Patents Assigned to Alfa Chemicals Italiana S.p.A.
  • Patent number: 5811586
    Abstract: A process for manufacturing 1-(3-trifluoromethyl)phenyl-propan-2-one intermediate in the synthesis of the anorexic drug fenfluramine consists of reacting the diazonium salt of 3-trifluoromethylaniline with isopropenyl acetate in a polar solvent in the presence of a catalytic amount of a cuprous salt and, optionally, of a base and purifying the crude product through the bisulfite complex or distillation under vacuum.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: September 22, 1998
    Assignee: Alfa Chemicals Italiana S.P.A.
    Inventors: Vincenzo Cannata, Barbara Galbiati, Angelo Spreafico
  • Patent number: 5808156
    Abstract: Process for the production of the isomers (R) and (S)-.alpha.-methyl-3-(trifluoromethyl)benzeneethanamine, the second being useful as intermediate in the synthesis of the anorexic drug dexfenfluramine (INN), which comprises carrying out a stereospecific reductive amination of 1-(3-trifluoromethyl)phenyl-2-propanone with (R) or (S)-.alpha.-methylbenzylamine under a hydrogen atmosphere in the presence of a catalyst and debenzylating the resulting diastereoisomer (R),(R) or (S),(S)-N-(1-phenylethyl)-.alpha.-methyl-3-(trifluoromethyl)benzeneethanam ine by treatment with hydrogen and a catalyst.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: September 15, 1998
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Barbara Galbiati, Tiziano Ferrario
  • Patent number: 5750793
    Abstract: New process for the synthesis of the antiinflammatory drug known as nabumetone that consists in reacting 2-acetyl-5-bromo-6-methoxynaphthalene with an alkyl acetate in presence of an alkaline alcoholate to get 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one that by catalytic hydrogenation in a polar solvent and in presence of a base gives 4-(6-methoxy-2-naphthyl)butan-2-one known as nabumetone.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: May 12, 1998
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Amilcare Bertoni, Stefano Bianchi
  • Patent number: 4724102
    Abstract: A new process for the optical resolution of racemic mixtures of .alpha.-naphthylpropionic acids of formula ##STR1## wherein R.sub.1 is (C.sub.1-6) alkyl and R.sub.2 represents hydrogen or a halogen atom comprises reacting a racemic mixture of a compound of formula II ##STR2## wherein R.sub.1 and R.sub.2 have the above seen meanings and R.sub.3 is a reactive group, with an optically active aminoacid of formula ##STR3## wherein R.sub.4 represents a (C.sub.1-8) alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl or carboxy, and m is an integer from 0 to 4, to give a pair of diastereoisomeric amides of formula ##STR4## wherein R.sub.1, R.sub.2, R.sub.4 and m have the above seen meanings, and M is a hydrogen atom or a cation of an alkali metal or a cation of an organic base. Compounds IV are resolved into the single diastereoisomeric amides d,d or 1,d, or d,1 or 1,1. Acid hydrolysis gives the optically active compound I.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: February 9, 1988
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti
  • Patent number: 4661628
    Abstract: A new process for the optical resolution of racemic mixtures of .alpha.-naphthyl-propionic acids of formula ##STR1## This process comprises reacting a racemic mixture of a compound of formula ##STR2## with an optically active substance of formula R.sub.4 --NH.sub.2 (III), said substance being a .beta.-aminoalcohol, thus forming a pair of diastereoisomeric amides which are resolved into the single diastereoisomers by fractional crystallization. The obtained single diastereoisomeric amide is then hydrolyzed to give the desired optically active .alpha.-naphthyl-propionic acid of formula ##STR3## In the above compound I.fwdarw.III and VI, R.sub.1 is (C.sub.1-6)alkyl, R.sub.2 stands for hydrogen, halogen, mercapto, (C.sub.1-6)alkylthio, phenylthio, benzylthio, (C.sub.1-6)alkylsulfonyl, benzenesulfonyl, benzenesulfonyl substituted by halogen or (C.sub.1-4)alkyl, R.sub.3 is a reactive group and R.sub.4 is the residue of a primary or secondary alcohol.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: April 28, 1987
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani
  • Patent number: 4622419
    Abstract: A process for the optical resolution of racemic mixtures of .alpha.-naphthyl-propionic acids of formula I ##STR1## which consists of reacting a racemic mixture of a compound of formula II ##STR2## with an optically active compound of formula IIIR.sub.4 --NH.sub.2wherein R.sub.4 is the residue of a primary or secondary alcohol which, taken with the NH.sub.2 radical, forms an optically active .beta.-aminoalcohol, to give a pair of diastereoisomeric amides, which is resolved into the single diastereoisomeric amides. Acid hydrolysis gives the optically active d or l .alpha.-naphthyl-propionic acids. The meaning of R.sub.1, R.sub.2, R.sub.3 is given.
    Type: Grant
    Filed: November 6, 1985
    Date of Patent: November 11, 1986
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani
  • Patent number: 4423244
    Abstract: A new process for the preparation of the d-2-(6-methoxy-2-naphthyl)-propionic acid of formula ##STR1## which comprises resolving a racemic mixture of the d- and 1-2-(5-halo-6-methoxy-2-naphthyl)-propionic acids of formula ##STR2## wherein halo stands for a halogen atom, recovering the d-isomer and subjecting this isomer to catalytic dehalogenation. Compound I is obtained in very high yields and with a high purity degree.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: December 27, 1983
    Assignee: Alfa Chemicals Italiana S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani