The Sulfur Is Double Bonded Directly To The Chalcogen Patents (Class 540/359)
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Patent number: 11912700Abstract: The invention relates to substituted pyrridinobenzodiazepines (PDDs) of formula (XV) and pharmaceutically acceptable salts thereof, which are useful as medicaments, in particular as anti-proliferative agents.Type: GrantFiled: February 24, 2021Date of Patent: February 27, 2024Assignee: PHEON THERAPEUTICS LTDInventors: Paul Joseph Mark Jackson, David Edwin Thurston, Khondaker Mirazur Rahman
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Patent number: 6908996Abstract: The present invention relates to novel intermediates for the preparation of 3-methylenecephams of the formula IIA. wherein: R is a carboxylic acid protecting group; R1 is a group of the formula; R10 is C1-C6 alkyl, C1-C6 polyfluoroalkyl, C3-C6 cycloalkyl, adamantyl, phenyl, substituted phenyl, phenyl(C1-C3 alkyl), diphenylmethyl, or substituted phenyl(C1-C3 alkyl), or a group of the formula Z is solid polymer support; and Z1 is one or two groups independently selected from the group consisting of hydrogen, halo, hydroxy, protected hydroxy, nitro, cyano, trifluoromethyl, C1-C4 alkyl, and C1-C4 alkoxy.Type: GrantFiled: November 12, 2003Date of Patent: June 21, 2005Assignee: Imperial College of LondonInventors: Robin D. G. Cooper, Anthony G. M. Barrett
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Patent number: 6683176Abstract: The present invention relates to novel processes for the preparation of 3-methylenecephams. More specifically, the present invention relates to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone derivatives with organometallic catalysts of the formula III. MEx(H2O)y (III) wherein: M is Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, or In; E is O[SO2(C1-C6 polyfluoroalkyl)], N[SO2(C1-C6 polyfluoroalkyl)]2, or C[SO2(C1-C6 polyfluoroalkyl)]3; x is 3; y is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.Type: GrantFiled: December 31, 2001Date of Patent: January 27, 2004Inventors: Robin D. G. Cooper, Anthony G. M. Barrett
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Patent number: 6569847Abstract: This invention relates to substituted azetidin-2-ones and to pharmaceutical compositions containing such compounds. Their use in medicine as inhibitors of cysteine proteases, particularly the cathepsins is also described. The invention includes a compound of formula (I), Y represents —C(O)— or —S(O2)—; R represents an allyl (ie CH2═CHCH2—) group or a radical. R1 represents —OCOR5, —OR5, —SR5, —S(O)R5, or —S(O)2R5; R2 represents a radical. R3 represents —OR5 or R5; or a pharmaceutically acceptable salt, hydrate or solvate thereof.Type: GrantFiled: October 5, 2001Date of Patent: May 27, 2003Assignee: NAEJA Pharmaceuticals Inc.Inventors: Rajeshwar Singh, Andhe V. Narender Reddy, Jadwiga Kaleta, Ronald G. Micetich, Mark Whittaker, Philip Huxley
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Patent number: 6335324Abstract: Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.Type: GrantFiled: December 13, 1999Date of Patent: January 1, 2002Assignee: Bristol-Myers Squibb Co.Inventors: Gregory S. Bisacchi, William A. Slusarchyk, Uwe Treuner, James C. Sutton, Robert Zahler, Steven Seiler, David R. Kronenthal, Michael E. Randazzo, Mark D. Schwinden, Zhongmin Xu, Zhongping Shi
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Patent number: 6221860Abstract: This invention relates to methods for treating diseases or disorders mediated by lipid inflammatory mediators, arachidonic acid, its metabolites and/or platelet activating factor (PAF), which method comprises administration to a mammal in need thereof of an effective Coenzyme A independent transacylase (CoA-IT) inhibiting amount of a triphenylmethylazetidinone. This invention also relates to a method of treating or reducing inflammation in a mammal in need thereof, which comprises administering to said mammal an effective amount of a triphenylmethylazetidinone.Type: GrantFiled: November 8, 1999Date of Patent: April 24, 2001Assignee: SmithKline Beecham CorporationInventors: William E. Bondinell, James David Winkler
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Patent number: 6071899Abstract: Azetidinone derivatives of formula (I) in which R.sup.1 and R.sup.2, which may be the same or different, is each selected from hydrogen or C.sub.(1-8) alkyl; R.sup.3 is C.sub.(1-8) alkyl or C.sub.(3-8) cycloalkyl each of which may be optionally substituted; X is a linker group; Y is an aryl group; and n is 0, 1 or 2; and excluding benzyl (4-methylthio-2-oxo-azetidin-1-yl)acetate are inhibitors of the enzyme Lp PLA2 and are of use in therapy, in particular treating atherosclerosis.Type: GrantFiled: September 30, 1997Date of Patent: June 6, 2000Assignee: SmithKline Beecham p.l.c.Inventors: Deirdre Mary Bernadette Hickey, Dashyant Dhanak, Colin Andrew Leach, Robert John Ife, David Graham Tew
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Patent number: 5916887Abstract: In accordance with the present invention, there are provided 4-substituted-3-(2-amino-2-cycloalkyl methyl)-acetamido azetidin-2-one derivatives of the formula: ##STR1## wherein n is 1, 2 or 3; in which R.sub.1, R.sub.2 and R.sub.3 are as defined herein, and salts thereof, which exhibit excellent cysteine proteinase inhibitory activity and which can be used for treatment of different diseases such as muscular dystrophy, myocardial infarction, bone resorption, arthritis, cancer metastasis, pulmonary emphysema, septic shock, cerebral ischemia, memory function, Alzheimer and cataract, malaria, glomerular basement membrane degradation, bacterial infection, inflammatory diseases, parasitic infections, and viral infections.Type: GrantFiled: September 22, 1997Date of Patent: June 29, 1999Assignee: National Research Council of CanadaInventors: Rajeshwar Singh, Nian E. Zhou, Enrico O. Purisima, Ronald G. Micetich
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Patent number: 5770729Abstract: The present invention provides an ozonide reducing agent for use in the ozonolysis reaction of an organic compound, the ozonide reducing agent finding wide applications, and being safe and inexpensive from a commercial viewpoint and easy to treat for disposal.The ozonide reducing agent of the invention is a compound wherein sulfur has, at both ends of its molecule, a hydrocarbon residue substituted by a polar functional group.Type: GrantFiled: January 22, 1996Date of Patent: June 23, 1998Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Daisuke Suzuki, Takashi Shiroi
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Patent number: 5744467Abstract: Sulfur-substituted azetidinone hypocholesterolemic agents of the formula ##STR1## or a pharmaceutically acceptable salt thereof are disclosed, as well as pharmaceutical compositions containing them, and a method of lowering serum cholesterol by administering said compounds, alone or in combination with a cholesterol biosynthesis inhibitor.Type: GrantFiled: January 8, 1997Date of Patent: April 28, 1998Assignee: Schering CorporationInventors: Brian A. McKittrick, Sundeep Dugar, Duane A. Burnett
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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: 5466686Abstract: The invention relates to the novel 4-oxo-azetidine-2-sulfonic acid amides and their salts of the formula I ##STR1## wherein the radicals have the meanings: R.sup.1 =hydrogen, halogen;R.sup.2 =hydrogen, halogen, NH.sub.2, C.sub.6 H.sub.5 CH.sub.2 CONH, C.sub.6 H.sub.5 OCH.sub.2 CONH, phthalimido, o-MeNHCOC.sub.6 H.sub.4 CONH, isoxazolylcarbonylamino;R.sup.3 =hydrogen, Me.sub.2 C.dbd.C--COOMe, H.sub.2 C.dbd.C(Me)--CH--COOMe, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.5, H.sub.2 C.dbd.C(Me)CH--COOCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 -p, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 -p, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.4 Me-m, H.sub.2 C.dbd.C(Me)--CH--COOCH.sub.2 C.sub.6 H.sub.4 Me-m, Me.sub.2 C.dbd.C--COOH;R.sup.4 =hydrogen or sodium andR.sup.5 =hydrogen, alkyl, benzyl or heterocycle, i.e. isoxazole or pyrazole etc.Type: GrantFiled: September 3, 1993Date of Patent: November 14, 1995Assignee: PLIVA and PLIVA Handels GmbHInventors: Mice Kovacevic, Jure J. Herak, Zora Mandic, Irena Lukic, Mirjana Tomic, Zinka Brkic
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Patent number: 5453502Abstract: The invention provides 1,3,4 substituted and bicyclic derivatives of 2-azetidinones and processes therefor. These compounds are valuable intermediates useful in the preparation of 1-carba(dethia)cephalosporin antibiotics.Type: GrantFiled: March 16, 1994Date of Patent: September 26, 1995Assignee: Eli Lilly and CompanyInventors: James A. Aikins, Larry C. Blaszczak, Kevin P. Lund, John R. Rizzo
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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: 5250525Abstract: The invention relates to novel 4-oxo-azetidine-2-sulfonic acids and their salts or the formula I ##STR1## wherein: R.sup.1 =hydrogen, halogen, phenylacetamido;R.sup.2 =hydrogen, halogen, phenylacetamido, phenoxyacetamido, phthalimido, 5-methyl-3-o-chlorophenyl-isoxazole-4-carboxamido;R.sup.3 =hydrogen, alkali metal, alkaline earth metal, quaternary ammonium group;R.sup.4 =hydrogen, SO.sub.2 O.sup.-+ NBu.sub.4 -n, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.3, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 -Ph, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 --C.sub.6 H.sub.4 --NO.sub.2 -p, (CH.sub.3).sub.2 C.dbd.C--COOCH.sub.2 --C.sub.6 H.sub.4 --CH.sub.3 -m.The products (I) may be used as intermediates in the synthesis of beta-lactamic antibiotics or as components in antimicrobial preparations.Type: GrantFiled: February 11, 1992Date of Patent: October 5, 1993Assignee: Pliva Handels GmbHInventors: Mice Kovacevic, Zorica Mandic, Mirjana Tomic, Zinka Brkic, Jure J. Herak, Irena Lukic
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Patent number: 5250677Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: October 6, 1992Date of Patent: October 5, 1993Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 5229381Abstract: New substituted azetidinones of the general formula (A') which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described.Type: GrantFiled: September 20, 1991Date of Patent: July 20, 1993Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Conrad P. Dorn, Paul E. Finke, William K. Hagmann, Malcolm MacCoss, Shrenik K. Shah
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Patent number: 5175283Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: February 11, 1992Date of Patent: December 29, 1992Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 5116972Abstract: The invention provides novel compounds of the formula ##STR1## wherein R is a protected amino group and R1 is a carboxy protected group.Type: GrantFiled: August 14, 1991Date of Patent: May 26, 1992Assignee: Eli Lilly and CompanyInventor: Robert J. Ternansky
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Patent number: 5106475Abstract: A process for preparing 3-4-cis-.beta.,.beta.-(4)-substituted and 3-4-trans,.beta.,.alpha.-(4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.Type: GrantFiled: October 16, 1990Date of Patent: April 21, 1992Assignee: Eli Lilly and CompanyInventors: John M. Morin, Jr., Robert J. Ternansky, David A. Hall
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Patent number: 5075439Abstract: Improved processes for preparation of racemic, cis- and optically active (3S,4R)-3[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(t hiocarbonyl)thio]azetidin-2-ones, process improvements for certain intermediates therefor and a novel intermediate for said racemic, cis- and trans-compounds, which compounds are useful as intermediates for antibacterial 5R,6S-6-[1(R)-hydroxyethyl]-2-(1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids and the pharmaceutically-acceptable salts and the pivaloyloxymethyl esters thereof.Type: GrantFiled: January 18, 1991Date of Patent: December 24, 1991Assignee: Pfizer Inc.Inventors: Frank R. Busch, Robert W. Dugger, George J. Quallich
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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: 5037819Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: June 4, 1990Date of Patent: August 6, 1991Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 4992545Abstract: A process for preparing 3-4-cis-.beta.,.beta.-(4)-substituted and 3-4-trans,.beta.,.alpha.- (4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.Type: GrantFiled: September 20, 1989Date of Patent: February 12, 1991Assignee: Eli Lilly and CompanyInventors: David A. Hall, deceased, John M. Morin, Jr., Robert J. Ternansky
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Patent number: 4855421Abstract: The invention relates to new 2-oxoazetidines having the formulas ##STR1## where R.sub.1 stands for a lower fluoroalkyl or an optionally protected lower hydroxyalkyl group; R.sub.2 for chlorine, bromine, iodine, fluorine, an ##STR2## group in which n is 0, 1 or 2 and R.sub.5 is a lower alkyl, lower alkenyl, an optionally substituted benzyl group, optionally substituted phenyl group, a --CH.sub.2 COX group in which X means a lower alkyl, lower alkoxy or the amino group, or a ##STR3## group in which Y and Z are the same or different and in each case stand for oxygen, nitrogen or sulphur and R.sub.6 stands for a lower alkyl, lower alkoxy, lower alkylthio, lower dialkylamino, an aryl, aryloxy or arylthio group, or for a group having the formula ##STR4## where W stands for --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or C.sub.6 H.sub.4 ; R.sub.3 stands for bromine, chlorine, iodine, SeC.sub.6 H.sub.5 or SC.sub.6 H.sub.5 ; and R.sub.4 stands for hydrogen, a group having the formula ##STR5## in which R.sub.Type: GrantFiled: April 20, 1988Date of Patent: August 8, 1989Assignee: Sanraku IncorporationInventors: Hans Fliri, Ching Pong Mak
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Patent number: 4816581Abstract: The novel compounds of the formula ##STR1## wherein R.sup.11 signifies hydrogen, acyl or tri(lower alkyl)silyl, R.sup.2 signifies a phenyl group which is substituted in the o- and/or the p-position by halogen, lower alkyl, lower alkylthio or lower alkoxy and n signifies the number 0 or 2, and mixtures thereof with the corresponding optical antipodes are valuable intermediates for the manufacture of antimicrobially active penems and carbapenems which have as a common structural element a (R)-1-hydroxyethyl group in the 6-position. They can be manufactured by reacting a compound of the formula ##STR2## wherein R.sup.12 signifies acyl, tri(lower alkyl)silyl or a group of the formula --BR.sup.3 R.sup.4 and R.sup.3 and R.sup.4 have the same significance and each signify a branched-open chain, cyclic or bicyclic hydrocarbon residue with 5-10 carbon atoms or together signify an open chain or cyclic hydrocarbon residue with 5-10 carbon atoms and two free valencies and R.sup.Type: GrantFiled: September 28, 1987Date of Patent: March 28, 1989Assignee: Hoffman-La Roche Inc.Inventor: Gerard Schmid
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Patent number: 4725678Abstract: Certain 2-substituted-2-penem-3-carboxylic acid compounds and pharmaceutically-acceptable salts thereof can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization and addition of an electrophilic sulfur compound followed by halogenation and ring closure. The corresponding desulfurized and halogenated olefinic intermediates are disclosed.Type: GrantFiled: April 4, 1986Date of Patent: February 16, 1988Assignee: Pfizer Inc.Inventor: Ernest S. Hamanaka
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Patent number: 4689411Abstract: This invention provides azetidinone derivatives represented by the formula ##STR1## and processes for preparing the same. The azetidinone derivatives are used as the intermediates for producing cephalosporin compounds useful as antibiotic agents.Type: GrantFiled: May 15, 1986Date of Patent: August 25, 1987Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Kenji Uneyama, Hideo Tanaka, Junzo Nokami, Michio Sasaoka, Norio Saito, Takashi Shiroi
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Patent number: 4680391Abstract: New substituted azetidinones are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: April 10, 1985Date of Patent: July 14, 1987Assignee: Merck & Co., Inc.Inventors: Raymond A. Firestone, Peter L. Barker
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Patent number: 4619783Abstract: Certain substituted-2-penem-3-carboxylic acid compounds, and pharmaceutically-acceptable salts thereof, can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization, followed by halogenation and ring closure. The corresponding desulfurized and halogenated intermediates are disclosed.Type: GrantFiled: June 10, 1983Date of Patent: October 28, 1986Assignee: Pfizer Inc.Inventor: Ernest S. Hamanaka
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Patent number: 4614614Abstract: The present invention relates to an improved process for the manufacture of (3S)-3,4-trans-disubstituted azetidinones of the formula ##STR1## in which R.sub.1 represents hydrogen or lower alkyl,R.sub.2 represents hydrogen or a hydroxy-protecting group,Y represents the group --S(.dbd.O)--R.sub.3 or --S(.dbd.O).sub.2 --R.sub.3 wherein R.sub.3 represents an organic radical bonded to the sulphur atom by a carbon atom that is not bonded to hydrogen, or the group --C(.dbd.O)--O--R.sub.3 ' wherein R.sub.3 ' represents an organic radical bonded to the oxygen atom of the carboxy group by a carbon atom that is not bonded to hydrogen, or a carboxy-protecting group, andR.sub.4 represents hydrogen or an amino-protecting group R.sub.4 '.The process according to the invention is carried out under particularly favorable reaction conditions and yields compounds (I) in particularly high yields.Type: GrantFiled: March 22, 1984Date of Patent: September 30, 1986Assignee: Ciba-Geigy CorporationInventors: Ivan Ernest, Jaroslav Kalvoda, Wolfgang Frostl