Patents Assigned to Zaklady Farmaceutyczne Polpharma
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Publication number: 20220213037Abstract: This invention relates to 4-(4-fluorobenzylamino)-1-methylpiperidine trihydrate and a process for the preparation of 4-(4-fluorobenzylamino)-1-methylpiperidine trihydrate comprising treating 4-(4-fluorobenzylamino)-1-methylpiperidine with water. The invention also relates to a process for the preparation of pimavanserin comprising reacting 4-(4-fluorobenzylamino)-1-methylpiperidine trihydrate with 1-isobutoxy-4-(isocyanatomethyl)benzene; to a process for the preparation of a pimavanserin acid addition salt comprising reacting 4-(4-fluorobenzylamino)-1-methylpiperidine trihydrate with 1-isobutoxy-4-(isocyanatomethyl)benzene and converting pimavanserin into a pimavanserin acid addition salt, pimavanserin and pimavanserin acid addition salts obtainable by the process, and to the use of 4-(4-fluorobenzylamino)-1-methylpiperidine trihydrate for preparing pimavanserin or an acid addition salt thereof.Type: ApplicationFiled: May 20, 2020Publication date: July 7, 2022Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Adam HALUSZCZUK, Dorota POGODA
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Publication number: 20220033356Abstract: This invention relates to a process for the preparation of pimavanserin comprising: (i) providing an acid addition salt of pimavanserin; (ii) dissolving the acid addition salt of pimavanserin in an aqueous solvent to form an aqueous solution; (iii) washing the aqueous solution obtained in step (ii) with an organic solvent; and (iv) adding a base to the washed aqueous solution to form pimavanserin. The invention also relates to a process for the preparation of an acid addition salt of pimavanserin additionally comprising step (v) of converting pimavanserin into an acid addition salt of pimavanserin. The invention also relates to pimavanserin or an acid addition salt thereof obtainable by the process, and to the use of pimavanserin hydrochloride, pimavanserin hydrogen sulfate or pimavanserin acetate for preparing pimavanserin or an acid addition salt thereof.Type: ApplicationFiled: October 18, 2021Publication date: February 3, 2022Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Adam HALUSZCZUK, Kamil KOSIK, Barbara PIOTRKOWSKA
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Patent number: 10774042Abstract: The invention particularly relates to crystalline (solid) forms of N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]acetamide), i.e. Form N, Form M, Form O and Form P. It also refers to a pharmaceutical composition or dosage form comprising said crystalline forms. The invention also concerns said pharmaceutical composition or dosage form for use in a method of treating a disease or disorder defined in the claims. Finally, the invention pertains to the use of said novel crystalline forms for the preparation of a pharmaceutical composition or dosage form.Type: GrantFiled: November 21, 2016Date of Patent: September 15, 2020Assignee: ZAKLADY FARMACEUTYCZNE POLPHARMA SAInventors: Monika Oracz, Piotr Garczarek, Przemyslaw Skoczen, Dominika Podwysocka, Marcin Szulc, Arkadiusz Majewski
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Publication number: 20190276400Abstract: The invention particularly relates to crystalline (solid) forms of N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]acetamide), i.e. Form N, Form M, Form O and Form P. It also refers to a pharmaceutical composition or dosage form comprising said crystalline forms. The invention also concerns said pharmaceutical composition or dosage form for use in a method of treating a disease or disorder defined in the claims. Finally, the invention pertains to the use of said novel crystalline forms for the preparation of a pharmaceutical composition or dosage form.Type: ApplicationFiled: November 21, 2016Publication date: September 12, 2019Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA SAInventors: Monika ORACZ, Piotr GARCZAREK, Przemyslaw SKOCZEN, Dominika PODWYSOCKA, Marcin SZULC, Arkadiusz MAJEWSKI
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Patent number: 9845328Abstract: The method of synthesizing vardenafil base, in anhydrous conditions, by chlorosulfonation of 2-(2-etoxy-phenyl)-5 -methyl-7-propyl-iH-imidazo[5,1-fJ[1,2,4]triazin-4-one in a mixture of thionyl chloride and sulfurochloridic acid followed by amidation of the product, 4-etoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)benzene-sulfonic acid chloride with N-ethylpiperazine, in an aprotic solvent, in the presence of an inorganic base and the method of conversion the product, vardenafil base, to yield vardenafil monohydrochloride trihydrate having a melting point of 234° C. by contacting with water of the anhydrous modification V of vardenafil monohydrochloride in an organic solvent. The subject of the invention is also the anhydrous modification V of vardenafil monohydrochloride and its use in the preparation of vardenafil monohydrochloride trihydrate having a melting point of 234° C.Type: GrantFiled: December 8, 2014Date of Patent: December 19, 2017Assignee: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Roman Szramka, Jerzy Drygas, Marcin Szulc, Robert Rynkiewicz
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Patent number: 8524912Abstract: A process for the preparation of [1-hydroxy-2-(1H-imidazol-1-yl)-ethylidene]bisphosphonic acid consists of the reaction of aqueous solution of 1H-imidazole-1-acetic acid hydrochloride with phosphorus trichloride followed by removal of the excess of phosphorus trichloride, addition of water and hydrolysis of the reaction products. In order to isolate the product the post-reaction mixture is filtered and the anti-solvent is added to the aqueous filtrate in order to crystallize out [1-hydroxy-2-(1H-imidazol-1-yl)-ethylidene]bisphosphonic acid monohydrate.Type: GrantFiled: October 17, 2009Date of Patent: September 3, 2013Assignee: Zaklady Farmaceutyczne Polpharma SAInventors: Leszek Dembkowski, Mariusz Krzyzanowski, Robert Rynkiewicz, Roman Szramka, Zdzislaw Roznerski, Daniel Zyla, Janusz Rachon, Slawomir Makowiec
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Patent number: 8450488Abstract: The invention relates to a novel process for the preparation of [1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid and hemipentahydrate monosodium salt thereof comprising (a) reacting an aqueous solution of 3-pyridyl acetic acid hydrochloride with phosphorus trichloride; (b) removing unreacted phosphorus trichloride; (c) adding water and hydrolyzing; (d) isolating crystalline [1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid; (e) suspending said crystalline [1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid in water; (f) adding sodium hydroxide, filtering off, and washing; and (g) drying obtained hemipentahydrate monosodium salt of 1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid.Type: GrantFiled: December 28, 2005Date of Patent: May 28, 2013Assignee: Zaklady Farmaceutyczne Polpharma S.A.Inventors: Leszek Dembkowski, Robert Rynkiewicz, Janusz Rachoń, Slawomir Makowiec, Witold Przychodzeń, Dariusz Witt
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Patent number: 8436182Abstract: A process for the preparation of solifenacin and/or the pharmaceutically acceptable salts thereof of high pharmaceutical purity is characterized in that 3-(R)-quinuclidinoloxy anion generated in situ from 3-(R)-quinuclidinol in a presence of strong base in polar organic solvent is subject to acylation with (S)-1-phenyl-1,2,3,4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98%, while maintaining constant anion excess in a reaction mixture, and after reaction completion solifenacin base is optionally transformed into solifenacin salt according to standard procedures. (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98% is obtained in a reaction of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline and molar excess of phosgene in a presence of tertiary aromatic amine in aromatic hydrocarbon, and isolated in a crystalline form.Type: GrantFiled: May 22, 2009Date of Patent: May 7, 2013Assignee: Zaklady Farmaceutyczne Polpharma SAInventors: Oliwia Zegrocka-Stendel, Joanna Zagrodzka, Marta Laszcz
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Publication number: 20120116092Abstract: A process for the preparation of [1-hydroxy-2-(1H-imidazol-1-yl)-ethylidene]bisphosphonic acid consists of the reaction of aqueous solution of 1H-imidazole-1-acetic acid hydrochloride with phosphorus trichloride followed by removal of the excess of phosphorus trichloride, addition of water and hydrolysis of the reaction products. In order to isolate the product the post-reaction mixture is filtered and the anti-solvent is added to the aqueous filtrate in order to crystallize out [1-hydroxy-2-(1H-imidazol-1-yl)-ethylidene]bisphosphonic acid monohydrate.Type: ApplicationFiled: October 17, 2009Publication date: May 10, 2012Applicants: POLITECHNIKA GDANSKA, ZAKLADY FARMACEUTYCZNE POLPHARMA S.AInventors: Leszek Dembkowski, Mariusz Krzyzanowski, Robert Rynkiewicz, Roman Szramka, Zdzislaw Roznerski, Daniel Zyla, Janusz Rachon, Slawomir Makowiec
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Patent number: 7928063Abstract: Growth hormone-releasing hormone analogs having the amino acid sequence of the formula: Dat-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr10-R11-R12-VAL-Leu-Ala-Gln-Leu-Ser-Ala-R20-R21-Leu-Leu-Gln-Asp-Ile-Nle-Asp-R29-NH2 (I), wherein R11 is hArg, Gab or Gap; R12 is hArg, Orn, Gab or Gap; R20 is hArg, hArg, Gab or Gap; R21 is hArg, Orn, Gab or Gap; R29 is D-Arg, hArg, Gab or Gap; and their pharmaceutically acceptable salts. Said peptides are potent and selective stimulators of GH release and they are highly resistant to enzymatic degradation.Type: GrantFiled: October 30, 2002Date of Patent: April 19, 2011Assignees: Instytut Farmaceutyczny, Zaklady Farmaceutyczne PolpharmaInventors: Jan Izdebski, Danuta Kunce, Alicja Orlowska, Ewa Witkowska, Wieslaw Szelejewski, Andrzej Kutner, Krzysztof Bankowski, Elzbieta Frackiewicz
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Publication number: 20110065922Abstract: A process for the preparation of solifenacin and/or the pharmaceutically acceptable salts thereof of high pharmaceutical purity is characterized in that 3-(R)-quinuclidinoloxy anion generated in situ from 3-(R)-quinuclidinol in a presence of strong base in polar organic solvent is subject to acylation with (S)-1-phenyl-1,2,3,4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98%, while maintaining constant anion excess in a reaction mixture, and after reaction completion solifenacin base is optionally transformed into solifenacin salt according to standard procedures. (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinolinecarbonyl chloride of chemical purity at least 98% is obtained in a reaction of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline and molar excess of phosgene in a presence of tertiary aromatic amine in aromatic hydrocarbon, and isolated in a crystalline form.Type: ApplicationFiled: May 22, 2009Publication date: March 17, 2011Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA SAInventors: Oliwia Zegrocka-Stendel, Joanna Zagrodzka, Marta Laszcz
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Publication number: 20110045085Abstract: The invention relates to a novel process for the manufacture of stable, meeting relevant quality requirements pharmaceutical compositions in the form of encapsulated powder comprising Orlistat and pharmaceutically acceptable additives. The invention further relates to pharmaceutical compositions of Orlistat in the form of encapsulated powder obtained in accordance with the process of the present invention.Type: ApplicationFiled: March 19, 2009Publication date: February 24, 2011Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Jaroslaw Mazgalski, Anna Szemecka-Golabek, Anna Kaminska
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Publication number: 20100255105Abstract: An extended release pharmaceutical composition comprising metoprolol succinate and at least two pharmaceutically acceptable excipients, wherein the first pharmaceutically acceptable excipient is an extended release agent; the second pharmaceutically acceptable excipient is selected from a binder, a diluent and mixtures thereof; and metoprolol succinate is in a crystalline form having a D50 ranging from 5 to 16 microns and a D90 below 50 microns.Type: ApplicationFiled: March 31, 2010Publication date: October 7, 2010Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: CHITRA SHAH, FRANCISCO GUAL PUJOL, JOAQUÍN AMELA-NAVARRO, JOSÉ-LUIS RUIZ-CÓRDOBA
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Publication number: 20100069641Abstract: A novel process for the preparation of a sodium salt of 1-(((1(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methyl-ethyl)phenyl)propyl)sulfanyl)methyl)cyclopropaneacetic acid, comprising: a) reacting a compound of Formula 1 with methanesulfonyl chloride in the presence of a tertiary amine to yield a crude solution of a compound of Formula 2; b) filtering the crude solution of compound of Formula 2 obtained in a) to remove solid amine hydrochloride, reacting the filtrate without isolation or further purification with a compound of Formula 3, and isolating 1-(((1(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)sulfanyl)methyl)cyclopropaneacetic acid; c) reacting the 1-(((1(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)sulfanyl)methyl)cyclopropaneacetic acid isolated in b) with tert-butylamine to yield a compound of formula 4; d) isolating and purifying the compound of formula 4; and e) converting thType: ApplicationFiled: April 30, 2008Publication date: March 18, 2010Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Daniel Zyla, Robert Rynkiewicz, Mariusz Krzyzanowski, Jan Ramza
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Publication number: 20090281320Abstract: The invention relates to a novel process for the preparation of [1-hydroxy-2-(3-pyridinyl)ethylidene] bisphosphonic acid and hemipentahydrate monosodium salt thereof comprising (a) reacting an aqueous solution of 3-pyridyl acetic acid hydrochloride with phosphorus trichloride; (b) removing unreacted phosphorus trichloride; (c) adding water and hydrolyzing; (d) isolating crystalline [1-hydroxy-2-(3-pyridinyl)ethylidene] bisphosphonic acid; (e) suspending said crystalline [1-hydroxy-2-(3-pyridinyl)ethylidene] bisphosphonic acid in water; (f) adding sodium hydroxide, filtering off, and washing; and (g) drying obtained hemipentahydrate monosodium salt of 1-hydroxy-2-(3-pyridinyl)ethylidene] bisphosphonic acid.Type: ApplicationFiled: December 28, 2005Publication date: November 12, 2009Applicants: ZAKLADY FARMACEUTYCZNE POLPHARMA SA, POLITECHNIKA GDANSKAInventors: Leszek Dembkowski, Robert Rynkiewicz, Janusz Rachon, Slawomir Makowiec, Witold Przychodzen, Dariusz Witt
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Publication number: 20090005413Abstract: The invention relates to a novel salt of montelukast with tert-butylamine and its use in the process for the preparation of highly pure free montelukast acid and/or pharmaceutically acceptable salts thereof, in particular montelukast sodium.Type: ApplicationFiled: October 21, 2005Publication date: January 1, 2009Applicants: INSTYTUT FARMACEUTYCZNY, ZAKLADY FARMACEUTYCZNE POLPHARMA SAInventors: Osman Achmatowicz, Krzysztof Wisniewski, Jan Ramza, Wieslaw Szelejewski, Barbara Szechner
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Publication number: 20080242872Abstract: The subject of the invention is amorphous carvedilol phosphate and a method of manufacturing amorphous carvedilol phosphate comprising removing solvent from carvedilol phosphate solution by means of spray drying.Type: ApplicationFiled: October 3, 2007Publication date: October 2, 2008Applicant: ZAKLADY FARMACEUTYCZNE POLPHARMA S.A.Inventors: Jerzy DRYGAS, Jolanta PAWLOWSKA, Roman SZRAMKA, Jan RAMZA