Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/453)
  • Patent number: 5137913
    Abstract: The invention concerns a diaryl ether cyclic ether of the formula I, or a pharmaceutically-acceptable salt thereof, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C) alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl and substituted (1-4C)alkyl.The invention also concerns processes for the manufacture of a diaryl ether cyclic ether of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said cyclic ether. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: August 11, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Thomas G. C. Bird, Philip N. Edwards
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5120864
    Abstract: New intermediates and processes for the preparation of vitamins A and E, which are the acetals of 5,6-dihalo-3-methyl-3-hydroxyhexanal or of 6-halo-3-hydroxy-3-methyl-5-hexenal or 3-methyl-3-hydroxy-5-hexenal, as well as processes for making the intermediates. After dehydrohalogenation and dehydration these intermediates are condensed directly with .beta.-ionone or with 2-methyl-2-heptene-6-one to synthesize vitamins A and E respectively.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: June 9, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5098932
    Abstract: The invention concerns a cyclic ether derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-6C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: March 24, 1992
    Assignee: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: Annie Hamon
  • Patent number: 5049585
    Abstract: Insecticidal compounds with effective knockdown activity against public health pests and having the general formula: ##STR1## wherein Z is selected from 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl; 3-propargyl-2-methyl-4-oxocyclopent-2-en-1-yl; 1-ethynyl-2-methylpent-2-en-1-yl; 3,4,5,6-tetrahydrophthalimidomethyl; (6-phenoxypyrid-2-yl)methyl; 1-cyano-1-(6-phenoxypyrid-2-yl)methyl; 1-propargylimidazolin-2,4-dione-3-ylmethyl; 5-benzylfur-3-ylmethyl; and a group of formula: ##STR2## wherein X represents hydrogen, hydroxy, methoxy or ethynyl. The invention also provides processes for the preparation of, and insecticidal compositions comprising, the compounds of formula (I).
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: September 17, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, Mark A. Spinney
  • Patent number: 5036061
    Abstract: The present invention provides novel derivatives of vitamin D.sub.2 and more specifically 1 alpha,25-dihydroxylated compounds of the vitamin D series. A process for the preparation of such derivatives is also provided as are certain intermediates in such process.The derivatives of this invention find ready application as substitutes for vitamin D.sub.3 or D.sub.2 or various of the known vitamin metabolites of these vitamins in their various applications to the correction of disorders involving calcium metabolism and associated bone disease.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: July 30, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Rafal R. Sicinski, Yoko Tanaka
  • Patent number: 4990682
    Abstract: A process for the preparation of 5-chloro-2-pentanone starting from a ketal of a levulinic ester, followed by hydrogenation, and then reaction with hydrochloric acid. The process involves first purifying the ketal of the levulinic ester by distillation, making the hydrogenation catalysts for the ketal alkaline, and reacting the 3-(2-methyl-1,3-dioxolan-2-yl)propan-1-ol formed in this hydrogenation with hydrochloric acid to obtain 5-chloro-2-pentanone.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: February 5, 1991
    Assignee: Huels AG
    Inventors: Manfred Kaufhold, Werner Otte
  • Patent number: 4981989
    Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: January 1, 1991
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
  • Patent number: 4973714
    Abstract: There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: November 27, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4971981
    Abstract: Novel substituted 1,3-dioxolan and 1,4-dioxan derivatives of formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 each independently of the others represents hydrogen or C.sub.1 -C.sub.4 -alkyl or, if n=1,R.sub.2 and R.sub.4 together represent one of the radicals ##STR2## R.sub.7 represents hydrogen, halogen, methyl, ethyl, C.sub.1 -C.sub.2 -alkyl substituted by 1 to 5 halogen atoms, methoxy, ethoxy or C.sub.1 -C.sub.2 -alkoxy substituted by 1 to 5 halogen atoms;R.sub.8 represents a halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl substituted by 1 to 7 halogen atoms, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkoxy substituted by 1 to 7 halogen atoms, or cyano;U represents a grouping --CH.dbd. or --N.dbd.;X represents --O--, --S-- or --N(R.sub.9)--;Y represents --O--, --S--, --S(O)--, --S(O.sub.2)--, --CH.sub.2 --, --CO-- or --N(R.sub.9)--, whereinR.sub.9 represents hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 4971995
    Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: November 20, 1990
    Assignee: Delande S.A.
    Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
  • Patent number: 4968820
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 = in any two cases (a) hydroxy and MC--CO--O or, independently of each other, MC--CO--O and (b), independently of each other (C.sub.1 -C.sub.10)alkoxy, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group, and it being possible for Y.sup.2 and Y.sup.3, in the case of (C.sub.1 -C.sub.10)alkoxy, also to be jointly part of a dioxolane ring, or Y.sup.1 and Y.sup.4 jointly = 0 as part of a tetrahydrofuran ring, and Y.sup.2 and Y.sup.3 = hydroxy and MC--CO--O or, independently of each other, MC--CO--O. Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: November 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4968706
    Abstract: Compounds of formula I ##STR1## wherein Ar is an optionally substituted phenyl ring; B is a single bond, a group --(CH.sub.2 OCH.sub.2).sub.n being n=1 or 2, a 2,4-disubstituted-1,3-dioxolane ring or a 2,4-disubstituted-1,3-thioxolane ring, R is a single bond, an optionally substituted methylene or ethylene group and T is 2-, 3- or 4-pyridyl, an optionally salified or esterified carboxy group or a carboxyamide group. Said compounds are useful in treatment of respiratory diseases.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: November 6, 1990
    Assignee: Boehringer Mannhein Italia, S.p.A.
    Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
  • Patent number: 4947005
    Abstract: 1,1,2-Trialkoxyethanes of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each independently of the others C.sub.1 -C.sub.20 -alkyl or cycloalkyl, or R.sup.1 and R.sup.2 may be linked together to form a 5-, 6- or 7-membered ring, are prepared by reacting formaldehyde dialkyl acetals of the general formula II ##STR2## where R.sup.1 and R.sup.2 are each as defined above, or compounds which are capable of forming formaldehyde dialkyl acetals under the reaction conditions, with carbon monoxide, hydrogen and alkanols R.sup.3 OH under superatmospheric pressure at elevated temperature in the presence of a catalyst composed of a cobalt carbonyl compound and a promotor, wherein the promotor is an alkali metal, alkaline earth metal or ammonium salt of a protogenic compound having an acid constant K.sub.a of from 10.sup.-2 to 10.sup.-14, an alkali metal or alkaline earth metal hydroxide or an aminocarboxylic acid.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: August 7, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Koeffer, Werner Bertleff
  • Patent number: 4940806
    Abstract: Novel substituted 2-(1H-1,2,4-triazolyl)-1-phenylethan-1-one ketals of the general formula ##STR1## wherein one of the two phenyl substituents is in 2-position and the other is in 4-position, and wherein R.sub.a is halogen, methyl or C.sub.1 -C.sub.3 haloalkoxy, and U and V are each independently of the other C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.6 alkoxy, or together are an alkylene bridge selected from ##STR2## wherein R.sub.1 to R.sub.5 are as defined herein, and the acid addition salts and metal complex salts, have microbicidal properties and are especially suitable for controling phytopathogenic microorganisms. They can be used in the form of plant protective or seed dressing agents for preventing or controlling plant pathogens.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: July 10, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4931575
    Abstract: Enantiomerically pure glycerol derivatives, e.g. S-1,2-O-isopropylidene, S-1,2-O-benzylidene, and R-1,2-O-dibenzyl glycerol, have been prepared from 1,2R-O-protected erythritols in high yields. The latter compounds are easily obtained from erythorbic acid and are useful building blocks in the synthesis of a host of optically active compounds having biological activity.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: June 5, 1990
    Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence Plantations
    Inventor: Elie Abushanab
  • Patent number: 4910220
    Abstract: The present invention relates to pharmaceutical compositions containing thiodioxolane derivatives having an interesting mucolytic activity, and to a process for the preparation of said thiodioxolane derivatives of the general structural formula ##STR1## in which the carbon atom marked with an asterisk indicates a asymmetry center in the molecule,X represents an hydroxy group or --SR" and R" is hydrogen or a suitable acylic radical,R represents hydrogen, a lower alkyl, a lower hydroxy alkyl, or phenyl,R' represents a lower alkyl, a lower hydroxy alkyl, phenyl, --(CH.sub.2).sub.n SR" where n is a whole number between 1 and 3 and R" has the above indicated meaning, with condition that X and R' can never be both type of groups.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: March 20, 1990
    Assignee: Proter Spa
    Inventor: Piercarlo Braga
  • Patent number: 4877891
    Abstract: 1,1-dialkoxy- or 1,1-(.alpha.,.omega.-methylenedioxy)-non-2-yn-9-ol and their OH-protected derivatives of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl or together form an alkylene chain of 2 to 5 carbon atoms and X is hydrogen or a protective group which can be eliminated, their preparation and their use as intermediates.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: October 31, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Walter Seufert, Ernst Buschmann, Christiane Bruchner
  • Patent number: 4876368
    Abstract: A process is provided for the production of a monohydroxy monocyclic acetal, e.g., trimethylolpropane cyclic formal, of a trihydroxy alcohol, e.g., trimethylolpropane, and an aldehyde, e.g., formaldehyde, by subjecting a "heavier condensation product" of the trihydroxy alcohol and the aldehyde than the desired cyclic acetal, i.e., one having a higher molecular weight and boiling point, to acetal formation conditions. In a preferred embodiment, the product of reaction of the trihydroxy alcohol and aldehyde is treated to remove the desired monohydroxy monocyclic acetal product and at least part of the remainder comprising the heavier condensation product is recycled to the reaction together with a flesh supply of trihydroxy alcohol and aldehyde. The monohydroxy monocyclic acetal product may be further reacted to obtain a desired ester, e.g. trimethylolpropane cyclic formal acrylate, such as by transesterifying the acetal with a low boiling ester of the esterifying acid, e.g.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: October 24, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry A. Broussard, Wayne C. Fuqua, James H. George
  • Patent number: 4861903
    Abstract: A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula ##STR1## in which the substituents have the meaning given in the description of the invention.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: August 29, 1989
    Assignee: Zambon spa
    Inventors: Claudio Giordano, Graziano Castaldi
  • Patent number: 4855318
    Abstract: Iodopropargyl ethers of the formula ##STR1## wherein A represents oxygen or a methylene group,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, lower alkyl, alkenyl or unsubstituted or halogen-substituted phenyl, or R.sup.2 and R.sup.3 together form a carbocyclic ring with 4 to 7 C atoms,l and m represent 0, 1 or 2,k denotes 0 or 1 andn denotes an integer from 0 to 4, with the proviso that if l is 0, n represents 1, 2, 3 or 4,can be prepared by reaction of the corresponding propargyl ethers with iodinating agents. The iodopropargyl ethers are active compounds in microbicidal agents.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: August 8, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
  • Patent number: 4847392
    Abstract: A method of conducting a Diels-Alder reaction is provided comprising reacting a Diels-Alder diene comprising a 1,3-conjugated diene with a dienophile comprising an alpha,beta-unsaturated acetal or ketal in the presence of a protonating acid to yield a [4+2] cycloadduct.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: July 11, 1989
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Daniel A. Singleton
  • Patent number: 4845119
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent of each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 4, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 4833258
    Abstract: Novel intermediates and a novel process for their preparation, where said intermediates are useful in the preparation of 6-hydroxymethyl and related oxidation derivatives of mevinolin and analogs thereof, are disclosed.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: May 23, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Robert L. Smith, Ta Jyh Lee
  • Patent number: 4812582
    Abstract: This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 14, 1989
    Assignee: The Upjohn Company
    Inventor: Stephen J. Nelson
  • Patent number: 4810806
    Abstract: There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: March 7, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4780479
    Abstract: Derivatives of carbonyl-group containing behavior modifying compounds, in which said carbonyl group has been converted to a photolabile group which regenerates the carbonyl group on exposure to radiation, are of value in various methods for the control of animal, and in particular insect, species.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: October 25, 1988
    Assignee: National Research Development Corporation
    Inventors: John A. Pickett, Ewen D. M. Macaulay
  • Patent number: 4774344
    Abstract: Described herein are novel monomers, polyketals derived from such monomer, improved process for the production of such monomers and a process for producing the polyketals.
    Type: Grant
    Filed: July 8, 1987
    Date of Patent: September 27, 1988
    Assignee: Amoco Corporation
    Inventor: Donald R. Kelsey
  • Patent number: 4755625
    Abstract: 1,1,2-trialkoxyethanes I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.8 -alkyl and R.sup.1 and R.sup.2 may furthermore be bonded to one another to form a 5-membered to 7-membered ring, are prepared by reacting a formaldehyde dialkyl acetal II with carbon monoxide and hydrogen, from 0.5 to 1.5 moles of hydrogen being used per mole of carbon monoxide, and with not less than 1 mole of alcohol R.sup.3 OH per mole of formaldehyde dialkyl acetal under superatmospheric pressure and at elevated temperatures in the presence of a catalyst which is formed from a cobalt carbonyl compound and a trivalent organic compound of the formula III ##STR2## where A is phosphorus, arsenic, antimony or bismuth and R.sup.4, R.sup.5 and R.sup.6 are each an organic radical.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: July 5, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Robert Maerkl, Werner Bertleff, Rudolf Kummer
  • Patent number: 4748256
    Abstract: A process is described for the preparation of (6-methoxy-2-naphthyl)-(1-bromoethyl)-ketone or ketals thereof (I), by selective debromination of (5-bromo-6-methoxy-2-naphthyl)-(1-bromoethyl)-ketone or ketals thereof (III) by means of a bromine acceptor in the presence of an acid and of an inert organic solvent. The bromine acceptor is preferably a phenol, a phenol ether or an aromatic ketone. The acid is preferably an halogenidric acid.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: May 31, 1988
    Assignee: Zambon SpA
    Inventors: Daniele Donati, Claudio Giordano, Graziano Castaldi
  • Patent number: 4748257
    Abstract: The new compound ##STR1## is prepared and converted to the new acetal ##STR2## which is reacted with an alkali phenolate or alkaline earth metal phenolate in the presence of copper or a copper compound as a catalyst and in the presence of a diluent at a temperature between about 100.degree. and 200.degree. C. to produce the new acetal ##STR3## which can be hydrolyzed to the corresponding aldehyde which is a known intermediate for pyrethroid-like insecticides.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
  • Patent number: 4745200
    Abstract: A new process for the production of salts of 1,3-dioxolane-4-carboxylic acid corresponding to the following formula ##STR1## using as a starting material an isomer mixture of a 4-hydroxymethyl-1,3-dioxolane and a 5-hydroxy-1,3-dioxane obtained by reacting glycerin with an aldehyde or ketone having the formula R.sup.1 R.sup.2 CO. The 4-hydroxymethyl-1,3-dioxolane may be selectively oxidized from the isomer mixture in the presence of a platinum metal catalyst at an alkaline pH. The unreacted 5-hydroxy-1,3-dioxane may be extracted from the reaction mixture and the 1,3-dioxolane-4-carboxylic acid salt isolated in pure form.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: May 17, 1988
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Hinrich Moeller
  • Patent number: 4719227
    Abstract: Iodopropargyl ethers of the formula ##STR1## wherein A represents oxygen or a methylene group,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, lower alkyl, alkenyl or unsubstituted or halogen-substituted phenyl, or R.sup.2 and R.sup.3 together form a carbocyclic ring with 4 to 7 C atoms,L and m represent 0, 1 or 2,k denotes 0 or 1 andn denotes an integer from 0 to 4, with the proviso that if 1 is 0, n represents 1, 2, 3 or 4,can be prepared by reaction of the corresponding propargyl ethers with iodinating agents. The iodopropargyl ethers are active compounds in microbicidal agents.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: January 12, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
  • Patent number: 4714710
    Abstract: There are described new compounds of general formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkylaryloxy, or nitro-C.sub.1-4 -alkylaryloxy,R.sub.2 and R.sub.3 are the same or different and are hydrogen, fluorine, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.1-4 -alkoxy, halo-C.sub.
    Type: Grant
    Filed: September 9, 1986
    Date of Patent: December 22, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinrich Franke, Hartmut Joppien, Helga Franke
  • Patent number: 4709059
    Abstract: Epoxy compounds for use as epoxy resins are prepared from relatively inexpensive and renewable resources via a selective halogenation process. Primary pendant hydroxyl groups on straight carbon chain compounds with oxygen atoms pendant to each carbon are selectively halogenated with, for example, carbon tetrachloride. A scavenger agent, triphenylphosphine and pyridine, is used to complex the residual portion of reacted halogenating agent. One additional step with the halogenated intermediate yields epoxy compounds which, when cured, yield epoxy resins.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: November 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Stoil K. Dirlikov, Connie J. Schneider
  • Patent number: 4701540
    Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 20, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4691033
    Abstract: 3-Phenoxybenzaldehyde acetals can be prepared by reacting a 3-bromobenzalkehyde acetal with an alkali metal phenolate at a temperature of about 130.degree.-165.degree. C. in the presence of a copper catalyst and a phenol as the sole solvent. The product acetals can be converted to the corresponding 3-phenoxybenzaldehydes by hydrolysis.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: September 1, 1987
    Assignee: Hardwicke Chemical Company
    Inventor: James E. Hardwicke, III
  • Patent number: 4671816
    Abstract: Acetylene compounds of the formula ##STR1## where R.sup.1, R.sup.2 and X have the meanings given in the description, a process for their preparation and their use for regulating plant growth.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: June 9, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Jens-Uwe Bliesener, Manfred Baumann, Werner Hoffmann, Hubert Sauter, Johann Jung
  • Patent number: 4657926
    Abstract: Derivatives of carbonyl-group containing behavior modifying compounds, in which said carbonyl group has been converted to a photolabile group which regenerates the carbonyl group on exposure to radiation, are of value in various methods for the control of animal, and in particular insect, species.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: April 14, 1987
    Assignee: National Research Development Corporation
    Inventors: John A. Pickett, Ewen D. M. Macaulay
  • Patent number: 4642372
    Abstract: A process for the preparation of cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein Z is selected from the group consisting of --CN, --COOH and --COOR.sub.1, R.sub.1 is alkyl of 1 to 6 carbon atoms and R.sub.2 and R.sub.3 are alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms comprising reacting at low temperatures in a solvent in the presence of a strong base a compound of the formula ##STR2## wherein Z has the above definitions and R is alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms with a sulfone of the formula ##STR3## wherein R.sub.2 and R.sub.3 have the above definitions and Y is an aromatic group followed by aqueous treatment to obtain a compound of the formula ##STR4## wherein Y, R, R.sub.2, R.sub.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: February 10, 1987
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4628108
    Abstract: It has been surprisingly discovered in accordance with the present invention that when 1,3-dioxolane is reacted with formaldehyde in the presence of an organic peroxide and an ionizable, at least sparingly soluble metal salt, the reaction preferentially involves an addition of the formaldehyde to the 2-methylene group of the 1,3-dioxolane with only minor reaction with the 4-methylene and 5-methylene groups of the 1,3-dioxolane whereby the reaction product that is formed contains significant quantities of 2-hydroxyalkyl-1,3-dioxolanes. 2-Hydroxyalkyl-1,3-dioxolanes are hydrolyzed with comparative ease to ethylene glycol and the corresponding glycol aldehyde (CHO--CH.sub.2 --OH). The glycol aldehyde in turn can be catalytically hydrogenated to form additional quantities of ethylene glycol.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: December 9, 1986
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Ernest L. Yeakey
  • Patent number: 4626601
    Abstract: The new compound ##STR1## is prepared and converted to the new acetal ##STR2## which is reacted with an alkali phenolate or alkaline earth metal phenolate in the presence of copper or a copper compound as a catalyst and in the presence of a diluent at a temperature between about 100.degree. and 200.degree. C. to produce the new acetal ##STR3## which can be hydrolyzed to the corresponding aldehyde which is a known intermediate for pyrethroid-like insecticides.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: December 2, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
  • Patent number: 4616092
    Abstract: An optically active or inactive .beta.-formyl-.beta.-hydroxy ester of the formula (1), ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.14 aralkyl group, R.sup.2 represents a C.sub.1 -C.sub.4 alkyl group and R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, and a method for producing the same which comprises reacting an optically active or inactive compound of the formula (2), ##STR2## wherein A represents a C.sub.6 -C.sub.14 aryl group and R.sup.1 is as defined above, with an .alpha.-halo ester of the formula (3), ##STR3## wherein X represents a halogen atom and R.sup.2 and R.sup.3 are as defined above, in the presence of zinc, followed by hydrolysis, or reacting an ester of the formula (4),R.sup.3 CH.sub.2 COOR.sup.2 (4)wherein R.sup.2 and R.sup.
    Type: Grant
    Filed: February 18, 1981
    Date of Patent: October 7, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4603208
    Abstract: Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.
    Type: Grant
    Filed: February 10, 1983
    Date of Patent: July 29, 1986
    Assignee: Kuraray Co., Ltd.
    Inventors: Takashi Onishi, Shigeaki Suzuki, Fumio Mori, Tetsuo Takigawa, Yoshiji Fujita, Masao Mizuno, Takashi Nishida
  • Patent number: 4594456
    Abstract: 3-Hydroxy-.alpha.-cyclocitral derivatives of the general formula I ##STR1## where R.sup.1 is ##STR2## wherein R.sup.2 and R.sup.3 can be identical or different and are each straight-chain or branched alkyl of 1 to 6 carbon atoms, or R.sup.2 and R.sup.3 together form an ethylene or propylene group which can be substituted by methyl or ethyl, processes for their preparation and their use for the preparation of safranal and 3-hydroxy-.beta.-cyclocitral, as well as optically active - cyclocitral derivatives of the general formulae A and B ##STR3## where R.sup.1 is ##STR4## if X is hydrogen and Y is OH, but is otherwise ##STR5## where R.sup.2 and R.sup.3 have the above meanings, and X and Y together are oxygen, or X is hydrogen if Y is OH, and a process for the preparation of optically active 3-oxo-.alpha.-cyclocitral acetals, wherein a mixture of the corresponding racemic 3-oxo-.alpha.-cyclocitral acetals is separated into the optically active compounds by chromatography over a suitable chiral adsorbent.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schaefer-Luederssen, Hagen Jaedicke, Joachim Paust, Manfred Eggersdorfer
  • Patent number: 4591601
    Abstract: Sulfamates of the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as herein defined have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and intermediates form part of the present invention.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: May 27, 1986
    Assignee: McNeilab, Inc.
    Inventors: Bruce E. Maryanoff, Samuel O. Nortey
  • Patent number: 4590282
    Abstract: Dioxolane and benzodioxin derivatives, intermediates therefor, synthesis thereof, and the use of the compounds for the control of pests.
    Type: Grant
    Filed: September 24, 1984
    Date of Patent: May 20, 1986
    Assignee: Sandoz Ltd.
    Inventor: Clive A. Henrick
  • Patent number: 4588824
    Abstract: Processes for preparing (S) or (R) epihalohydrin and an (S) substituted glycerol intermediate are disclosed.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: May 13, 1986
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, David E. McClure
  • Patent number: 4575558
    Abstract: Described is a process for preparing 2,2'-disubstituted-1,3-dioxolane-4-methanol compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, cycloalkyl or R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 6 member cycloalkyl group, or aryl, the process comprising: reacting D- or L-serine with a nitrosating agent in an aqueous solution in the presence of formic acid, acetic acid, or propanoic acid to prepare 2,3-dihydroxypropanoic acid (D- or L-glyceric acid), the aqueous solution comprising from about 0.1 to 0.5 liter of water per mole of the serine starting material; reacting the glyceric acid so formed with 2,2-dimethoxypropane in the presence of a loweralkyl alcohol to prepare the D- or L-glyceric acid alkyl ester which is reacted with a selected aldehyde or ketone or the acetal or ketal derivative to prepare the corresponding 1,3-dioxolane derivative.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: March 11, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Khuong H. X. Mai, Ghanshyam Patil