Ring Expansion To Produce The Bicyclo Ring System Patents (Class 540/218)
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Patent number: 10059722Abstract: This invention provides cephalosporin derivatives for killing or inhibiting the spread of microorganisms such as non-replicating Mycobacterium tuberculosis and in the treatment of infectious disease.Type: GrantFiled: November 4, 2013Date of Patent: August 28, 2018Assignee: UNIVERSITY OF KANSASInventors: Jeffrey Aube, Carl Nathan, Robert Smith, Ben S. Gold, Paul Hanson, Chunjing Liu, Lester Allen Mitscher, Maneesh Pingle, Frank John Schoenen
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Publication number: 20040002600Abstract: The present invention relates to a new process for the preparation of cephalosporin derivative of formula (I) 1Type: ApplicationFiled: July 30, 2002Publication date: January 1, 2004Applicant: Orchid Chemicals and Pharmaceuticals LimitedInventors: Pandurang Balwant Deshpande, Senthilkumar Udayampalayam Palanisamy, Padmanabhan Ramar
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Patent number: 6100393Abstract: Process for purifying 7-substituted aminodeacetoxycephalosporins through the use of filter membranes. A process for purification by ultrafiltration and/or nanofiltration with a cut-off for molecular weights over 10,000 Dalton and preferably over 2000 Dalton is described. For example cephalosporin-G of increased purity, represented by a 6-8% increase in the HPLC titre, with a reduction of 50% in absorbance, is obtained using this technique. The invention makes it possible for the purified products to be used directly in the synthesis of other antibiotic compounds without the need for intermediate isolation.Type: GrantFiled: February 25, 1998Date of Patent: August 8, 2000Assignee: Antibioticos, S.A.Inventors: Juan Francisco Lopez Ortiz, Oscar Ferrero Barruego, Emiliano Gonzalez de Prado, Alejandro Vitaller Alba, Francisco Salto Maldonado
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Patent number: 5731165Abstract: An overall process for the preparation and recovery of 7-aminodesacetoxycephalosporanic acid (7-ADCA) via enzymatic ring expansion activity on penicillin G, using a Penicillium chrysogenum transformant strain expressing expandase.Type: GrantFiled: June 2, 1995Date of Patent: March 24, 1998Assignee: Gist-brocades, B.V.Inventors: Roelof Ary Lans Bovenberg, Bertus Pieter Koekman, Dirk Schipper, Adrianus Wilhelmus Vollebregt
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Patent number: 5604222Abstract: An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one of the formula: ##STR1## wherein R is: hydrogen; C.sub.1 -C.sub.3 alkyl; halomethyl; cyanomethyl; phenyl; substituted phenyl; phenoxy, benzyloxy- or substituted benzyl; a group of the formula R.sub.2 --O--wherein R.sub.2 is t-butyl, 2,2,2-trichloroethyl, benzyl or substituted benzyl; a group of the formula R.sub.3 --(O).sub.n --CH.sub.2 wherein R.sub.3 is phenyl or substituted phenyl. The 2-chlorosulfinylazetidin-4-one is prepared by reacting a penicillin sulfoxide ester of the general formula ##STR2## wherein R and R.sub.1 have the meanings defined above with an N-chloro halogenating agent in an inert organic solvent. The reaction is carried out in the presence of an acid scavenging amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures thereof.Type: GrantFiled: December 27, 1993Date of Patent: February 18, 1997Assignee: Lupin Laboratories, Ltd.Inventors: Niranjan L. Gupta, Ramanathan Sankaran, Sakina Sitabkhan
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Patent number: 5347000Abstract: A process for preparing a 2-chlorosulfinylazetidinone comprises heating in an inert organic solvent a penicillin sulfoxide ester, at a temperature between about 75.degree. C. and 140.degree. C., with an N-chlorohalogenating agent in the presence of a weakly basic N-alkali metal salt of a cyclic imide. The weakly basic N-alkali metal salt of a cyclic imide acts as an acid scavenger to bind the hydrogen chloride which is produced as a byproduct of the reaction. Preferably, the N-chlorohalogenating agent is N-chlorosuccinimide or N-chlorophthalimide, and the weakly basic N-alkali metal salt of a cyclic imide is the sodium or potassium salt of succinimide or phthalimide.Type: GrantFiled: April 21, 1993Date of Patent: September 13, 1994Assignee: Ranbaxy Laboratories Ltd.Inventors: Jag M. Khanna, Yatendra Kumar, Arun Malhotra
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Patent number: 5229509Abstract: The process comprises a series of stages essentially comprising the protection of the functional groups of the side chain of Ampicillin, esterification of the acid group, oxidation to sulphoxide, expansion of the thiazole ring to a thiazine ring, ozonolysis of the exomethylene cefam derivative obtained, substitution of the hydroxyl group by chlorine and de-protection of the functional groups, in which the order of some stages can be varied without affecting the final result.Type: GrantFiled: March 11, 1992Date of Patent: July 20, 1993Assignee: Antibioticos, S.A.Inventors: Rosa M. Nieves Elvira, Santiago Conde Ruzafa, Jose R. Fernandez Lizarbe
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Patent number: 5070195Abstract: An improved method for preparing 2-chlorosulfinyl azetidine-4-one comprises heating a penicillin sulfoxide ester with an N-chlorohalogenating agent at a temperature of about 75.degree. C. to about 140.degree. in an inert organic solvent, and in the presence of an organic solvent insoluble, strongly basic ion exchange resin. Desirably, the ion exchange resin comprises a styrene-divinyl benzane copolymer which is about 2 to 16% cross-linked and incorporates a quaternary ammonium functionality. Such ion exchange resins are commercially available. The 2-chlorosulfinyl azetidine-4-one which is produced by this method can be cyclized in the presence of a Friedel-Crafts catalysts to afford the 3-exomethylene cepham sulfoxide ester in yields of 80-90%.Type: GrantFiled: March 7, 1990Date of Patent: December 3, 1991Assignee: Ranbaxy Laboratories LimitedInventors: Jag M. Khanna, Naresh Kumar, Kiran Bala, Yatendra Kumar
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Patent number: 5053501Abstract: 3-Exomethylenecepham sulfoxide derivatives and intermediates therefor, viz. 2-chlorosulfinylazetidin-4-ones are prepared in high yield and purity by reaction of a penam sulfoxide ester with a N-chloro halogenating agent in the presence of molecular sieves.Type: GrantFiled: March 21, 1990Date of Patent: October 1, 1991Assignee: Gist-Brocades N.V.Inventors: Jagdfish C. Kapur, Jan J. De Koning, Roland P. Bezemer
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Patent number: 4767851Abstract: An improved process is disclosed for the preparation of 7-amino and 7-substituted amino-desacetoxycephalosporins in which the corresponding 6-substituted amino penicillin sulphoxide is heated in the presence of an acidic substance which causes expansion of the penam ring in the reactant to the .DELTA..sup.3 cephem ring in the product in the presence of a silicon containing compound. The process comprises adding sulphamide or a silylsulphamide or a silylsulphamoyl to the reaction or utilizing a silylsulphamide or silylsulphamoyl as the silicon containing compound.Type: GrantFiled: July 8, 1985Date of Patent: August 30, 1988Assignee: Gema, S.A.Inventor: Alberto Palomo-Coll