Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/453)
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Patent number: 5137913Abstract: 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: GrantFiled: December 12, 1991Date of Patent: August 11, 1992Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Thomas G. C. Bird, Philip N. Edwards
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Patent number: 5128479Abstract: 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: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5120864Abstract: 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: GrantFiled: December 3, 1990Date of Patent: June 9, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
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Patent number: 5098932Abstract: 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: GrantFiled: December 22, 1989Date of Patent: March 24, 1992Assignee: Imperial Chemical Industries PLC, ICI PharmaInventor: Annie Hamon
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Certain 3,3-bis-(difluoro methyl)2,2-dimethyl-cyclopropane carboxylates having insecticidal activity
Patent number: 5049585Abstract: 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: GrantFiled: October 6, 1989Date of Patent: September 17, 1991Assignee: Imperial Chemical Industries PLCInventors: Michael J. Robson, Mark A. Spinney -
Patent number: 5036061Abstract: 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: GrantFiled: November 22, 1989Date of Patent: July 30, 1991Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Rafal R. Sicinski, Yoko Tanaka
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Patent number: 4990682Abstract: 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: GrantFiled: November 21, 1989Date of Patent: February 5, 1991Assignee: Huels AGInventors: Manfred Kaufhold, Werner Otte
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Patent number: 4981989Abstract: 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: GrantFiled: November 8, 1989Date of Patent: January 1, 1991Assignee: American Cyanamid CompanyInventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
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Patent number: 4973714Abstract: There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.Type: GrantFiled: November 22, 1988Date of Patent: November 27, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4971981Abstract: 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: GrantFiled: January 19, 1988Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4971995Abstract: 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: GrantFiled: January 26, 1989Date of Patent: November 20, 1990Assignee: Delande S.A.Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
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Patent number: 4968820Abstract: 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: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Scherowsky, Manel Gunaratne
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Patent number: 4968706Abstract: 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: GrantFiled: August 11, 1988Date of Patent: November 6, 1990Assignee: Boehringer Mannhein Italia, S.p.A.Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
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Patent number: 4947005Abstract: 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: GrantFiled: August 25, 1989Date of Patent: August 7, 1990Assignee: BASF AktiengesellschaftInventors: Dieter Koeffer, Werner Bertleff
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Patent number: 4940806Abstract: 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: GrantFiled: June 21, 1989Date of Patent: July 10, 1990Assignee: Ciba-Geigy CorporationInventor: Adolf Hubele
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Patent number: 4931575Abstract: 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: GrantFiled: March 13, 1987Date of Patent: June 5, 1990Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence PlantationsInventor: Elie Abushanab
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Patent number: 4910220Abstract: 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: GrantFiled: April 20, 1988Date of Patent: March 20, 1990Assignee: Proter SpaInventor: Piercarlo Braga
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Patent number: 4877891Abstract: 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: GrantFiled: August 5, 1988Date of Patent: October 31, 1989Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Walter Seufert, Ernst Buschmann, Christiane Bruchner
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Patent number: 4876368Abstract: 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: GrantFiled: May 24, 1988Date of Patent: October 24, 1989Assignee: Hoechst Celanese CorporationInventors: Jerry A. Broussard, Wayne C. Fuqua, James H. George
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Patent number: 4861903Abstract: 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: GrantFiled: July 31, 1986Date of Patent: August 29, 1989Assignee: Zambon spaInventors: Claudio Giordano, Graziano Castaldi
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Patent number: 4855318Abstract: 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: GrantFiled: June 26, 1987Date of Patent: August 8, 1989Assignee: Bayer AktiengesellschaftInventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
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Patent number: 4847392Abstract: 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: GrantFiled: March 17, 1987Date of Patent: July 11, 1989Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, Daniel A. Singleton
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Patent number: 4845119Abstract: 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: GrantFiled: February 18, 1986Date of Patent: July 4, 1989Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 4833258Abstract: 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: GrantFiled: February 17, 1987Date of Patent: May 23, 1989Assignee: Merck & Co., Inc.Inventors: Robert L. Smith, Ta Jyh Lee
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Patent number: 4812582Abstract: 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: GrantFiled: May 6, 1987Date of Patent: March 14, 1989Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4810806Abstract: There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.Type: GrantFiled: July 31, 1987Date of Patent: March 7, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4780479Abstract: 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: GrantFiled: January 14, 1987Date of Patent: October 25, 1988Assignee: National Research Development CorporationInventors: John A. Pickett, Ewen D. M. Macaulay
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Patent number: 4774344Abstract: 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: GrantFiled: July 8, 1987Date of Patent: September 27, 1988Assignee: Amoco CorporationInventor: Donald R. Kelsey
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Patent number: 4755625Abstract: 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: GrantFiled: July 16, 1987Date of Patent: July 5, 1988Assignee: BASF AktiengesellschaftInventors: Robert Maerkl, Werner Bertleff, Rudolf Kummer
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Patent number: 4748256Abstract: 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: GrantFiled: May 29, 1986Date of Patent: May 31, 1988Assignee: Zambon SpAInventors: Daniele Donati, Claudio Giordano, Graziano Castaldi
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Patent number: 4748257Abstract: 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: GrantFiled: July 21, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
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Patent number: 4745200Abstract: 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: GrantFiled: December 13, 1985Date of Patent: May 17, 1988Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Hinrich Moeller
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Patent number: 4719227Abstract: 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: GrantFiled: February 27, 1986Date of Patent: January 12, 1988Assignee: Bayer AktiengesellschaftInventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
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Patent number: 4714710Abstract: 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: GrantFiled: September 9, 1986Date of Patent: December 22, 1987Assignee: Schering AktiengesellschaftInventors: Heinrich Franke, Hartmut Joppien, Helga Franke
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Patent number: 4709059Abstract: 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: GrantFiled: August 12, 1985Date of Patent: November 24, 1987Assignee: The Dow Chemical CompanyInventors: Stoil K. Dirlikov, Connie J. Schneider
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Patent number: 4701540Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.Type: GrantFiled: March 12, 1984Date of Patent: October 20, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4691033Abstract: 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: GrantFiled: December 20, 1985Date of Patent: September 1, 1987Assignee: Hardwicke Chemical CompanyInventor: James E. Hardwicke, III
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Patent number: 4671816Abstract: 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: GrantFiled: August 23, 1985Date of Patent: June 9, 1987Assignee: BASF AktiengesellschaftInventors: Jens-Uwe Bliesener, Manfred Baumann, Werner Hoffmann, Hubert Sauter, Johann Jung
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Patent number: 4657926Abstract: 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: GrantFiled: May 14, 1984Date of Patent: April 14, 1987Assignee: National Research Development CorporationInventors: John A. Pickett, Ewen D. M. Macaulay
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Patent number: 4642372Abstract: 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: GrantFiled: July 29, 1985Date of Patent: February 10, 1987Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4628108Abstract: 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: GrantFiled: December 19, 1984Date of Patent: December 9, 1986Assignee: Texaco Inc.Inventors: John R. Sanderson, Ernest L. Yeakey
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Patent number: 4626601Abstract: 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: GrantFiled: September 18, 1981Date of Patent: December 2, 1986Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
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Patent number: 4616092Abstract: 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: GrantFiled: February 18, 1981Date of Patent: October 7, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4605758Abstract: 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: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4603208Abstract: 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: GrantFiled: February 10, 1983Date of Patent: July 29, 1986Assignee: Kuraray Co., Ltd.Inventors: Takashi Onishi, Shigeaki Suzuki, Fumio Mori, Tetsuo Takigawa, Yoshiji Fujita, Masao Mizuno, Takashi Nishida
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Patent number: 4594456Abstract: 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: GrantFiled: January 20, 1984Date of Patent: June 10, 1986Assignee: BASF AktiengesellschaftInventors: Ulrich Schaefer-Luederssen, Hagen Jaedicke, Joachim Paust, Manfred Eggersdorfer
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Patent number: 4591601Abstract: 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: GrantFiled: April 12, 1985Date of Patent: May 27, 1986Assignee: McNeilab, Inc.Inventors: Bruce E. Maryanoff, Samuel O. Nortey
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Patent number: 4590282Abstract: Dioxolane and benzodioxin derivatives, intermediates therefor, synthesis thereof, and the use of the compounds for the control of pests.Type: GrantFiled: September 24, 1984Date of Patent: May 20, 1986Assignee: Sandoz Ltd.Inventor: Clive A. Henrick
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Patent number: 4588824Abstract: Processes for preparing (S) or (R) epihalohydrin and an (S) substituted glycerol intermediate are disclosed.Type: GrantFiled: June 16, 1983Date of Patent: May 13, 1986Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David E. McClure
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Patent number: 4575558Abstract: 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: GrantFiled: February 15, 1984Date of Patent: March 11, 1986Assignee: American Hospital Supply CorporationInventors: Khuong H. X. Mai, Ghanshyam Patil