Acetic Acid Utilized In Pretreatment Patents (Class 536/71)
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Patent number: 4794173Abstract: Mycaminosyl tylonolide derivatives represented by the following general formula ##STR1## (wherein R.sup.1 denotes hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azido group, or amino group which mat optionally be substituted with a lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 expresses hydrogen atom or formyl group; and means a double bond or a radical represented by ), and salts thereof.Type: GrantFiled: May 9, 1986Date of Patent: December 27, 1988Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto
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Patent number: 4766112Abstract: There are disclosed macrolides isolated from the fermentation broth, with avermectin Bla, avermectin Blb or 22,23-dihydro avermectin Bla as a substrate, of a known microorganism identified as MA-6181. The structure of the novel compounds isolated from the microorganism are presented based upon analytical studies. The compounds are highly potent antiparasitic, insecticidal, and anthelmintic agents. Compositions for such uses are also disclosed.Type: GrantFiled: April 30, 1986Date of Patent: August 23, 1988Assignee: Merck & Co. Inc.Inventors: Robert T. Goegelman, Edward S. Inamine, Raymond F. White
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Patent number: 4764602Abstract: A novel antibiotic of the formula: ##STR1## wherein R is a hydrogen atom or a methyl group and preparation of the antibiotic by cultivating Nocardia sp. SC-4710.Type: GrantFiled: December 19, 1986Date of Patent: August 16, 1988Assignees: Sumitomo Chemical Company, Sumitomo Pharmaceuticals Company, LimitedInventors: Kazuo Kumagai, Kiyoshi Taya, Shin Tanaka, Koichi Moriguchi, Masatomo Fukasawa, Akio Fukui
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Patent number: 4760054Abstract: 5-Carbonate derivatives of milbemycins A.sub.3, A.sub.4 and A.sub.5 have valuable acaricidal, anthelmintic and other activities, especially against endo- and exoparasites.Type: GrantFiled: September 26, 1985Date of Patent: July 26, 1988Assignee: Sankyo Company LimitedInventors: Junya Ide, Noritoshi Kitano
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Patent number: 4734492Abstract: Disclosed is a novel macrolide antibiotic, M 119, of the formula (A): ##STR1## wherein the substituent R designates either (a) or (d): (a) R: H(d) R: OH.The antibiotic M 119 has antimicrobial activity, particularly against Gram-positive bacteria, typical pathogenic bacteria falling under Gram-negative bacteria such as Haemophilus influenzae, and mycoplasmas, and is effective against infections induced by such bacteria.Type: GrantFiled: July 11, 1986Date of Patent: March 29, 1988Assignee: Kirin Beer Kabushiki KaishaInventors: Hiroyuki Tanba, Kazuyoshi Adachi, Tomiko Kawasaki
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Patent number: 4730039Abstract: New compound, designated as leucanicidin, is now provided and is useful as insecticide. Leucanicidin is fermentatively produced by a microorganism Streptomyces halstedii No. 3002-14 (identifiable as FERM BP-493).Type: GrantFiled: January 24, 1985Date of Patent: March 8, 1988Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Akinori Suzuki, Akira Isogai, Shogo Matsumoto, Shohei Sakuta, Mitsuo Ogura, Haruo Seto, Kazuo Furihata
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Patent number: 4717718Abstract: A device for the controlled delivery of a beneficial agent is disclosed. The device comprises (a) a formulation layer and (b) a layer comprising means for pushing the formualtion layer from said device. The formulation layer comprises the beneficial agent avermectin or ivermectin.Type: GrantFiled: August 11, 1986Date of Patent: January 5, 1988Assignee: ALZA CorporationInventors: James B. Eckenhoff, Richard Cortese, Felix A. Landrau
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Patent number: 4661588Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl, phenyl substituted by one or more lower alkyl or halogen, phenyl-lower alkyl optionally substituted in its side chain by lower alkyl or lower alkoxycarbonyl, thienylmethyl or thiazolyl, R.sub.2 is hydrogen or lower alkyl, or ##STR2## constitutes a 3-7-membered nitrogen-containing heterocyclic ring in which R.sub.1 and R.sub.2 are connected, R.sub.3 is hydrogen or hydroxyl, and X is oxygen or sulfur, or a non-toxic salt thereof. These compounds have stronger antibacterial activity as compared with known clinically used macrolide antibiotics such as erythromycin, oleandomycin, josamycin and leucomycin, and also have strong antibacterial activity against all macrolide antibiotic-resistant strains such as macrolide-resistant A group strains (clinical isolates or erythromycin, oleandomycin and 16-membered macrolide antibiotic resistant strains).Type: GrantFiled: October 25, 1985Date of Patent: April 28, 1987Assignee: Toyo Jozo Kabushiki KaishaInventors: Tatsuro Fujiwara, Kazuyo Ohta, Eiichi Honda, Takao Hirano, Hideo Sakakibara
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Patent number: 4656258Abstract: New macrocin and lactenocin ester derivatives of the formula: ##STR1## wherein R is formyl or hydroxymethyl; R.sup.1 is hydrogen, acetyl or propionyl; R.sup.2 is hydrogen or ##STR2## and R.sup.3 is hydrogen, acetyl, propionyl, n-butyryl or isovaleryl; provided that one of R.sup.1 or R.sup.3 must be other than hydrogen; and the acid addition salts thereof; prepared by bioconversion of macrocin or lactenocin with an acylating enzyme system produced by Streptomyces thermotolerans strains, have improved activity against Mycoplasma species.Type: GrantFiled: June 11, 1985Date of Patent: April 7, 1987Assignee: Eli Lilly and CompanyInventors: Jan R. Turner, Veronica M. Krupinski, David S. Fukuda, Richard H. Baltz
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Patent number: 4652638Abstract: Novel 3-O-acyl-4"-deoxydesmycosin derivatives of the formula ##STR1## wherein R.sub.1 is lower alkyl, phenyl, substituted phenyl, phenyl-lower alkyl or substituted phenyl-lower alkyl, R.sub.2 is hydrogen or --CHO and R.sub.3 is hydrogen or hydroxyl, or a non-toxic salt thereof, can be produced by acylating the hydroxyl group at position-3 of the corresponding intermediate while protecting the hydroxyl at position-2' or positions-2' and -4' with acetyl, and then removing the protective group or groups. These derivatives have antibiotic utility against Gram positive and Gram negative bacteria.Type: GrantFiled: September 30, 1985Date of Patent: March 24, 1987Assignee: Toyo Jozo Kabushiki KaishaInventors: Tatsuro Fujiwara, Kazuyo Ohta, Takao Hirano
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Patent number: 4629786Abstract: C-20-Modified derivatives of macrolide antibiotics which include demycinosyltylosin (DMT), 20-dihydro-23-demycinosyltylosin (dihydro-DMT), 23-de(mycinosyloxy)tylosin (DMOT), 20-dihydro-23-de(mycinosyloxy)tylosin (dihydro-DMOT), 5-O-mycaminosyltylonolide (OMT), 20-dihydro-5-O-mycaminosyltylonolide (dihydro-OMT), 23-deoxy-5-O-mycaminosyltylonolide (DOMT), and 20-dihydro-23-deoxy-5-O-mycaminosyltylonolide (dihydro-DOMT) inhibit pathogenic bacteria, especially gram-positive bacteria, and Mycoplasma species; and pharmaceutical compositions thereof.Type: GrantFiled: May 25, 1984Date of Patent: December 16, 1986Assignee: Eli Lilly and CompanyInventors: Manuel Debono, Herbert A. Kirst
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Patent number: 4624945Abstract: A dispensing device is disclosed for delivering a beneficial agent. The device comprises (1) a housing defining an internal space, (2) heat responsive means containing a beneficial agent in the space, (3) means for increasing the amount of beneficial agent delivered from the device in the space, (4) expandable means in the space, (5) an optional dense means in the space, and (6) means in the housing for delivering the beneficial agent from the dispensing device.Type: GrantFiled: August 9, 1985Date of Patent: November 25, 1986Assignee: ALZA CorporationInventors: James B. Eckenhoff, Richard Cortese, Felix A. Landrau
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Patent number: 4622313Abstract: There are disclosed novel O-sulfate derivatives of avermectin and milbemycin. The avermectin and milbemycin O-sulfate derivatives have improved water solubility compared to the parent avermectin and milbemycin compounds and have utility as anti-parasitic agents and as potent insecticides against agricultural pests.Type: GrantFiled: August 1, 1985Date of Patent: November 11, 1986Assignee: Merck & Co., Inc.Inventor: Matthew J. Wyvratt, Jr.
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Patent number: 4612372Abstract: Novel tylosin derivatives are represented by formula: ##STR1## wherein R represents a hydrogen atom, an acetyl group or a propionyl group; X represents a group --CO-- or --SO.sub.2 --; Y represents a fluorine atom, an acetyl group, a methanesulfonyl group, a methylthio group, a benzoyl group or a methoxy group bound to the benzyl group at the 2-position or 4-position; and Z represents a hydrogen atom or a D-mycinose residue: ##STR2## The tylosin derivatives which are antibiotics of macrolide type provide improved antibacterial activity and improved ability of absorption and excretion in vivo.Type: GrantFiled: July 12, 1985Date of Patent: September 16, 1986Assignee: Sanraku IncorporatedInventors: Takeo Yoshioka, Miharu Maeda, Rokuro Okamoto, Yasutaka Shimauchi, Tomoyuki Ishikura, Tsutomu Sawa, Tomio Takeuchi, Hamao Umezawa
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Patent number: 4609645Abstract: Macrolides PTL-448 A and B, which can be prepared by aerobic cultivation of Streptomyces ambofaciens ATCC 15154 in the presence of a macrolide intermediate selected from protylonlide, 5-O-mycaminosylprotylonolide, 20-hydroxy-5-O-mycaminosylprotylonolide and 20-oxo-5-O-mycaminosylprotylonodide, and macrolides PTL-448 C and D, which can be prepared by acidic hydrolysis of PTL-448 A and B are useful antibiotics.Type: GrantFiled: March 26, 1984Date of Patent: September 2, 1986Inventor: Satoshi Omura
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Patent number: 4607024Abstract: A new salt of the macrolide antibiotic Josamycin with (-)-cis-1,4-epoxypropionylphosphonic acid, of formula (I) ##STR1## The salt (I), prepared from Josamycin base and phosphomycin, possesses favorable antimicrobial and pharmacokinetics properties.Type: GrantFiled: October 9, 1984Date of Patent: August 19, 1986Assignee: Schering S.p.A.Inventor: Alberto Bertelli
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Patent number: 4604380Abstract: C-23-bicyclic or tricyclic amino derivatives of OMT and 4'-deoxy-OMT, and pharmaceutical compositions comprising and methods of treating infections with these compounds, are provided.Type: GrantFiled: January 18, 1985Date of Patent: August 5, 1986Assignee: Eli Lilly and CompanyInventor: Manuel Debono
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Patent number: 4594187Abstract: The present invention is directed to a chemical process for preparing the antibiotic substance denominated antibiotic L 17054 and its pharmaceutically acceptable salts by selectively hydrolyzing teicoplanin or a factor or component thereof with a concentrated strong organic acid.Type: GrantFiled: December 11, 1984Date of Patent: June 10, 1986Assignee: Gruppo Lepetit S.p.A.Inventors: Paolo Strazzolini, Adriano Malabarba, Bruno Cavalleri
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Patent number: 4594338Abstract: 11-Thioether and certain C-20 acetal and thioacetal derivatives of tylosin and demycarosyltylosin are effective antibacterial agents. Processes for preparing, formulations containing, and methods of treating bacterial infections with these derivatives are provided.Type: GrantFiled: February 19, 1985Date of Patent: June 10, 1986Inventors: Satoshi Omura, Kazuo Tsuzuki
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Patent number: 4590266Abstract: Cellulose acetate is effectively prepared from cellulose and acetic anhydride in a solvent of acetic acid in the presence of a catalyst of sulfuric acid, when the reaction system is being evacuated at least before the reaction mixture reaches a boiling point thereof until the reaction completes, so that the vapor evolved from the reaction mixture may be condensed to distill off and the reaction product may be concentrated.Type: GrantFiled: December 28, 1984Date of Patent: May 20, 1986Assignee: Daicel Chemical Industries, Ltd.Inventors: Mitsuru Yamashita, Kouji Shima
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Patent number: 4581345Abstract: There are disclosed novel avermectin 8,9-cyclopropyl compounds (also referred to as 8,9-dihydro-8,9-methano avermectin compounds). The 8,9-cyclopropyl compounds are prepared by treating an avermectin compound with an iodohalomethane compound in the presence of an activated form of zinc. The avermectin 8,9-cyclopropyl compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.Type: GrantFiled: April 8, 1985Date of Patent: April 8, 1986Assignee: Merck & Co., Inc.Inventor: Matthew J. Wyvratt, Jr.
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Patent number: 4581346Abstract: C-8, 20-cyclo-derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, lactenocin, 2'"-O-demethylmacrocin and 2"-O-demethyllactenocin, which inhibit pathogenic bacteria, especially gram-positive bacteria, and Mycoplasma species, and pharmaceutical compositions thereof, are provided.Type: GrantFiled: July 12, 1984Date of Patent: April 8, 1986Assignee: Eli Lilly and CompanyInventor: Joseph H. Kennedy
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Patent number: 4579940Abstract: A compound of the formula ##STR1## wherein R.sub.1 is hydrogen, --COOR.sub.11 or ##STR2## R.sub.11 is optionally substituted lower alkyl, R.sub.12 is optionally substituted hydrocarbon, heterocyclic or heterocyclic-lower alkyl, R.sub.13 is hydrogen or lower alkyl, or R.sub.12 and R.sub.13 together constitute a heterocyclic ring together with the attached nitrogen atom, and R.sub.2 is hydrogen or hydroxyl, or a pharmaceutically-acceptable salt thereof, has stronger antibacterial activity against Gram-positive bacteria than does tylosin. It is produced by deformylation, or by oxidizing a formyl at position-14, or by amidating the latter compound.Type: GrantFiled: November 30, 1984Date of Patent: April 1, 1986Assignee: Toyo Jozo Kabushiki KaishaInventors: Tatsuro Fujiwara, Hideyuki Watanabe, Takao Hirano
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Patent number: 4576931Abstract: Novel 23-C-substituted mycaminosyl tylonolide of the general formula (I) ##STR1## wherein R.sup.1 represents a lower alkyl group, an aryl group, a lower alkenyl group or a lower alkynyl group, R.sup.2 represents a hydrogen atom or a hydroxyl group.These compounds have excellent antibacterial activities.Type: GrantFiled: April 3, 1985Date of Patent: March 18, 1986Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai (Microbial Chemistry Research Foundation)Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto
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Patent number: 4575497Abstract: 3, 3", 4"-Tri-O-acylspiramycin I represented by the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different groups, and at least one of the groups is a straight or branched chain alkylcarbonyl group represented by --COC.sub.m H.sub.2m+1 wherein m is an integer of 2-4 and the other group(s) are straight or branched chain alkylcarbonyl group(s) represented by --COC.sub.n H.sub.2n+1 wherein n is an integer of 1-4, and its pharmacologically acceptable acid addition salts.Type: GrantFiled: December 11, 1984Date of Patent: March 11, 1986Assignee: Kyowa Hakko Kogyo Co., LtdInventors: Satoshi Omura, Hiroshi Sano, Kinya Yamashita, Ryo Okachi
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Patent number: 4568740Abstract: Disclosed is a process for purifying Tylosin by selective adsorption of the fermentation broth previously brought to 7.5-10.0 pH on polymeric resins and by subsequent deadsorption of the purified product with a aqueous-alcoholic or aqueous-acetonic solution and further purification of the eluate by filtration through macroreticular weak anion resins.Type: GrantFiled: March 28, 1984Date of Patent: February 4, 1986Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Ernesto Oppici, Onorino G. Rosa, Carlo Varesio, Giovanni Lazzari, Danillo Fabris
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Patent number: 4560677Abstract: There is disclosed a novel combination of avermectin compounds and agricultural spray oil which has been found to be synergistic in such a manner as to allow for a drastic reduction in the amount of active ingredient which is fully effective and also a dramatic extension of the time period over which such a combination is fully effective. The synergistic combination is useful as an agricultural insecticide and miticide against a variety of insects and mites which infest a variety of plants.Type: GrantFiled: January 31, 1984Date of Patent: December 24, 1985Assignee: Merck & Co., Inc.Inventor: Richard A. Dybas
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Patent number: 4559301Abstract: New macrocin and lactenocin ester derivatives of the formula: ##STR1## wherein R is formyl or hydroxymethyl; R.sup.1 is hydrogen, acetyl or propionyl; R.sup.2 is hydrogen or ##STR2## and R.sup.3 is hydrogen, acetyl, propionyl, n-butyryl or isovaleryl; provided that one of R.sup.1 or R.sup.3 must be other than hydrogen; and the acid addition salts thereof; prepared by bioconversion of macrocin or lactenocin with an acylating enzyme system produced by Streptomyces thermotolerans strains, have improved activity against Mycoplasma species.Type: GrantFiled: March 3, 1983Date of Patent: December 17, 1985Assignee: Eli Lilly and CompanyInventors: Jan R. Turner, Veronica M. Krupinski, David S. Fukuda, Richard H. Baltz
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Patent number: 4552701Abstract: Desvancosaminyl- and des(vancosaminyl-O-glucosyl) glycopeptides, and methods for their preparation by treating a glycopeptide selected from vancomycin, A51568A, A51568B, M43A and M43D with trifluoroacetic acid under controlled conditions, are provided. The new glycopeptides are useful antibacterial agents.Type: GrantFiled: April 16, 1984Date of Patent: November 12, 1985Assignee: Eli Lilly and CompanyInventors: Ramakrishnan Nagarajan, Amelia A. Schabel
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Patent number: 4550160Abstract: The C-076 compounds are a series of four pairs of macrolides in which the members of each pair are homologous. The instant processes convert the C-076 A2 and B2 compounds isolated from a fermentation broth into the biologically preferred B1 and A1 compounds or into the dihydro derivatives thereof.Type: GrantFiled: August 13, 1979Date of Patent: October 29, 1985Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4547491Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the 8a position is oxidized to a ketone group. The 8a-oxo compounds are prepared by oxidizing an avermectin or milbemycin compound. The avermectin and milbemycin 8a-oxo compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.Type: GrantFiled: July 18, 1984Date of Patent: October 15, 1985Assignee: Merck & Co., Inc.Inventors: Helmut H. Mrozik, Frank S. Waksmunski
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Patent number: 4543334Abstract: An antibiotic complex, consisting of one major and two minor components, has been isolated from fermentation of a new Streptomyces culture. The components from the complex are three new macrolides which are active as antibacterial agents against certain gram-negative and gram-positive microorganisms.Type: GrantFiled: December 16, 1983Date of Patent: September 24, 1985Assignee: Pfizer Inc.Inventors: Walter D. Celmer, Walter P. Cullen, Hiroshi Maeda, Junsuke Tone
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Patent number: 4530921Abstract: There are disclosed novel avermectin compounds wherein certain double bonds are oxidized to epoxides. The epoxides are prepared by oxidizing an avermectin compound with a mild oxidizing agent. The avermectin epoxide compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.Type: GrantFiled: October 3, 1983Date of Patent: July 23, 1985Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4528369Abstract: 20-Dihydro-20-deoxy-23-de(mycinosyloxy)tylosin (20-deoxo-DMOT), specified 2'-acyl ester derivatives, and their acid addition salts are useful intermediates and antibacterial agents. Methods of preparing 20-deoxo-DMOT and 5-O-mycaminosyltylactone by fermentation of Streptomyces fradiae ATCC 31733 are included.Type: GrantFiled: August 22, 1983Date of Patent: July 9, 1985Assignee: Eli Lilly and CompanyInventor: Gene M. Wild
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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: 4510133Abstract: Insecticidally active compositions comprising a combination of a C-076 or B-41 macrolide antibiotic with an insect feeding stimulant. The combination shows substantially enhanced activity compared with combinations of pyrethroid insecticides with feeding stimulants.Type: GrantFiled: March 28, 1983Date of Patent: April 9, 1985Assignee: Imperial Chemical Industries PLCInventor: David D. Evans
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Patent number: 4497803Abstract: Inclusion compound of lankacidin-group antibiotic with cyclodextrin, having enhanced water-solubility and stability and a veterinary composition containing the same, which is useful for curing swine dysentery. The compound is prepared by adding lankacidin-group antibiotic to an aqueous cyclodextrin solution and stirring.Type: GrantFiled: April 6, 1983Date of Patent: February 5, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Setsuo Harada, Junya Okada
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Patent number: 4490524Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is optionally substituted phenyl, thienyl, 2-amino-4-thiazolyl or 2-chloroacetamido-4-thiazolyl; A is lower alkylene, lower alkenylene, or lower alkylene substituted by lower alkyl, amino, lower alkoxyimino or phenyl-Z-group wherein Z is a single bond or --S-- or --SO.sub.2 --, but when R.sub.1 is 2-amino-4-thiazolyl or 2-chloroacetamido-4-thiazolyl then A is lower alkylene substituted by lower alkoxyimino; R.sub.2 is hydrogen or hydroxyl; X is oxygen or sulfur and n=0 or 1, or a non-toxic salt thereof. These compounds have a stronger antibacterial activity against Gram positive bacteria as compared with known macrolide antibiotics such as erythromycin and tylosin, and also have an equivalent level of antibacterial activity against Gram negative bacteria as compared with that of erythromycin, and hence may be useful for clinical use. These compounds are also useful for feed additives and growth stimulants.Type: GrantFiled: January 24, 1983Date of Patent: December 25, 1984Assignee: Toyo Jozo Kabushiki KaishaInventors: Tatsuro Fujiwara, Hideyuki Watanabe, Takao Hirano, Hideo Sakakibara
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Patent number: 4487923Abstract: An improved method of preparing 23-monoester derivatives of 5-O-mycaminosyl tylonolide (OMT) and demycinosyltylosin (DMT) is provided. This method comprises esterifying the antibiotic with an acylating agent in the presence of an external base, such as pyridine or 2,4,6-collidine, until acylation of the 23-hydroxyl group is substantially complete, and separating the 23-monoester derivative. 23-Monoester derivatives of OMT and DMT are useful antibiotics and/or intermediates to antibiotics.Type: GrantFiled: March 14, 1983Date of Patent: December 11, 1984Assignee: Eli Lilly and CompanyInventors: Herbert A. Kirst, John E. Toth
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Patent number: 4486584Abstract: 2'"-O-demethylmacrocin (DOMM) which has the formula: ##STR1## 20-dihydro-DOMM, 2'"-O-demethyllactenocin (DOML), 20-dihydro-DOML, specified acyl ester derivatives, and their acid addition salts are useful antibacterial agents.Type: GrantFiled: December 20, 1982Date of Patent: December 4, 1984Assignee: Eli Lilly and CompanyInventors: Richard H. Baltz, Gene M. Wild, Eugene T. Seno
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Patent number: 4480090Abstract: The present invention relates to a method of preparing lower fatty acid esters of cellulose which comprises esterifying at a temperature of between about 75.degree. C. and about 110.degree. C. a cellulose compound having esterifiable hydroxyl groups with an esterifying bath comprising an organic acid anhydride, a diluent, and a catalyst comprising from 0.2 to 2.0 parts phosphoric acid, from 0.1 to 1.2 parts sulfuric acid, and from 0.05 to 0.6 parts of a hindered aliphatic alcohol by weight per 100 parts of the cellulose to be esterified.Type: GrantFiled: October 21, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: Chung-Ming Kuo, Alan P. Leonard
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Patent number: 4477443Abstract: Tylosin compounds of the formula ##STR1## wherein R.sub.1 represents a hydroxyl group; a halogen atom; ##STR2## group (wherein R.sub.5 is a hydrogen atom or a lower alkyl group which may be substituted by a hydroxyl group and R.sub.6 is a hydrogen atom, a lower alkyl group which may be substituted by a hydroxyl group, an aryl group, an aralkyl group, a cycloalkyl group having 3-10 carbon atoms, --CO(O).sub.m --R.sub.7 group (wherein m is 0 or 1 and R.sub.7 is a lower alkyl group, an aryl group, an aralkyl group, a furanyl group, or a pyridyl group), or --CH.sub.2 --R.sub.13 group (wherein R.sub.13 is a mono-, di-, or trifluoromethyl group)); --N(CH.sub.2).sub.n group (wherein n is an integer of 2-15) which may be substituted by an oxo group, a hydroxyl group, a lower alkyl group, or a hydroxy lower alkyl group; an imidazolyl group, a morpholino group, or a piperazino group each may be substituted by a lower alkyl group; or --OOCCH.sub.2 --R.sub.8 group (wherein R.sub.8 is ##STR3## group (wherein R.sub.Type: GrantFiled: July 6, 1982Date of Patent: October 16, 1984Assignee: Zaidan Hojin Biselbutsu Kagaku Kenkyu Kai (Microbial Chemistry Research Foundation)Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Hidenori Iwamoto, Shuichi Sakamoto
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Patent number: 4469682Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the various hydroxy groups are substituted with a phosphate ester group. The phosphate esters are prepared by reacting an avermectin or milbemycin compound with one or more unprotected hydroxy groups with a disubstituted halo phosphate. The avermectin and milbemycin phosphate esters have increased water solubility when compared with the parent compounds. The phosphate ester compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests.Type: GrantFiled: January 28, 1983Date of Patent: September 4, 1984Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4468511Abstract: C-20- and C-23-Modified macrolide derivatives of demycinosyltylocin (DMT), 5-O-mycaminosyltylonolide (OMT) 23-de(mycinosyloxy)tylosin, 23-deoxy-OMT, 20-dihydro-20-deoxy-DMT and 20-dihydro-20-deoxy-OMT are useful antibiotics or intermediates to antibiotics.Type: GrantFiled: February 28, 1983Date of Patent: August 28, 1984Assignee: Eli Lilly and CompanyInventors: Herbert A. Kirst, John E. Toth
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Patent number: 4463171Abstract: Compounds of the following general formula ##STR1## wherein R.sup.1 and R.sup.2 represent a hydrogen atom or a lower alkanoyl group;R.sup.3 represents a hydrogen atom or the group --COCH.sub.2 R.sup.5 in which R.sup.5 represents a lower alkyl group or an aryl or pyridyl group bonded through a sulfur atom;R.sup.4 represents a methyl group which may be substituted by aryl, pyridyl, pyridylthio, hydroxyl or arylthioamino, an aryl group, a nitrile group, a 5- or 6-membered heterocyclic group having 1 to 4 hetero atoms selected from nitrogen and sulfur atoms, or a tetrahydropyranyl group which may be substituted by methoxy;A represents the group --OCO--, --OSO.sub.2 --, --O-- or --S--, or A and R.sup.4, taken together, represent a halogen atom, a nitrile group or a group of the formula ##STR2## in which R.sup.Type: GrantFiled: June 9, 1983Date of Patent: July 31, 1984Assignee: Sanraku-Ocean Co., Ltd.Inventors: Hamao Umezawa, Tomio Takeuchi, Kuniaki Tatsuta, Tomoyuki Ishikura, Rokuro Okamoto, Masao Yamamoto, Kohki Kiyoshima
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Patent number: 4459290Abstract: C-23-Modified derivatives of 5-O-mycaminosyl-tylonolide (OMT) of the formula: ##STR1## wherein R is chloro, fluoro, --S--R.sup.4, azido, --NHR.sup.5, pyridinium, or --OSO.sub.2 CF.sub.3 ;R.sup.1 is hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl, phenylpropionyl, phenoxyacetyl or phenylthioacetyl;R.sup.2 and R.sup.3 are hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl or phenylpropionyl;R.sup.4 is hydrogen, optionally substituted C.sub.1 -C.sub.6 -alkyl, cyclohexyl, C.sub.1 -C.sub.5 alkanoyl, optionally substituted phenyl or benzyl, or an optionally substituted heteroaryl group selected from imidazolyl, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, thienyl and furanyl; andR.sup.5 is hydrogen or an acyl group selected from optionally substituted C.sub.1 -C.sub.Type: GrantFiled: July 19, 1982Date of Patent: July 10, 1984Assignee: Eli Lilly and CompanyInventors: Herbert A. Kirst, John E. Toth
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Patent number: 4457920Abstract: There are disclosed novel avermectin compounds wherein the 4-methyl group is substituted with hydroxy or various groups connected through the hydroxy oxygen atom. The hydroxy compounds are prepared by oxidation of the 4-methyl group and the hydroxy substituents prepared by a substitution process selective for primary alcohols. The compounds have utility as antiparasitic agents and compositions for that use are also disclosed.Type: GrantFiled: August 4, 1982Date of Patent: July 3, 1984Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4454314Abstract: Antibacterial and intermediate substances which are derived by selective chemical transformation of partially hydrolyzed tylosin and related macrolide derivatives in which only the mycaminose sugar remains attached to the macrocyclic lactone ring. Compounds having particular utility as antibacterial agents have C-6 side chain aldehyde converted to a hydrazone, the C-3 ring hydroxy group acylated, and/or the C-14 hydroxymethyl group converted to a sulfonate or carboxylate ester, or to a halomethyl, aminomethyl, sulfonamidomethyl or carboxamidomethyl group. Compounds whose prime utility is as intermediates have side chain aldehyde group protected as an acetal, mycaminose sugar hydroxyls protected as carboxylate ester and/or C-14 hydroxymethyl converted to a formyl or azidomethyl group.Type: GrantFiled: August 2, 1982Date of Patent: June 12, 1984Assignee: Pfizer Inc.Inventor: Arthur A. Nagel
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Patent number: RE32006Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted or substituted by a halogen atom. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis. This is followed by substitution of the 13-hydroxy group with a halogen, and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaracidal agents.Type: GrantFiled: July 18, 1984Date of Patent: October 15, 1985Assignee: Merck & Co., Inc.Inventors: John C. Chabala, Michael H. Fisher, Helmut H. Mrozik
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Patent number: RE32034Abstract: Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis, followed by halogenation and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaricidal agents.Type: GrantFiled: July 18, 1984Date of Patent: November 19, 1985Assignee: Merck & Co., Inc.Inventors: John C. Chabala, Michael H. Fisher, Helmut H. Mrozik