Chalcogen Or Nitrogen Attached Directly To The Hetero Ring By Nonionic Bonding Patents (Class 549/21)
  • Patent number: 5032312
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.4 --Z.sup.3 -- and R.sup.2 denotes a group R.sup.4 or --Z.sup.4 --A.sup.5 --R.sup.4 ; m and n each individually stand for the number 0 or 1; A.sup.1, A.sup.2, A.sup.3, A.sup.4 and A.sup.5 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen, trans-1,4-cyclohexylene in which optionally 2 non-adjacent methylene groups are replaced by oxygen and/or sulphur, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2, --C.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans form of --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--; R.sup.3 and R.sup.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: July 16, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4988459
    Abstract: Optically active oxirane-2-carboxylic acid esters with a mesogenic molecular component suitable as dopants in liquid-crystal mixtures. They result in liquid-crystalline ferroelectric phases with short switching times and in electroclinic phases with large electroclinic coefficients. A further advantage lies in the fact that they induce a helix with a very small pitch so that they are also suitable for helix compensation in LC mixtures.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: January 29, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Jurgen Gay, Hans-Rolf Dubal, Claus Escher, Wolfgang Hemmerling, Ingrid Muller, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 4985411
    Abstract: The present invention provides compounds of the formula (I): ##STR1## wherein m and n are independently selected from 0, 1 or 2, ##STR2## R is selected from hydrogen, methyl or ethyl; R.sup.1 is selected from C.sub.1-4 hydrocarbyl substituted by one to five halo atoms, and a group --C.tbd.C--R.sup.9 wherein R.sup.9 is a group S(O).sub.w --R.sup.10 wherein R.sup.10 is trifluoromethyl, methyl or ethyl and w is 0, 1 or 2 or R.sup.9 is a C.sub.3-5 aliphatic group or an aliphatic group containing up to 5 carbon atoms atoms substituted by C.sub.1-4 alkoxy, C.sub.2-6 alkoxyalkoxy, C.sub.1-8 acyloxy, halo or hydroxy, a group COR.sup.11 wherein R.sup.11 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or a group NR.sup.12 R.sup.13 wherein R.sup.12 and R.sup.13 are independently selected from hydrogen, methyl or ethyl, or R.sup.9 is SiR.sup.14 R.sup.15 R.sup.16 wherein R.sup.14 to R.sup.16 are the same or different and each is a C.sub.1-4 aliphatic group or R.sup.14 and R.sup.15 are C.sub.1-4 aliphatic groups and R.sup.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: January 15, 1991
    Assignees: The Wellcome Foundation Ltd., The Regents of the University of California
    Inventors: John E. Casida, Michael Elliott
  • Patent number: 4946861
    Abstract: The invention relates to the use of ketenethioacetals of the formula ##STR1## in which R.sub.1 represents aryl or heteroaryl, R.sub.2 represents hydrogen, an optionally substituted hydrocarbon radical, heteroaryl, an acyl radical, a group of the formula --S(O).sub.m --R.sub.a, wherein m is 0, 1 or 2 and R.sub.a is an optionally substituted hydrocarbon radical; or optionally functionally modified sulpho, A represents an optionally substituted bivalent aliphatic hydrocarbon radical and n is 0 or 1, and pharmaceutically acceptable salts of such compounds that contains a salt-forming group, for the treatment of liver diseases, respiratory tract diseases and vascular diseases pharmaceutical preparations containing compounds of the formula I and novel compounds of the formula I. The compounds have liver-protecting and immunomodulating properties.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: August 7, 1990
    Assignee: Zyma SA
    Inventors: Andre J. Weith, Philippe M. Narld
  • Patent number: 4927845
    Abstract: Anthralin analogues containing a thio-substituent, especially in one or more of the positions 2-, 7- and 10- of the anthralin ring. They may be made by reacting an anthralin derivative (e.g. 10-bromoanthralin) with a thiol or a compound containing a group convertible to a thio-group. Alternatively, a 1,8-dihydroxy anthraquinone containing a thio-substituent may be reduced. Reactive intermediates may be made by introducing one or more nuclear allylic groups into a 1,8-dihydroxy anthraquinone and then converting them into a reactive form, e.g. by epoxidation or halide addition. The intermediate can then reduced to the oxidation state corresponding to anthralin.Additional products having the 10-carbon atom of the anthralin ring as part of a heterocyclic ring, may be made by anthralins containing various substitutes thioalkyl groups as the 10-substituent.The compounds are useful for treatment of psoriasis, and may be formulated in the conventional vehicles for topical application, for example petrolatum.
    Type: Grant
    Filed: August 15, 1989
    Date of Patent: May 22, 1990
    Assignee: The Victoria University of Manchester
    Inventor: John M. Bruce
  • Patent number: 4925590
    Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: May 15, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4846998
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
  • Patent number: 4806604
    Abstract: The present invention discloses a new class of calcium chelating compounds which have a decreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca.sup.2+ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. However unlike EGTA or BAPTA-like compounds, in which the two halves of the chelator are linked by a simple 1,2-ethanediyl moiety, the compounds of the present invention modify the stereochemical conformation of this linkage by adding bulky substituents or incorporating the linkage into a carbocyclic or heterocyclic ring. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: February 21, 1989
    Assignee: Regents of the University of California
    Inventors: Roger Yonchien Tsien, Stephen R. Adams
  • Patent number: 4803286
    Abstract: Certain amino-2-hydroxypropyloximinoheterocycles are .beta.-adrenoceptor antagonists useful in the treatment of elevated intraocular pressure, hypertension, angina and arrhythmia.
    Type: Grant
    Filed: August 19, 1987
    Date of Patent: February 7, 1989
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello, David C. Remy, David A. Claremon, Stella W. King
  • Patent number: 4726911
    Abstract: Compounds of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --OCO-- groups and/or --COO-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, --A.sup.4 --A-- or --A--A.sup.4 --,A is a 1,3-dioxane-2,5-diyl or 1,3-dithiane-2,5-diyl group which is monosubstituted or polysubstituted in the 2-position and/or 4-position by alkyl each having 1-10 C atoms and/or in the 5-position by alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy each having 1-5 C atoms, or by F, Cl, Br or CN,A.sup.2, A.sup.3 and A.sup.4 each are 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2,2,2]octylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 1,4-phenylene which is substituted by one or two F and/or Cl atoms and/or CH.sub.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: February 23, 1988
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Peter Fuss, Reinhard Hittich, Bernhard Scheuble
  • Patent number: 4725682
    Abstract: Sulfur-containing bis-amino carbamate compounds exhibit outstanding acaricidal, nematocidal and insecticidal activity.
    Type: Grant
    Filed: December 2, 1986
    Date of Patent: February 16, 1988
    Assignee: Rhone-Poulenc Nederland, B.V.
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4704227
    Abstract: Compounds of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, --A.sup.4 --A--or --A--A.sup.4 --,A is a 1,3-dioxane-2,5-diyl or a 1,3-dithiane-2,5-diyl group,A.sup.2, A.sup.3 are each a 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl,and A.sup.4 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl or 1,4-bicyclo(2,2,2)octylene group, or a 1,4-phenylene, pyrimidine-2,5-diyl or pyridazine-3,6-diyl group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups,Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O or a single bond andR.sup.3 is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br or CN, with the proviso that(a) at least one group A.sup.2, A.sup.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: November 3, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Reinhard Hittich, Georg Weber, Bernhard Scheuble
  • Patent number: 4675340
    Abstract: Pesticidal oxime N-alkyl-N-.alpha.-haloacyl-carbamates represented by the structure: ##STR1## wherein R represents an imino radical, R' and R" represent alkyl radicals and X is chlorine, fluorine or bromine.
    Type: Grant
    Filed: December 11, 1985
    Date of Patent: June 23, 1987
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4659502
    Abstract: Ethane derivatives of the formula IR.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 IwhereinR.sup.1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R.sup.3 --A.sup.4 --Z.sup.1 --,R.sup.2 is --CN or --Z.sup.2 --A.sup.4 --CN,A.sup.1 is --A--, --A--A.sup.5 -- or --A.sup.5 --A--,A.sup.2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms,A is a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group,A.sup.3, A.sub.4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.
    Type: Grant
    Filed: January 17, 1985
    Date of Patent: April 21, 1987
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Julie E. Fearon, Wendy E. Smith, George W. Gray, David Lacey, Kenneth J. Toyne, Georg Weber
  • Patent number: 4640929
    Abstract: A novel 1,3-dithiane of the formula ##STR1## wherein R.sup.1 is a di-substituted amino group; R.sup.2 and R.sup.3 are such that one of them is an electron-withdrawing group with the other being a hydrogen atom, a hydrocarbon group or heterocyclic group of the class consisting of thienyl, triazolyl, and pyridyl, which may optionally be substituted or that R.sup.2 and R.sup.3 taken together with the adjacent carbon atom form a spiro ring provided that at least one of R.sup.2 and R.sup.3 is a carbonyl group; X.sup.1 and X.sup.2 each is a sulfur atom and at least one of X.sup.1 and X.sup.2 may be oxidized, or a salt thereof, possesses very useful pesticidal actions.
    Type: Grant
    Filed: August 23, 1983
    Date of Patent: February 3, 1987
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroyuki Mitsudera, Kazuo Konishi, Yasuo Sato
  • Patent number: 4639328
    Abstract: Thienothiophene derivatives of the formula IR.sup.1 --(A.sup.1).sub.m --Z.sup.1 --A--(Z.sup.2 --A.sup.2).sub.n --R.sup.2 Iin which R.sup.1 and R.sup.2 are each H or an alkyl group having 1-12 C atoms, in which, furthermore, one or two non-adjacent CH.sub.2 groups can be replaced by O atoms, --CO-- or --CH.dbd.CH-- groups, or are each F, Cl, Br, CN, --COOR or --O--COR, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl, tetrahydropyran-2,5-diyl, pyridazine-3,6-diyl or the corresponding N-oxide, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by one or two F, Cl or Br atoms and/or CN groups and/or CH.sub.3 groups, A is a group of the formula 1 or 2 ##STR1## which is unsubstituted or substituted by one or two Cl and/or Br atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.
    Type: Grant
    Filed: November 26, 1984
    Date of Patent: January 27, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Michael Romer, Georg Weber
  • Patent number: 4638064
    Abstract: Unsaturated heterocyclic carbonyl-containing compounds, such as 2-oxathiolone, are prepared by the oxylation of saturated heterocyclic carbonyl-containing precursors of the above compounds in a C.sub.1-4 alcohol or carboxylic acid solvent in the presence of a supporting electrolyte followed by dehydroxylation of the oxylated intermediate.The products formed may be polymerized or copolymerized with other ethylenically unsaturated monomers to prepared resins, films, etc. or they may be employed as reaction intermediates.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: January 20, 1987
    Assignee: The Dow Chemical Company
    Inventors: Pen-Chung Wang, James M. Renga
  • Patent number: 4638060
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4612036
    Abstract: Cyclohexane-1,3-dione derivatives of the formula ##STR1## where A is an unsubstituted or substituted, saturated or unsaturated 4-membered to 7-membered ring which contains 1 or 2 sulfinyl or sulfonyl groups, R.sup.1 is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, R.sup.2 is alkyl and R.sup.3 is alkyl, alkenyl, haloalkenyl or propargyl, and salts of these compounds are used for controlling undesirable plant growth.
    Type: Grant
    Filed: July 2, 1985
    Date of Patent: September 16, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Rainer Becker, Michael Keil, Bruno Wuerzer
  • Patent number: 4612326
    Abstract: Sulfur-containing bis-amino carbamate compounds exhibit outstanding acaricidal, nematocidal and insecticidal activity.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: September 16, 1986
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. D'Silva
  • Patent number: 4576965
    Abstract: Pesticidal oxime N-alkyl-N-.alpha.-haloacyl-carbamates represented by the structure: ##STR1## wherein R represents an imino radical, R' and R" represent alkyl radicals and X is chlorine, fluorine or bromine.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: March 18, 1986
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4551472
    Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4535092
    Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are substituents defined in claim 1; wherein R.sup.4 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R.sup.5 as stated below;wherein R.sup.5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R.sup.4 to form an oxycarbonyl group such that together with the --N--CO--C-- part of the molecule it forms an oxazolidinedione group;wherein R.sup.6 is alkyl or halogenoalkyl of up to 4 carbon atoms;and wherein R.sup.7 is 5- or 6- membered saturated or unsaturated heterocyclic which contains one, two or three hetero atoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two substituents defined in claim 1;processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: August 13, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Leslie R. Hughes
  • Patent number: 4496721
    Abstract: Symmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: January 29, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4486447
    Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: December 4, 1984
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4479002
    Abstract: Carbamate-carbamoyl fluoride compounds are useful intermediates for the production of insecticidal bis-carbamate compounds.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: October 23, 1984
    Assignee: Union Carbide Corporation
    Inventor: Wei C. Liang
  • Patent number: 4473580
    Abstract: This invention pertains to some new organic compounds, to a process for preparing them, and to formulations of them suitable for pesticidal use. The invention is more particularly directed to imidic acid derivatives of N-thio(methyl)carbamates.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: September 25, 1984
    Assignee: The Upjohn Company
    Inventors: Fred E. Dutton, Stephen J. Nelson
  • Patent number: 4469877
    Abstract: This invention relates to photographic products and processes employing silver halide solvent precursors of the formula ##STR1## wherein R.sup.1 is a monovalent organic radical; R.sup.2 is hydrogen or a monovalent organic radical; Z is a moiety that undergoes .beta.-elimination in aqueous alkaline solution and preferably is a moiety that undergoes .beta.-elimination in aqueous alkaline solution to release a photographically useful reagent; and n is an integer 3, 4 or 5.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: September 4, 1984
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Ernest W. Ellis
  • Patent number: 4400389
    Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: August 23, 1983
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4394383
    Abstract: A novel class of chemical compounds useful as pesticides consists of N-alkoxysulfenylcarbamate esters. The preparation of these compounds, their physical properties, formulations, and use to control both household insects and crop pests are exemplified.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: July 19, 1983
    Assignee: Regents of the University of California
    Inventors: Mitsuyasu Kawata, Noriharu Umetsu, Tetsuo R. Fukuto
  • Patent number: 4390707
    Abstract: A method for the preparation of cyclopentenones of the general formula (VIII): ##STR1## wherein n is 5-7, has been developed which proceeds via the acid catalyzed deprotection and rearrangement of novel substituted-.alpha.-hydroxymethylfurans of general formula (VII): ##STR2## wherein R is a hydroxyl protecting group, R.sub.1 and R.sub.2 are methyl or ethyl or together form --(CH.sub.2).sub.3 -- and n is as above described. Cyclopentenones of formula VIII are useful intermediates in prostaglandin analog synthesis.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: June 28, 1983
    Assignee: American Cyanamid Company
    Inventor: Steven L. Peake
  • Patent number: 4357329
    Abstract: N-Phosphonylcarbonyl-N-methylcarbamic acid esters of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and each represents alkyl, alkenyl or alkynyl, it being possible for any of these radicals to be substituted by halogen, andR.sup.3 represents alkyl, phenyl, naphthyl, benzodioxolanyl, dihydrobenzofuranyl or indanyl, it being possible for any of these radicals to carry one or more substituents selected from alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, alkylthio, alkenylthio, alkynylthio, dialkylamino, halogenoalkyl, halogen, nitro, cyano, cycloalkyl, formamidino, dioxanyl and dioxolanyl, orR.sup.3 represents a radical of the formula ##STR2## in which R.sup.4 and R.sup.5 can be identical or different and each represents alkyl, alkoxy, alkylthio, alkylthioalkyk, cyano, alkoxycarbonyl, dialkylcarbamoyl, dialkoxyphosphoryl or triazolyl, orR.sup.4 and R.sup.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: November 2, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Heywang, Engelbert Kuhle, Ingeborg Hammann, Bernhard Homeyer
  • Patent number: 4341795
    Abstract: Asymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: July 27, 1982
    Assignee: Union Carbide Corporation
    Inventor: Wei C. Liang
  • Patent number: 4338450
    Abstract: Carbamate-sulfenyl-carba moyl fluoride compounds are valuable insecticidal compositions and are also useful intermediates in the production of bis-carbamate compounds.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: July 6, 1982
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4335138
    Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.
    Type: Grant
    Filed: September 15, 1980
    Date of Patent: June 15, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
  • Patent number: 4330674
    Abstract: Carbamoyl sulfides such as dimethyl N,N'-[2,3-butanediylidenebis[nitrilooxycarbonyl(N-methylimino)thio(N-methy limino)carbonyloxy]]bis[ethanimidothioate] useful for control of insects and nematodes.This application is a divisional of application Ser. No. 139,836, filed Apr. 24, 1980, now U.S Pat. No. 4,254,141, which is a continuation-in-part of application Ser. No. 18,293, filed Mar. 6, 1979, and now abandoned.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: May 18, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4327110
    Abstract: Symmetrical N-substituted bis-carbamoyloximino disulfide compounds exhibit outstanding nematocidal, miticidal and insecticidal activity, coupled with substantially reduced mammalian toxicity and phytotoxicity as compared to known pesticidal compounds having a comparable spectrum of activity against insect, arachnid and nematode pests.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: April 27, 1982
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4319033
    Abstract: A method of making certain 2,3-dihydro-1,4-dithiins of the following formula by the action of alpha-hydroxyketones (acyloins) of 1,2-dithiols: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl having 1 to 6 carbon atoms or are joined together to form a ring with 3 or 4 methylene groups, and R.sup.3 and R.sup.4 are hydrogen or the same or different alkyl groups having 1 to 10 carbon atoms, which alkyl groups may be substituted with lower alkoxy groups.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: March 9, 1982
    Assignee: Uniroyal Ltd.
    Inventors: Allan K. S. Tsai, Duncan D. Lennox, Arthur D. Brewer
  • Patent number: 4315027
    Abstract: A novel class of chemical compounds useful as pesticides consists of symmetrical and asymmetrical N,N'-sulfinyldicarbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.
    Type: Grant
    Filed: May 9, 1980
    Date of Patent: February 9, 1982
    Assignee: The Regents of the University of California
    Inventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
  • Patent number: 4307238
    Abstract: Derivatives of 2-imino-1,3-dithiolane, 1,3-dithiole, 1,3-dithiane, 1,3-dithietane and 1,3-oxathiole have been found to reduce herbicidal injury to crop plants due to thiocarbamate and acetanilide herbicides. This is a division, of application Ser. No. 960,987 filed Nov. 15, 1978, now U.S. Pat. No. 4,231,783.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: December 22, 1981
    Assignee: Monsanto Company
    Inventor: Frederic G. Bollinger
  • Patent number: 4283335
    Abstract: Disclosed is a method for improving the yield of dialkyl dithiophosphoric acid esters produced by the Lewis acid catalyzed reaction of an O,O-dialkyl dithiophosphoric acid and an organic chloride. More specifically, the method concerns the improvement wherein the reaction is carried out in the presence of from 0.1 to 1.5 moles, per mole of organic chloride, of an anhydride of a fatty acid containing 2 to 5 carbon atoms.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: August 11, 1981
    Assignee: Boots Hercules Agrochemicals Co.
    Inventor: James Minn
  • Patent number: 4283338
    Abstract: Disclosed is a method for improving the yield of dialkyl dithiophosphoric acid esters produced by the Lewis acid catalyzed reaction of an O,O-dialkyl dithiophosphoric acid and an organic chloride. More specifically, the method concerns the improvement wherein the reaction is conducted under sufficient pressure to maintain the liberated hydrogen chloride in the reaction system during the course of the reaction.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: August 11, 1981
    Assignee: Boots Hercules Agrochemicals Co.
    Inventor: James Minn
  • Patent number: 4276422
    Abstract: Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre- and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: June 30, 1981
    Assignees: Uniroyal, Inc., Uniroyal Ltd.
    Inventors: Arthur D. Brewer, Robert W. Neidermyer, William S. McIntire
  • Patent number: 4265807
    Abstract: Disclosed is a method of disproportionating rosin comprising heating said rosin in the presence of a dithiin derivative such, for example, as 2,5-diphenyl dithiin. The method can be carried out at about 150.degree. C. to about 300.degree. C. for about 1 hour to about 10 hours with the longer reaction time corresponding to the lower temperatures. Preferably, the process is run at about 260.degree. C. to about 300.degree. C. for about 3 to 8 hours.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: May 5, 1981
    Assignee: Hercules Incorporated
    Inventor: David S. Breslow
  • Patent number: 4264625
    Abstract: Bis-[N-Alkyl-N-arylcarbamate] sulfide compounds exhibit outstanding miticidal and insecticidal activity, coupled with substantially reduced mammalian toxicity, and phytotoxicity.
    Type: Grant
    Filed: October 26, 1978
    Date of Patent: April 28, 1981
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4254141
    Abstract: Carbamoyl sulfides such as dimethyl N,N'-[2,3-butanediylidenebis[nitrilooxycarbonyl(N-methylimino)thio(N-methy limino)carbonyloxy]]bis[ethanimidothioate] useful for control of insects and nematodes.
    Type: Grant
    Filed: April 24, 1980
    Date of Patent: March 3, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4234580
    Abstract: Carbamate thiosulfenylcarbamoyl fluoride compounds are insecticidal and miticidal compounds and are also useful intermediates in the preparation of pesticidally active bis-carbamate disulfide compounds.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: November 18, 1980
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4231783
    Abstract: Derivatives of 2-imino-1,3-dithiolane, 1,3-dithiole, 1,3-dithiane, 1,3-dithietane and 1,3-oxathiole have been found to reduce herbicidal injury to crop plants due to thiocarbamate and acetanilide herbicides.
    Type: Grant
    Filed: November 15, 1978
    Date of Patent: November 4, 1980
    Assignee: Monsanto Company
    Inventor: Frederic G. Bollinger