Halogen Containing Compound Utilized In Process Patents (Class 536/72)
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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: 4686207Abstract: Disclosed herein are erythromycin derivatives of the formula ##STR1## wherein R.sub.1 is lower alkyl, aryl, alkene, aryl halide, alkylamino, hydroxyalkyl and furanyl, and pharmaceutically acceptable salts thereof. These compounds have improved oral absorption, reduced effects on gastrointestinal motility, increased acid stability and longer serum half-lives.Type: GrantFiled: November 12, 1985Date of Patent: August 11, 1987Assignee: Abbott LaboratoriesInventors: Leslie A. Freiberg, David J. Bacino
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Patent number: 4681872Abstract: An erythromycin A derivative with high antimicrobial activity and improved pharmacokinetics is disclosed. 4"-Deoxyerythromycin A 11,12-carbonate and derivatives show superior in vitro and in vivo antimicrobial activity compared to erythromycin A, and when administered to animals has a serum half-life much prolonged over that of erythromycin A.Type: GrantFiled: November 12, 1985Date of Patent: July 21, 1987Assignee: Abbott LaboratoriesInventors: Leslie A. Freiberg, Howard E. Gracey, Andre G. Pernet
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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: 4677097Abstract: A pharmaceutical composition for inducing contractile motility of the gastrointestinal tract in humans and animals, comprising as active ingredient 8,9-anhydroerythromycin 6,9-hemiketals, anhydroerythromycins, derivatives thereof and/or pharmaceutically acceptable salts thereof, in association with a pharmaceutically acceptable carrier or excipient. The active compounds may be produced by chemical modification of erythromycin and exhibit no or little antimicrobial activity. By administering the present composition to humans and animals, contractile motility of the gastrointestinal tract similar to the motility occurring naturally under normal conditions may be effectively induced.Type: GrantFiled: October 4, 1985Date of Patent: June 30, 1987Assignee: Kitasato KenkyushoInventors: Satoshi Omura, Zen Itoh
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Patent number: 4673736Abstract: For the synthesis of (8S)-8-fluoroerythromycins the corresponding 8,9-anhydroerythromycins 6,9-hemiketal are directly fluorinated with perchloryl fluoride.Type: GrantFiled: July 11, 1984Date of Patent: June 16, 1987Assignee: Pierrel SpAInventor: Luciano Toscano
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Patent number: 4672109Abstract: A method for the selective methylation of a hydroxy group at the 6-position of an erythromycin A derivative which comprises converting an erythromycin A derivative into an erythromycin A 9-oxime derivative, and reacting the resulting ethythromycin A 9-oxime derivative with an methylating agent.Type: GrantFiled: April 5, 1985Date of Patent: June 9, 1987Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoshiaki Watanabe, Shigeo Morimoto, Masami Goi, Morihiro Mitsukuchi, Takashi Adachi, Jozi Nakagami, Toshifumi Asaka, Tadashi Eguchi, Kaoru Sota
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Patent number: 4672055Abstract: The erythromycin salt of 5-(3-carboxy-1-oxopropoxy)-.alpha.,.alpha., 4-trimethyl-3-cyclohesene-1-methanol acid is described.This salt shows a mucosecretolytic and fluidizing activity. There is further described a process for the preparation of said salt, as well as pharmaceutical compositions with mucosecretolytic and fluidizing action which contain the novel salt.Type: GrantFiled: March 14, 1985Date of Patent: June 9, 1987Assignee: Camillo Corvi S.p.A.Inventor: Camillo Corvi Mora
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Patent number: 4672056Abstract: Erythromycin A derivatives with high antimicrobial activity are disclosed. 14-hydroxyerythromycin A and derivatives show superior in vitro antimicrobial activity compared to the parent compounds.Type: GrantFiled: November 12, 1985Date of Patent: June 9, 1987Assignee: Abbott LaboratoriesInventors: Prabhavathi Fernandes, Leslie A. Freiberg
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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: 4668664Abstract: Linear bi- or tri-enic fatty esters of erythromycin A have the formula ##STR1## wherein one of R and R' represents a linear bi- or tri-enic C.sub.18 acyl radical having an all cis (Z) stereochemical configuration and the other of R and R' represents hydrogen.Type: GrantFiled: May 14, 1986Date of Patent: May 26, 1987Assignee: L'OrealInventors: Andr/e/ Rougier, Didier Dupuis, Michel Philippe, Henri Sebag, Didier S. Leger
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Patent number: 4640910Abstract: Novel O-alkylsilyl derivatives of macrolide antibiotics are disclosed. These compounds have markedly superior taste properties when compared to the corresponding parent compounds.Type: GrantFiled: November 12, 1985Date of Patent: February 3, 1987Assignee: Abbott LaboratoriesInventors: Hermann Faubl, Robert G. Stein
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Patent number: 4599326Abstract: The invention relates to a new antibiotic compound, acetyl erythromycin stearate having formula I ##STR1## The compound according to the invention is absorbed readily from the alimentary tract. Gastric acid does not convert the compound according to the invention to an uneffective form as is the case with some other erythromycin antibiotics. Absorbing is good also when the patient eats when taking the new medicine.The compound according to the invention is prepared by reacting erythromycin base with acetyl halide in an organic solvent in the presence of an acid acceptor. The stearate salt is prepared from the obtained ester without in between isolating the ester.Type: GrantFiled: December 27, 1984Date of Patent: July 8, 1986Assignee: Orion-yhtyma OyInventors: Martti L. A. Marvola, Esko V. Marttila, Jaakko A. Uotila, Aino K. Pippuri, Pekka J. Kairisalo, Erkki J. Honkanen
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Patent number: 4594439Abstract: Methods and compositions are provided for asymmetrically donating an oxygen atom to a pair of electrons to produce an asymmetric product. Specifically, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms. The metal catalyst is employed in conjunction with a hydroperoxide and an alkanol having a functionality with a pair of electrons capable of accepting an oxygen atom. The resulting product is enriched in one enantiomer due to the enantioselective introduction of an asymmetric center or an enhanced rate of reaction of one of the enantiomers of a chiral alkanol.Type: GrantFiled: August 23, 1984Date of Patent: June 10, 1986Assignee: The Board of Trustees of the Leland Stanford Jr. UniversityInventors: Tsutomu Katsuki, Karl B. Sharpless
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Patent number: 4588712Abstract: (8S)-8-fluoroerythromycin derivatives of formula ##STR1## wherein R is an optionally substituted alkyl, alkenyl or phenyl groupR' is hydrogen or methyl andR" is hydrogen or hydroxy,may be prepared by fluorination of the corresponding 8,9-anhydroerythromycin 6,9-hemiketals with perchloryl fluoride in the presence of a compound ROH in strictly anhydrous conditions.The new compounds as well as their pharmaceutically acceptable esters, salts and salt-esters may be employed as the active ingredients of pharmaceutical compositions for antibacterial use suitable for oral administration.Type: GrantFiled: February 28, 1985Date of Patent: May 13, 1986Assignee: Pierrel S.p.A.Inventor: Luciano Toscano
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Patent number: 4585759Abstract: New antibacterial agents from a neutral macrolide wherein the keto group of the beta-D-4,6-dideoxy-3-ketoallose unit is converted to the corresponding hydroxy, amino, methylamino and dimethylamino functions.Type: GrantFiled: January 22, 1985Date of Patent: April 29, 1986Assignee: Pfizer inc.Inventor: Arthur A. Nagel
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Patent number: 4575496Abstract: The present invention concerns the new erythromycin salt of the o-carbonyl(1-thiazolidinyl)-benzoic acid having the formula ##STR1## wherein X represents the monovalent cation of erythromycin. The new salt constitutes a novel antibiotic complex for the selective therapy of the respiratory tract.Type: GrantFiled: December 15, 1983Date of Patent: March 11, 1986Assignee: Camillo Corvi S.p.A.Inventor: Camillo C. Mora
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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: 4515941Abstract: Novel 23-demycinosyldesmycosin derivatives are disclosed of the formula ##STR1## wherein A is oxygen or sulfur, R.sub.1 is optionally substituted phenyl or ##STR2## group, in which R.sub.3 is optionally substituted phenyl and R.sub.4 and R.sub.5 are the same or different and are hydrogen, lower alkyl or optionally substituted phenyl, and R.sub.2 is hydrogen or hydroxyl. The compounds or non-toxic salts thereof are useful as antibiotics.Type: GrantFiled: March 30, 1983Date of Patent: May 7, 1985Assignee: Toyo Jozo Kabushiki KaishaInventors: Tatsuro Fujiwara, Hideyuki Watanabe, Takao Hirano, Hideo Sakakibara
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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: 4496546Abstract: Fermentation of a culture of Nocardia sp. ATCC 39043 produces an antibiotic complex comprising erythromycin D, 3",4"-di-O-acetylerythromcyin D, 3"-O-acetyl-4"-O-propionylerythromycin D and 4"-O-acetylerythromycin D. The components are separated and are each useful in vitro and in vivo as antibacterial agents. If erythromycin D is the desired product, the esters can be hydrolyzed prior to the separation of the erythromycin D.Type: GrantFiled: April 12, 1982Date of Patent: January 29, 1985Assignee: Pfizer Inc.Inventors: Walter D. Celmer, Walter P. Cullen, Paul C. Watts, Riichiro Shibakawa, Junsuke Tone
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Patent number: 4496717Abstract: Novel erythromycin B derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are each hydrogen or methyl, and the pharmaceutically acceptable acid addition salts thereof are disclosed. They exhibit excellent in vivo antibacterial activity against Gram-positive bacteria.Type: GrantFiled: November 24, 1982Date of Patent: January 29, 1985Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Takashi Adachi, Shigeo Morimoto, Yoko Takahashi, Yoshiaki Watanabe, Sadafumi Omura
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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: 4476298Abstract: Novel erythromycin A derivatives of the formula ##STR1## wherein R is hydrogen or methyl, and the pharmaceutically acceptable acid addition salts thereof are disclosed. They exhibit excellent antibacterial activity against erythromycin resistant bacteria, Gram-positive bacteria and Mycoplasma species.Type: GrantFiled: November 24, 1982Date of Patent: October 9, 1984Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Shigeo Morimoto, Yoko Takahashi, Yoshiaki Watanabe, Sadafumi Omura
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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: 4471130Abstract: Methods and compositions are provided for asymmetrically donating an oxygen atom to a pair of electrons to produce an asymmetric product. Specifically, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms. The metal catalyst is employed in conjunction with a hydroperoxide and an alkanol having a functionality with a pair of electrons capable of accepting an oxygen atom. The resulting product is enriched in one enantiomer due to the enantioselective introduction of an asymmetric center or an enhanced rate of reaction of one of the enantiomers of a chiral alkanol.Type: GrantFiled: July 27, 1981Date of Patent: September 11, 1984Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Tsutomu Katsuki, Karl B. Sharpless
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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: 4439426Abstract: From the fermentation carried, out with mutants blocked in the synthesis respectively of erythromycin and of oleandomycin, namely Streptomyces erythreus ATCC 31772 and Streptomyces antibioticus ATCC 31771, using as the substrate a derivative of erythronolide A, namely (8S)-8-fluoroerythronolide A, a derivative of erythronolide B, namely (8S)-8-fluoroerythronolide B, or a derivative of 3-O-mycarosyl-erythronolide B, namely 3-O-mycarosyl-(8S)-fluoroerythronolide B, the corresponding (8S)-8-fluoro derivatives of the erythromycins A, B, C and D, as well as 3-O-oleandrosyl-5-desosaminyl-(8S)-8-fluoroerythronolide A and 3-O-oleandrosyl-5-O-desosaminyl-(8S)-8-fluoroerythronolide B, all belonging to the class of the macrolide antibiotics are obtained.Type: GrantFiled: January 8, 1982Date of Patent: March 27, 1984Assignee: Pierrel S.p.A.Inventors: Luciano Toscano, Leonardo M. Cappelletti
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Patent number: 4429116Abstract: A process for the alkylation of the C.sub.3 " position of oleandomycin and antibacterial agents derived therefrom.Type: GrantFiled: December 27, 1982Date of Patent: January 31, 1984Assignee: Pfizer Inc.Inventor: Arthur A. Nagel
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Patent number: 4429115Abstract: The fermentation of a substrate selected among erythronolide B, erythronolide A and erythronolide A oxime with a novel mutant, Streptomyces antibioticus ATCC 31771, obtained from an industrial stock for the production of oleandomycin, said novel mutant being incapable of producing the same oleandomycin, permits novel macrolide antibiotics to be produced, having not only an activity range like that of erythromycin, but characterized by a greater stability in acidic environment, whereby for the administration of antibiotic it is no longer necessary to have recourse to esters and/or salts highly toxic for the organism.Type: GrantFiled: January 8, 1982Date of Patent: January 31, 1984Assignee: Pierrel S.p.A.Inventors: Leonardo M. Cappelletti, Roberto Spagnoli, Luciano Toscano
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Patent number: 4413119Abstract: The reaction product of dimethyl diazomethylphosphonate with 4"-deoxy-4"-oxo-oleandomycin and erythromycin A derivatives as antibacterial agents, and intermediates leading thereto.Type: GrantFiled: April 26, 1982Date of Patent: November 1, 1983Assignee: Pfizer Inc.Inventor: James R. Hauske
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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: 4382086Abstract: Antibacterial macrolides derived from 9-dihydro-11,12-O-isopropylidene-erythromycin A and 9-dihydro-11,12-O-isopropylidene-4"-epi-erythromycin A.Type: GrantFiled: March 1, 1982Date of Patent: May 3, 1983Assignee: Pfizer Inc.Inventors: Frank C. Sciavolino, James R. Hauske
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Patent number: 4382085Abstract: 4"-Epi erythromycin A and 9-dihydro-4"-epi erythromycin A and derivatives thereof as useful antibacterial agents.Type: GrantFiled: March 1, 1982Date of Patent: May 3, 1983Assignee: Pfizer Inc.Inventors: Frank C. Sciavolino, Mark A. Guadliana
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Patent number: 4363803Abstract: The reaction product of dimethyl diazomethylphosphonate with 4"-deoxy-4"-oxo-oleandomycin and erythyromycin A derivatives as antibacterial agents.Type: GrantFiled: March 1, 1982Date of Patent: December 14, 1982Assignee: Pfizer Inc.Inventor: James R. Hauske
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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: 4331803Abstract: Novel erythromycin compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or methyl, and a pharmaceutically acceptable salt thereof are disclosed. They exhibit excellent antibacterial activity against Gram-positive bacteria, acid stability and in vivo activity.Type: GrantFiled: May 19, 1981Date of Patent: May 25, 1982Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoshiaki Watanabe, Shigeo Morimoto, Sadafumi Omura