Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/462)
  • Patent number: 4994474
    Abstract: The present invention relates to aminoalkoxyphenyl derivatives of formula: ##STR1## and its N-oxide and pharmaceutically acceptable salts, in which: B represents a--S--, --SO-- or --SO.sub.2 -- group,R.sub.1 and R.sub.2, which are identical or different, each denote hydrogen, a methyl or ethyl radial or a halogen atom,A denotes a straight-or branched-alkylene radical having from 2 to 5 carbon atoms or a 2-hydroxypropylene radial in which the hydroxy is optionally substituted by a lower alkyl radical,R.sub.3 denotes an alkkyl radical or a radical of formula:--Alk--Arin which Alk denotes a single bond or a linear- or branched-alkylene radical having from 1 to 5 carbon atoms and Ar denotes a pyridyl, phenyl, 2,3-methylenedioxyphenyl or 3,4-methylenedioxyphenyl radical or a phenyl group substituted with one or more substituents, which may be identical or different, selected from halogen atoms, lower alkyl group or lower alkoxy groups,R.sub.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: February 19, 1991
    Assignee: Sanofi
    Inventors: Jean Gubin, Pierre Chatelain, Henri Inion
  • Patent number: 4983779
    Abstract: An improved process for the preparation of vinyl ethers by the coupling reaction of an ester of the formula ##STR1## with a carbonyl containing compound of the formula ##STR2## wherein A and R are passive organic groups and OY is a hydroxyl group or OP where P is a protecting group is described. The ester and the carbonyl containing compound are reacted in an organic solvent with a titanium salt, a metallic reducing agent and an amine base to provide the vinyl ether. The reaction is safe and produces high yields. The vinyl ethers are useful for producing dioxetanes which produce light upon triggering.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: January 8, 1991
    Assignee: The Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • Patent number: 4978761
    Abstract: The present invention relates to a compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or a lower alkyl; R.sup.2 is methyl which is substituted by a carboxy, alkoxycarbonyl, cyano, halogen, aryl or heterocyclic group of C.sub.2-15 chain hydrocarbon residue having no lower alkyl at the .alpha.-position which may be substituted by a carboxy, alkoxycarbonyl, cyano, halogen, aryl or heterocyclic group; R.sup.3 is a lower alkyl; R.sup.4 is hydrogen or acyl; and R.sup.5 and R.sup.6 each is a lower alkyl or lower alkoxy, or R.sup.5 and R.sup.6 combinedly are butadienylene or a salt thereof.The compound (I) of the present invention has a strong 5- and 12-lipoxygenase inhibiting action, is of high safety and is useful as, among others, an agent for ameliorating dysfunction circulatory system, an anti-allergic agent and a pharmaceutical agent for central nervous system.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: December 18, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
  • Patent number: 4977276
    Abstract: Novel heteroarotinoid compositions characterized by the formulae: ##STR1## where: X is S or O; OAc is the acetate group ##STR2## and R is --H, --OH, --OCH.sub.3, or --OC.sub.2 H.sub.5 and includes ##STR3## for formulae (1) and (2). Such compositions exhibit activity as anticancer agents.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 11, 1990
    Assignee: The Board of Regents for the Oklahoma Agricultural and Mechanical Colleges acting for and on behalf of Oklahoma State Univ.
    Inventors: Kenneth D. Berlin, Warren T. Ford, Shirish N. Rajadhyaksha, Jonathan B. Gale, Lyle W. Spruce
  • Patent number: 4975457
    Abstract: Certain trans-2,3-disubstituted-2,3-dihydro-5-hydroxybenzofurans are described. The synthesis involves an intramolecular Michael addition to yield the thermodynamic trans isomer. The compounds were found to be inhibitors of 5-lipoxygenase, an enzyme crucial to the biosynthesis of leukotrienes and useful for the treatment of various inflammatory diseases.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: December 4, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Kathleen M. Rupprecht, Joshua S. Boger
  • Patent number: 4975451
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; and Ar.sup.1 is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 2-methyl[1-1'-biphenyl]-3-yl, or 6-phenoxy-2-pyridyl, exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively nontoxic to fish.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: December 4, 1990
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
  • Patent number: 4971620
    Abstract: Disclosed herein is a sulfonamide compound represented by the formula (I): ##STR1## wherein A represents a phenyl group which may be substituted, B represents a phenyl group which may be substituted, R represents a lower alkyl group, a lower alkoxy group or a lower haloalkyl group, W represents a hydroxyl group or a halogen atom, and z represents a halogen atom, a lower alkysulfonyloxy group which may be substituted, or a phenylsulfonyloxy group which may be substituted, and a herbicidal composition containing the sulfonamide compound as an effective ingredient.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: November 20, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Manabu Katsurada, Toyohiko Shike, Osamu Ikeda, Hisao Watanabe, Tetsuo Takematsu, Koichi Yoneyama
  • Patent number: 4966907
    Abstract: Novel position-4 and/or position-6 substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs of the following general structural formula (I) are disclosed: ##STR1## These compounds are found to be potent inhibitors of leukotriene biosynthesis.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: October 30, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Charles G. Caldwell, Milton L. Hammond, Ihor E. Kopka, Stanley H. B. Wright, Robert A. Zambias
  • Patent number: 4966973
    Abstract: The present invention relates to a compound of the formula ##STR1## wherein R.sup.1 stands for hydrogen or a lower alkyl; n denotes an integer of 1 to 6; X stands for an optionally oxidized sulphur atom, oxygen atom or an optionally substituted imino; R.sup.2 stands for methyl or an organic residual group bonded through methylene, methine a quaternary carbon; R.sup.3 stands for a lower alkyl; R.sup.4 stands for hydrogen or acyl; R.sup.5 and R.sup.6 each stand for a lower alkoxy or a lower alkyl, or R.sup.5 and R.sup.6 combinedly stand for butadienylene, and salts thereof.The compound (I) of the present invention has a strong 5-lipoxygenase inhibiting action, is of high safety and is useful as, among others, an agent for ameliorating dysfunction of circulatory system, an anti-allergic agent and a pharmaceutical agent for central nervous system.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: October 30, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
  • Patent number: 4959092
    Abstract: The present invention relates to a substituted phenyl(or pyridyl)urea compound and a herbicidal composition containing the substituted phenyl(or pyridyl)urea compound as an active ingredient.The compound has the formula: ##STR1## wherein A represents an alkylene group; B represents a nitrogen atom or CH; R represents a hydrogen atom, a lower alkyl group or a lower alkoxy group;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent a hydrogen atom or a methyl group; and n is 0 or 1.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: September 25, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hiroki Ohta, Katsutoshi Sato, Susumu Matsumoto, Kazuo Ishii, Yumiko Miura, Hisao Watanabe, Seiichi Suzuki, Yoichiro Umeki, Hiroshi Hanabe
  • Patent number: 4956382
    Abstract: A series of novel N-alkyl-N-(alkanesulphonamidoheterocyclicmethyl)-4-alkanesulphonamidophene tyl mines have been prepared, including their pharmaceutically acceptable salts and various key novel intermediates therefor. The heterocyclic moiety present in these compounds is a benzo-fused heterocyclic group derived from either benzofuran, benzothiophene, benzoxazole or quinoline, and it is attached to the adjacent methyl group of the molecule by means of the available ring carbon atom which is situated alpha to the hetero atom. These particular compounds are useful in therapy as highly effective anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Preferred member compounds include N-methyl-N-(5-methanesulphonamidobenzofur-2-ylmethyl)-4-methanesulphonamid op henethylamine and N-methyl-N-(6-methanesulphonamidoquinol-2-ylmethyl)-4-methanesulphonamidop hen thylamine. Methods for preparing all these compounds from known starting materials are provided.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: September 11, 1990
    Assignee: Pfizer Inc.
    Inventors: John E. Arrowsmith, Peter E. Cross, Roger P. Dickinson, Geoffrey N. Thomas
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4950766
    Abstract: A method for preparing a benzamide by reacting an aromatic acid with an amine having a primary amino group and a secondary amino group wherein the reaction is directed to the primary amino group by first reacting the acid with N,N'-carbonyldiimidazole.
    Type: Grant
    Filed: September 21, 1989
    Date of Patent: August 21, 1990
    Assignee: Erbamont, Inc.
    Inventor: Jung-Hui Sun
  • Patent number: 4950773
    Abstract: Process is disclosed for the selective epoxidation of olefins having no allylic hydrogens. Such olefins are contacted with an oxygen-containing gas in the presence of a silver catalyst and an organic halide under defined reaction conditions, thereby selectively producing epoxides in good yield.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: August 21, 1990
    Assignee: Eastman Kodak Company
    Inventors: John R. Monnier, Peter J. Muehlbauer
  • Patent number: 4939141
    Abstract: A (fused) benz(thio)amides of the general ##STR1## (wherein, symbol A represents a single bond or a group of methylene, ethylene, trimethylene, tetramethylene, vinylene, propenylene, butenylene, butadienylene or ethynylene group optionally being substituted by one, two or three of straight or branched alkyl groups(s) of from 1 to 10 carbon atom(s) and/or phenyl group(s);Symbol B represents(i) a heterocyclic ring of from 4 to 8 members containing one, two or three hetero atoms selected from oxygen, nitrogen and/or sulphur atom(s), wherein the ring may optionally be substituted by group(s) of oxo, thioxo and/or hydroxy group(s) with the exclusion of a ring of the formula: ##STR2## Symbol T represents an oxygen atom or a sulphur atom; R.sup.1 represents a group of general formula:(i) ##STR3## (ii) ##STR4## or (iii) ##STR5## or (iv) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 20 carbon atom(s);(wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: July 3, 1990
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
  • Patent number: 4923641
    Abstract: Highly concentrated stable solutions of color-forming agents of the general formula ##STR1## wherein x denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkylamino, dialkylamino, acylamino, aralkylamino or arylamino andR denotes alkyl, alkenyl or aralkyl,further isocyclic or heterocyclic rings can be fused onto the rings A, B, C and D and the cyclic and acyclic radicals and the rings A, B, C and D can carry further non-ionic substituents which are customary in dyestuff chemistry, or mixtures thereof, in water-insoluble organic solvents from the group comprising optionally chlorinated hydrocarbons, vegetable oils and phthalic acid esters are used for the preparation of pressure-sensitive recording materials.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: May 8, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Eckstein, Hubertus Psaar
  • Patent number: 4921982
    Abstract: This invention provides bicyclic carboxylic esters and amides, their pharmaceutical formulations, and a method for their use in treating migraine, emesis, gastrointestinal disorders, schizophrenia, or anxiety in mammals.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: May 1, 1990
    Assignee: Eli Lilly and Company
    Inventors: Marlene L. Cohen, William B. Lacefield, David W. Robertson
  • Patent number: 4918092
    Abstract: Compounds having the formula I: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: April 17, 1990
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Richard Frenette, Robert N. Young, Masatoshi Kakushima
  • Patent number: 4897498
    Abstract: Process is disclosed for the selective mono epoxidation of olefins having no allylic hydrogens. Such olefins are contacted with an oxygen-containing gas in the presence of a silver catalyst under defined reaction conditions, thereby selectively producing monoepoxides in good yield.
    Type: Grant
    Filed: January 28, 1988
    Date of Patent: January 30, 1990
    Assignee: Eastman Kodak Company
    Inventors: John R. Monnier, Peter J. Muehlbauer
  • Patent number: 4895871
    Abstract: Benzoheterocyclyl ketone hydrazones of the formula ##STR1## in which Y is methylene, difluoromethylene or oxygen and n is 0 or 1, compositions thereof and their use as insecticides are disclosed and exemplified.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: January 23, 1990
    Assignee: FMC Corporation
    Inventors: Kathryn A. Lutomski, Angelina J. Duggan, John F. Engel
  • Patent number: 4888353
    Abstract: Carboxamides represented by the formula (I): ##STR1## wherein Z represents the carbon atoms necessary to complete a 5- to 7-membered ring,R.sup.1, R.sup.2, and R.sup.3 may be the same or different and are selected from the group consisting of a hydrogen atom, a lower alkyl group, a cycloalkyl group, a halogen atom, an amino group, a lower alkylamino group, an alkoxy group, an acylamido group, a sulfonamido group, and a nitro group; andA represents an aminoalkyl moiety and acid addition salts thereof.
    Type: Grant
    Filed: May 23, 1986
    Date of Patent: December 19, 1989
    Assignee: Erbamont, Inc.
    Inventors: Daniel Lednicer, Jung-Hui Sun
  • Patent number: 4874878
    Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, each denote a hydrogen atom, a benzyl radical, a cyclohexylmethyl radical or a linear or branched alkyl radical containing from 1 to 10 carbon atoms, optionally substituted with a hydroxy radical, with a carboxy radical or with an alkoxy radical having 1 to 5 carbon atoms, with an alkoxycarbonyl radical having 2 to 6 carbon atoms, with an alkylphenyl radical having 7 to 16 carbon atoms or with a 2-alkylthienyl radical having 5 to 14 carbon atoms,R.sub.3 denotes a hydrogen atom or a linear or branched alkyl radical containing from 1 to 4 carbon atoms,A denotes a single bond or a methylene radical, or a radical of formula ##STR2## in which R.sub.4 is a linear or branched alkyl radical containing from 1 to 4 carbon atoms.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: October 17, 1989
    Assignee: Adir Et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4873259
    Abstract: Compounds of the formula: ##STR1## wherein R.sub.1 is (1) hydrogen, (2) C.sub.1 to C.sub.4 alkyl, (3) C.sub.2 to C.sub.4 alkenyl, or (4) NR.sub.2 R.sub.3, wherein R.sub.2 and R.sub.3 are independently selected from (1) hydrogen, (2) C.sub.1 to C.sub.4 alkyl and (3) hydroxyl, but R.sub.2 and R.sub.3 are not simultaneously hydroxyl;wherein X is oxygen, sulfur, SO.sub.2, or NR.sub.4, wherein R.sub.4 is (1) hydrogen, (2) C.sub.1 to C.sub.6 alkyl, (3) C.sub.1 to C.sub.6 alkoyl, (4) aroyl, or (5) alkylsulfonyl;A is selected from C.sub.1 to C.sub.6 alkylene and C.sub.2 to C.sub.6 alkenylene;n is 1-5;Y is selected independently at each occurrence from (1) hydrogen, (2) halogen, (3) hydroxy, (4) cyano, (5) halosubstituted alkyl, (6) C.sub.1 to C.sub.12 alkyl, (7) C.sub.2 to C.sub.12 alkenyl, (8) C.sub.1 to C.sub.12 alkoxy, (9) C.sub.3 to C.sub.8 cycloalkyl, (10) C.sub.1 -C.sub.8 thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C.sub.1 to C.sub.12 arylalkyl, (15) C.sub.2 to C.sub.12 arylalkenyl, (16) C.sub.1 to C.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: October 10, 1989
    Assignee: Abbott Laboratories
    Inventors: James B. Summers, Jr., Bruce P. Gunn, Dee W. Brooks
  • Patent number: 4868318
    Abstract: The present invention relates to novel perfluoro chemicals (PFC), particularly perfluorocyclic ethers and polyfluorinated compounds containing a few chlorine atoms and to a method for the preparation thereof.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: September 19, 1989
    Assignee: The Green Cross Corporation
    Inventors: Kirby V. Scherer, Jr., Taizo Ono, Kouichi Yamanouchi, Kazumasa Yokoyama
  • Patent number: 4857516
    Abstract: A compound of the formula ##STR1## wherein R is a lower alkyl group, R.sup.0 is hydrogen or an acyl group, R.sup.1 and R.sup.2 are lower alkyl groups which may optionally be substituted or wherein R.sup.1 and R.sup.2 are combined to form a butadienylene group which may optionally be substituted, R.sup.3 and R.sup.4 are hydrogen or alkyl groups which may optionally be substituted or wherein R.sup.3 and R.sup.4 are combined to form a polymethylene group, and R.sup.5 is a lower alkyl, aromatic or heterocyclic group which may optionally be substituted or a pharmaceutically acceptable salt thereof, exerts cardiovascular system improving action and antiallergic action and can be used as pharmaceutics, e.g. antithromotics, antiallergic agents etc.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: August 15, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Yoshitaka Maki
  • Patent number: 4855426
    Abstract: The synthesis of epoxybenzazepin compounds is described. The novel compounds have anti-ulcer activity.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: August 8, 1989
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Michael P. Wachter, Donald S. Karanewsky
  • Patent number: 4851587
    Abstract: 2-Methallyloxyphenol precursor to 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared selectively and in good yield in the etherification of an alkali metal catecholate by methallyl chloride in an improved process using the same solvent medium for both the precursor and the hydroxybenzofuran, the process characterized by a solvent medium comprising an aromatic hydrocarbon solvent, the medium also containing an amine selected from alkylamines and N-heterocyclic amines. The amine forms a quaternary salt with the methallyl chloride in situ to catalyze the etherification and the aromatic solvent permits rearrangement of the product and Claisen closure to a benzofuran intermediate without solvent exchange.
    Type: Grant
    Filed: May 31, 1988
    Date of Patent: July 25, 1989
    Assignee: FMC Corporation
    Inventors: Borivoj Franko-Filipasic, James Snyder
  • Patent number: 4851552
    Abstract: 13-oxabicyclo[10.3.0]pentadecane, a valuable ambergris fragrance, is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a Knoevenagel catalyst to form cyclododecenylacetonitrile, the nitrile is hydrolyzed to cyclododecenylacetic acid, and the acid is cyclized to the lactone, and the lactone is reduced to the corresponding diol which is cyclized to 13-oxabicyclo[10.3.0]pentadecane.
    Type: Grant
    Filed: January 10, 1985
    Date of Patent: July 25, 1989
    Assignee: Huels Aktiengesellschaft
    Inventor: Manfred Kaufhold
  • Patent number: 4849428
    Abstract: The present invention involves compounds having the structure: ##STR1## (a) --A-- is selected from the group consisting of ##STR2## (b) --Y is selected from certain low molecular weight moieties which terminate in specific functional groups: --C.tbd.CH, ##STR3## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: July 18, 1989
    Assignee: The Procter & Gamble Company
    Inventors: Roy L. M. Dobson, Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
  • Patent number: 4838924
    Abstract: This invention relates to novel compounds of formula [I], a process for their production, and their use as a herbicide. ##STR1## wherein A represents the bond ##STR2## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group;B represents a hydrogen atom, a methyl group or a methoxy group; andAr represents one member selected from the group consisting of ##STR3## in which R.sup.1 to R.sup.38, are as defined hereinafter.
    Type: Grant
    Filed: April 1, 1987
    Date of Patent: June 13, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Takematsu, Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 4826984
    Abstract: Novel heteroarotinoid compositions characterized by the formulae: ##STR1## where R is H, CH.sub.3 or C.sub.2 H.sub.5 and X is S, S O, O, NCH.sub.3, Si(CH.sub.3).sub.2, N.sup.+ (H)CH.sub.3 [Cl.sup.- ], N.sup.+ (H)CH.sub.3 [Br.sup.- ] or N.sup.+ (alkyl) CH.sub.3 [Cl.sup.- or Br.sup.-) where alkyl is CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 .dbd.CHCH.sub.2 or C.sub.6 H.sub.5 CH.sub.2. Such compositions exhibit activity as anticancer agents.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: May 2, 1989
    Assignee: The Board of Regents for the Oklahoma Agricultural and Mechanical College acting for and on behalf of Oklahoma State University
    Inventors: Kenneth D. Berlin, Elizabeth M. Holt, Warren T. Ford, Mark D. Thompson
  • Patent number: 4820851
    Abstract: The present invention particularly provides novel benzofuran compounds which are useful in the synthesis of khellin and antiatherosclerotic furochromones.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: April 11, 1989
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4816592
    Abstract: A process for the production of benzofuran derivatives having the general formula, ##STR1## wherein R is alkyl, in particular of 2,3-dihydro-2,2-dimethyl benzofuran-7-ol, starting from pyrocatechol ethers in one step operation.The process essentially consists of heating a solution of pyrocatechol ether in an inert organic solvent in the presence of a catalyst comprising metals of 3.degree. and 4.degree. group of the Periodic System in form of carboxylates or of modified zeolites.The products are known intermediates for the production of insecticides.
    Type: Grant
    Filed: January 31, 1984
    Date of Patent: March 28, 1989
    Assignee: Enichem Sintesi Spa
    Inventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
  • Patent number: 4816473
    Abstract: Novel aroyl-substituted benzofuran and benzothiophene acetic and propionic acids are disclosed herein. These compounds are useful as analgesic, anti-inflammatory, and antipyretic agents.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: March 28, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: James P. Dunn
  • Patent number: 4780469
    Abstract: A (fused) benz(thio)amide of the formula: ##STR1## wherein B represents(i) a carbocyclic ring of from 4 to 8 members being unreplaced or replaced one, two or three of optional carbon atom(s) by oxygen, nitrogen and/or sulphur atom(s) or(ii) a divalent group of the formula: ##STR2## R.sup.1 represents a group of formula: ##STR3## (iv) a straight or branched alkyl, alkenyl, or alkynyl of from 1 to 20 carbon atoms,R.sup.4 represents(i) when B represents a closed ring, a group of the formula: ##STR4## (ii) when B does not represent a ring, a group of formula: ##STR5## with the proviso that compounds of formula: ##STR6## wherein A' is a vinylene or an ethylene group optionally substituted by straight or branched alkyl groups of from 1 to 4 carbon atom(s);R.sup.4' is--(CH.sub.2).sub.n --COOR.sup.8andR.sup.1' is(i) a group of the formula: ##STR7## or (ii) a group of the formula: ##STR8## are excluded, wherein A, R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, U, n, m, p, q, R.sup.5', and R.sup.
    Type: Grant
    Filed: August 20, 1985
    Date of Patent: October 25, 1988
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
  • Patent number: 4772730
    Abstract: Benzofurans of the formula ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetamido, R.sup.2 is at least one of halo, cyano, alkyl(C.sub.1 -C.sub.8), cycloalkyl(C.sub.3 -C.sub.8), hydroxy, alkoxy(C.sub.1 -C.sub.8), acyl(C.sub.1 -C.sub.8), acyloxy(C.sub.1 -C.sub.8), alkoxy(C.sub.1 -C.sub.8)carbonyl, alkoxy(C.sub.1 -C.sub.8)carbonylalkyl(C.sub.1 -C.sub.8), phenyl, phenyloxy, trifluoromethyl or dialkyl(C.sub.1 -C.sub.8)amino, m is 0-3, and at least one of the carbon atoms of the benzene ring of said benzofuran is substituted. The compounds are intermediates in the preparation of pyrazoline insecticides.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: September 20, 1988
    Assignee: FMC Corporation
    Inventors: David E. Seelye, Ernest L. Plummer
  • Patent number: 4766146
    Abstract: The invention relates to novel unsubstituted or substituted 2-fluorocarbonyl-2-(2,3-dihydrobenzofuran-7-yl)hydrazinecarboxylic acid esters of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen orC.sub.1-C.sub.3 alkyl,R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 -alkoxy, andR.sub.5 is C.sub.1 -C.sub.4 alkyl to the preparation of said compounds and to compositions containing them for use in pest control, especially for controlling insects that attack plants and animals. The novel compounds are particularly effective for controlling plant destructive sucking insects.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: August 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4742077
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## whereby R.sub.4 and R.sub.5 are the same or different and represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl and X represents oxygen, sulfur, imino, lower alkylimino, --(CH.sub.2)--, --(S.CH.sub.2)-- or --(O.CH.sub.2)--,R.sub.2 represents hydrogen or lower alkyl,R.sub.3 represents a group of formula ##STR3## whereby R.sub.6, R.sub.7 and R.sub.8 are the same or different and represent hydrogen or alkyl or R.sub.6 together with R.sub.7 or R.sub.7 together with R.sub.8 represent --(CH.sub.2).sub.m -- wherein m is 3 to 6,R.sub.9 represents alkyl, alkenyl, trialkylsilyl or alkyl substituted by hydroxy, lower alkoxy, lower halogenalkyl or aryl andn stands for 1, 2 or 3,which possess pharmaceutical in particular antimycotic activity as well as activity against phytopathogenic fungi.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: May 3, 1988
    Assignee: Sandoz Ltd.
    Inventor: Anton Stutz
  • Patent number: 4737509
    Abstract: Compounds of the formula ##STR1## wherein Z is ##STR2## compositions containing the compounds, and their utility as dietary and foliar insecticides are disclosed and exemplified.
    Type: Grant
    Filed: December 4, 1986
    Date of Patent: April 12, 1988
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4730062
    Abstract: Tetrafluorobenzofurans of the formula ##STR1## are prepared by contacting, at elevated temperature in an aprotic solvent, an ether of the formula ##STR2## with a catalytic mixture of metallic cooper and a polydentate or other ligand, wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetylimido, R.sup.2 is at least one of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, acyl, acyloxy, alkoxycarbonyl, alkoxycarbonylalkyl, phenyl, phenyloxy, trifluoromethyl or dialkylamino. The products are intermediates in the preparation of pyrazoline insecticides.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: March 8, 1988
    Assignee: FMC Corporation
    Inventors: David E. Seelye, Ernest L. Plummer
  • Patent number: 4725680
    Abstract: The invention relates to a process for preparing carbamic acid derivatives of formula: ##STR1## in which R.sup.1 or R.sup.2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R.sup.1 and R.sup.2 together form a ring, and Y denotes OR, SR, ##STR2## groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R.sup.3 and R.sup.4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R.sup.6 and R.sup.7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical.According to the process, a compound of formula ##STR3## is reacted with an .alpha.-halogenated derivative of formula ##STR4## at a temperature of -5.degree. to 150.degree. C.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: February 16, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
  • Patent number: 4720559
    Abstract: There are disclosed novel benzofurans having the following structural formula: ##STR1## wherein R is alkenyl of 1 to 6 carbon atoms or aryl of from 6 to 10 carbon atoms; R.sub.1 is H, alkali metal, or alkyl of 1 to 4 carbon atoms; and R.sub.2 is alkyl or alkoxy of from 1 to 5 carbon atoms, hydrogen, amino or dialkylamino, nitro, sulfonyl, alkyl or aryl thioether or halide. Also disclosed is a novel process of making the benzofurans, comprising the step of cyclizing an o-(2-carboxyvinyl)phenyl unsaturated alkyl ether in the presence of a base selected from the group consisting of KOH, NaOH, LiOH, dimsyl sodium, lithium diisopropylamide, potassium tert-butoxide, and mixtures thereof, at room temperature.
    Type: Grant
    Filed: October 9, 1986
    Date of Patent: January 19, 1988
    Assignee: Eastman Kodak Company
    Inventor: Thomas R. Welter
  • Patent number: 4713393
    Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: December 15, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
  • Patent number: 4705554
    Abstract: A benzofuranyloxyphenylurea derivative having the formula: ##STR1## wherein X is a halogen atom or a trifluoromethyl group, n is an integer of from 0 to 2, Y is a hydrogen atom, a halogen atom or a trifluoromethyl group, R.sup.1 is a lower alkyl group, and R.sup.2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxy group. The compounds are useful as herbicides.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: November 10, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Susumu Matsumoto, Shigeru Suzuki, Hisao Watanabe, Hiroshi Hanabe
  • Patent number: 4694019
    Abstract: The present invention relates to therapeutic compositions for the treatment of gastric disorders, said compositions containing a compound of the formula ##STR1## in which R is a mono- or poly-cyclic heterocyclic radical, possibly substituted, containing an oxygen atom, R' is a hydrogen atom or a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing up to 18 carbon atoms, and,either A represents a hydrogen atom and B represents a hydroxyl radicalor A and B together form a carbon-carbon double bond, as well as the pharmaceutically acceptable alkaline, alkaline-earth or amine salts thereof.
    Type: Grant
    Filed: August 14, 1985
    Date of Patent: September 15, 1987
    Assignee: Roussel UCLAF
    Inventors: Mario Bianchi, deceased, Fernando Barzaghi
  • Patent number: 4689336
    Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]-furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: August 25, 1987
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4686235
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: August 11, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4659709
    Abstract: Highly effective diuretic antihypertensives, i.e., 2,3-dihydrobenzofuran-5-sulfonamide derivatives which is classified to loop diuretics with less adverse side-effects and can be administered orally at a daily dosage of 0.5-200 mg or parenterally of 0.01-50 mg.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: April 21, 1987
    Assignee: Shionogi & Co.
    Inventors: Hiroshi Harada, Yoshihiro Matsushita, Masuhisa Nakamura, Yukio Yonetani
  • Patent number: 4652635
    Abstract: A method for converting ether groups such as alkyl or aryl ether groups including hydroquinone ether groups to hydroxyl groups and ester groups such as alkyl or aryl ester groups to carboxylic acid groups which comprises reacting a compound including at least one ether and/or ester group with a 2-halo-1,3,2-benzodioxaborole to form an intermediate and hydrolyzing the intermediate such as by quenching it into water to form the desired final product.
    Type: Grant
    Filed: June 15, 1984
    Date of Patent: March 24, 1987
    Assignee: Polaroid Corporation
    Inventor: Patrick F. King