Spiro Patents (Class 549/264)
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Patent number: 4791134Abstract: The invention relates to milbemycin derivatives of formula I ##STR1## wherein R.sub.1 is an aliphatic or aromatic radical or is a pyridyl ring or a heterocyclic oxygen-containing 5- or 6-membered ring, all of which may also be bound through oxygen, and R.sub.2 is methyl, ethyl or isopropyl. These compounds are suitable for controlling arthropode species such as injurious insects or endo- or ectoparasites of animals and are employed in the form of compositions. The compounds can also be used as intermediates for obtaining further milbemycin derivatives.Type: GrantFiled: June 4, 1985Date of Patent: December 13, 1988Assignee: Ciba-Geigy CorporationInventor: Urs Burckhardt
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Patent number: 4789684Abstract: There is disclosed a series of macrolides isolated from the fermentation broth of a microorganism identified as MA-5920. This novel microorganism is formed by the protoplast fusion of strains of Streptomyces avermitilis and Streptomyces hygroscopicus. The structure of the novel compounds isolated from the microorganism is presented based upon analytical studies. The compounds are highly potent antiparasitic, insecticidal, and anthelmintic agents. Compositions for such uses are also disclosed.Type: GrantFiled: May 2, 1985Date of Patent: December 6, 1988Assignee: Merck & Co., Inc.Inventor: Robert T. Goegelman
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Patent number: 4778809Abstract: The invention relates to ecto- and endoparasitic milbemycins of formula I ##STR1## wherein R is methyl, ethyl, isopropyl or sec-butyl;R.sub.1 is hydrogen, fluorine or C.sub.1 -C.sub.4 alkyl;R.sub.2 is one of the groups ##STR2## in which formulaeis a value from 2 to 6;X is oxygen or sulfur;R.sub.3 is halogen; andR.sub.4 is hydrogen, C.sub.1 -C.sub.12 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy or C.sub.2 -C.sub.6 alkenyloxy; or C.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy, hydroxy and/or COOG, G being hydrogen, an alkali metal cation or an alkaline earth metal cation; or R.sub.4 is C.sub.3 -C.sub.7 cycloalkyl which is unsubstituted or substituted by halogen and/or C.sub.1 -C.sub.4 alkyl;C.sub.2 -C.sub.18 alkenyl which is unsubstituted or substituted by halogen;C.sub.2 -C.sub.18 alkynyl which is unsubstituted or substituted by halogen;phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 alkoxy, nitro, cyano and/or C.sub.Type: GrantFiled: August 13, 1986Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Elmar Sturm
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Patent number: 4757132Abstract: Cyclic polyester and especially polyarylate oligomers, typically having degrees of polymerization from 2 to about 7, are prepared by reacting a bisphenol such as bisphenol A or 6,6'-dihydroxy-3,3,3',3'-tetramethylspiro(bis)indane with a dicarboxylic acid chloride such as isophthaloyl or terephthaloyl chloride in the presence of a catalyst, under conditions of low concentration. The cyclic oligomers may be polymerized to linear polyesters by contact with a transesterification catalyst at a temperature in the range of about 200.degree.-300.degree. C.Type: GrantFiled: October 20, 1986Date of Patent: July 12, 1988Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon
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Patent number: 4696945Abstract: The invention relates to parasiticidally and insecticidally highly active compounds of formula I ##STR1## wherein R.sub.1 is hydrogen or a protecting group;R.sub.2 is methyl, ethyl, isopropyl or sec-butyl; andR is a radical R.sub.3 which is bound through oxygen or sulfur and is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.1 -C.sub.10 mercaptoalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.3 -C.sub.10 alkoxyalkoxyalkyl, hydroxy- or mercapto-substituted C.sub.3 -C.sub.10 alkoxyalkyl, C.sub.4 -C.sub.15 alkoxyalkoxyalkoxyalky, hdroxy- or mercapto-substituted C.sub.4 -C.sub.15 alkoxyalkoxyalkoxyalkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 haloalkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.2 -C.sub.10 haloalkynyl, phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: July 14, 1986Date of Patent: September 29, 1987Assignee: Ciba-Geigy CorporationInventors: Bruno Frei, Anthony C. O'Sullivan
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Patent number: 4696922Abstract: The present invention relates to milbemycin derivatives of the formula I ##STR1## wherein X is hydrogen or .beta.-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C.sub.1 -C.sub.6 alkyl groups. These compounds, and the acid addition salts and metal complexes thereof, are effective pesticides for controlling endo-and ectoparasites, especially for controlling neamatodes which are parasites of animals. The may be obtained by appropriate esterification in 5-position of milbemycin derivatives. The selective .beta.-halogenation of 14,15-epoxymilbemycin derivatives can be effected via the intermediate .DELTA..sup.13,14 -15-hydroxymilbemycins with appropriate halogenating agents.Type: GrantFiled: November 18, 1985Date of Patent: September 29, 1987Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Peter Maienfisch
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Patent number: 4668696Abstract: There is disclosed a macrolide isolated from the fermentation broth, with 22,23-dihydro avermectin Bla aglycone as a substrate, of a known microorganism identified as MA-5853. The structure of the novel compound isolated from the microorganism is presented based upon analytical studies. The compound is a highly potent antiparasitic, insecticidal, and anthelmintic agent. Compositions for such uses are also disclosed.Type: GrantFiled: July 29, 1985Date of Patent: May 26, 1987Assignee: Merck & Co., Inc.Inventors: Robert T. Goegelman, Raymond F. White, Edward S. Inamine
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Patent number: 4666937Abstract: There are disclosed novel compounds which are derived from 22,23-dihydro avermectin Bla aglycone, 13-deoxy-22,23 dihydro overmectin Bla aglycone and 13-deoxy-22,23-dihydro overmectin Blb aglycone. The six compounds are hydroxy adducts of the substrate avermectin compound at the 12a, 24, 24a, 26, 26a and 27 positions. The hydroxy adducts are prepared by incubating the substrate with the microorganism Cunninghamella blakesleeana and isolating the hydroxy adducts from the fermentation broth. The compounds are highly potent antiparasitic, insecticidal and anthelmintic agents.Type: GrantFiled: February 20, 1986Date of Patent: May 19, 1987Assignee: Merck & Co., Inc.Inventors: Robert T. Goegelman, Edward S. Inamine, Raymond F. White
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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: 4587247Abstract: Novel substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones are useful as anthelmintic and antiparasitic agents. The compounds are also useful as pesticides and insecticides against agricultural pests. Included herein are novel intermediates useful in the process for preparing said avermectin aglycone derivatives. Compositions of said derivatives and methods of administering said compositions are also disclosed.Type: GrantFiled: February 25, 1985Date of Patent: May 6, 1986Assignee: Merck & Co., Inc.Inventors: Bruce O. Linn, Helmut H. Mrozik
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Patent number: 4584314Abstract: The compound of formula I ##STR1## wherein R.sub.2 is methyl, ethyl, isopropyl or sec-butyl, can be prepared by selective chlorination of an appropriate milbemycin derivative either with hypochlorous acid (HOCl) or sulfuryl chloride (SO.sub.2 Cl.sub.2) in the temperature range from -10.degree. to +60.degree. C. It is employed as pesticide for controlling Arthropode species such as injurious insects or ecto- or endoparasites of animals, and is applied in the form of compositions. This compound is also used as intermediate for obtaining further milbemycin derivatives.Type: GrantFiled: November 16, 1984Date of Patent: April 22, 1986Assignee: Ciba-Geigy CorporationInventor: Urs Burckhardt
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Patent number: 4582852Abstract: Milbemycin derivatives of the formula I ##STR1## wherein A has the structure ##STR2## or the structure ##STR3## X is either --CH(OR.sub.1)-- or --CO--, R.sub.1 is hydrogen, a silyl group or an acyl group, and R.sub.2 is methyl, ethyl, isopropyl or sec-butyl, can be prepared by singulett oxygen oxidation of the milbemycin derivatives of the formula II herein, wherein X and R.sub.2 have the above meanings, and subsequent reduction of the 15- and 14-peroxides obtained as intermediates. Compounds of the formula I can be prepared as such or in the form of compositions for controlling endo- and ectoparasites, in particular nematodes which are parasites of animals.Type: GrantFiled: October 25, 1984Date of Patent: April 15, 1986Assignee: Ciba-Geigy CorporationInventor: Jean-Claude Gehret
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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: 4579864Abstract: There are disclosed novel avermectin and milbemycin compounds wherein the 13-position is oxidized to a keto function. The 13-keto derivatives are prepared from the 13-hydroxy compounds by oxidizing the 13-position with a suitable oxidizing agent. The avermectin and milbemycin 13-keto derivatives are active in their own right and also serve as intermediates in the preparation of 13-imino and 13-amino derivatives. The 13-keto, imino and amino 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: June 11, 1984Date of Patent: April 1, 1986Assignee: Merck & Co., Inc.Inventors: Bruce O. Linn, Helmut H. Mrozik
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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: 4547520Abstract: Oxime derivatives of 5-didehydromilbemycins A.sub.3, A.sub.4 and D are represented by the formula: ##STR1## (wherein R.sup.1 represents methyl, ethyl or isopropyl, and R.sup.2 represents hydrogen, lower alkyl, optionally substituted aralkyl or --CH.sub.2 COOR.sup.3, wherein R.sup.3 represents hydrogen or lower alkyl). These and their salts and esters have valuable anthelmintic, acaricidal and insecticidal activity.Type: GrantFiled: November 25, 1983Date of Patent: October 15, 1985Assignee: Sankyo Company LimitedInventors: Junya Ide, Shigeki Muramatsu, Yasuo Nakada, Noritoshi Kitano
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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: 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: 4463182Abstract: The present invention relates to roridin E-2 which is represented by Formula I and a process for the production of said compound.Type: GrantFiled: June 26, 1978Date of Patent: July 31, 1984Assignee: Warner-Lambert CompanyInventors: William G. Freckman, Zbigniew L. Jakubowski, Richard H. Bunge, James C. French, Lucia E. Balta
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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: 4439426Abstract: From the fermentation carried, out with mutants blocked in the synthesis respectively of erythromycin and of oleandomycin, namely Streptomyces erythreus ATCC 31772 and Streptomyces antibioticus ATCC 31771, using as the substrate a derivative of erythronolide A, namely (8S)-8-fluoroerythronolide A, a derivative of erythronolide B, namely (8S)-8-fluoroerythronolide B, or a derivative of 3-O-mycarosyl-erythronolide B, namely 3-O-mycarosyl-(8S)-fluoroerythronolide B, the corresponding (8S)-8-fluoro derivatives of the erythromycins A, B, C and D, as well as 3-O-oleandrosyl-5-desosaminyl-(8S)-8-fluoroerythronolide A and 3-O-oleandrosyl-5-O-desosaminyl-(8S)-8-fluoroerythronolide B, all belonging to the class of the macrolide antibiotics are obtained.Type: GrantFiled: January 8, 1982Date of Patent: March 27, 1984Assignee: Pierrel S.p.A.Inventors: Luciano Toscano, Leonardo M. Cappelletti
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Patent number: 4436750Abstract: The present invention relates to the novel trichothecenes, 12'-hydroxyverrucarin J and iso-satratoxin H, and a fermentation process for the production of said compounds.The invention also relates to pharmaceutical compositions comprising said compounds and methods for using said compositions.Type: GrantFiled: October 4, 1982Date of Patent: March 13, 1984Assignee: Warner-Lambert CompanyInventors: Tim A. Smitka, Richard H. Bunge, James C. French, Russell J. Bloem
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Patent number: 4423209Abstract: There is disclosed a process for converting avermectin compounds (formerly identified as C-076 compounds) of the A-type, into avermectin compounds of the B-type. The process is carried out on the naturally occuring avermectin compounds as well as on derivatives thereof. The process involves selectively cleaving the 5-methoxy group, converting it into the hydroxy group, through the intermediate 5-keto group.Type: GrantFiled: February 26, 1982Date of Patent: December 27, 1983Assignee: Merck & Co., Inc.Inventor: Helmut H. Mrozik
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Patent number: 4408059Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.Type: GrantFiled: December 4, 1981Date of Patent: October 4, 1983Assignee: University Patents, Inc.Inventors: Amos B. Smith, III, Steven R. Schow
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Patent number: 4378353Abstract: There are disclosed certain new compounds related to C-076 compounds which have been produced by a mutant of the culture that produced the original C-076 compounds and isolated from the fermentation broth thereof. The compounds retain the C-076 16-membered cyclic backbone, however, the groups attached thereto are considerably modified from the original C-076 compounds. The new compounds have been found to retain the biological activity of the parent C-076 compounds. The compounds are thus potent antiparasitic agents and compositions and methods for such uses are also disclosed.Type: GrantFiled: February 17, 1981Date of Patent: March 29, 1983Assignee: Merck & Co., Inc.Inventors: Robert T. Goegelman, Vincent P. Gullo, Louis Kaplan
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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