The Spiro Includes The Lactone Ring Patents (Class 549/265)
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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: 4650881Abstract: Arenes, such as benzoic acid and substituted benzoic acids, are readily thallated by thallium(III) compounds such as the trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, dienes, allylic halides, vinyl halides, vinyl esters, or unsaturated cyclopropanes or unsaturated cyclobutanes to give isocoumarins.Type: GrantFiled: April 1, 1985Date of Patent: March 17, 1987Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larock, Sudarsanan Varaprath
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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: 4582913Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.Type: GrantFiled: June 11, 1984Date of Patent: April 15, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4578475Abstract: The novel D-homosteroids of the formula ##STR1## wherein R.sup.1 represents a --CN, .dbd.NOH or .dbd.CH--NHOH group; R.sup.2 represents oxo or, where R.sup.1 represents a --CN group, R.sup.2 represents oxo or a --OAc group; or R.sup.1 and R.sup.2 together with carbon atoms 2 and 3 of the steroid skeleton represents a [2,3-d]-fused isoxazole ring, a [3,2-c]-fused pyrazole ring, a [3,2-c]-fused N-acylated pyrazole ring or a [2,3-c]-fused furazan ring; Ac represents an acyl group; R.sup.3 and R.sup.4 represent methyl and R.sup.5 and R.sup.6 together represent an additional bond between carbon atoms 5 and 6 of the steroid skeleton; or R.sup.4 and R.sup.5 together represent --O--, R.sup.3 represents hydrogen or methyl, and R.sup.6 represents hydrogen; R.sup.7 represents hydrogen, lower-alkyl or ethynyl; R.sup.8 represents hydroxy or acyloxy; or R.sup.7 and R.sup.Type: GrantFiled: January 26, 1984Date of Patent: March 25, 1986Assignee: Hoffman-La Roche Inc.Inventors: Andor Furst, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
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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: 4532058Abstract: Motor oil dispersants are disclosed which are made by heating alkenyl succinic anhydrides in the presence of bases and heating the resulting products with a polyamine H.sub.2 N(RNH).sub.n H or a polyamine alcohol HO(RNH).sub.n H.Also disclosed are motor oils containing from 0.10 to 10.00 weight percent of at least one such dispersant.Type: GrantFiled: February 4, 1982Date of Patent: July 30, 1985Assignee: Texaco Inc.Inventor: Harry Chafetz
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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: 4524019Abstract: Spiro-lactones of formula ##STR1## which could possess a supplemental bond at the position indicated by the dotted lines and wherein index n stands for integers 1 or 2, possess useful organoleptic properties and consequently can be utilized as perfume ingredients in the preparation of fragrance compositions and the perfuming of various articles such as e.g. soaps, cosmetics, detergents and household materials.A process for their preparation starting from p-mentha-1,8-dien-4-ol is disclosed.Type: GrantFiled: July 25, 1983Date of Patent: June 18, 1985Assignee: Firmenich, SAInventors: Wolfgang K. Giersch, Gunther Ohloff
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Patent number: 4519944Abstract: Fragrance compositions comprising 8-alkyl-1-oxaspiro[4.5]decan-2-ones wherein the alkyl group contains from one to four carbon atoms.Type: GrantFiled: May 16, 1983Date of Patent: May 28, 1985Assignee: Givaudan CorporationInventors: Robert T. Dahill, Kenneth L. Purzycki, Erlinda F. Golle
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Patent number: 4507427Abstract: The present invention relates to a process for the production of organic polyisocyanates containing at least partly blocked isocyanate groups characterized in that specific cyclic dicarbonyl compounds are used as the blocking agent. The present invention also relates to the polyisocyanates containing at least partly blocked isocyanate groups obtainable by this process and to the use of the polyisocyanates containing at least partly blocked isocyanate groups obtainable by this process as reactants for isocyanate-reactive compounds for the production of isocyanate polyaddition products.The present invention also relates to the use of polyisocyanates containing at least partly blocked isocyanate groups obtainable by the above process for the production of aqueous stoving lacquers and to the use of these polyisocyanates for the production of aqueous polyisocyanate solutions or dispersions.Type: GrantFiled: July 5, 1984Date of Patent: March 26, 1985Assignee: Bayer AktiengesellschaftInventors: Terry A. Potter, Klaus Nachtkamp, Franz Weider
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Patent number: 4492797Abstract: The present disclosure is directed to 5-oxo- or methylene 17.beta.-hydroxy saturated or unsaturated deA-steroids wherein the 17.alpha.-position contains a propionic acid or propanol substituent and derivatives thereof wherein the hydroxy group at the 17-position forms a lactone ring with the carboxy substituent when the substituent at position 21 is carboxy. The deA-steroids and derivatives of the present disclosure are useful as potassium-sparing diuretics or for flushing oedemas.Type: GrantFiled: October 4, 1982Date of Patent: January 8, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Andor Furst, Peter Keller, Marcel Muller
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Patent number: 4447625Abstract: The invention relates to novel 4-(1H-azolylmethyl)-1,3-dioxolan-5-one derivatives of the formula I ##STR1## and to the production and use of these compounds. In formula I, R.sub.1 and R.sub.2 are unsubstituted or substituted alkyl or phenyl, or together form a 3- to 7-membered carbocyclic ring which is unsubstituted or substituted, A is an unsubstituted or substituted phenyl radical, and X is --CH.dbd. or --N.dbd.. The compounds of the formula I can be used in the form of appropriate compositions for regulating plant growth and/or for controlling and/or protecting plants from attack by phytopathogenic microorganisms.Type: GrantFiled: September 23, 1982Date of Patent: May 8, 1984Assignee: Ciba-Geigy CorporationInventor: Walter Kunz
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Patent number: 4444591Abstract: Novel chromogenic fluoran compounds of the formula: ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl radicals of from five to eight carbon atoms; R.sub.2 is selected from the group consisting of alkyl radicals of from one to eight carbon atoms; R.sub.3 is selected from the group consisting of hydrogen atom and lower alkyl radicals of from one to four carbon atoms; X.sub.1 and X.sub.2 are independently selected from the group consisting of hydrogen atom and lower alkyl radicals of from one to four carbon atoms, X.sub.3 is selected from the group consisting of hydrogen atom, lower alkyl radicals of from one to four carbon atoms, halogen atoms and trifluoromethyl radical; and n is an integer of a value of 1 or 2; providing that R.sub.1 does not represent an amyl radical when R.sub.2 is selected from the group consisting of alkyl radicals of from one to five carbon atoms, X.sub.1 and X.sub.2 are each a hydrogen atom, X.sub.Type: GrantFiled: February 23, 1982Date of Patent: April 24, 1984Assignee: Yamada Chemical Co., Ltd.Inventors: Hajime Kawai, Katsuhiko Tsunemitsu, Yoshiharu Fujino, Yoji Shimizu
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Patent number: 4413133Abstract: Process for manufacturing chlorolactones by reacting, within an ahydrous organic solvent, a metal N-chlorosulfonamidate of the formula ##STR1## wherein R is a hydrogen or halogen atom or an alkyl radical, Ar is a mono- or polycyclic divalent aromatic radical and M is an alkali metal, with a substantially stoichiometrical proportion of an aliphatic or alicyclic carboxylic acid having at least one double bond separated from the COOH group by at least 2 carbon atoms, in the presence of a substantially stoichiometrical amount of a strong acid whose conjugate base is weakly nucleophilic.Type: GrantFiled: November 13, 1981Date of Patent: November 1, 1983Assignee: Institut Francais du PetroleInventors: Bernard Damin, Alain Forestiere, Bernard Sillion
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Patent number: 4398032Abstract: Novel compounds of the formula I ##STR1## in which each of Y.sup.1 and Y.sup.2 independently represents a fluorine, chlorine or bromine atom and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an alkyl group having up to 10 carbon atoms, or R.sup.1 and R.sup.2 together represent an alkylene group having from 2 to 5 carbon atoms, may be converted by the action of base into the corresponding dihalovinylcyclopropane carboxylic acids.Type: GrantFiled: June 7, 1982Date of Patent: August 9, 1983Assignee: Shell Oil CompanyInventor: Petrus A. Kramer
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Patent number: 4395416Abstract: Derivatives of formula: ##STR1## in which Z< represents: either an amino group of struture >N-R.sub.1 where R.sub.1 represents a linear or branched alkyl group with 1 to 5 carbon atoms or a phenyl group possibly substituted by a chlorine atom, in which case:n=1 or 2,the pair (A, C X) assumes the following values: (S, C.dbd.O), (S, CH.sub.2), (O, CH.sub.2), (O, CH--C.sub.6 H.sub.5), andR represents a hydrogen or halogen atom, one or more methoxy groups or the butadiene-1,3 ylene chain ##STR2## fixed in position 5,6 of the phenyhl nucleus and thus forming with this latter a naphthyl nucleus;or a methylene group (--CH.sub.2 --), in which case:n=1 or 2,A represents the oxygen atom,>C X represents a carbonyl group (>C.dbd.O) or thiocarbonyl group (>C.dbd.S), andR has the same meanings as previously,as well as the mineral or organic acid addition salts thereof. The compounds exhibit anti-convulsion and analgesic activity.Type: GrantFiled: January 21, 1982Date of Patent: July 26, 1983Assignee: Delalande S.A.Inventors: Michel Langlois, Bernard P. Bucher, Philippe L. Dostert, Alain P. Lacour, Gerard H. Moinet
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Patent number: 4393056Abstract: New antibacterial tetronolide compounds F-1 and F-2 are produced by fermentation of a microorganism belonging to the genus Micromonospora. The antibiotics F-1 and F-2 are accumulated in the culture liquor and are isolated therefrom respectively and the acyl derivatives of F-1 and F-2, that is, F-1-21-O-acetate, F-1-21-O-propionate, F-1-21-O-n-butylate, F-1 diacetate, F-1 dipropionate, F-2 triacetate, F-2 tripropionate and F-2 tri-n-butylate, etc., are synthesized from F-1 and F-2 by known means.Type: GrantFiled: June 15, 1981Date of Patent: July 12, 1983Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Fusao Tomita, Tatsuya Tamaoki, Kunikatsu Shirahata, Masaji Kasai, Noriaki Hirayama, Makoto Morimoto, Masanori Fukui
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Patent number: 4390616Abstract: Recording members having excellent light resistance are obtained by using as a dye precursor specific diarylaminofluoran compounds.Type: GrantFiled: December 1, 1980Date of Patent: June 28, 1983Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Ken Iwakura, Akira Igarashi
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Patent number: 4384879Abstract: The invention relates to novel 4-(1H-azolylmethyl)-1,3-dioxolan-5-one derivatives of the formula I ##STR1## and to the production and use of these compounds. In formula I, R.sub.1 and R.sub.2 are unsubstituted or substituted alkyl or phenyl, or together form a 3- to 7-membered carbocyclic ring which is unsubstituted or substituted, A is an unsubstituted or substituted phenyl radical, and X is --CH.dbd. or --N.dbd.. The compounds of the formula I can be used in the form of appropriate compositions for regulating plant growth and/or for controlling and/or protecting plants from attack by phytopathogenic microorganisms.Type: GrantFiled: July 6, 1981Date of Patent: May 24, 1983Assignee: Ciba-Geigy CorporationInventor: Walter Kunz
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Patent number: 4377689Abstract: The invention relates to new derivatives of spiro compounds represented by the general formula (I) ##STR1## wherein R is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R.sub.1 and R.sub.2 represent a hydrogen atom or an alkyl group or together form a nitrogen-containing heterocyclic ring; A is a>CH.sub.2 group or a>CO group; n is 4 or 5. These compounds can be prepared from .beta.-hydroxyacids by intramolecular rearrangement by the action of a strong acid, in order to form a .gamma.-spirolactone which is converted into an .alpha.-carboxy .gamma.-spirolactone to form the compounds of formula (I) using a Mannich reaction. As necessary, a reduction is then carried out. These compounds are useful medically, in particular, as an antidepressant, a stimulant, and a neuroleptic.Type: GrantFiled: October 23, 1981Date of Patent: March 22, 1983Assignee: Etablissements Nativelle S.A.Inventors: Georges Tsatsas, Evan E. Costakis, Georges V. Foscolos
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Patent number: 4371538Abstract: The invention relates to new derivatives of spiro compounds represented by the general formula (I) ##STR1## wherein R is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R.sub.1 and R.sub.2 represent a hydrogen atom or an alkyl group or together form a nitrogen-containing heterocyclic ring; A is a >CH.sub.2 group or a >CO group; n is 4 or 5. These compounds can be prepared from .beta.-hydroxyacids by intramolecular rearrangement by the action of a strong acid, in order to form a .gamma.-spirolactone which is converted into an .alpha.-carboxy .gamma.-spirolactone to form the compounds of formula (I) using a Mannich reaction. As necessary, a reduction is then carried out. These compounds are useful medically, in particular, as an antidepressant, a stimulant, and a neuroleptic.Type: GrantFiled: October 9, 1980Date of Patent: February 1, 1983Assignee: Etablissements Nativelle S.A.Inventors: Georges Tsatsas, Evan E. Costakis, Georges V. Foscolos
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Patent number: 4362872Abstract: A method is provided for preparing intermediates for use in prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate: ##STR1## and subjecting same to a Wittig reaction to form the difluoro dihydroxy prostacyclin intermediate: ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.Type: GrantFiled: September 24, 1981Date of Patent: December 7, 1982Assignee: E. R. Squibb & Sons, Inc.Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger