Patents Assigned to Antibioticos S.p.A.
  • Patent number: 6458558
    Abstract: A process for the preparation of Cefuroxime acid (I), which comprises the following steps: (1) Extraction of deacetyl 7-glutaryl ACA (II) aqueous solution at acid pH with organic solvents (for example according to the procedures disclosed in U.S. Pat. No. 5,801,241); (2) drying the resulting solution while preventing lactonization of the intermediate; (3) carbamoylation of the hydroxymethyl group at the 3-position by reaction with chlorosulfonyl isocyanate or similar products; (7) extraction of the carbamoyl derivative from step 3 with water at neutral pH; (8) enzymatic hydrolysis of the amide at the 7-position of the cephalosporanic ring with glutaryl acylase; (6) acylation of the amnino group by condensation with 2-furanyl(sin-methoxyimino)acetic acid chloride or mixed anhydride.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: October 1, 2002
    Assignee: Antibioticos S.p.A.
    Inventors: Enrico Siviero, Walter Cabri, Daniele Mario Terrassan
  • Patent number: 6005101
    Abstract: A compound having the following general formula (I): ##STR1## where R is a hydrogen atom; a linear or branched C.sub.1 -C.sub.4 alkyl group, unsubstituted or substituted by at least a phenyl group or at least a hydrogen atom; a benzyl group substituted by at least a linear or branched C.sub.1 -C.sub.4 alkyl or alkoxy group or a nitro group; a silyl substituted by at least a linear or branched, unsubstituted or substituted C.sub.1 -C.sub.4 alkyl group; n is 0 or 1; and Y is a radical of formula ##STR2## wherein A is H, OH, Cl, CH.sub.2, CH.sub.2 X, where X is F, Cl, Br, I, OH or OR' and R' is COCH.sub.3 or a linear or branched, unsubstituted or substituted C.sub.1 -C.sub.4 alkyl group and - - - represents a single or a double bond, with the proviso that when n=0 and R is H, R' is not a methyl group.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: December 21, 1999
    Assignee: Antibioticos S.p.A.
    Inventors: Loris Sogli, Davide Longoni, Giovanni Pozzi, Enrico Siviero, Daniele Mario Terrassan, Ermanno Bernasconi, Francisco Salto
  • Patent number: 5945414
    Abstract: Cefazolin, cefazedone, cefoperazone, cefamandole, cefatrizine or ceftriaxone is prepared by reacting glutaryl 7-ACA of the formula: ##STR1## with a compound of formula (II):R--SH (II)wherein R is 5-methyl-1,3,4-thiadiazol-2-yl, 1H-1,2,3-triazol-4-yl, 1-methyl-tetrazol-5-yl or1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl group, and R.sup.1 and R.sup.2 are both hydrogen and the other is an acyl group, in an aqueous solution in an amount of 3-5 mols per mol of glutaryl 7-ACA to about 90.degree. C. and for a time from about 2 to about 10 hours;optionally recovering the excess of the compound of formula (II), thereby preparing a compound of formula (III) in an aqueous solution: ##STR2## wherein R is as above defined and optionally deacylating said compound of formula (III); andconverting the resulting compound of formula (I) ##STR3## wherein R, R.sup.1 and R.sup.2 are as defined above in the presence of a non-chlorinated solvent into one of said cephalosporins.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: August 31, 1999
    Assignee: Antibioticos S.p.A.
    Inventors: Loris Sogli, Daniele Terrassan, Ermanno Bernasconi, Francisco Salto
  • Patent number: 5750682
    Abstract: There are disclosed new compounds of formula (I), wherein R is: a hydrogen atom: a linear or branched C1-C4 alkyl group, unsubstituted or substituted by at least a phenyl group or at least a hydrogen atom: a benzyl group substituted by at least a linear or branched C1-C4 alkyl or alkoxy group or a nitro group; a silyl substituted by at least a linear or branched, unsubstituted or substituted C1-C4 alkyl group; n is 0 or 1; and Y is a radical of formula (II), wherein A is H, OH, Cl, CH2, CH2X, where X is F, Cl, Br, I, OH or OR' and R' is COCH3 or a linear or branched, unsubstituted or substituted C1-C4 alkyl group and . . . represents a single or a double bond, with the proviso that when n=0 and R is H, R' is not a methyl group; and processes for obtaining them.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: May 12, 1998
    Assignee: Antibioticos S.p.A.
    Inventors: Loris Sogli, Davide Longoni, Giovanni Pozzi, Enrico Siviero, Daniele Mario Terrassan, Ermanno Bernasconi, Francisco Salto
  • Patent number: 5424196
    Abstract: Transformation of Cephalosporin C or its derivatives and salts into 7-aminocephalosporanic acid or its derivatives by an enzymatic two stage process with enzymes immobilized on a solid matrix.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: June 13, 1995
    Assignee: Antibioticos S.p.A.
    Inventors: Stefano Cambiaghi, Sergio Tomaselli, Roberto Verga
  • Patent number: 5387679
    Abstract: The present invention relates to a process for preparing a compound of formula (I) ##STR1## wherein R is an heterocyclic group which contains at least one nitrogen atom with or without oxygen or sulphur and R.sup.1 and R.sup.2 are both hydrogen atoms or one of them is an hydrogen atom and the other is an acyl group; the process comprising reacting a compound of formula (II) ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, and wherein, if necessary, any reactive group is protected by a suitable protective group, or a salt thereof, with a compound of formula (III)R--SH (III)wherein R is as defined above, or a salt thereof, in the presence of an acid and of a compound of formula (IV) ##STR3## wherein each of R.sup.3 and R.sup.4 is a C.sub.1 -C.sub.4 alkyl group or R.sup.3 and R.sup.4 taken together are a C.sub.2 or C.sub.3 alkylene chain and, if necessary, removing the protective groups possibly present.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: February 7, 1995
    Assignee: Antibioticos S.p.A.
    Inventors: Loris Sogli, Daniele Terrassan, Giuseppe Ribaldone
  • Patent number: 5354667
    Abstract: A process for the production of an E. coli strain producing high yields of 7.beta.-(4-carboxybutanamido) cephalosporin acylase, comprises: (a) digesting the DNA of a microorganism whose DNA includes the sequence encoding 7.beta.-(4-carboxybutanamido) cephalosporin acylase, and forming a plasmidic library; (b) transforming, with the sequences in the plasmidic library, an auxotrophic E. coli host; (c) selecting for transformed E. coli hosts containing the acylase sequence by growth on a suitable medium; (d) isolating the vector containing the acylase sequence, digesting the vector, and ligating the DNA sequences obtained into an E. coli vector under control of an E. coli promoter; (e) repeating selection procedure of step (c) ; (f) using the vectors from the selected E. coli hosts to transform an E. coli host lacking substantial .beta.-lactamase activity. 7-Aminocephalosporanic acid and its derivatives can be prepared by reaction of substrates like 7.beta.-(4-carboxybutanamido) cephalosporanic acid with 7.beta.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: October 11, 1994
    Assignee: Antibioticos, S.p.A.
    Inventors: Christian Croux, Javier C. Perez, Jose L. B. Fuentes, Francisco S. Maldonado