Sulfur Containing Compound Utilized In Pretreatment Patents (Class 536/74)
  • Patent number: 4963528
    Abstract: New 2:1 complexes of N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A or 11-aza-10-deoxo-10-dihydroerythromycin A with bivalent metals chosen form the group comprising Cu.sup.+2, Zn.sup.+2, Co.sup.+2, Ni.sup.+2 and Ca.sup.+2, a process for their manufacture and their use in the manufacture of antibiotically active pharmaceuticals.New 2:1 complexes of N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A or 11-aza-10-deoxo-10-dihydroerythromycin A with bivalent metals chosen from the group comprising Cu.sup.+2, Zn.sup.+2, Co.sup.+2, Ni.sup.+2 and Ca.sup.+2 are made by reacting N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A or 11-aza-10-deoxo-10-dihydroerythromycin A in its free base form or in its water-soluble salt form with salts of said bivalent metals. The compounds possess antibiotic activity.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: October 16, 1990
    Assignee: Sour Pliva
    Inventors: Zlatko Vajtner, Nevenka Lopotar, Slobodan Djokic
  • Patent number: 4957905
    Abstract: 9-(N'-substituted hydrazone) derivatives of certain erythromycin compounds are novel, antibacterially active compounds which can be prepared by treatment of the corresponding 9-imine derivative with an N'-substituted hydrazine.
    Type: Grant
    Filed: September 7, 1988
    Date of Patent: September 18, 1990
    Assignee: Beecham Group p.l.c.
    Inventor: Eric Hunt
  • Patent number: 4948782
    Abstract: A growth promoting composition for animals containing an erythromycin derivative wherein a dimethylamino radical of the 3'-position is converted into a primary amino radical, a secondary amino radical, a tertiary amino radical other than the dimethyl amino radical, or a quaternary ammonio radical.This composition does not exhibit the antimicrobial activity at all or show the extremely decreased antimicrobial activity, and has the excellent effect to improve the feed efficiency of domestic animals.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: August 14, 1990
    Assignee: Kitasato Kenkyusho
    Inventors: Satoshi Omura, Zen Itoh
  • Patent number: 4945080
    Abstract: Novel macrolide, AS-E 136 metabolite, is obtained from the body fluids of animals receiving AS-E 136 or erythromycylamine. Methods for treating infections caused by pathogenic bacteria, especially Gram-positive bacteria, and pharmaceutical compositions containing the metabolite are provided.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: July 31, 1990
    Assignee: Eli Lilly and Company
    Inventors: Terry D. Lindstrom, Gary W. Whitaker
  • Patent number: 4921839
    Abstract: Antibacterially active 11,12-carbonate derivatives of erythromycin 9-(optionally substituted)oxime and 9-imino compounds and their pharmaceutically acceptable ester or acid addition salt thereof: ##STR1## wherein R.sup.1 denotes an oxime group, a substituted oxime group, or an imino group;R.sup.3 denotes a hydrogen atom or an unsubstituted or substituted alkyl group;R.sup.7 denotes hydrogen or methyl;one of R.sup.8 and R.sup.9 denotes hydrogen, hydroxy, alkoxy, alkanoyloxy, amino, substituted amino, or a group of the formula R.sup.A --SO.sub.2 --O--, in which R.sup.A denotes an organic group, and the other of R.sup.8 and R.sup.9 denotes hydrogen, orR.sup.8 and R.sup.9 together denote an oxo group, an oxime group, or a substituted oxime group.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: May 1, 1990
    Assignee: Beecham Group p.l.c.
    Inventors: Edward G. Brain, Eric Hunt, Andrew K. Forrest
  • Patent number: 4906579
    Abstract: A method to selectively oxidize a polyglucose, on the oxygen of the hydroxy groups of the C-6 position of the glucose rings, while substantially maintaining the degree of polymerization of the polyglycosidic units, comprising heating a 6-sulfonyl polyglucose, for instance 6-O-para-(P)-toluene sulfonyl polyglucose with dimethyl sulfoxide (DMSO) in the presence of at least a catalytic amount of a catalyst selected from a member of the group consisting of: symmetrical--collidine, sodium bicarbonate and pyridine, to produce a polyglucose having aldehyde groups on the oxygen of the hydroxyl on the C-6 position of the glucose rings. In a preferred embodiment when pyridine is selected, this method enables use of that reaction to obtain other new products having other functional groups, mainly on the C-6 position of the glucose rings, without having to purify the aldehyde which may serve as intermediate.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: March 6, 1990
    Assignee: Domtar Inc
    Inventors: Manssur Yalpani, Magdy M. Abdel-Malik
  • Patent number: 4847242
    Abstract: 11-ether derivatives of erythromycin, and corresponding 9-(optionally substituted)-amino, 9-imino, and 9-(optionally substituted)-oxime derivatives are novel antibacterially active compounds, and can be prepared by alkylation of the 11-hydroxy group under mild conditions.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: July 11, 1989
    Assignee: Beecham Group p.l.c.
    Inventor: John S. Davies
  • Patent number: 4826820
    Abstract: Antibacterially active 6-carbamate erythromycin derivatives of formula I and their pharmaceutically acceptable esters and acid addition salts; ##STR1## wherein: R.sup.1 or R.sup.2 is optionally substituted amino, or R.sup.1 or R.sup.2 +R.sup.5 is --O--C(R.sup.A)(R.sup.B)--O--, and R.sup.2 or R.sup.1 is H, or R.sup.1 +R.sup.2 is oxo, oxime, substituted oxime, or imino;R.sup.3 is carbamoyl or N-substituted carbamoyl;R.sup.4 is H or OH, and R.sup.5 is OH, or etherified hydroxy, or R.sup.4 +R.sup.5 is --O--CO--O-- or --O--C(R.sup.A) (R.sup.B)--O--;R.sup.6 is H, F or OH;R.sup.7 is H or CH.sub.3 ;R.sup.8 or R.sup.9 is H, OH, alkoxy, optionally substituted NH.sub.2, alkanoyloxy, or R.sup.C --SO.sub.2 O--, and R.sup.9 or R.sup.8 is H, or R.sup.8 +R.sup.9 is oxo or optionally substituted oxime;R.sup.A, R.sup.B are H or hydrocarbon; andR.sup.C is organic.
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: May 2, 1989
    Assignee: Beecham Group p.l.c.
    Inventor: Edward G. Brain
  • Patent number: 4742049
    Abstract: Semisynthetic antibiotics with improved therapeutic properties made from erythromycin are disclosed. 11,12-Cyclic carbamates of erythromycin, its derivatives, and their salts and esters show superior in vitro antimicrobial activity and reduced hepatotoxicity compared to the parent compounds.
    Type: Grant
    Filed: June 4, 1986
    Date of Patent: May 3, 1988
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, Jerry D. Clark
  • Patent number: 4740502
    Abstract: Semisynthetic antibiotics with improved therapeutic properties made from erythromycin are disclosed. Certain 4"-carbamates of erythromycin, its derivatives, and their salts and esters show superior in vitro antimicrobial activity and reduced gastrointestinal stimulation compared to the parent compounds.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: April 26, 1988
    Assignee: Abbott Laboratories
    Inventors: Steven M. Hannick, Larry L. Klein
  • Patent number: 4697007
    Abstract: The preparation of microcrystalline triacetylcellulose by acid-catalyzed acetylation of microcrystalline cellulose, perfluoroalkanesulfonic acids with 1 to 8 carbon atoms are used as the catalyst, resulting in a non-hazardous process and high yields of exceptionally high purity product, the latter being particularly suitable for chromatographic purposes, in particular for the chromatographic resolution of racemates.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: September 29, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Georg Seitz, Rainer Wernicke
  • Patent number: 4680386
    Abstract: A novel 6-O-methylerythromycin A derivative represented by the formula ##STR1## and the salts thereof are disclosed. These compounds are useful as intermediates for preparation of 6-O-methylerythromycin A and useful as antibiotics.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: July 14, 1987
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Shigeo Morimoto, Takashi Adachi, Toshifumi Asaka, Yoshiaki Watanabe, Kaoru Sota
  • Patent number: 4670549
    Abstract: A method for the selective methylation of the hydroxy group at the 6-position of erythromycin A derivatives which comprises reacting a compound represented by the formula R-X (wherein R is a 2-alkenyl group, a benzyl group or a substituted benzyl group, and X is a halogen atom), reacting the resulting quaternary salt compound with a methylating agent, and then eliminating R groups of the resulting compound to give 6-O-methylerythromycin A 9-oxime, is disclosed.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: June 2, 1987
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Shigeo Morimoto, Takashi Adachi, Toshifumi Asaka, Masato Kashimura, Yoshiaki Watanabe, Kaoru Sota
  • Patent number: 4668776
    Abstract: There is disclosed a novel protected des-N-methylerythromycin derivative, in which 2', 3' and 9-positions are protected with new substituents that can provide stabler derivative and can be eliminated in a single reaction under neutral condition.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: May 26, 1987
    Assignees: Nippon Zeon Co. Ltd., Taisho Pharmaceutical Co. Ltd.
    Inventors: Toshiro Yamada, Hiroshi Fujisawa, Kuniaki Goto, Shigeo Morimoto, Takashi Adachi, Yoshiaki Watanabe
  • Patent number: 4575497
    Abstract: 3, 3", 4"-Tri-O-acylspiramycin I represented by the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different groups, and at least one of the groups is a straight or branched chain alkylcarbonyl group represented by --COC.sub.m H.sub.2m+1 wherein m is an integer of 2-4 and the other group(s) are straight or branched chain alkylcarbonyl group(s) represented by --COC.sub.n H.sub.2n+1 wherein n is an integer of 1-4, and its pharmacologically acceptable acid addition salts.
    Type: Grant
    Filed: December 11, 1984
    Date of Patent: March 11, 1986
    Assignee: Kyowa Hakko Kogyo Co., Ltd
    Inventors: Satoshi Omura, Hiroshi Sano, Kinya Yamashita, Ryo Okachi
  • Patent number: 4567163
    Abstract: The thioester of N-acetylcysteine with salicylic acid and the pharmacologically acceptable and non-toxic organic and inorganic salts thereof, exhibit anti-pyretic, anti-inflammatory and analgesic activity as well as mucolytic activity. The compounds are prepared by the reaction of N-acetylcysteine with either the acid chloride of acetylsalicylic acid or with the mixed anhydride formed from acetylsalicylic acid and ethyl chloroformate, the reaction taking place in an aqueous medium and at low temperature.
    Type: Grant
    Filed: November 16, 1982
    Date of Patent: January 28, 1986
    Assignee: Pietro Ismardi & C. S.p.A.
    Inventor: Osvaldo Ponchiroli
  • Patent number: 4563443
    Abstract: Acetylsalicylic acid thioesters having antipyretic activity and useful for the symptomatic treatment of influenza of formula: ##STR1## wherein n is zero or 1, R.sub.1 is hydrogen, methyl or carboxy and R.sub.2 is hydrogen or an acetamido group; a process for their preparation by reacting a functional derivative of acetylsalicylic acid with the suitable thiol; and pharmaceutical compositions containing them as active ingredient.
    Type: Grant
    Filed: August 9, 1983
    Date of Patent: January 7, 1986
    Assignee: Edmond Pharma S.r.l.
    Inventors: Marino Gobetti, Guido Vandoni
  • Patent number: 4526889
    Abstract: Antibacterial 4"-epi-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A, pharmaceutically-acceptable salts thereof, pharmaceutical compositions comprising antibacterially-effective amounts thereof, a method of treatment of bacterial infections with antibacterially effective amounts thereof, and intermediates for the synthesis thereof from erythromycin A.
    Type: Grant
    Filed: April 17, 1984
    Date of Patent: July 2, 1985
    Assignee: Pfizer Inc.
    Inventor: Gene M. Bright
  • Patent number: 4518590
    Abstract: Certain novel 9-deoxo-4"-deoxy-4"-amino-9a-aza-9a-homoerythromycin A derivatives; a method of treating a bacterial infection in a mammalian subject using the novel erythromycin A derivatives; pharmaceutical compositions containing the novel erythromycin A derivatives; and intermediates and processes for making the novel erythromycin A derivatives.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: May 21, 1985
    Assignee: Pfizer Inc.
    Inventors: James R. Hauske, Arthur A. Nagel
  • Patent number: 4517359
    Abstract: 11-Methyl-11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl-7,13,14-trihydroxy -3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one and derivatives thereof, such as the 13,14-carbonate and C.sub.1 -C.sub.3 -alkanoyl derivatives thereof. The compounds exhibit antibacterial activity.
    Type: Grant
    Filed: September 22, 1981
    Date of Patent: May 14, 1985
    Assignee: Sour Pliva farmaceutska, kemijska prehrambena i kozmeticka industrija, n.sol.o.
    Inventors: Gabrijela Kobrehel, Slobodan Djokic
  • Patent number: 4514562
    Abstract: Fluorinated derivatives of erythromycins A, B, C and D, having antibiotic activity, are prepared, starting from 8,9-anhydroerythromycin 6,9-hemiacetals or their N-oxides, through the reaction with a compound capable of generating electrophilic reactive fluorine, the resulting reaction product undergoing thereafter a reduction, possibly together with a methylation, to the corresponding (8S)-8-fluoroerythomycins.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 30, 1985
    Assignee: Pierrel Spa
    Inventor: Luciano Toscano
  • Patent number: 4512982
    Abstract: Certain novel 9-deoxo-4"-deoxy-4"-amino-9a-aza-9a-homoerythromycin A derivatives; a method of treating a bacterial infection in a mammalian subject using these novel erythromycin A derivatives; pharmaceutical compositions containing the novel erythromycin A derivatives; and intermediates and processes for making the novel erythromycin A derivatives.
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: April 23, 1985
    Assignee: Pfizer Inc.
    Inventors: James R. Hauske, Arthur A. Nagel
  • Patent number: 4492688
    Abstract: Antibacterial 9,11-deoxo-11beta,9a-(epoxyalkano)9a-aza-9a-homoerythromycin A compounds, pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising antibacterially-effective amounts thereof and a pharmaceutically acceptable carrier, the treatment of bacterial infections with antibacterially effective amounts thereof; and intermediates and processes therefor.
    Type: Grant
    Filed: November 25, 1983
    Date of Patent: January 8, 1985
    Assignee: Pfizer Inc.
    Inventor: Gene M. Bright
  • Patent number: 4480090
    Abstract: The present invention relates to a method of preparing lower fatty acid esters of cellulose which comprises esterifying at a temperature of between about 75.degree. C. and about 110.degree. C. a cellulose compound having esterifiable hydroxyl groups with an esterifying bath comprising an organic acid anhydride, a diluent, and a catalyst comprising from 0.2 to 2.0 parts phosphoric acid, from 0.1 to 1.2 parts sulfuric acid, and from 0.05 to 0.6 parts of a hindered aliphatic alcohol by weight per 100 parts of the cellulose to be esterified.
    Type: Grant
    Filed: October 21, 1983
    Date of Patent: October 30, 1984
    Assignee: Eastman Kodak Company
    Inventors: Chung-Ming Kuo, Alan P. Leonard
  • Patent number: 4476120
    Abstract: The thiolic salts of erythromycin and of the propionic ester of erythromycin with thenoyl alpha-mercaptopropionylglycine find therapeutical use in the cases in which erythromycin or its propionic ester are used and are generally endowed with very low toxicity and high hematic levels.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: October 9, 1984
    Assignee: Sigma Tau Indistrie Farmaceutiche Riunites, p.A
    Inventor: Jacques Gonella
  • Patent number: 4474768
    Abstract: Antibacterial N-methyl 11-aza-10-deoxo-10-dihydroerythromycin A and pharmaceutically acceptable acid addition salts thereof, intermediates therefor, and processes for their preparation.
    Type: Grant
    Filed: November 15, 1982
    Date of Patent: October 2, 1984
    Assignee: Pfizer Inc.
    Inventor: Gene M. Bright
  • Patent number: 4465674
    Abstract: Antibacterial 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin D, pharmaceutically-acceptable salts thereof, pharmaceutical compositions comprising antibacterially-effective amounts thereof, a method of treatment of bacterial infections with antibacterially effective amounts thereof, and intermediates for the synthesis thereof from erythromycin D.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: August 14, 1984
    Assignee: Pfizer Inc.
    Inventors: Gene M. Bright, James R. Hauske
  • Patent number: 4464527
    Abstract: Antibacterial 9-deoxo-9a-ethyl and propyl-9a-aza-9a-homoerythromycin A compounds, pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising antibacterially effective amounts thereof and a pharmaceutically acceptable carrier, the treatment of bacterial infections with antibacterially effective amounts thereof, and intermediates and processes for their preparation.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: August 7, 1984
    Assignee: Pfizer Inc.
    Inventor: Gene M. Bright
  • Patent number: 4393053
    Abstract: The thiolic salts of erythromycin and of the propionic ester of erythromycin with thenoyl alpha-mercaptopropionylglycine find therapeutical use in the cases in which erythromycin or its propionic ester are used and are generally endowed with very low toxicity and high hematic levels.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: July 12, 1983
    Assignee: Refarmed S.A.
    Inventor: Jacques Gonella
  • Patent number: 4349545
    Abstract: Novel erythromycin derivatives in the syn form or anti form or mixtures of the syn and anti forms of the formula ##STR1## wherein A is a linear or branched alkylene of 1 to 6 carbon atoms, R is selected from the group consisting of optionally substituted alkoxy of 1 to 6 carbon atoms, optionally substituted alkenyloxy and alkynyloxy of 2 to 6 carbon atoms, optionally substituted alkylthio of 1 to 6 carbon atoms, optionally substituted alkenylthio and alkynylthio of 2 to 6 carbon atoms with the thio group optionally oxidized to the sulfoxide or sulfone form, optionally substituted aryloxy and arylthio, optionally substituted aralkyloxy and arylalkylthio, the thio derivatives optionally oxidized to sulfoxide or sulfone, ##STR2## optionally substituted quaternary ammonium group, halogen, optionally substituted 1,2-epoxyethyl and the group resulting from opening of the epoxy with a nucleophilic reactant, ##STR3## a free or protected formyl, --COOR', thiocyanate, --CN, acyl and carbamoyl, R.sub.1 and R.sub.
    Type: Grant
    Filed: January 8, 1981
    Date of Patent: September 14, 1982
    Assignee: Roussel Uclaf
    Inventors: Solange Gouin d'Ambrieres, Andre Lutz, Jean-Claude Gasc
  • Patent number: 4336368
    Abstract: Derivatives of oleandomycin, its 11-trimethylsilyl ether and 11-trimethylsilyl-2'-alkanoyl esters and processes for preparation thereof wherein the L-oleandrosyl moiety is modified at the 4"-position to provide derivatives thereof wherein said moiety has formula ##STR1## wherein A and B when taken together are .dbd.CHX wherein X is H, --CN, --COOR.sub.3, --SR.sub.3 ', --S(O)R.sub.3 ', --S(O).sub.2 R.sub.3 ' or ##STR2## A when taken individually is hydrogen; B when taken individually is --CHO or --CH.sub.2 Z wherein Z is hydrogen, --OR.sub.3, --COOR.sub.3, --SR.sub.3 ', --S(O)R.sub.3 ', --S(O).sub.2 R.sub.3 ', --CN or --(CH.sub.2).sub.n --NR.sub.5 R.sub.6 ;R.sub.3 is hydrogen, ##STR3## R.sub.3 ' is (C.sub.1-4)alkyl or ##STR4## R.sub.4 is hydrogen, chloro, bromo, (C.sub.1-4)alkyl or (C.sub.1-4)alkoxy; R.sub.5 is hydrogen or ##STR5## R.sub.6 is hydrogen, --COCH.sub.3, ##STR6## R.sub.5 and R.sub.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: June 22, 1982
    Assignee: Pfizer Inc.
    Inventor: Arthur A. Nagel
  • Patent number: 4328334
    Abstract: 11-aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof, and process for preparation thereof.
    Type: Grant
    Filed: March 28, 1980
    Date of Patent: May 4, 1982
    Assignee: PLIVA Pharmaceutical and Chemical Works
    Inventors: Gabrijela Kobrehel, Gordana Radobolja, Zrinka Tamburasev, Slobodan Djokic