Sulfur Containing Compound Utilized In Pretreatment Patents (Class 536/74)
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Patent number: 5780605Abstract: Novel multicyclic erythromycin compounds and pharmaceutically acceptable salts and esters thereof having antibacterial activity having a formula ##STR1## compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, as well as a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically-effective amount of a compound of the invention.Type: GrantFiled: September 8, 1997Date of Patent: July 14, 1998Assignee: Abbott LaboratoriesInventors: Yat Sun Or, Richard F. Clark, Daniel T. Chu, Jacob J. Plattner
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Patent number: 5770726Abstract: The present invention relates to a process for preparing a substituted cellulose acetoacetate alkanoate without using a carboxamide/lithium chloride solvent system. The process involves contacting cellulose in a carboxylic acid diluent with an acetylating compound selected from the group consisting of a carboxylic acid anhydride and an acid chloride, an acetoacetylating compound selected from the group consisting of diketene, an alkyl acetoacetate and 2,2,6-trimethyl-4H-1,3-dioxin-4-one, and a mineral acid catalyst under conditions and in a molar ratio sufficient to cause the cellulose, acetylating compound and acetoacetylating compound to react to produce a substituted cellulose acetoacetate alkanoate.Type: GrantFiled: March 10, 1997Date of Patent: June 23, 1998Assignee: Eastman Chemical CompanyInventors: Chung Ming Kuo, Kevin Joseph Edgar
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Patent number: 5770579Abstract: Compounds of the formula ##STR1## wherein X and X' form C.dbd.O or C.dbd.NOR, R is selected from the group consisting of hydrogen, heterocycle, alkyl, alkenyl, alkynyl, all optionally substituted, ##STR2## R.sub.a and R.sub.b are hydrogen or a hydrocarbon group or form together with the nitrogen a heterocycle, or with A forms a 9-N, 11-O ring, and X' is hydrogen, --Y and Y' have the same definition as X and X', b is hydrogen or OR.sub.4, R.sub.4 is hydrogen or forms together with A a carbonate or a carbamate, A forms with C a double bond or A is OR'.sub.4, R'.sub.4 is hydrogen or forms together with B a carbonate or ##STR3## R.sub.2 is alkyl or --CONH.sub.2, --CONHCOR.sub.11 or --CONHSO.sub.2 R.sub.11, R.sub.11 is a hydrocarbon up to 18 carbon atoms, R.sub.3 is hydrogen, ##STR4## and Z is hydrogen or a carboxylic acid remainder and their non-toxic, pharmaceutically acceptable acid addition salts, their preparation and intermediates useful as antibiotics.Type: GrantFiled: January 25, 1995Date of Patent: June 23, 1998Assignee: Roussel UclafInventors: Constantin Agouridas, Yannick Benedetti, Jean-Fran.cedilla.ois Chantot, Alexis Denis, Claude Fromentin, Odile Le Martret
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Patent number: 5747466Abstract: A compound selected from the group: ##STR1## wherein A, B, V, W, X and R.sup.8 are specifically defined; pharmaceutical compositions thereof; a method of treating or preventing bacterial infections by administering therapeutically effective pharmaceutical compositions thereof; and a process for the preparation thereof.Type: GrantFiled: October 10, 1996Date of Patent: May 5, 1998Assignee: Abbott LaboratoriesInventors: Richard L. Elliott, Yat Sun Or, Daisy Pireh, Daniel T. Chu
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Patent number: 5747467Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein X is selected from the group consisting of --(NH).sub.a --, --CH.sub.2 --, --SO.sub.2 -- and --O--, a is 0 or 1, Y is --(CH.sub.2).sub.m - (CH.dbd.CH).sub.n --(CH.sub.2).sub.o -, m+n+o.ltoreq.8, n=o or 1, Ar is aryl optionally substituted with at least one member of the group consisting of --OH, halogen, --NO.sub.2, --CN, ##STR2## and alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, -N-alkyl, -N-alkenyl and N-alkynyl of up to 12 carbon atoms, R.sub.a and R.sub.b individually are hydrogen or alkyl of up to 12 carbon atoms, R.sub.Type: GrantFiled: December 19, 1996Date of Patent: May 5, 1998Assignee: Roussel UclafInventors: Constantin Agouridas, Fran.cedilla.ois Bretin, Jean-Fran.cedilla.ois Chantot
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Patent number: 5721346Abstract: The present invention refers to the new compounds of the secomacrolide and secoazalide class, a process for the preparation thereof as well as to new intermediates for the preparation of these seco derivatives.Type: GrantFiled: March 7, 1996Date of Patent: February 24, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Gorjana Lazarevski, Gabrijela Kobrehel
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Patent number: 5719272Abstract: A process of preparing a 6-O-methyl erythromycin A derivative using a 2'-protected, 9-etheroxime erythromycin A intermediate is provided. A preferred protecting group for the 2'-position is acetyl. 2'-protected, 9-etheroxime erythromycin A derivatives are also provided. Also disclosed is a method for inhibiting quaternary salt formation at the 3' amine without the need for 3'N-protecting groups.Type: GrantFiled: April 2, 1996Date of Patent: February 17, 1998Assignee: Abbott LaboratoriesInventors: Chengxi Yang, Hemantkumar H. Patel, Yi-Yin Ku, Jih-Hua Liu
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Patent number: 5658888Abstract: Compounds represented by the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an acyl group; R.sub.2 and R.sub.3 may be the same or different, and each represents a hydrogen atom, hydroxyl group, acyloxy group or amino group, or, in combination, they represent .dbd.O or .dbd.NOR.sub.10, where R.sub.10 represents a hydrogen atom or lower alkyl group;R.sub.4 represents a hydrogen atom or lower alkyl group; andY represents --NR.sub.5 R.sub.6 or --N.sup.+ R.sub.7 R.sub.8 R.sub.9 X.sup.-, where R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 may be the same or different, and each represents a hydrogen atom or an unsubstituted or substituted lower alkyl group, lower alkenyl group, lower alkinyl group, cycloalkyl group or 3-7-membered heterocyclic group comprising an oxygen atom, nitrogen atom or sulphur atom as an heteroatom, and X represents an anion, where R.sub.5 and R.sub.6, or R.sub.7 and R.sub.Type: GrantFiled: October 19, 1994Date of Patent: August 19, 1997Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Hiroshi Koga, Tsutomu Sato, Hisanori Takanashi
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Patent number: 5656607Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and an optionally unsaturated hydrocarbon of up to 24 carbon atoms optionally interrupted by at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen and optionally having at least one functional group or taken together form ##STR2## and R'.sub.1 and R'.sub.Type: GrantFiled: March 31, 1995Date of Patent: August 12, 1997Assignee: Roussel UclafInventors: Constantin Agouridas, Yannick Benedetti, Jean-Francois Chantot, Alexis Denis, Odile Le Martret
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Patent number: 5654411Abstract: 4"-Deoxy derivatives of erythromycin having the Formula (I) ##STR1## and pharmaceutically acceptable salts thereof, which are enhancers of gastric motility but have minimal antibacterial activity, as well as pharmaceutical compositions containing the same and methods for their use and preparation.Type: GrantFiled: May 4, 1995Date of Patent: August 5, 1997Assignee: Abbott LaboratoriesInventors: Paul A. Lartey, Larry L. Klein, Ramin Faghih, Hugh N. Nellans
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Patent number: 5635485Abstract: An erythromycin compound of Formula I or its non-toxic acid addition salt having antibiotic activity.Type: GrantFiled: April 21, 1995Date of Patent: June 3, 1997Assignee: Roussel UclafInventors: Constantin Agouridas, Jean-Francois Chantot, Alexis Denis, Solange G. D'Ambrieres, Odile L. Martret
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Patent number: 5635613Abstract: The invention provides Form II dirithromycin, a novel polymorph of dirithromycin. Also disclosed are the acetone, 1-butanol, 1-propanol, and 2-propanol solvates of dirithromycin, which provide an efficient means for preparing and isolating Form II. Processes for preparing and isolating Form II dirithromycin from these solvates or from Form I dirithromycin are provided. A process for obtaining Form II dirithromycin from non-solvated dirithromycin is also provided. Another aspect of the invention is an improved tablet containing Form II dirithromycin as the active ingredient.Type: GrantFiled: May 19, 1995Date of Patent: June 3, 1997Assignee: Eli Lilly and CompanyInventors: James M. Greene, Holly M. Hankins, Gregory A. Stephenson, David D. Wirth
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Patent number: 5631355Abstract: Object: To provide novel macrolide antibiotics having a strong antibacterial activity. Constitution: 5-O-desosaminylerythronolide A derivatives represented by the formula: ##STR1## [wherein -A- - is a group of --N(R.sup.3)-- (wherein R.sup.3 is a hydrogen atom or an alkyl group having 1-3 carbon atoms) or a group represented by --N.dbd., and R.sup.1 and R.sup.2 are each a hydrogen atom or an alkyl group having 1-3 carbon atoms] which is a tricyclic carbamate of 5-0-desosaminylerythronolide A derivative having a ketone at the 3-position, being substituted by a methoxy group at the 6-position, and a pharmaceutically acceptable acid addition salt thereof; and a compound represented by the formula: ##STR2## (wherein R.sup.4 is an acetyl group or a propionyl group) which is an intermediate useful for the preparation of the 3-ketone forms of 5-O-desosaminylerythronolide A derivatives.Type: GrantFiled: October 17, 1994Date of Patent: May 20, 1997Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshifumi Asaka, Masato Kashimura, Yoko Misawa, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5631354Abstract: Object:Provision of novel macrolide antibiotics having a strong antibacterial activity.Construction:Compounds represented by the formula: ##STR1## which are obtained by introducing a certain substituted carbonyloxy group into 5-O-desosaminylerythronolide derivatives at the 3-position; and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: June 21, 1994Date of Patent: May 20, 1997Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshifumi Asaka, Yoko Misawa, Masato Kashimura, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5629296Abstract: The invention relates to 9a-N-(N'-carbamoyl) and 9a-N-(N'-thiocarbamoyl) derivatives of 9-deoxo-9a-aza-9a-homoerythromycin A, novel semisynthetic macrolide antibiotics of the azalide series, of the formula (I) ##STR1## wherein R represents a C.sub.1 -C.sub.3 alkyl, aryl or aralkyl group and X represents O or S, and pharmaceutically acceptable addition salts thereof with inorganic or organic acids, to the intermediates and processes for the preparation thereof, to a process for the preparation of pharmaceutical compositions as well as to the use of pharmaceutical compositions in the treatment of bacterial infections.Type: GrantFiled: November 29, 1994Date of Patent: May 13, 1997Assignee: Pliva farmaceutiska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo ZagrebInventors: Nedjeliko Kujund zi c, Gabrijela Kobrehel, Zeljko Kelneri c
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Patent number: 5608050Abstract: The specification discloses a process for the manufacture of cellulose acetate. The process reacts, at a temperature suitable for acetylation, an acetic acid activated pretreated cellulose raw material containing 100 parts cellulose by dry weight, and 0.5 to 40 parts of a bisulfate catalyst by dry weight of the cellulose. The bisulfate catalyst is selected from lithium bisulfate, sodium bisulfate, and potassium bisulfate. To enhance mixing with the activated and pretreated cellulose, the catalyst may be mixed with 2 to 4 parts of acetic anhydride by dry weight of the cellulose, and 4 to 6 parts of acetic acid by dry weight of the cellulose. In a further embodiment, 0.05 to 10 parts of a strong Bronsted acid by weight of the dry cellulose may be added as a co-catalyst.Type: GrantFiled: December 18, 1995Date of Patent: March 4, 1997Assignee: Eastman Chemical CompanyInventors: Chung M. Kuo, Richard T. Bogan
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Patent number: 5602239Abstract: A novel macloride antibiotic having a potent antibacterial activity, represented by the formula: ##STR1## which is obtained by introducing a specific aryloxy or alkoxy group into the 3-position of a 5-O-desosaminylerythronolide derivative; or phamaceutically acceptable acid addition salts thereof.Type: GrantFiled: July 13, 1995Date of Patent: February 11, 1997Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoko Misawa, Toshifumi Asaka, Masato Kashimura, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5591837Abstract: Object: To provide a novel macrolide antibiotic having a strong antibacterial activity.Constitution: 11-Amino-3,11-dideoxy-3-oxo-5-O-desosaminyl-6-O-methylerythronolide A 11-N,12-O-cyclic carbamate which has a ketone at the 3-position and a methylated hydroxyl group at the 6-position of a 5-O-desosaminylerythronolide A derivative, and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: October 14, 1994Date of Patent: January 7, 1997Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshifumi Asaka, Masato Kashimura, Yoko Misawa, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5578579Abstract: 4"-Deoxy derivatives of erythromycin having the Formula (I) ##STR1## and pharmaceutically acceptable salts thereof, which are enhancers of gastric motility but have minimal antibacterial activity, as well as pharmaceutical compositions containing the same and methods for their use and preparation.Type: GrantFiled: August 2, 1994Date of Patent: November 26, 1996Assignee: Abbott LaboratoriesInventors: Paul A. Lartey, Larry L. Klein, Ramin Faghih, Hugh N. Nellans
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Patent number: 5578713Abstract: The disclosure relates to a new process for the synthesis of the macrolide antibiotic dirithromycin in crystalline form. The process is carried out in a single reaction vessel whereby an acetal dissolved in acetonitrile, in the presence of an acid catalyst, is hydrolyzed to the related hemiacetal which then reacts directly with erythromycylamine to form crystalline dirithromycin.Type: GrantFiled: July 20, 1993Date of Patent: November 26, 1996Assignee: Eli Lilly and CompanyInventor: John M. McGill, III
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Patent number: 5561118Abstract: Compounds of the formula ##STR1## wherein X and X' form C.dbd.O or C.dbd.NOR, R is selected from the group consisting of hydrogen, heterocycle, alkyl, alkenyl, alkynyl, all optionally substituted, or X is ##STR2## R.sub.a and R.sub.b are hydrogen or a hydrocarbon group or form together with the nitrogen a heterocycle, or with A forms a 9-N, 11-0 ring, and X' is hydrogen, --Y and Y' have the same definition as X and X', B is hydrogen or OR.sub.4, R.sub.4 is hydrogen or forms together with A a carbonate or a carbamate, A forms with C a double bond or A is OR'.sub.4, R'.sub.4 is hydrogen or forms together with B a carbonate or A is ##STR3## R.sub.2 is alkyl or --CONH.sub.2, --CONHCOR.sub.11 or --CONHSO.sub.2 R.sub.11, R.sub.11 is a hydrocarbon up to 18 carbon atoms, R.sub.3 is hydrogen, ##STR4## and Z is hydrogen or a carboxylic acid remainder and their non-toxic, pharmaceutically acceptable acid addition salts, their preparation and intermediates useful as antibiotics.Type: GrantFiled: March 31, 1994Date of Patent: October 1, 1996Assignee: Roussel UclafInventors: Constantin Agouridas, Yannick Benedetti, Jean-Francois Chantot, Alexis Denis, Claude Fromentin, Odile Le Martret
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Patent number: 5559098Abstract: A stable topical formulation with good active ingredient release characteristics, comprising at least one macrolide antibiotic which is lipophilized with at least one former of oppositely charged ions which is selected from the group consisting of alkyl sulfates, alkylsulfonates, and alkyl salicylates, RX, where R represents a linear and/or branched alkyl group with 6-32 C atoms, and X represents a sulfate, sulfonate, or salicylate group.Type: GrantFiled: January 30, 1995Date of Patent: September 24, 1996Assignee: Roehm Pharma GmbHInventors: Wolfgang A. Wohlrab, Reinhard Neubert, Sybille Matschiner, Katrin Wellner
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Patent number: 5556839Abstract: The invention provides Form II dirithromycin, a novel polymorph of dirithromycin. Also disclosed are the acetone, 1-butanol, 1-propanol, and 2-propanol solvates of dirithromycin, which provide an efficient means for preparing and isolating Form II. Processes for preparing and isolating Form II dirithromycin from these solvates or from Form I dirithromycin are provided. A process for obtaining Form II dirithromycin from non-solvated dirithromycin is also provided. Another aspect of the invention is an improved tablet containing Form II dirithromycin as the active ingredient.Type: GrantFiled: January 9, 1995Date of Patent: September 17, 1996Assignee: Eli Lilly and CompanyInventors: James M. Greene, Holly M. Hankins, Gregory A. Stephenson
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Patent number: 5543400Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is ##STR2## m and n are individually integers from 0 to 6, A and B are individually a member selected from the group consisting of hydrogen, halogen and alkyl of 1 to 8 carbon atoms, the double bond geometry being E or Z or E+Z or A and B form a third bond between the carbon atoms to which they are attached, Ar is selected from the group consisting of a) carbocyclic aryl of up to 18 carbon atoms optionally substituted with at least one member of the group consisting of free carboxy, alkoxycarbonyl, carboxy salified with a non-toxic, pharmaceutically acceptable base, amidified carboxy, --OH, halogen, --NO.sub.2, --CN, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio and alkynylthio of up to 12 carbon atoms, N-alkyl, N-alkenyl and N-alkynyl of up to 12 carbon atoms and cycloalkyl of 3 to 12 carbon atoms, all optionally substituted with at least one halogen and ##STR3## R.sub.1 and R.sub.Type: GrantFiled: November 1, 1993Date of Patent: August 6, 1996Assignee: Roussel UclafInventors: Constantin Agouridas, Alain Bonnefoy, Jean-Fran.cedilla.ois Chantot, Alexis Denis, Odile Le Martret
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Patent number: 5527780Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is --(CH.sub.2).sub.n --Ar.sub.1 or --XAr.sub.2, n is an integer from 1 to 6, Ar.sub.1 and Ar.sub.2 are individually selected from the group consisting of a) carbocyclic aryl of up to 18 carbon atoms substituted by at least one member of the group consisting of free carboxy, alkoxy carbonyl and carboxyl salified with a pharmaceutically acceptable base, --OH, halogen, --NO.sub.2, --CN, ##STR2## and alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, N-alkyl, N-alkenyl and N-alkynyl of up to 12 carbon atoms optionally substituted with at least one halogen, R.sub.1 and R.sub.2 are individually hydrogen or alkyl of 1 to 12 carbon atoms, b) ##STR3## wherein R.sub.Type: GrantFiled: November 1, 1993Date of Patent: June 18, 1996Assignee: Roussel UclafInventors: Constantin Agouridas, Alain Bonnefoy, Jean-Francois Chantot, Alexis Denis, Odile Le Martret
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Patent number: 5523399Abstract: Provision of novel macrolide antibiotics having a strong antibacterial activity.Construction:Compounds represented by the formula: ##STR1## which are obtained by introducing a carbamoyl group into 5-O-desosaminyl-6-O-methylerythronolide derivatives at the 3-position; and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: June 20, 1994Date of Patent: June 4, 1996Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshifumi Asaka, Yoko Misawa, Masato Kashimura, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5476843Abstract: A stable topical formulation with good active ingredient release characteristics, comprising at least one macrolide antibiotic which is lipophilized with at least one former of oppositely charged ions which is selected from the group consisting of alkyl sulfates, alkylsulfonates, and alkyl salicylates, RX, where R represents a linear and/or branched alkyl group with 6-32 C atoms, and X represents a sulfate, sulfonate, or salicylate group.Type: GrantFiled: October 4, 1993Date of Patent: December 19, 1995Assignee: Roehm Pharma GmbHInventors: Wolfgang A. Wohlrab, Reinhard Neubert, Sabine Matschiner, Katrin Wellner
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Patent number: 5470961Abstract: Disclosed are (1) a structurally novel 6,9-hemiacetal-erythromycin derivative having a hydroxyl group at at least one of the 14- and 15-positions or a salt thereof, which has an excellent gastrointestinal function promoting effect and is low in toxicity; (2) a process for preparing a 6,9-hemiacetal-erythromycin derivative having a hydroxyl group at at least one of the 14- and 15-positions or a salt thereof, which comprises reacting a 6,9-hemiacetal-erythromycin derivative or a salt thereof with an organism-derived oxidase; and (3) a gastrointestinal function promoting agent containing a 6,9-hemiacetal-erythromycin derivative having a hydroxyl group at at least one of the 14- and 15-positions or a salt thereof.Type: GrantFiled: March 19, 1993Date of Patent: November 28, 1995Assignees: Takeda Chemical Ind., Ltd., Kitasato KenkyushioInventors: Setsuo Harada, Yasunori Funabashi, Nobuhiro Inatomi, Shigeharu Tanayama, Seiichi Tanida
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Patent number: 5444051Abstract: Compounds of the formula ##STR1## wherein X and X' form C.dbd.O or C.dbd.NOR, R is selected from the group consisting of hydrogen, heterocycle, alkyl, alkenyl, alkynyl, all optionally substituted,or X is ##STR2## R.sub.a and R.sub.b are hydrogen or a hydrocarbon group or form together with the nitrogen a heterocycle, or with A forms a 9-N, 11-O ring, and X' is hydrogen, --Y and Y' have the same definition as X and X', B is hydrogen or OR.sub.4, R.sub.4 is hydrogen or forms together with A a carbonate or a carbamate, A forms with C a double bond or A is OR'.sub.4, R'.sub.4 is hydrogen or forms together with B a carbonate or ##STR3## R.sub.2 is alkyl or --CONH.sub.2, --CONHCOR.sub.11 or --CONHSO.sub.2 R.sub.11, R.sub.11 is a hydrocarbon up to 18 carbon atoms, R.sub.3 is hydrogen, ##STR4## and Z is hydrogen or a carboxylic acid remainder and their non-toxic, pharmaceutically acceptable acid addition salts, their preparation and intermediates useful as antibiotics.Type: GrantFiled: June 28, 1993Date of Patent: August 22, 1995Assignee: Roussel UCLAFInventors: Constantin Agouridas, Yannick Benedetti, Jean-Francois Chantot, Alexis Denis, Claude Fromentin, Odile Le Martret
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Patent number: 5441939Abstract: A compound having the formula ##STR1## wherein Z is CH.sub.2 --N(CH.sub.3), N(CH.sub.3)--CH.sub.2, or ##STR2## R.sup.1 and R.sup.2 are selected from 1) one of R.sup.1 and R.sup.2 is OH and the other of R.sup.1 and R.sup.2 is (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, or phenyl, with the proviso that Z is not CO;2) one of R.sup.1 and R.sup.2 is H and the other of R.sup.1 and R.sup.2 is NR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 are independently selected from H and (C.sub.1 -C.sub.6)alkyl, or is OR.sup.7 wherein R.sup.7 is H or (C.sub.1 -C.sub.6)alkyl; and3) R.sup.1 and R.sup.2 together form an oxo or oxime group;R.sup.3 and R.sup.4 are each hydroxyl or together form a carbonate or thiocarbonate group; and pharmaceutically acceptable salts thereof.Type: GrantFiled: March 4, 1994Date of Patent: August 15, 1995Assignee: Pfizer Inc.Inventor: Bingwei V. Yang
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Patent number: 5439889Abstract: All possible stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein the substituents are as defined in the specification and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties.Type: GrantFiled: March 7, 1994Date of Patent: August 8, 1995Assignee: Roussel UclafInventors: Constantin Agouridas, Yannick Benedetti, Jean-Francois Chantot, Alexis Denis
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Patent number: 5439890Abstract: A compound of the formula ##STR1## wherein A and B are both hydrogen or A is hydrogen and B is --OH or A and B form a carbon-carbon double bond and Z is hydrogen or acyl of an organic carboxylic acid of 1 to 6 carbon atoms and their nontoxic, pharmaceutically acceptable acid addition salts having antibiotic activity.Type: GrantFiled: November 14, 1994Date of Patent: August 8, 1995Assignee: Roussel-UclafInventors: Constantin Agouridas, Jean-Francois Chantot, Nicole Tessot
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Patent number: 5434140Abstract: The invention relates to 9-deoxo-9a-aza-11-deoxy-9a-homoerythromycin A 9a,11-cyclic carbamates, novel semisynthetic macrolide antibiotics from the genus of azalides, of the formula (I) ##STR1## whereinR.sup.1 .dbd.R.sup.2 .dbd.CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 .dbd.R.sup.4 .dbd.CH.sub.3, (IA)R.sup.1 .dbd.R.sup.2 .dbd.CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 .dbd.CH.sub.3, R.sup.4 .dbd.H, (IB)R.sup.1 .dbd.R.sup.2 .dbd.CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 .dbd.R.sup.4 .dbd.H, (IC)R.sup.1 .dbd.R.sup.2 .dbd.H, R.sup.3 .dbd.R.sup.4 .dbd.CH.sub.3,(ID)R.sup.1 .dbd.R.sup.2 .dbd.R.sup.4 .dbd.H, R.sup.3 .dbd.CH.sub.3,(IE)R.sup.1 .dbd.R.sup.2 .dbd.R.sup.3 .dbd.R.sup.4 .dbd.H, (IF)R.sup.1 .dbd.H, R.sup.2 .dbd.R.sup.3 .dbd.R.sup.4 .dbd.CH.sub.3,(IG)R.sup.1 .dbd.R.sup.4 .dbd.H, R.sup.2 .dbd.R.sup.3 .dbd.CH.sub.3,(IH)R.sup.1 .dbd.R.sup.3 .dbd.R.sup.4 .dbd.H, R.sup.2 .dbd.CH.sub.Type: GrantFiled: January 7, 1994Date of Patent: July 18, 1995Assignee: Pliva, Farmaceutska, Kemijska, Prehranbena I Kozmeticka Industrija Dionicko Drustvo ZagrebInventors: Gabrijela Kobrehel, Gorjana Lazarevski, Slobodan Djokic
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Patent number: 5403923Abstract: This invention provides 6-O-methylerythromycin A derivatives represented by the following formula ##STR1## (wherein R.sup.1 and R.sup.2 each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and A represents a nitrogen atom or a N.fwdarw.O group) and their pharmaceutically acceptable salts. The erythromycin A derivatives have a strong antimicrobial activity against Gram-negative bacteria and have a much stronger activity against Gram-positive bacteria than previously known compounds.Type: GrantFiled: May 20, 1993Date of Patent: April 4, 1995Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Masato Kashimura, Toshifumi Asaka, Shigeo Morimoto, Katsuo Hatayama
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Patent number: 5350839Abstract: Erythromycins showing an extremely relieved bitterness at administration and an improved absorbability in vivo when orally administered are provided.A compound having a group represented by the following formula:--O--CO--O--[(CH.sub.2).sub.m --O].sub.n --R(wherein R represents an alkyl group having from 1 to 12 carbon atoms, m represents an integer of from 2 to 4, and n represents an integer of from 1 to 7) at the 2'-position of erythromycins or a salt thereof.Type: GrantFiled: April 15, 1993Date of Patent: September 27, 1994Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshifumi Asaka, Yoko Misawa, Masato Kashimura, Shigeo Morimoto, Yoshiaki Watanabe, Katsuo Hatayama
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Patent number: 5332807Abstract: A process of producing 8a- and 9a- azalide compounds is disclosed, comprised of reacting an 8a- aza or 9a- aza azalide eastern fragment or a derivative thereof with a compound of the formula:X--A'--Ywherein X and Y are appropriate reactive groups and A' is a fragment or compound which forms the western portion of the azalide, andcyclizing this intermediate to form the target 8a- or 9a-azalide compound. Compounds of formula I, II and III as well as other azalides can be synthesized according to this process.Type: GrantFiled: April 14, 1993Date of Patent: July 26, 1994Assignee: Merck & Co., Inc.Inventors: Sherman T. Waddell, Timothy A. Blizzard
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Patent number: 5302705Abstract: A 6-O-methylerythromycin A oxime derivative represented by the formula ##STR1## wherein X is a substituted benzyl group, a substituted phenyl group, an .alpha.-methylbenzyl group, an .alpha.-methylphenethyl group, a diphenylmethyl group, a trityl group, a dibenzosuberanyl group, or a group of the formula --(CH.sub.2).sub.n --R, and Y is a hydrogen atom, a substituted phenyl group or a 2-aminothiazol-4-ylmethylcarbonyl group, and a pharmaceutically acceptable salt thereof are disclosed. These compounds have antibacterial activity against erythromycin resistant bacteria.Type: GrantFiled: October 1, 1990Date of Patent: April 12, 1994Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Yoko Misawa, Toshifumi Asaka, Masato Kashimura, Shigeo Morimoto, Yoshiaki Watanabe, Katsuo Hatayama
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Patent number: 5294703Abstract: Provided is a novel improved process for the preparation of .alpha.-D-cellobiose octaacetate via the acetylative degradation of cellulose or cellulose acetate. The title compound is provided in high yield and quality in a facile one-pot process, amenable to large-scale synthesis.Type: GrantFiled: April 7, 1993Date of Patent: March 15, 1994Assignee: Eastman Kodak CompanyInventors: John A. Hyatt, Tony L. Sander, D. Mark Naylor, Bobby L. Bernard
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Patent number: 5288709Abstract: New 9-deoxo-9,12-epoxy erythromycin derivatives are disclosed which have improved antibacterial properties. Compositions comprising the erythromycin derivatives and methods of treating mammalian patients with the erythromycin derivatives are also disclosed.Type: GrantFiled: August 21, 1991Date of Patent: February 22, 1994Assignee: Abbott LaboratoriesInventors: Leslie A. Freiberg, Larry L. Klein, Clinton M. Yeung, Carla M. Edwards, David J. Bacino
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Patent number: 5274085Abstract: A process for preparing erythromycin A oxime or a salt thereof which comprises reacting erythromycin A with hydroxylamine using an acid, is disclosed. Erythromycin A oxime and the salts thereof are useful as intermediates for the synthesis of macrolide antibiotics.Type: GrantFiled: May 12, 1989Date of Patent: December 28, 1993Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa
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Patent number: 5268462Abstract: Oleandomycin oximes ##STR1## wherein R.sup.1 stands for hydrogen or --CH.sub.3, R.sup.2 stands for --CH.sub.3 or hydrogen or R.sup.1 and R.sup.2 stand together for an epoxide group or for .dbd.CH.sub.2, R.sup.3 stands for --OH, whereas the line stands for a single or a double bond, a process for the preparation thereof and their use in antimicrobial agents.Type: GrantFiled: March 14, 1991Date of Patent: December 7, 1993Assignee: Pliva FarmaceutskaInventors: Gorjana Lazarevski, Slobodan Djokic
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Patent number: 5250518Abstract: The invention relates to O-methyl derivatives of azithromycin A of the formula (I) ##STR1## wherein Ia R.sup.1 =R.sup.2 =CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 =CH.sub.3, R.sup.4 =R.sup.5 =HIb R.sup.1 =R.sup.2 =CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 =R.sup.4 =CH.sub.3, R.sup.5 =HIc R.sup.1 =R.sup.2 =CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 =R.sup.5 =H, R.sup.4 =C.sub.3Id R.sup.1 =R.sup.2 =CO.sub.2 CH.sub.2 C.sub.6 H.sub.5, R.sup.3 =R.sup.4 =R.sup.5 =CH.sub.3Ie R.sup.1 =R.sup.2 =R.sup.4 =R.sup.5 =H, R.sup.3 =CH.sub.3If R.sup.1 =R.sup.2 =R.sup.5 =H, R.sup.3 =R.sup.4 =CH.sub.3Ig R.sup.1 =R.sup.2 =R.sup.3 =R.sup.5 =H, R.sup.4 =CH.sub.3Ih R.sup.1 =R.sup.2 =H, R.sup.3 =R.sup.4 =R.sup.5 =CH.sub.3Ii R.sup.1 =R.sup.4 =R.sup.5 =H, R.sup.2 =R.sup.3 =CH.sub.3Ij R.sup.1 =R.sup.5 =H, R.sup.2 =R.sup.3 =R.sup.4 =CH.sub.3Ik R.sup.1 =R.sup.3 =R.sup.5 =H, R.sup.2 =R.sup.4 =CH.sub.3Il R.sup.1 =H, R.sup.2 =R.sup.3 =R.sup.4 =R.sup.5 =CH.sub.Type: GrantFiled: July 18, 1991Date of Patent: October 5, 1993Assignee: Pliva Farmaceutska, Kemijska, Prehrambena I KozmetickaInventors: Gabrijela Kobrehel, Slobodan Djokic, Gorjana Lazarevski
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Patent number: 5217960Abstract: Antibacterial compounds are disclosed having the formula ##STR1## and pharmaceutically acceptable salts thereof, wherein R.sup.1 is --NR.sup.4 R.sup.6, where R.sup.4 and R.sup.6 are independently selected from the group consisting of hydrogen, loweralkyl and arylalkyl or, together, R.sup.4 and R.sup.6 form a nitrogen-containing heterocycle attached at the nitrogen atom; R.sup.2 is selected from the group consisting of hydrogen, --OH and, when R.sup.3 is methylene, oxygen so as to form an epoxide; and R.sup.3 is selected from the group consisting of --CH.sub.2 OH, --NR.sup.4 R.sup.6, --(CH.sub.2).sub.n NR.sup.4 R.sup.6 and, when R.sup.2 is oxygen, methylene so as to form an epoxide, where n is 1-4 and R.sup.4 and R.sup.6 are as previously defined, with the proviso that when R.sup.2 is --OH, R.sup.3 may not be --NR.sup.4 R.sup.6 ; or R.sup.2 and R.sup.3 together are.dbd.CH.sub.2.Type: GrantFiled: May 3, 1991Date of Patent: June 8, 1993Assignee: Abbott LaboratoriesInventors: Paul A. Lartey, Ramin Faghih, Shari DeNinno
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Patent number: 5175150Abstract: Disclosed are novel erythromycin derivatives, or salts thereof, represented by the following general formula: ##STR1## and processes for preparing the same. The erythromycin derivatives described above have an excellent effect of stimulating the gastrointestinal contractile motion and have low toxicity, and the preparations containing these compounds can be advantageously used as digestive tract contractile motion stimulants.Type: GrantFiled: December 17, 1990Date of Patent: December 29, 1992Assignee: Kitasato, KenkyushoInventors: Satoshi Omura, Zen Itoh
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Patent number: 5141929Abstract: Ethers and/or esters of D-desosamine having the formula ##STR1## whereinn represents 0 or 1; R and R', each independently, represent linear or branched alkyl having 1-30 carbon atoms, alkenyl having 5-21 carbon atoms, cycloalkyl having 4-10 carbon atoms, cycloalkylalkyl having 5-11 carbon atoms or phenyl or arylalkyl optionally substituted; or R can represent hydrogen when n=1 and R' can represent hydrogen when n=0, the number of carbon atoms of R, R' or R+R' being equal to 9 to 33 inclusive; or R represents the aglyconic part of erythralosamine and R' represents linear or branched alkyl having 9-30 carbon atoms or alkenyl having 11-21 carbon atoms; and the .alpha. and .beta. anomers, their mixture and their salts.These compounds are usefully employed as anti-bacteria and anti-fungus agents in pharmaceutical and cosmetic compositions.Type: GrantFiled: December 6, 1989Date of Patent: August 25, 1992Assignee: Societe Anonyme dite: L'OrealInventors: Michel Phillippe, Henri Sebag
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Patent number: 5110800Abstract: Three new groups of 9-N-substituted derivatives of erythromycylamine with superior oral activity against Gram-positive pathogens, new processes for preparing derivatives of erythromycylamine and aliphatic aldehydes by controlling the pH of the reaction and by catalytic hydrogenation, and pharmaceutical compositions and methods using the new compounds are provided.Type: GrantFiled: August 18, 1989Date of Patent: May 5, 1992Assignee: Eli Lilly and CompanyInventors: Rosanne Bonjouklian, Manuel Debono, Herbert A. Kirst, Julie A. Wind
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Patent number: 5075289Abstract: Semisynthetic antibiotics with improved therapeutic properties are disclosed. In particular, 9-R-azacyclic derivatives of erythromycin, its derivatives, and their salts and esters show superior antimicrobial activity compared to other macrolide compounds.Type: GrantFiled: June 7, 1988Date of Patent: December 24, 1991Assignee: Abbott LaboratoriesInventors: Richard J. Pariza, Paul A. Lartey, Clarence J. Maring, Larry L. Klein
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Patent number: 5008249Abstract: Disclosed are digestive tract contractile motion stimulants containing compounds, or salts thereof, represented by the following general formula: ##STR1## The compounds described above have an excellent effect of stimulating the gastrointestinal contractile motion, and the preparation of the present invention containing these compounds can be advantageously used as digestive tract contractile motion stimulants.Type: GrantFiled: August 25, 1986Date of Patent: April 16, 1991Assignee: Kitasato KenkyushoInventors: Satoshi Omura, Zen Itoh
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Patent number: 4990602Abstract: Erthromycin A derivatives represented by the general formula ##STR1## wherein R.sup.1 is a group of the formula R.sup.7 CH.sub.2 -- (wherein R.sup.7 is a hydrogen group or a lower alkyl group) or a group of the formula R.sup.8 O-- (wherein R.sup.8 is a lower alkyl group), R.sup.2 is R.sup.8, a cycloalkyl group, a phenyl group or an aralkyl group.), or R.sup.2 and R.sup.7 together form an alkylene group, R.sup.3 is a hydrogen atom, a lower alkyl group, a phenyl group or an aralkyl group, or R.sup.3 and R.sup.7 together form an alkylene group, or R.sup.2 and R.sup.3 together form an alkylene group, R.sup.4 is a lower alkyl group, R.sup.5 is a substituted silyl group, and R.sup.6 is a hydrogen atom or R.sup.5, are disclosed. These compounds are useful as intermediates for the synthesis of antibacterial agents.Type: GrantFiled: December 12, 1988Date of Patent: February 5, 1991Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Shigeo Morimoto, Takashi Adachi, Tohru Matsunaga, Masato Kashimura, Toshifumi Asaka, Yoshiaki Watanabe, Kaoru Sota, Kazuto Sekiuchi
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Patent number: 4963531Abstract: A method of use of azithromycin or derivatives of azithromycin in the treatment of infection caused by Toxoplasma gondii in mammals is disclosed.Type: GrantFiled: August 16, 1988Date of Patent: October 16, 1990Assignee: Pfizer Inc.Inventor: Jack S. Remington