Patents by Inventor Domenico Vergani
Domenico Vergani 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: 9403770Abstract: A process for preparing fexofenadine is described, which provides for the hydrolysis of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidyl]-1-oxobutyl]-?,?-dimethylbenzeneacetic acid-alkyl ester, in a mixture of water and optionally an organic solvent, in the presence of a base; the carboxylate salt of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidyl]-1-oxobutyl]-?,?-dimethylbenzeneacetic acid is thus obtained, which is then directly reduced as carboxylate in a basic environment with hydrogen in the presence of a suitable hydrogenation catalyst to give the carboxylate of fexofenadine, which is precipitated by neutralization of the solution.Type: GrantFiled: July 25, 2007Date of Patent: August 2, 2016Assignee: Euticals SPAInventors: Giorgio Bertolini, Maurizio Gallina, Giuseppe Motta, Domenico Vergani
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Patent number: 8796488Abstract: A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-carcinogenic, such as methyl p-toluenesulfonate; the R enantiomer is isolated from the racemic mixture of Lacosamide after selective hydrolysis of the acetamide, salification of the racemic mixture with a chiral acid (HX*) in an organic solvent, resolution of the diastereoisomeric mixture, preferably by precipitation of the R enantiomer, and subsequent acetylation of the optically pure intermediate.Type: GrantFiled: December 22, 2010Date of Patent: August 5, 2014Assignee: Euticals S.p.A.Inventors: Alberto Bologna, Patrizia Castoldi, Domenico Vergani, Giorgio Bertolini
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Patent number: 8791287Abstract: The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention.Type: GrantFiled: June 20, 2011Date of Patent: July 29, 2014Assignee: Euticals S.p.A.Inventors: Giuseppe Motta, Domenico Vergani, Giorgio Bertolini, Nicola Landoni
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Patent number: 8729308Abstract: The present invention refers to a new process for the synthesis of tapentadol comprising the quantitative resolution of the racemic mixture (V) to obtain the stereoisomer of (S)-3-(dimethylamino)-2-methyl-1-(3-nitrophenyl)-propan-1-one (VII) according to the Scheme 2 below using the (2R,3R)—O,O?-dibenzoyltartaric chiral acid wherein said resolution is quantitative. The present invention also refers to some intermediate compounds of the new synthesis process of tapentadol.Type: GrantFiled: November 30, 2010Date of Patent: May 20, 2014Assignee: Euticals S.p.A.Inventors: Giuseppe Motta, Domenico Vergani, Giorgio Bertolini
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Publication number: 20130178644Abstract: The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high stereoselectivity due to the presence of the benzyl group as substituent of the amino group. It was surprisingly found that this substitution shifts the keto-enol equilibrium towards the desired enantiomer and amplifies the capacity of the stereocenter present in the compound (VII) to orient the nucleophilic addition of the organometallic compound at the carbonyl towards the desired stereoisomer. This substitution thus allows obtaining a considerable increase of the yields in this step, and consequently allows significantly increasing the overall yield of the entire tapentadol synthesis process. A further object of the present invention is constituted by the tapentadol free base in solid form, obtainable by means of the process of the invention.Type: ApplicationFiled: June 20, 2011Publication date: July 11, 2013Applicant: EUTICALS S.P.A.Inventors: Giuseppe Motta, Domenico Vergani, Giorgio Bertolini, Nicola Landoni
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Patent number: 8367868Abstract: The present invention relates to a process for the synthesis of aryloxypropylamine and heteroaryloxypropylamine of formula I: where: A is aryl or heteroaryl, where the aryl is preferably a phenyl, optionally substituted, selected from benzyl and tolyl and the heteroaryl is preferably thiophenyl; Y is an aryl, preferably phenyl, a substituted phenyl or a naphthyl, where the substituted phenyl is preferably selected from tolyl, trihalomethyltolyl and alkoxytolyl, starting from a suitable amino alcohol of formula II:Type: GrantFiled: October 4, 2007Date of Patent: February 5, 2013Assignee: Archimica S.r.l.Inventors: Giorgio Bertolini, Barbara Verzola, Domenico Vergani
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Publication number: 20130030216Abstract: A novel process for the synthesis of Lacosamide using D,L-serine as starting material is described, where the methylation reaction of hydroxyl is carried out using an inexpensive base such as NaOH and an inexpensive alkylating agent, non-toxic and non-carcinogenic, such as methyl p-toluenesulfonate; the R enantiomer is isolated from the racemic mixture of Lacosamide after selective hydrolysis of the acetamide, salification of the racemic mixture with a chiral acid (HX*) in an organic solvent, resolution of the diastereoisomeric mixture, preferably by precipitation of the R enantiomer, and subsequent acetylation of the optically pure intermediate.Type: ApplicationFiled: December 22, 2010Publication date: January 31, 2013Applicant: EUTICALS S.P.A.Inventors: Alberto Bologna, Patrizia Castoldi, Domenico Vergani, Giorgio Bertolini
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Publication number: 20120322996Abstract: A novel method for the preparation of stavudine polymorphic form I and form II is described. 5?-acetate-2?,3?-diacetyl-5-methyluridine is reacted with catalytic amounts of sodium methoxide in a C1-C4 alcoholic solvent, resulting in crude stavudine form II. Crude stavudine form II can be converted into polymorphic stavudine form I by slurry at reflux in isopropanol, without isolating or purifying the crude stavudine form II.Type: ApplicationFiled: February 26, 2007Publication date: December 20, 2012Inventors: Gianluca Di Lernia, Alfredo Mancini, Franco Mancini, Maurizio Serra, Domenico Vergani
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Publication number: 20120232306Abstract: The present invention refers to a new process for the synthesis of tapentadol comprising the quantitative resolution of the racemic mixture (V) to obtain the stereoisomer of (S)-3-(dimethylamino)-2-methyl-1-(3-nitrophenyl)-propan-1-one (VII) according to the Scheme 2 below using the (2R,3R)—O,O?-dibenzoyltartaric chiral acid wherein said resolution is quantitative. The present invention also refers to some intermediate compounds of the new synthesis process of tapentadol.Type: ApplicationFiled: November 30, 2010Publication date: September 13, 2012Applicant: Euticals S.P.A.Inventors: Giuseppe Motta, Domenico Vergani, Giorgio Bertolini
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Patent number: 8124769Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: GrantFiled: August 17, 2010Date of Patent: February 28, 2012Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Patent number: 8101758Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: GrantFiled: August 17, 2010Date of Patent: January 24, 2012Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Publication number: 20110190504Abstract: A process for preparing fexofenadine is described, which provides for the hydrolysis of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidyl]-1-oxobutyl]-?,?-dimethylbenzeneacetic acid-alkyl ester, in a mixture of water and optionally an organic solvent, in the presence of a base; the carboxylate salt of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidyl]-1-oxobutyl]-?,?-dimethylbenzeneacetic acid is thus obtained, which is then directly reduced as carboxylate in a basic environment with hydrogen in the presence of a suitable hydrogenation catalyst to give the carboxylate of fexofenadine, which is precipitated by neutralisation of the solution.Type: ApplicationFiled: July 25, 2007Publication date: August 4, 2011Inventors: Giorgio Bertolini, Maurizio Gallina, Giuseppe Motta, Domenico Vergani
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Publication number: 20100311784Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: ApplicationFiled: August 17, 2010Publication date: December 9, 2010Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITIE SPAInventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Publication number: 20100311783Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: ApplicationFiled: August 17, 2010Publication date: December 9, 2010Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITIE SPAInventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Patent number: 7799921Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: GrantFiled: December 16, 2005Date of Patent: September 21, 2010Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Publication number: 20100105942Abstract: The present invention relates to a process for the synthesis of aryloxypropylamine and heteroaryloxypropylamine of formula I: where: A is aryl or heteroaryl, where the aryl is preferably a phenyl, optionally substituted, selected from benzyl and tolyl and the heteroaryl is preferably thiophenyl; Y is an aryl, preferably phenyl, a substituted phenyl or a naphthyl, where the substituted phenyl is preferably selected from tolyl, trihalomethyltolyl and alkoxytolyl, starting from a suitable amino alcohol of formula II:Type: ApplicationFiled: October 4, 2007Publication date: April 29, 2010Inventors: Giorgio Bertolini, Barbara Verzola, Domenico Vergani
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Publication number: 20100016599Abstract: A process for preparing fexofenadine is described that includes the purification of 4-[4-chloro-1-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.Type: ApplicationFiled: July 25, 2007Publication date: January 21, 2010Inventors: Giuseppe Motta, Domenico Vergani
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Publication number: 20090239893Abstract: A stereoselective process for preparing 7-[(E)-t-butyloxyiminomethyl]-camptothecin (also known as gimatecan) is herein disclosed. With the addition of further dissolution and precipitation steps carried out in appropriate different solvent mixtures, four new crystalline forms of gimatecan are also obtainable by using the same stereoselective process.Type: ApplicationFiled: December 16, 2005Publication date: September 24, 2009Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.Inventors: Paolo Carminati, Maria Ornella Tinti, Mauro Marzi, Fabrizio Giorgi, Walter Cabri, Marco Alpegiani, Domenico Vergani, Paolo Ghetti
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Publication number: 20080269494Abstract: A process for the preparation of -aryl-piperid-2-yl-acetamides of formula (I) in which Ar is as defined in the disclosure, by catalytic reduction of ?-aryl-?-pyridin-2-yl-acetamides (II) with rhodium catalysts. Acetamides of formula (II) can subsequently by hydrolysed to the corresponding arylacetic acids, e.g. ritalinic acid, a direct precursor of methylphenidate.Type: ApplicationFiled: December 16, 2005Publication date: October 30, 2008Inventors: Marco Frigerio, Sara Maculan, Domenico Vergani
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Publication number: 20050272934Abstract: The invention relates to a process for the preparation of thalidomide (I) comprising the reaction between glutamine (II) and a phthaloylating agent, preferably phthalic anhydride, to give N-phthaloyl-glutamine, which is directly transformed in thalidomide.Type: ApplicationFiled: May 31, 2005Publication date: December 8, 2005Applicant: ANTIBIOTICOS S.p.A.Inventors: Marco Alpegiani, Andrea Mazzoni, Domenico Vergani, Walter Cabri