Patents by Inventor Oreste Piccolo
Oreste Piccolo 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: 6566552Abstract: The present invention describes a process for the industrial production of L-carnitine, comprising the enantioselective reduction of an alkyl 4-chloro-3-oxobutyrate or 4-chloro-3-oxobutyramide. The optically active 3-hydroxy derivative thus obtained is reacted with trimethylamine, obtaining crude L-carnitine, which is then finally purified. The catalyst used for the reduction is a complex of ruthenium bound to a penta-atomic bis-heteroaromatic system. The reduction reaction, performed in controlled conditions of hydrogen pressure, substrate concentration, temperature, and substrate: catalyst molar ratio, enables 4-chloro-3-hydoxybutyrate or 4-chloro-hydroxybutyamide to be obtained in a high yield. The process described, which leads to L-carnitine being obtained, is easily applicable on an industrial scale.Type: GrantFiled: May 7, 2001Date of Patent: May 20, 2003Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Maria Ornella Tinti, Oreste Piccolo, Fausto Bonifacio, Cristina Crescenzi, Sergio Penco
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Patent number: 6548693Abstract: Carnitine derivatives of formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease. Also described is a process for producing the (R)-carnitine enantiomer from (S)-carnitine (or vice versa), using the derivatives of formula (I).Type: GrantFiled: April 11, 2002Date of Patent: April 15, 2003Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
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Publication number: 20030032818Abstract: 1 A new, more efficient and highly stereospecific process is described for the preparation of compounds with general formula (R)-(I) and of absolute configuration (R), where the groups M, W, Q and Q1 are as defined in the description, starting from compounds of absolute configuration (S) by hydrolysis, in the presence of acids, of the corresponding esterified derivatives. The (R)-(I) products obtained with the process described herein are chiral synthons useful for the production of enanthiomerically pure drugs. The preparation of (R)-carnitine is also provided.Type: ApplicationFiled: June 24, 2002Publication date: February 13, 2003Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
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Publication number: 20020165408Abstract: The present invention describes a process for the industrial production of L-carnitine, comprising the enantioselective reduction of an alkyl 4-chloro-3-oxobutyrate or 4-chloro-3-oxobutyramide. The optically active 3-hydroxy derivative thus obtained is reacted with trimethylamine, obtaining crude L-carnitine, which is then finally purified. The catalyst used for the reduction is a complex of ruthenium bound to a penta-atomic bis-heteroaromatic system. The reduction reaction, performed in controlled conditions of hydrogen pressure, substrate concentration, temperature, and substrate: catalyst molar ratio, enables 4-chloro-3-hydoxybutyrate or 4-chloro-hydroxybutyamide to be obtained in a high yield. The process described, which leads to L-carnitine being obtained, is easily applicable on an industrial scale.Type: ApplicationFiled: May 7, 2001Publication date: November 7, 2002Inventors: Maria Ornella Tinti, Oreste Piccolo, Fausto Bonifacio, Cristina Crescenzi, Sergio Penco
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Patent number: 6444822Abstract: Described herein is the process for the preparation of 3-substituted 4-phenyl-piperidine derivatives of formula (I) in which X is selected from H and F, and R is selected from the group consisting of H, C1-C6 alkyl, C3-C6 alkenyl, and benzyl, comprising three steps starting from the monoamide of malonic acid and cinnamic aldehyde, or derivatives thereof.Type: GrantFiled: July 28, 2000Date of Patent: September 3, 2002Assignee: Chemi S.p.A.Inventors: Lorenzo De Ferra, Pietro Massardo, Oreste Piccolo, Giorgio Cignarella
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Publication number: 20020119965Abstract: Carnitine derivatives of formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease.Type: ApplicationFiled: April 11, 2002Publication date: August 29, 2002Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.p.A.Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
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Patent number: 6395923Abstract: Carnitine derivatives of formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease. Also described is a process for producing the (R)-carnitine enantiomer from (S)-carnitine (or vice versa), using the derivatives of formula (I).Type: GrantFiled: March 13, 2001Date of Patent: May 28, 2002Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
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Publication number: 20010011074Abstract: New camitine derivatives of general formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease.Type: ApplicationFiled: March 13, 2001Publication date: August 2, 2001Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
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Patent number: 5700668Abstract: The invention relates to a process for the preparation of phosphatidylserines by reacting racemic or enantiomerically pure serine, preferably (L)-serine, with natural phosphatides, such as soybean or egg lecithin, or with synthetic phosphatides, in the presence of a phospholipase D, having transphosphatidylating activity, in an aqueous/organic diphasic system.Type: GrantFiled: December 8, 1995Date of Patent: December 23, 1997Assignee: Italfarmaco Sud S.p.A.Inventors: Lorenzo De Ferra, Pietro Massardo, Oreste Piccolo, Stefano Servi
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Patent number: 5433833Abstract: A process for fractionating deacylated glycerophospholipids of the formula (I): ##STR1## wherein R is a negative charge; a hydrogen atom; a CH.sub.2 CH.sub.2 NR.sup.1 R.sup.2 residue wherein R.sup.1 and R.sup.2, which are the same or different, are H or C.sub.1 -C.sub.4 alkyl; a CH.sub.2 CH.sub.2 N.sup.+ (CH.sub.3).sub.3 residue; a CH.sub.2 CH(NH.sub.2)COOH residue or a residue of the formula: ##STR2## and X is OH or 0.sup.-, is described. The process involves subjecting an aqueous or hydroalcoholic mixture of two or more of the deacylated glycerophospholipids to electrodialysis in an electrolytic cell comprising a number of compartments. The compartments are separated by cation-exchange membranes, anion-exchange membranes or both cation-exchange and anion-exchange membranes, at a pH effective to differentiate the deacylated glycerophospholipids.Type: GrantFiled: May 10, 1994Date of Patent: July 18, 1995Assignee: Italfarmaco Sud S.p.A.Inventors: Lorenzo de Ferra, Sandra Rondinini, Patrizia R. Mussini, Fausto Bonifacio, Pietro Massardo, Oreste Piccolo
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Patent number: 5315023Abstract: A process for the preparation of highly pure deacylated glycerophosphorylcholine, glycerophosphorylethanolamine and glicerophosphorylserine starting from mixtures of the corresponding acylated derivatives.The process according to the invention is characterized in that the deacylation reaction, by means of alcoholysis, and the fractionation are carried out in a single step in a reactor containing a basic ion-exchange resin.Type: GrantFiled: March 8, 1993Date of Patent: May 24, 1994Assignee: Chemi S.p.A.Inventors: Lorenzo De Ferra, Fausto Bonifacio, Guido Cifarelli, Pietro Massardo, Oreste Piccolo
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Patent number: 5089661Abstract: A new process is described for the preparation of a 2-aryl-propionic acid, such as for instance 2-[4-(2-methyl-propyl)phenyl]propionic or 2-(6'-methoxy-2'-naphthyl)propionic acid, through hydrogenation of a complex salt which consists of the mono- and/or di-valent anion of the corresponding 2-hydroxy-2-aryl-propionic acid, a di- or tri-valent metal cation, such as for instance Al(+3), Fe(+3), Zn(+2), or Mg(+2), and optionally other anonic or neutral ligands.This new process is particularly advantageous in that the starting salt can be obtained directly via electrocarboxylation of the corresponding aryl methyl ketone, e.g. 4-(2-methyl-propyl)acetophenone or (6-methoxy-2-naphthyl) methyl ketone, with metal anodes which dissolve during the electrolysis.Type: GrantFiled: September 10, 1990Date of Patent: February 18, 1992Assignee: Enichem Synthesis S.p.A.Inventors: Federico Maspero, Oreste Piccolo, Ugo Romano, Salvatore Gambino
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Patent number: 4864063Abstract: Process for preparing Naproxen via a sequence of stereospecific reactions which comprises: condensation of 1-chloro-2-methoxy-naphthalene with a (S)-2-halo-propionyl halide according to the Friedel-Crafts reaction, ketalization of the thus obtained (S)-2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)propan-1-one, rearrangement of said ketal to afford an ester, hydrolysis of the ester and removal of the chlorine atom in 5-position by hydrogenolysis.New (S) 2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)propan-1-ones.Type: GrantFiled: December 23, 1987Date of Patent: September 5, 1989Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
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Patent number: 4834919Abstract: The keto group at the 7-position of a bile keto acid is stereoselectively reduced to a beta-hydroxy group with hydrogen in the presence of nickel, a base (the quantity of which is at least 0.3 mole for each mole of keto acid), and an alcohol having from 3 to 10 C atoms, selected from the group consisting of secondary alcohols, tertiary alcohols and beta-branched alcohols.Type: GrantFiled: January 6, 1987Date of Patent: May 30, 1989Assignee: Blaschim S.p.A.Inventors: Ambrogio Magni, Oreste Piccolo, Antonio Ascheri
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Patent number: 4736061Abstract: Process for preparing Naproxen via a sequence of stereospecific reactions which comprises: condensation of 1-chloro-2-methoxy-naphthalene with a (S)-2-halo-propionyl halide according to the Friedel-Crafts reaction, ketalization of the thus obtained (S)-2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)-propan-1-one, rearrangement of said ketal to afford an ester, hydrolysis of the ester and removal of the chlorine atom in 5-position by hydrogenolysis.New (S) 2-halo-1-(5'-chloro-6'-methoxy-2'-naphthyl)-propan-1-ones.Type: GrantFiled: May 10, 1985Date of Patent: April 5, 1988Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
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Patent number: 4698432Abstract: A process for the resolution of (.+-.) 2-[2'-(p-fluorophenyl)-5'-benzoxazolyl]-propionic acid, indicated for brevity as (.+-.)-FBP, by treatment with (-)N-R-glucamine, indicated for brevity as NRG and in which R is an alkyl or cycloalkyl radical, followed by fractional crystallization of the mixture of the diastereoisomer salts obtained, and by separation of the precipitate, from which, by hydrolysis, (.+-.)-FBP is obtained with the required purity characteristics. The levorotatory antipode, (-)-FBP, is racemized, preferably by the formation of one of its esters, which is then hydrolyzed to give the (.+-.)-FBP, which is recycled to the treatment with NRG. (+)-FBP and (-)-FBP salts with NRG obtained by said process.Type: GrantFiled: July 19, 1985Date of Patent: October 6, 1987Assignee: Ravizza SpAInventors: Alberto Verga, Oreste Piccolo, Ermanno Valoti
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Patent number: 4670603Abstract: Preparation of aryl alkyl ketones by reaction of an aryl compound with an aliphatic acid and/or a functional derivative thereof in anhydrous hydrofluoric acid.Type: GrantFiled: September 24, 1985Date of Patent: June 2, 1987Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Giuseppina Visentin, Pietro Blasina, Franca Spreafico
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Patent number: 4546201Abstract: Process for the optical resolution of (.+-.)2-(6'methoxy-2'-naphthyl)-propionic acid by adding from 0.45 to 0.65 mole of (S)-alpha-phenylethylamine to each mole of said acid in chloroform.Type: GrantFiled: April 23, 1984Date of Patent: October 8, 1985Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Giovanni Villa, Enrico Zen
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Patent number: 4542233Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.Type: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio