically acceptable salts with high optic purity, wherein the crude solifenacin base is transformed to the hydrogen tartrate, which is then optionally transformed to another pharmaceutically acceptable salt or the base of solifenacin. A crystalline salt of solifenacin hydrogen tartrate.Type: ApplicationFiled: December 21, 2007Publication date: June 10, 2010Inventors: Josef Jirman, Richard Junek
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Publication number: 20100087661Abstract: A method for the preparation of 5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole of formula (1) by reaction of 2-bromo-4?-benzyloxypropiophenone and 4-benzyloxyaniline hydrochloride, in which high purity of the product is achieved by isolation of the intermediate, N-(4-benzyloxyphenyl)-?-amino-4-benzyloxypropiophenone of formula (10), in the solid state. The method may be used for the preparation of bazedoxifen of formula (2).Type: ApplicationFiled: February 11, 2007Publication date: April 8, 2010Inventors: Josef Jirman, Jindrich Richter
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Patent number: 7618953Abstract: The monosodium salt of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid in new amorphous forms, methods of preparation and a pharmaceutical formulation.Type: GrantFiled: February 28, 2005Date of Patent: November 17, 2009Assignee: Zentiva, a.s.Inventors: Jindrich Richter, Josef Jirman, Hana Petrickova
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Publication number: 20090203914Abstract: A process for the preparation of (1S)-QR)-I -azabicyclo[2.2.2.]oct-3-yl 3,4-dihydro-1-phenyl- 2(1H)-isoquino-line carboxylate by reacting (1S)-alkyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinoline carboxylate with 3-(R)-quinuclidol in an inert solvent, where a primary alkyl ester of the carboxylate whose alkyl length is C1-C4 is used and the reaction is catalyzed by a non-nu-cleophilic base.Type: ApplicationFiled: June 21, 2007Publication date: August 13, 2009Inventors: Josef Jirman, Richard Junek, Petr Lustig, Jindrich Richter, Lukas Placek
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Patent number: 7276604Abstract: The present invention relates to a crystalline, hydrated form of the sodium salt of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid. The hydrate contains from 6.4 up to 22 weight % of sodium and 15 up to 23 weight % of crystalline water if the sodium content is lower than 7.5 weight %, based on the whole molecule, or 4.5 up to 18 weight % of crystalline water if the sodium content is equal to or higher than 13 weight %, based on the anhydrous substance. Due to stability in humid environments, the hydrate is useful as an active substance for the treatment of diseases associated with bone resorption disorders.Type: GrantFiled: October 21, 2003Date of Patent: October 2, 2007Assignee: Zentiva A.S.Inventors: Jindrich Richter, Josef Jirman
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Publication number: 20070142332Abstract: The monosodium salt of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid in new amorphous forms, methods of preparation and a pharmaceutical formulation.Type: ApplicationFiled: February 28, 2005Publication date: June 21, 2007Applicant: ZENTIVA , A.S.Inventors: Jindrich Richter, Josef Jirman, Hana Petrichova
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Publication number: 20060148762Abstract: The present invention relates to a crystalline, hydrated form of the sodium salt of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid. The hydrate contains from 6.4 up to 22 weight % of sodium and 15 up to 23 weight % of crystalline water if the sodium content is lower than 7.5 weight %, based on the whole molecule, or 4.5 up to 18 weight % of crystalline water if the sodium content is equal to or higher than 13 weight %, based on the anhydrous substance. Due to stability in humid environments, the hydrate is useful as an active substance for the treatment of diseases associated with bone resorption disorders.Type: ApplicationFiled: October 21, 2003Publication date: July 6, 2006Applicant: Zentiva, A.S.Inventors: Jindrich Richter, Josef Jirman
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Patent number: 7009057Abstract: A method for obtaining antidiabetic of formula (I), wherein the method comprises condensing of a 4-derivatized phenol or phenolate of general formula (II), wherein R is an amino group-containing organic residue, selected from the group comprising a residue of the following formula —NHR3, wherein R3 is hydrogen or a protecting group, which is removed before further treatment, and a residue of general formula (A), wherein Rb represents a carboxy group either in the free acid form or in the form of a salt or ester or another functional derivative or the nitrile group CN, and M represents a hydrogen or alkali metal atom, with a pyridine base of general formula (III, wherein Z is a leaving group other than a halogen, wherein, before or after carrying out the condensation, the following operations are carried out: (a) diazotizing the amino group present in organic residue R; (b) converting the diazotised residue R into a derivative of 2-halopropionate or 2-halopropionitrile of formula (B), wherein Rb is as definedType: GrantFiled: April 25, 2002Date of Patent: March 7, 2006Assignee: Zentiva A.S.Inventors: Ale{hacek over (s)} Halama, Ludmila Hejtmánková, Petr Lustig, Jind{hacek over (r)}ich Richter, Lucie Sr{hacek over (sn)}ová, Josef Jirman
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Publication number: 20050043360Abstract: A method for obtaining antidiabetic of formula (I), wherein the method comprises condensing of a 4-derivatized phenol or phenolate of general formula (II), wherein R is an amino group-containing organic residue, selected from the group comprising a residue of the following formula —NHR3, wherein R3 is hydrogen or a protecting group, which is removed before further treatment, and a residue of general formula (A), wherein Rb represents a carboxy group either in the free acid form or in the form of a salt or ester or another functional derivative or the nitrile group CN, and M represents a hydrogen or alkali metal atom, with a pyridine base of general formula (III, wherein Z is a leaving group other than a halogen, wherein, before or after carrying out the condensation, the following operations are carried out: (a) diazotizing the amino group present in organic residue R; (b) converting the diazotised residue R into a derivative of 2-halopropionate or 2-halopropionitrile of formula (B), wherein Rb is as definedType: ApplicationFiled: April 25, 2002Publication date: February 24, 2005Applicant: LECIVA, A.S.Inventors: Ales Halama, Ludmila Hejtmankova, Petr Lustig, Jindrich Richter, Lucie Srsnova, Josef Jirman