Sulfur Containing Compound Utilized In Pretreatment Patents (Class 536/74)
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Patent number: 4963528Abstract: 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: GrantFiled: September 9, 1987Date of Patent: October 16, 1990Assignee: Sour PlivaInventors: Zlatko Vajtner, Nevenka Lopotar, Slobodan Djokic
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Patent number: 4957905Abstract: 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: GrantFiled: September 7, 1988Date of Patent: September 18, 1990Assignee: Beecham Group p.l.c.Inventor: Eric Hunt
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Patent number: 4948782Abstract: 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: GrantFiled: February 18, 1988Date of Patent: August 14, 1990Assignee: Kitasato KenkyushoInventors: Satoshi Omura, Zen Itoh
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Patent number: 4945080Abstract: 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: GrantFiled: May 26, 1987Date of Patent: July 31, 1990Assignee: Eli Lilly and CompanyInventors: Terry D. Lindstrom, Gary W. Whitaker
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Patent number: 4921839Abstract: 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: GrantFiled: February 22, 1988Date of Patent: May 1, 1990Assignee: Beecham Group p.l.c.Inventors: Edward G. Brain, Eric Hunt, Andrew K. Forrest
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Patent number: 4906579Abstract: 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: GrantFiled: April 26, 1988Date of Patent: March 6, 1990Assignee: Domtar IncInventors: Manssur Yalpani, Magdy M. Abdel-Malik
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Patent number: 4847242Abstract: 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: GrantFiled: March 10, 1986Date of Patent: July 11, 1989Assignee: Beecham Group p.l.c.Inventor: John S. Davies
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Patent number: 4826820Abstract: 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: GrantFiled: August 26, 1986Date of Patent: May 2, 1989Assignee: Beecham Group p.l.c.Inventor: Edward G. Brain
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Patent number: 4742049Abstract: 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: GrantFiled: June 4, 1986Date of Patent: May 3, 1988Assignee: Abbott LaboratoriesInventors: William R. Baker, Jerry D. Clark
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Patent number: 4740502Abstract: 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: GrantFiled: June 20, 1986Date of Patent: April 26, 1988Assignee: Abbott LaboratoriesInventors: Steven M. Hannick, Larry L. Klein
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Patent number: 4697007Abstract: 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: GrantFiled: March 1, 1985Date of Patent: September 29, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Georg Seitz, Rainer Wernicke
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Patent number: 4680386Abstract: 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: GrantFiled: October 21, 1985Date of Patent: July 14, 1987Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Shigeo Morimoto, Takashi Adachi, Toshifumi Asaka, Yoshiaki Watanabe, Kaoru Sota
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Patent number: 4670549Abstract: 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: GrantFiled: February 24, 1986Date of Patent: June 2, 1987Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Shigeo Morimoto, Takashi Adachi, Toshifumi Asaka, Masato Kashimura, Yoshiaki Watanabe, Kaoru Sota
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Patent number: 4668776Abstract: 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: GrantFiled: March 31, 1986Date of Patent: May 26, 1987Assignees: Nippon Zeon Co. Ltd., Taisho Pharmaceutical Co. Ltd.Inventors: Toshiro Yamada, Hiroshi Fujisawa, Kuniaki Goto, Shigeo Morimoto, Takashi Adachi, Yoshiaki Watanabe
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Patent number: 4575497Abstract: 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: GrantFiled: December 11, 1984Date of Patent: March 11, 1986Assignee: Kyowa Hakko Kogyo Co., LtdInventors: Satoshi Omura, Hiroshi Sano, Kinya Yamashita, Ryo Okachi
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Patent number: 4567163Abstract: 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: GrantFiled: November 16, 1982Date of Patent: January 28, 1986Assignee: Pietro Ismardi & C. S.p.A.Inventor: Osvaldo Ponchiroli
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Patent number: 4563443Abstract: 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: GrantFiled: August 9, 1983Date of Patent: January 7, 1986Assignee: Edmond Pharma S.r.l.Inventors: Marino Gobetti, Guido Vandoni
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Patent number: 4526889Abstract: 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: GrantFiled: April 17, 1984Date of Patent: July 2, 1985Assignee: Pfizer Inc.Inventor: Gene M. Bright
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9.alpha.-Aza-9.alpha.-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
Patent number: 4518590Abstract: 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: GrantFiled: June 4, 1984Date of Patent: May 21, 1985Assignee: Pfizer Inc.Inventors: James R. Hauske, Arthur A. Nagel -
Patent number: 4517359Abstract: 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: GrantFiled: September 22, 1981Date of Patent: May 14, 1985Assignee: Sour Pliva farmaceutska, kemijska prehrambena i kozmeticka industrija, n.sol.o.Inventors: Gabrijela Kobrehel, Slobodan Djokic
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Patent number: 4514562Abstract: 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: GrantFiled: November 22, 1982Date of Patent: April 30, 1985Assignee: Pierrel SpaInventor: Luciano Toscano
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Patent number: 4512982Abstract: 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: GrantFiled: April 13, 1984Date of Patent: April 23, 1985Assignee: Pfizer Inc.Inventors: James R. Hauske, Arthur A. Nagel
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Patent number: 4492688Abstract: 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: GrantFiled: November 25, 1983Date of Patent: January 8, 1985Assignee: Pfizer Inc.Inventor: Gene M. Bright
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Patent number: 4480090Abstract: 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: GrantFiled: October 21, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: Chung-Ming Kuo, Alan P. Leonard
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Patent number: 4476120Abstract: 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: GrantFiled: February 2, 1982Date of Patent: October 9, 1984Assignee: Sigma Tau Indistrie Farmaceutiche Riunites, p.AInventor: Jacques Gonella
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Patent number: 4474768Abstract: 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: GrantFiled: November 15, 1982Date of Patent: October 2, 1984Assignee: Pfizer Inc.Inventor: Gene M. Bright
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Patent number: 4465674Abstract: 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: GrantFiled: September 6, 1983Date of Patent: August 14, 1984Assignee: Pfizer Inc.Inventors: Gene M. Bright, James R. Hauske
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Patent number: 4464527Abstract: 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: GrantFiled: June 30, 1983Date of Patent: August 7, 1984Assignee: Pfizer Inc.Inventor: Gene M. Bright
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Patent number: 4393053Abstract: 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: GrantFiled: February 2, 1982Date of Patent: July 12, 1983Assignee: Refarmed S.A.Inventor: Jacques Gonella
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Patent number: 4349545Abstract: 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: GrantFiled: January 8, 1981Date of Patent: September 14, 1982Assignee: Roussel UclafInventors: Solange Gouin d'Ambrieres, Andre Lutz, Jean-Claude Gasc
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Patent number: 4336368Abstract: 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: GrantFiled: April 20, 1981Date of Patent: June 22, 1982Assignee: Pfizer Inc.Inventor: Arthur A. Nagel
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Patent number: 4328334Abstract: 11-aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof, and process for preparation thereof.Type: GrantFiled: March 28, 1980Date of Patent: May 4, 1982Assignee: PLIVA Pharmaceutical and Chemical WorksInventors: Gabrijela Kobrehel, Gordana Radobolja, Zrinka Tamburasev, Slobodan Djokic