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).

  • Patent number: 6566552
    Abstract: 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: Grant
    Filed: May 7, 2001
    Date of Patent: May 20, 2003
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Maria Ornella Tinti, Oreste Piccolo, Fausto Bonifacio, Cristina Crescenzi, Sergio Penco
  • Patent number: 6548693
    Abstract: 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: Grant
    Filed: April 11, 2002
    Date of Patent: April 15, 2003
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Publication number: 20030032818
    Abstract: 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: Application
    Filed: June 24, 2002
    Publication date: February 13, 2003
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Publication number: 20020165408
    Abstract: 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: Application
    Filed: May 7, 2001
    Publication date: November 7, 2002
    Inventors: Maria Ornella Tinti, Oreste Piccolo, Fausto Bonifacio, Cristina Crescenzi, Sergio Penco
  • Patent number: 6444822
    Abstract: 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: Grant
    Filed: July 28, 2000
    Date of Patent: September 3, 2002
    Assignee: Chemi S.p.A.
    Inventors: Lorenzo De Ferra, Pietro Massardo, Oreste Piccolo, Giorgio Cignarella
  • Publication number: 20020119965
    Abstract: 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: Application
    Filed: April 11, 2002
    Publication date: August 29, 2002
    Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.p.A.
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Patent number: 6395923
    Abstract: 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: Grant
    Filed: March 13, 2001
    Date of Patent: May 28, 2002
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Publication number: 20010011074
    Abstract: 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: Application
    Filed: March 13, 2001
    Publication date: August 2, 2001
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Patent number: 5700668
    Abstract: 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: Grant
    Filed: December 8, 1995
    Date of Patent: December 23, 1997
    Assignee: Italfarmaco Sud S.p.A.
    Inventors: Lorenzo De Ferra, Pietro Massardo, Oreste Piccolo, Stefano Servi
  • Patent number: 5433833
    Abstract: 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: Grant
    Filed: May 10, 1994
    Date of Patent: July 18, 1995
    Assignee: Italfarmaco Sud S.p.A.
    Inventors: Lorenzo de Ferra, Sandra Rondinini, Patrizia R. Mussini, Fausto Bonifacio, Pietro Massardo, Oreste Piccolo
  • Patent number: 5315023
    Abstract: 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: Grant
    Filed: March 8, 1993
    Date of Patent: May 24, 1994
    Assignee: Chemi S.p.A.
    Inventors: Lorenzo De Ferra, Fausto Bonifacio, Guido Cifarelli, Pietro Massardo, Oreste Piccolo
  • Patent number: 5089661
    Abstract: 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: Grant
    Filed: September 10, 1990
    Date of Patent: February 18, 1992
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Federico Maspero, Oreste Piccolo, Ugo Romano, Salvatore Gambino
  • Patent number: 4864063
    Abstract: 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: Grant
    Filed: December 23, 1987
    Date of Patent: September 5, 1989
    Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
  • Patent number: 4834919
    Abstract: 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: Grant
    Filed: January 6, 1987
    Date of Patent: May 30, 1989
    Assignee: Blaschim S.p.A.
    Inventors: Ambrogio Magni, Oreste Piccolo, Antonio Ascheri
  • Patent number: 4736061
    Abstract: 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: Grant
    Filed: May 10, 1985
    Date of Patent: April 5, 1988
    Assignee: Blaschim S.p.A.
    Inventors: Oreste Piccolo, Ermanno Valoti, Giuseppina Visentin
  • Patent number: 4698432
    Abstract: 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: Grant
    Filed: July 19, 1985
    Date of Patent: October 6, 1987
    Assignee: Ravizza SpA
    Inventors: Alberto Verga, Oreste Piccolo, Ermanno Valoti
  • Patent number: 4670603
    Abstract: 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: Grant
    Filed: September 24, 1985
    Date of Patent: June 2, 1987
    Assignee: Blaschim S.p.A.
    Inventors: Oreste Piccolo, Giuseppina Visentin, Pietro Blasina, Franca Spreafico
  • Patent number: 4546201
    Abstract: 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: Grant
    Filed: April 23, 1984
    Date of Patent: October 8, 1985
    Assignee: Blaschim S.p.A.
    Inventors: Oreste Piccolo, Giovanni Villa, Enrico Zen
  • Patent number: 4542233
    Abstract: 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: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio