The Hetero Ring Has Exactly 15 Ring Carbons Patents (Class 514/30)
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Patent number: 6013636Abstract: A composition comprising an anthelmintic chosen from the class of macrocyclic lactones including but not limited to the avermectins, ivermectin, doramectin, abamectin, milbemycin and moxidectin, together with a vegetable oil and a co-solvent chosen from the group comprising alcohols having four or more carbons atoms. The compositions of the inventions may be formulated as injections, drenches or for topical administration and are suitable for treating helminthiasis in animals.Type: GrantFiled: March 25, 1998Date of Patent: January 11, 2000Assignee: Ashmont Holdings LimitedInventor: Colin Manson Harvey
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Patent number: 5989566Abstract: The invention relates to certain stable vaccine compositions comprising a macrocyclic lactone compound, a milbemycin compound, an avermectin compound or mixtures thereof; at least one antigen; a dispersing agent; an adjuvant; a water soluble organic solvent; and saline or water or mixtures thereof. The invention further relates to stable compositions as described above of a macrocyclic lactone compound, a milbemycin compound, an avermectin compound or mixtures thereof, but without an antigen. The invention also relates to a method for preventing or controlling helminthiasis, infection by acarids and arthropod endo-and ectoparasites and bacterial and viral disease in warm-blooded animals by the parenteral administration of compositions of the invention. The invention further relates to a process for the preparation of the invention compositions.Type: GrantFiled: June 28, 1996Date of Patent: November 23, 1999Assignee: American Cyanamid CompanyInventors: Ramune Marija Cobb, Christopher Leigh Schwartzkoff
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Patent number: 5981500Abstract: A 5-oximino-25-substituted avermectin B1 or B2 monosaccharide of formula I herein has use in the treatment of parasitic infections in animals and humans. The compounds may be prepared from corresponding 5-keto substituted derivatives.Type: GrantFiled: May 9, 1997Date of Patent: November 9, 1999Assignee: Pfizer Inc.Inventors: Bernard Frank Bishop, Michael Stephen Pacey, David Austen Perry
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Patent number: 5958888Abstract: Water miscible pharmaceutical compositions containing up to about 40% of a macrolide antibiotic are prepared by reaction of the macrolide with acid in a non-aqueous water miscible organic solvent system.Type: GrantFiled: July 9, 1998Date of Patent: September 28, 1999Assignee: Merial, Inc.Inventors: Lowell R. Macy, Raymond E. Hopponen, Roger A. Wilson, James B. Williams
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Patent number: 5922684Abstract: The invention relates to 13-hydroxy-tylosine derivatives, novel semisynthetic antibiotics from the class of macrolides, and to a process for the preparation thereof. According to the present invention by a reductive opening of the oxirane ring of tylosine 13-hydroxy compounds are obtained, which are then subjected to a hydrogenation of the double bond and then 13-hydroxy dihydro or tetrahydro compounds are subjected to an oximation reaction or 13-hydroxy oximes are subjected to the hydrogenation of the double bond.Type: GrantFiled: October 28, 1997Date of Patent: July 13, 1999Assignee: Pliva, Farmaceutska, Kemijska, Prehrambenai Kozmeticka Industrija, Dionicko DrustvoInventors: Amalija Narandja, Nevenka Lopotar
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Patent number: 5891855Abstract: This invention provides methods of inhibiting the export of a leaderless protein from a cell by contacting the cell with a cardiac glycoside or aglycone derivative. Leaderless proteins include FGF-1, FGF-2, IL,-1.alpha., IL-1.beta. and factor XIIIa. These methods are useful in treatment of conditions, including tumors and diabetes.Type: GrantFiled: February 12, 1996Date of Patent: April 6, 1999Assignee: The Scripps Research InstituteInventor: Robert Z. Florkiewicz
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Patent number: 5885601Abstract: The present invention relates to a method of female sterilization including delivery of a macrolide antibiotic or a pharmacologically acceptable salt of a macrolide antibiotic to the uterine cavity or fallopian tube of the female. The present invention also relates to a method of endometrial ablation including delivery of a macrolide antibiotic or a pharmacologically acceptable salt of a macrolide antibiotic to the uterine cavity of a female. The endometrial ablation effected in this manner may be used to treat the conditions of excessive menstrual bleeding or menstrual pain in women. A preferred macrolide antibiotic is erythromycin, or its pharmacologically acceptable salts.Type: GrantFiled: April 4, 1997Date of Patent: March 23, 1999Assignee: Family Health InternationalInventor: David C. Sokal
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Patent number: 5872104Abstract: Disclosed are novel methods, combinations of agents and kits for use in killing, or inhibiting the growth of, microorganisms. Enhanced antimicrobial action is provided by using a methylation inhibitor, as exemplified by using an agent that inhibits methylation or maturation of bacterial RNA in combination with, e.g., a macrolide lincosamide streptogramin B (MLS) antibiotic. The methods and compositions described may be employed to reduce the resistance of susceptible microorganisms to antimicrobial agents and thus to treat animals or patients with infections.Type: GrantFiled: December 27, 1994Date of Patent: February 16, 1999Assignee: Oridigm CorporationInventors: Nicolaas M. J. Vermeulen, Dennis E. Schwartz
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Patent number: 5866596Abstract: The present invention relates to the derivatives of formula: ##STR1## and to their use in therapeutics, especially as drugs with anti-inflammatory and analgesic properties.Type: GrantFiled: March 24, 1997Date of Patent: February 2, 1999Assignee: Laboratories UPSAInventors: Eric Sartori, Jean-Marie Teulon
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Patent number: 5840704Abstract: The invention provides novel compounds having the formula: ##STR1## wherein R when taken individually is H; R.sup.1 when taken individually is H or OH; R and R.sup.1 when taken together represent a double bond;R.sup.2 is an alpha-branched C.sub.3 -C.sub.8 alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl group; a C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl or C.sub.5 -C.sub.8 cycloalkylalkyl group, any of which may be substituted by methylene or one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms;R.sup.3 is hydrogen or methyl;R.sup.4 is H or 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy with the proviso that when R.sup.2 is alkyl it is not isopropyl or sec-butyl; when R.sup.4 is H, each of R and R.sup.1 is H, and R.sup.2 is not methyl or ethyl; and when R.sup.Type: GrantFiled: March 23, 1993Date of Patent: November 24, 1998Assignee: Pfizer Inc.Inventors: Stephen P. Gibson, Alexander C. Goudie, Kelvin S. Holdom, John D. Bu'Lock
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Patent number: 5830875Abstract: Novel avermectin and milbemycin derivatives are disclosed, where the C-24 and C-25 carbon atoms are substituted by hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl groups. These compounds can be further substituted at the 4"-, 5-, 13-, and 23-positions. The new C-24 and C-25 substituted avermect prepared by cleavage of known and suitably protected avermectin and milbemycin compounds. The new compounds are potent anti-parasitic agents, in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: October 30, 1989Date of Patent: November 3, 1998Assignee: Merck & Co., Inc.Inventors: Helmut Mrozik, Thomas L. Shih
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Patent number: 5824653Abstract: The Invention relates to an anthelmintic composition for oral use comprising an effective amount of praziquantel and an effective amount of at least one anthelmintic agent selected from avermectins, milbemycins or derivatives thereof and to a method for controlling and treating infestations by cestodes and nematodes in equine animals comprising orally administering such a composition to said animals.Type: GrantFiled: November 27, 1995Date of Patent: October 20, 1998Assignee: Virbac S.A.Inventors: Vincent Beuvry, Michael Forster
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Patent number: 5773422Abstract: Novel formulations are disclosed for the administration of an avermectin, based upon the use of N-methylpyrrolidone or 2-pyrrolidone or mixtures thereof to dissolve avermectin. Formulations can contain from 0.1 to 40% by weight dissolved in at least 5% by volume of N-methylpyrrolidone, 2-pyrrolidone or mixture thereof. Various formulations are suitable for administration by intramuscular or subcutaneous injection, by topical application, stomach intubation, oral and drench administration.Type: GrantFiled: January 29, 1996Date of Patent: June 30, 1998Inventor: Gene Komer
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Patent number: 5760011Abstract: Derivatives of 16-membered ring 3-deoxy macrolide antibiotic derivatives of rosaramicin, repromicin, 5-mycaminosyltylonolide, desmycosin, lactenocin, O-demethyllactenocin, cirramycin A.sub.1, and 23-deoxymycaminosyltylonolide, which are useful against bacterial and mycoplasmic pathogens in animals.Type: GrantFiled: November 26, 1996Date of Patent: June 2, 1998Assignee: Pfizer Inc.Inventors: Burton H. Jaynes, Martin R. Jefson, Kristin M. Lundy
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Patent number: 5756474Abstract: The invention is directed to a novel non-aqueous oral-drench composition comprising from 0.01% to 2.0% (w/v) of an avermectin compound; from 30% to 45% (w/w) of an oil, said oil being selected from the group consisting of corn oil, sunflower oil, peanut oil and safflower oil; from 0.01% to 1.0% (w/v) of an oil-soluble antioxidant; and from 50% to 70% (w/w) of a fatty acid ester, said fatty acid ester being selected from the group consisting of caprylic/capric triglyceride, octyl palmitate and propylene glycol dicaprylate/dicaprate. The invention is further directed to methods of using the non-aqueous composition to treat parasitic diseases in mammals.Type: GrantFiled: April 8, 1997Date of Patent: May 26, 1998Assignee: Pfizer, Inc.Inventor: Kai-Uwe Furstenau
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Patent number: 5723488Abstract: A compound of formula (I): ##STR1## wherein the broken lines represent independently optional bonds, R.sup.1 and R.sup.2 being absent when the C.sub.22 -C.sub.23 double bond is present.Type: GrantFiled: August 12, 1996Date of Patent: March 3, 1998Assignee: Pfizer Inc.Inventor: Nigel Derek Walshe
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Patent number: 5716939Abstract: The present invention relates to amide derivatives of formula (I) or (II) of 19-carboxy-19-deformyl 16-membered ring macrolide antibiotics rosaramicin, repromicin, tylosin, 5-O-mycaminosyltylonolide, 4-deoxy-O-mycaminosyltylonolide, desmycosin lactenocin, O-demethyllactenocin, cirramycin A.sub.1, and 23-deoxymycaminosyltylonolide, which are useful against bacterial and mycoplasmic pathogens in animals. Also claimed are a pharmaceutical composition of such derivatives and their use in treating bacterial and mycoplasmic infections in animals.Type: GrantFiled: December 22, 1995Date of Patent: February 10, 1998Assignee: Pfizer Inc.Inventors: Kristin Marie Lundy, Chi B. Vu
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Patent number: 5707839Abstract: The present invention relates to novel DNA sequences that encode for the branched-chain alpha-ketoacid dehydrogenase complex of an organism belonging to the genus Streptomyces and to novel polypeptides produced by the expression of such sequences. It also relates to novel methods of enhancing the production of natural avermectin, of producing a Streptomyces avermitilis bkd mutant and of producing novel avermectins through fermentation.Type: GrantFiled: June 6, 1995Date of Patent: January 13, 1998Assignee: Pfizer Inc.Inventors: Claudio D. Denoya, Kim J. Stutzman-Engwall
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Patent number: 5698420Abstract: Preparation of 4'-deoxy-O-mycaminosyltylonolide by feeding repromicin to a fermentation broth of a strain of the microorganism Streptomyces fradiae (ATCC 31733) under aerobic conditions in an aqueous nutrient medium containing inorganic salts and assimilable sources of carbon and nitrogen.Type: GrantFiled: November 26, 1996Date of Patent: December 16, 1997Assignee: Pfizer Inc.Inventor: Lapyuen H. Lam
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Patent number: 5698592Abstract: Methods and compositions for the control of nematodes are disclosed. Specifically, fatty acid ester compounds have been found to advantageously control nematodes at concentrations which are non-phytotoxic. The fatty acid ester compounds can be used in conjunction with other nematicidal agents such as free fatty acids, fatty acid salts, avermectins, ivermectin, and milbemycin.Type: GrantFiled: October 17, 1996Date of Patent: December 16, 1997Assignee: Mycogen CorporationInventors: Leo Kim, Jerald S. Feitelson, John Harvey, Paul S. Zorner
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Patent number: 5696095Abstract: New formulations of spiramycin suitable for oral administration, particularly for children, comprise spiramycin and potassium acesulfame. These formulations mask the bitterness of spiramycin without adversely affecting the bioavailability or stability of the spiramycin. Preparation by wet granulation followed by dry state mixing is also disclosed.Type: GrantFiled: June 6, 1995Date of Patent: December 9, 1997Assignee: Rhone-Poulenc Rorer S.A.Inventors: Francois-Xavier Piot, Robert Rona
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Patent number: 5686274Abstract: A process for separating a natural B avermectin from a natural avermectin containing fermentation broth by using an aqueous precipitation. The process comprises extracting natural avermectins from the fermentation broth with a water miscible solvent and adding sufficient water to precipitate the natural B avermectins. Preferably, the water miscible solvent is a C.sub.1 -C.sub.3 alcohol, acetone, or acetonitrile. In addition, an acid, base, salt or surfactant may be added to facilitate the precipitation. This invention provides an isolation technique that substitutes the use of an aqueous precipitation for nonaqueous solvent precipitations. The reduction in use of nonaqueous solvents provides economic, environmental and safety benefits.Type: GrantFiled: January 16, 1996Date of Patent: November 11, 1997Assignee: Pfizer Inc.Inventor: Abdullah R. Ali
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Patent number: 5677287Abstract: The present invention relates to C-20 olefin derivatives of 16-membered macrolide antibiotics repromicin, rosaramicin, 5-mycaminosyltylonolide, desmycosin, lactenocin, O-demethyllactenocin, 4'-deoxymycaminosyltylonolide and 23-deoxymycaminosyltylonolide, which are useful against bacterial and mycoplasmic pathogens in animals. Also claimed are a pharmaceutical composition of such derivatives and their use in treating bacterial and mycoplasmic infections in animals.Type: GrantFiled: September 11, 1995Date of Patent: October 14, 1997Assignee: Pfizer Inc.Inventor: Burton Humphrey Jaynes
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Patent number: 5674897Abstract: Methods and compositions for the control of nematodes are disclosed. Specifically, fatty acid ester compounds have been found to advantageously control nematodes at concentrations which are non-phytotoxic. The fatty acid ester compounds can be used in conjunction with other nematicidal agents such as free fatty acids, fatty acid salts, avermectins, ivermectin, and milbemycin.Type: GrantFiled: October 20, 1995Date of Patent: October 7, 1997Assignee: Mycogen CorporationInventors: Leo Kim, Jerald S. Feitelson, John Harvey, Paul S. Zorner
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Patent number: 5665708Abstract: Intermediates and a process for preparing doramectin, the compound of formula (I), semisynthetically from by-product in the fermentation procedure which also yields the compound of formula (I). The intermediates prepared by the process of this invention also have utility as antiparasitic agents. The process of this invention utilizes continuous reaction inert gas sparging during the pyrolysis step, resulting in a significant improvement in the overall yield of this conversion.Type: GrantFiled: March 8, 1996Date of Patent: September 9, 1997Assignee: Pfizer Inc.Inventors: Constantine Sklavounos, Thomas Charles Crawford, Neil Demers, Stephen Paul Gibson, Charles William Murtiashaw, deceased
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Patent number: 5643886Abstract: Avermectins and milbemycins to treat endo- and ectoparasitic infestations in dogs.Type: GrantFiled: January 7, 1994Date of Patent: July 1, 1997Assignee: Pfizer Inc.Inventor: John Dick Hood
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Patent number: 5637616Abstract: A method for the topical or systemic treatment of disorders mediated by proteases which result in skin or mucosal lesions, and in particular, pemphigus, cicatricial pemphigoid, bullous pemphigoid, lichen planus, and canker sores, is disclosed wherein the host is treated with an effective amount of N-acetyl ysteine or a derivative thereof, or its pharmaceutically acceptable salt, optionally in a pharmaceutically acceptable diluent or carrier for systemic or topical delivery.Type: GrantFiled: October 5, 1993Date of Patent: June 10, 1997Assignee: Arcturus Pharmaceutical CorporationInventors: Richard J. Sharpe, Maureen H. McAloon, Stephen J. Galli, Kenneth A. Arndt
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Patent number: 5631298Abstract: .beta.-Phenethanolamines are effective in promoting growth and improving feed efficiency and leanness in animals.Type: GrantFiled: May 25, 1995Date of Patent: May 20, 1997Assignee: Eli Lilly and CompanyInventors: David B. Anderson, Edward L. Veenhuizen
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Patent number: 5624935Abstract: Compounds of formula (I): ##STR1## [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.Type: GrantFiled: April 11, 1995Date of Patent: April 29, 1997Assignee: Sankyo Company, LimitedInventors: Takashi Fujita, Takao Yoshioka, Toshihiko Fujiwara, Minoru Oguchi, Hiroaki Yanagisawa, Hiroyoshi Horikoshi, Kunio Wada, Koichi Fujimoto
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Patent number: 5602106Abstract: 16-membered macrolide derivatives represented by the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a substituent group which protects a hydroxyl group; R.sup.2 represents a hydrogen atom or a substituent group which protects a hydroxyl group; R.sup.3 represents a hydrogen atom or a straight-chain aliphatic acyl group having 2 to 4 carbon atoms; and R.sup.4 represents a hydrogen atom or a straight-chain aliphatic or aromatic acyl group having 1 to 10 carbon atoms;or a pharmaceutically acceptable salt thereof are disclosed.A novel process for producing these 16-membered macrolide derivatives is also disclosed.Type: GrantFiled: July 8, 1994Date of Patent: February 11, 1997Assignee: Meiji Seika Kaisha, Ltd.Inventors: Keiichi Ajito, Osamu Hara, Ken-ichi Kurihara, Nobue Kikuchi, Minako Araake, Akira Shimizu, Tsuneo Okonogi, Shigeharu Inouye, Seiji Shibahara
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Patent number: 5602107Abstract: There is disclosed a topical pour-on formulation containing glycols, glycerides, or their derivatives and an avermectin compound (active ingredient) which has been discovered to provide superior efficacy against endoparasites and ectoparasites when compared to conventional formulations and to maintain the concentration of the active compound in the milk of dairy animals below a safe concentration for human consumption. The formulation contains the avermectin active ingredient and at least 50% of the glycol or glyceride.Type: GrantFiled: November 20, 1995Date of Patent: February 11, 1997Assignee: Merck & Co., Inc.Inventor: Hoo-Kyun Choi
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Patent number: 5578581Abstract: An active avermectin analogue which can be produced by directed biosynthesis is described. The compound, named 26-R-Avermectin B.sub.Type: GrantFiled: April 26, 1994Date of Patent: November 26, 1996Assignee: Merck & Co., Inc.Inventors: Prakash S. Masurekar, Wesley L. Shoop, Michael A. Wallace, Richard L. Monaghan
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Patent number: 5574020Abstract: An aqueous, injectable, sustained release tilmicosin formulation comprises 250-350 mg/ml of tilmicosin and 250 mg/ml of propylene glycol, and has a pH adjusted to 6.Type: GrantFiled: January 13, 1995Date of Patent: November 12, 1996Assignee: Eli Lilly and CompanyInventors: Paul R. Klink, Thomas D. Thomson
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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: 5556868Abstract: Avermectin and milbemycin derivatives of formula (I) ##STR1## having a double bond at the 3-4 position and a cyano substituent at the 3-position have outstanding anthelmintic properties. They may be prepared by allowing an avermectin or milbemycin derivative having a leaving group at the 5-position, or having double bonds at the 2-3 and 4-5 positions and no substituent at the 5-position, to react with an ionic cyanide.Type: GrantFiled: September 28, 1994Date of Patent: September 17, 1996Assignee: Pfizer IncInventor: Bernard J. Banks
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Patent number: 5516761Abstract: There is disclosed a topical multiple-point-application formulation containing a solution of a polymeric material and an avermectin compound (active ingredient) which has been discovered to provide superior efficacy against ectoparasites, such as fleas and ticks and endoparasites such as nematodes and heartworms, when compared to conventional formulations. The formulation contains the avermectin active ingredient and up to 50% of the polymeric material.Type: GrantFiled: November 3, 1994Date of Patent: May 14, 1996Assignee: Merck & Co., Inc.Inventors: Hoo-Kyun Choi, James B. Williams
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Patent number: 5499979Abstract: A dispenser for use in a fluid environment which is capable of delivery of plurality of drugs in any desired delivery pattern or profile.Type: GrantFiled: March 10, 1994Date of Patent: March 19, 1996Assignee: Alza CorporationInventors: Patrick S.-L. Wong, Felix Theeuwes, James B. Eckenhoff
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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: 5468735Abstract: Described is a novel animal feed premix including corn cob granules and, incorporated in the corn cob granules, a tylosin antibiotic agent. A pharmaceutically acceptable buffer is also incorporated in the corn cob granules so as to increase the stability of the tylosin antibiotic agent against hydrolysis. Also described are a method for preparing the animal feed premix and a feed composition including the premix.Type: GrantFiled: April 6, 1994Date of Patent: November 21, 1995Assignee: Eli Lilly and CompanyInventors: Mary B. Schadewald, Peter W. Vanevenhoven
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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: 5411946Abstract: Avermectin derivatives, wherein the C-17-21-25-dioxaspirane substructure has been modified to include substitutions of heteratomic nucleophilic thiols at the 23,24-.alpha.-epoxide. These compounds can be similarly substituted at the 4"-, 5-, 13, and 25-positions. The new C-23 and C-24 substituted avermectin derivatives are potent anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: February 24, 1993Date of Patent: May 2, 1995Assignee: Merck & Co., Inc.Inventors: Ronald C. Newbold, Thomas L. Shih
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Patent number: 5407918Abstract: 16-membered macrolide derivatives represented by the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a COR.sup.6 group, wherein R.sup.6 represents a straight-chain alkyl group having 1 to 3 carbon atoms; R.sup.2 represents a hydrogen atom or a COR.sup.6 group, wherein R.sup.6 is as defined above; R.sup.3 represents a hydrogen atom or a COR.sup.6 group, wherein R.sup.6 is as defined above; R.sup.4 represents a straight-chain alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted allyl group; and R.sup.5 represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or aralkyl group having 1 to 10 carbon atoms; and pharmaceutically acceptable salts thereof are disclosed. These compounds show excellent and long-acting antimicrobial activities. A novel process for producing these 16-membered macrolide derivatives is further disclosed.Type: GrantFiled: October 29, 1993Date of Patent: April 18, 1995Assignee: Meiji Seika Kaisha, Ltd.Inventors: Keiichi Ajito, Ken-ichi Kurihara, Akira Shimizu, Shuichi Gomi, Nobue Kikuchi, Minako Araake, Tsuneo Ishizuka, Aiko Miyata, Osamu Hara, Seiji Shibahara
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Patent number: 5387509Abstract: Avermectins wherein one or both of the 3'- and 3"-positions of the oleandrose disaccharide moiety is substituted by an ethoxy rather than a methoxy group, process for their preparation; and their use as antiparasitic agents.Type: GrantFiled: June 26, 1989Date of Patent: February 7, 1995Assignee: Pfizer Inc.Inventors: Steven J. Hawrylik, S. Edward Lee
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Patent number: 5369021Abstract: A microorganism for selective production of a specific compound of avermectin having one or more of the following properties:specific accumulation of avermectin compound "a",effective incorporation of isoleucine or its keto acid (3-methyl-2-oxovaleric acid) into avermectin molecule, andmarkedly suppressed incorporation of valine or its keto acid (2-oxoisovaleric acid) into avermectin molecule.Type: GrantFiled: December 30, 1992Date of Patent: November 29, 1994Assignee: The Kitasato InstituteInventors: Omura Satoshi, Ikeda Haruo
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Patent number: 5362862Abstract: An improved process for formation of a 5-oxime on avermectin derivatives comprises the treatment of the oxo compound with O-(trimethylsilyl)hydroxylamine in the presence of a Lewis acid.Type: GrantFiled: September 29, 1993Date of Patent: November 8, 1994Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Raymond Cvetovich
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Patent number: 5346698Abstract: Described and claimed are methods and compositions for the control of pests. According to the subject invention, a fatty acid or mixture of fatty acids can be combined with one or more avermectins or related compounds to achieve synergistic control of pests.Type: GrantFiled: March 8, 1993Date of Patent: September 13, 1994Assignee: Mycogen CorporationInventor: Kenneth D. Abercrombie
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Patent number: 5302583Abstract: A method of preventing, treating and/or controlling diseases caused by dysregulation and/or dysfunction of various portions of the nervous system which comprises administering to a patient, an effective amount of a compound of the avermectin family, e.g. ivermectin, in single or multiple doses of up to 1.6 mg/kg at intervals of from 3 days to 4 months.Type: GrantFiled: November 23, 1992Date of Patent: April 12, 1994Assignee: Fractal Laboratories, Inc.Inventors: Jonathan L. Costa, Jesus A. Diazgranados
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Patent number: 5290767Abstract: A method for treating laminitis in equine livestock with tylosin which comprises dosing the equine or delivering to the lower alimentary canal a pharmaceutically effective quantity of an agent comprising tylosin. The method may be used for treating equine livestock which are subjected to a high carbohydrate diet by controlling lactic acid concentration in the hind gut. The agent acts to improve efficiency of feed utilization in the equine by increasing the production of propionate during fermentative digestion in the hind gut and allows feeding to the equine diets containing high levels of a readily fermentable carbohydrate.Type: GrantFiled: September 30, 1992Date of Patent: March 1, 1994Inventor: James B. Rowe
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Patent number: 5288710Abstract: Certain salts of 4"-deoxy-4"-epi-methylamino avermectin Bla/Blb such as: the benzoic acid salt, gallic acid salt, citric acid salt, benzenesulfonic acid salt and salicyclic acid salt, phosphoric acid salt, tartaric acid salt or maleic acid salt, exhibit enhanced stability, a property which serves to provide greater shelf life and a product of greater safety for the user and the environment.Type: GrantFiled: April 2, 1992Date of Patent: February 22, 1994Assignee: Merck & Co., Inc.Inventor: Raymond Cvetovich
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Patent number: 5286763Abstract: Bioerodible polymers which degrade completely into nontoxic residues over a clinically useful period of time, including polyanhydrides, polyorthoesters, polyglycolic acid, polylactic acid, and copolymers thereof, are used for the delivery of bioactive agents, including antibiotics, chemotherapeutic agents, inhibitors of angiogenesis, and simulators of bone growth, directly into bone.Type: GrantFiled: June 30, 1992Date of Patent: February 15, 1994Assignee: Massachusetts Institute of TechnologyInventors: Tobin N. Gerhart, Cato T. Laurencin, Abraham J. Domb, Robert S. Langer, Wilson C. Hayes