The Spiro Includes The Lactone Ring Patents (Class 549/265)
  • Patent number: 4696945
    Abstract: 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: Grant
    Filed: July 14, 1986
    Date of Patent: September 29, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Bruno Frei, Anthony C. O'Sullivan
  • Patent number: 4650881
    Abstract: 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: Grant
    Filed: April 1, 1985
    Date of Patent: March 17, 1987
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Richard C. Larock, Sudarsanan Varaprath
  • Patent number: 4584314
    Abstract: 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: Grant
    Filed: November 16, 1984
    Date of Patent: April 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Burckhardt
  • Patent number: 4582852
    Abstract: 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: Grant
    Filed: October 25, 1984
    Date of Patent: April 15, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Claude Gehret
  • Patent number: 4582913
    Abstract: 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: Grant
    Filed: June 11, 1984
    Date of Patent: April 15, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Patent number: 4578475
    Abstract: 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: Grant
    Filed: January 26, 1984
    Date of Patent: March 25, 1986
    Assignee: Hoffman-La Roche Inc.
    Inventors: Andor Furst, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
  • Patent number: 4547491
    Abstract: 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: Grant
    Filed: July 18, 1984
    Date of Patent: October 15, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Helmut H. Mrozik, Frank S. Waksmunski
  • Patent number: 4532058
    Abstract: 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: Grant
    Filed: February 4, 1982
    Date of Patent: July 30, 1985
    Assignee: Texaco Inc.
    Inventor: Harry Chafetz
  • Patent number: 4530921
    Abstract: 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: Grant
    Filed: October 3, 1983
    Date of Patent: July 23, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Helmut H. Mrozik
  • Patent number: 4524019
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: June 18, 1985
    Assignee: Firmenich, SA
    Inventors: Wolfgang K. Giersch, Gunther Ohloff
  • Patent number: 4519944
    Abstract: Fragrance compositions comprising 8-alkyl-1-oxaspiro[4.5]decan-2-ones wherein the alkyl group contains from one to four carbon atoms.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: May 28, 1985
    Assignee: Givaudan Corporation
    Inventors: Robert T. Dahill, Kenneth L. Purzycki, Erlinda F. Golle
  • Patent number: 4507427
    Abstract: 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: Grant
    Filed: July 5, 1984
    Date of Patent: March 26, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Terry A. Potter, Klaus Nachtkamp, Franz Weider
  • Patent number: 4492797
    Abstract: 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: Grant
    Filed: October 4, 1982
    Date of Patent: January 8, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Andor Furst, Peter Keller, Marcel Muller
  • Patent number: 4447625
    Abstract: 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: Grant
    Filed: September 23, 1982
    Date of Patent: May 8, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Walter Kunz
  • Patent number: 4444591
    Abstract: 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: Grant
    Filed: February 23, 1982
    Date of Patent: April 24, 1984
    Assignee: Yamada Chemical Co., Ltd.
    Inventors: Hajime Kawai, Katsuhiko Tsunemitsu, Yoshiharu Fujino, Yoji Shimizu
  • Patent number: 4413133
    Abstract: 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: Grant
    Filed: November 13, 1981
    Date of Patent: November 1, 1983
    Assignee: Institut Francais du Petrole
    Inventors: Bernard Damin, Alain Forestiere, Bernard Sillion
  • Patent number: 4398032
    Abstract: 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: Grant
    Filed: June 7, 1982
    Date of Patent: August 9, 1983
    Assignee: Shell Oil Company
    Inventor: Petrus A. Kramer
  • Patent number: 4395416
    Abstract: 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: Grant
    Filed: January 21, 1982
    Date of Patent: July 26, 1983
    Assignee: Delalande S.A.
    Inventors: Michel Langlois, Bernard P. Bucher, Philippe L. Dostert, Alain P. Lacour, Gerard H. Moinet
  • Patent number: 4393056
    Abstract: 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: Grant
    Filed: June 15, 1981
    Date of Patent: July 12, 1983
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Fusao Tomita, Tatsuya Tamaoki, Kunikatsu Shirahata, Masaji Kasai, Noriaki Hirayama, Makoto Morimoto, Masanori Fukui
  • Patent number: 4390616
    Abstract: Recording members having excellent light resistance are obtained by using as a dye precursor specific diarylaminofluoran compounds.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: June 28, 1983
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Ken Iwakura, Akira Igarashi
  • Patent number: 4384879
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: May 24, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Walter Kunz
  • Patent number: 4377689
    Abstract: 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: Grant
    Filed: October 23, 1981
    Date of Patent: March 22, 1983
    Assignee: Etablissements Nativelle S.A.
    Inventors: Georges Tsatsas, Evan E. Costakis, Georges V. Foscolos
  • Patent number: 4371538
    Abstract: 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: Grant
    Filed: October 9, 1980
    Date of Patent: February 1, 1983
    Assignee: Etablissements Nativelle S.A.
    Inventors: Georges Tsatsas, Evan E. Costakis, Georges V. Foscolos
  • Patent number: 4362872
    Abstract: 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: Grant
    Filed: September 24, 1981
    Date of Patent: December 7, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger