Ortho Fused Patents (Class 560/134)
  • Patent number: 8969249
    Abstract: Bicyclic abscisic acid (ABA) analogs of Formula (I) and (II) and the process for their production are disclosed. The bicyclic ABA analogs include the structural elements and functional groups of the parent molecule that are required for activity, and have an aromatic ring fused to the ring replacing the vinyl methyl group of absicisie acid. Methods for using the bicyclic ABA analogs to inhibit cell growth and seed germination are also disclosed.
    Type: Grant
    Filed: May 10, 2005
    Date of Patent: March 3, 2015
    Assignee: National Research Council of Canada
    Inventors: Suzanne Abrams, Adrian J. Cutler, Patricia Rose, James Nyangulu, Ken M. Nelson
  • Publication number: 20140121187
    Abstract: Disclosed are 1,3-Dioxoindene derivatives, pharmaceutically acceptable salts thereof or enantiomers, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of viral diseases, comprising the same as an active ingredient. The 1,3-Dioxoindene derivatives have excellent inhibitory activity against picornaviruses including coxsackie-, entero-, echo-, Polio-, and rhinoviruses, as well as exhibiting low cytotoxicity, so that they can be useful as an active ingredient of a pharmaceutical composition for the prevention or treatment of viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular disease, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, herpangina, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.
    Type: Application
    Filed: June 18, 2012
    Publication date: May 1, 2014
    Applicants: KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R & D, KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
    Inventors: Young Sik Jung, Chong Kgo Lee, Ihl Young Choi, Hae Soo Kim, Pil Ho Kim, Soo Bong Han, Johan Neyts, Hendrik Jan Thibaut
  • Patent number: 6462222
    Abstract: This invention is directed to compounds of the following formula: wherein when a is 0, b is 1 or 2; when a is 1, b is 1, m is from 0-3, X is 0 or S, Y is halogeno, R1 is hydrogen C1-4 alkyl, R2 is hydrogen, C1-4 alkyl, or optionally substituted propargyl and R1 and R4 are each independently hydrogen, C1-6 alkyl, C6-12 aryl, C6-12 aralkyl each optionally substituted. This invention is also directed to the use of these compounds for treating depression, Attention Deficit Disorder (ADD), Attention Deficit and Hyperactivity Disorder (ADHD), Tourette's Syndrome. Alzheimer's Disease and other dementia's such as senile dementia, dementia of the Parkinson's type, vascular dementia and Lewy body dementia. This invention is further directed to a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: August 31, 2001
    Date of Patent: October 8, 2002
    Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem, Teva Pharmaceutical Industries, Ltd., Technion Research and Development Foundation, Ltd.
    Inventors: Michael Chorev, Tamar Goren, Yacov Herzig, Jeffrey Sterling, Marta Weinstock-Rosin, Moussa B. H. Youdim
  • Patent number: 6310248
    Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of: a) enantioselectively reducing the carbonyl function in a compound of formula (II): wherein R1, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulphamoyl or halogen, to form an enantiomerically enriched compound of formula (IIIa) or (IIIb): wherein R1, R2 and R3 are as defined above; b) subjecting the compound of formula (IIIa) or (IIIb) to a sigmatropic rearrangement to form a corresponding enantiomerically enriched compound of formula (IVa) or (IVb): wherein R1, R2 and R3 are as defined above; c) subjecting the compound of formula (IVa) or (IVb) to a Baeyer-Virliger oxidation to form a corresponding enantiomerically enriched compound of the general formula (Va) or (Vb): wherein R1, R2 and R3 are as defined above; d) converting the compo
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: October 30, 2001
    Assignee: Pharmacia AB
    Inventors: Pher G. Andersson, Christian Hedberg
  • Patent number: 5958971
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalyzed reactions.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: September 28, 1999
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
  • Patent number: 5714148
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalysed reactions.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: February 3, 1998
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger, Caroline Joy Springer
  • Patent number: 5660829
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalysed reactions.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: August 26, 1997
    Assignees: Zeneca Limited, Cancer Research Campaign Technology
    Inventors: Philip John Burke, Robert Ian Dowell, Anthony Brian Mauger
  • Patent number: 5587161
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT).
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: December 24, 1996
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
  • Patent number: 5407956
    Abstract: Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene and their use in therapeutic field are described.The compounds are particularly useful in the treatment of arterial hypertension, cardiac decompensation and renal failure, in the treatment of peripheral arteriopathies and in cerebrovascular insufficiency.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: April 18, 1995
    Assignee: Zambon Group S.p.A.
    Inventors: Francesco Santangelo, Giorgio Bertolini, Cesare Casagrande, Francesco Marchini, Stefania Montanari, Claudio Semeraro
  • Patent number: 5405990
    Abstract: Prodrugs, of generic formula I, are disclosed for use in antibody directed enzyme prodrug therapy (ADEPT). The prodrugs are substrates for carboxypeptidase G2 (CPG2) and yield more active cytotoxic drugs than known products of CPG2 catalyzed reactions.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: April 11, 1995
    Assignees: Zeneca Limited, Cancer Research Campaign Technology Limited
    Inventors: Philip J. Burke, Robert I. Dowell, Anthony B. Mauger, Caroline J. Springer
  • Patent number: 5254715
    Abstract: A compound of the following general formula which is useful in treating hypocholesterolemia and atherosclerosis: ##STR1## wherein X is oxygen or sulfur; R is hydrogen, alkyl having from 1 to 8 carbon atoms, or benzyl; R.sub.1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, an aralkyl group, a heterocyclic group, or a hydrocarbon chain of from 1 to 20 carbon atoms which is saturated or contains 1 to 3 double bonds and each of R.sub.2 and R.sub.3 is selected from hydrogen, provided both are not hydrogen, an aralkyl group, a hydrocarbon chain of from 1 to 20 carbon atoms which is saturated or contains 1 to 3 double bonds, an w-substituted alkylC.sub.1-6, a heterocyclic group, phenyl, substituted phenyl or NR.sub.2 R.sub.3 taken together form a monocyclic heterocyclic group.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: October 19, 1993
    Assignee: Warner-Lambert Company
    Inventors: Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5206417
    Abstract: The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R.sup.1, and R.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, OH, Oalkyl, SH, Salkyl, halogen, N(alkyl).sub.2 or N(alkyl)(aryl), and not less than one but not more than three of the radicals R.sup.2 to R.sup.6 are each a radical ##STR3## where X is alkylene or oxaalkylene, each of 2 to 10 carbon atoms, and Y is H or CH.sub.3. These compounds have particularly high photochemical reactivity in the medium-wavelength to relatively long-wavelength UV range.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: April 27, 1993
    Inventors: Andreas Boettcher, Gerd Rehmer
  • Patent number: 5101063
    Abstract: A process for preparation of urethanes by reacting an organic hydroxyl group-containing compound and carbon monoxide with a primary amine and oxygen in the presence of a non-noble metal or lanthanide metal catalyst system, particularly a cerium catalyst.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: March 31, 1992
    Assignee: Industrial Technology Research Institute
    Inventors: Kuo-Liang Loh, Puh Shieh, Jih-Liang Chen, Tsu-Kung Chuang
  • Patent number: 5098999
    Abstract: 3,4-Dihydroxyphenylalanine wherein the amino group is protected with a 9-fluorenylmethyloxycarbonyl group, or a derivative thereof can be produced by reacting 3,4-dihydroxyphenylalanine with a boron compound or phosphorus compound to stabilize the hydroxyl groups, followed by introduction of a 9-fluorenylmethyloxycarbonyl group thereinto.
    Type: Grant
    Filed: August 17, 1990
    Date of Patent: March 24, 1992
    Assignee: Hitachi Chemical Company
    Inventors: Yasuo Yamamoto, Yasuo Miyadera
  • Patent number: 5066674
    Abstract: Certain carbamate esters are used as inhibitors as cholesterol esterase and function as hypolipidemic and hypocaloric agents. The invention also relates to a method of decreasing the absorption of dietary cholesterol and fats through the wall of the intestinal tract.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: November 19, 1991
    Assignee: University of Iowa Research Foundation
    Inventor: Daniel M. Quinn
  • Patent number: 5066819
    Abstract: The invention relates to a process for the preparation of aryl esters of N-alkyl carbamic acids. The process comprises reacting an alkyl N-alkyl carbamate of the general formula:R.sub.1 --NH--COO--R.sub.3wherein R.sub.1 and R.sub.3 are both alkyl groups, with a substituted phenol in the presence of a halogen-containing phosphorous compound to produce an aryl ester of N-alkyl carbamic acid having the general formula:R.sub.1 --NH--COO--R.sub.2wherein R.sub.1 is an alkyl group and R.sub.2 is an aryl group derived from the substituted phenol. In a preferred embodiment of the invention, the process is used for the preparation of aryl esters of N-methyl carbamic acid.
    Type: Grant
    Filed: March 20, 1990
    Date of Patent: November 19, 1991
    Assignee: Council of Scientific & Industrial Research
    Inventors: Gurunath H. Kulkarni, Rajan H. Naik, Srinivasachari Rajappa
  • Patent number: 5021590
    Abstract: A process is provided for the preparation of N-alkyl-carbamates by directly reacting low-molecular weight alkyl-isocyanates, in particular methyl isocyanate, and a substituted phenolic precursor in solution in the presence of a basic catalyst compound selected from the class of bicyclic amidines or bicyclic guanidines.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: June 4, 1991
    Assignee: Enichem Synthesis SpA
    Inventors: Franco Mizia, Franco Rivetti, Ugo Romano
  • Patent number: 5008435
    Abstract: Process for producing urethanes, by reacting an organic hydroxyl group containing compound and carbon monoxide, either (i) with an organic nitro group containing compound, e.g. nitrobenzene, or (ii) with a primary amine, e.g. aniline, and oxygen, the reacting in both cases being carried out in the presence of a non-noble metal catalyst system comprising a copper catalyst, preferably mixed with a promoter such as a nitrogen or phosphorous containing organic compound for the (i) nitro compound reaction, or an alkali salt for the (ii) amine reaction, e.g. at 200-8000 psig and 100.degree.-300.degree. C., using 0.05-0.4 mole copper catalyst and 0.01-10 moles promoter per mole (i) nitro compound or (ii) amine, and 2-500 moles carbon monoxide, and (in the case of the (ii) amine) 0.5-5 moles oxygen, per mole of the (i) nitro compound or (ii) amine.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: April 16, 1991
    Assignee: Industrial Technology Research Institute
    Inventors: Kuo-Liang Loh, Puh Shieh, Y. S. Chao, Tsu-Kung Chuang
  • Patent number: 4946863
    Abstract: The present invention relates to 3-aminomethyl derivatives of indane, dihydrobenzofurane, dihydrobenzothiophene, and indoline, acid addition salts thereof, isomers thereof, methods of preparation, pharmaceutical compositions and method of treating CNS-disorders such as schizophrenia, Parkinson's disease, depression, anxiety, migraine and senile dementia, or in the cure of cardiovascular diseases, by administering such a derivative.
    Type: Grant
    Filed: January 18, 1989
    Date of Patent: August 7, 1990
    Assignee: H. Lundbeck A/S
    Inventors: Klaus P. Boegesoe, Jens K. Perregaard
  • Patent number: 4939169
    Abstract: Novel 1,4-naphthalenediol and 1,4-hydroquinone derivatives of formula I, II, III and IV and their therapeutic uses as 5-lipoxygenase inhibitors, leukotriene inhibitors, antiinflammatory and/or inhibitors of mucus secretion agents are described. Also provided are novel intermediates useful for the preparation of said derivatives.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: July 3, 1990
    Assignee: The Upjohn Company
    Inventors: Gordon L. Bundy, Chiu-Hong Lin
  • Patent number: 4925971
    Abstract: A method for producing aliphatic O-arylurethanes by the reaction of an aliphatic primary amine with an aromatic hydroxyl compound and urea. Ammonia produced as a by-product in the reaction is removed during the reaction so that the ammonia concentration of the reaction solution is maintained at 2 wt % or less.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: May 15, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Toshiya Aoki, Hiroshi Ishida, Shinsuke Fukuoka
  • Patent number: 4914124
    Abstract: A method of combating endoparasites which comprises applying thereto or to an endoparasite habitat an endoparasiticidally effective amount of an N-organooxycarbamic acid ester of the formula ##STR1## in which R.sup.1 represents alkyl, cycloalkyl, alkenyl, alkinyl or aryl, which can optionally be substituted,R.sup.2 represents alkyl, alkenyl or alkinyl, which can optionally be substituted, andR.sup.3 represents alkyl, alkenyl or alkinyl, which can optionally be substituted.Those compounds wherein one of R.sup.2 and R.sup.3 is alkinyl are new.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Nikolaus Muller, Peter Andrews
  • Patent number: 4786652
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy,R.sup.2 is the same as R.sup.1, or R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl,R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X is the same and is either --C(O)OR.sup.4 or --C(O)NR.sup.5 R.sup.6,whereinR.sup.4 is alkyl, phenyl or benzyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl, cycloalkyl or phenyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: November 22, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Michael C. Venuti
  • Patent number: 4782175
    Abstract: The molecule of the new urethanes contains an aliphatic fluoroalcohol, an isocyanate and an aromatic dihydroxy, diamino, aminohydroxy, aminocarboxy or hydroxycarboxy compound. They are prepared by reacting an aliphatic fluoroalcohol with a diisocyanate or triisocyanate to give the fluoroalcohol/isocyanate adduct and by reacting this adduct with said aromatic compound to give the desired urethanes composed of an aliphatic fluoroalcohol, an isocyanate and the bifunctional aromatic compound mentioned, and also be reacting a urethane of this type which also carries an active hydrogen atom on the bifunctional aromatic compound, with an isocyanate compound containing one or more isocyanate groups. The new urethanes are preferably used for imparting an oleophobic and hydrophobic finish to textiles and leather.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: November 1, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Frank Wehowsky, Rolf Kleber, Lothar Jaeckel
  • Patent number: 4758587
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy;R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X and Y are different and are either R.sup.4 or --C(O)W whereinR.sup.4 is lower alkyl or optionally substituted phenyl-lower-alkyl;W is --OR.sup.5 or --NR.sup.6 R.sup.7,whereinR.sup.5 is alkyl, optionally substituted phenyl or optionally substituted benzyl; andR.sup.6 and R.sup.7 are independently hydrogen, lower alkyl, cycloalkyl or optionally substituted phenyl.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: July 19, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Michael C. Venuti
  • Patent number: 4698438
    Abstract: A continuous, close-coupled method for making N-methyl carbamate pesticides which comprises contacting the methyl isocyanate in a vapor phase mixture containing methyl isocyanate and water with a selected oxime or phenol, said mixture being the reaction product formed by oxidizing monomethylformamide. An optional intermediate step for preparing the methyl isocyanate/water vapor phase reaction mixture for contact with the oxime or phenol is to remove therefrom a portion of the water without liquefying the methyl isocyanate by cooling the mixture to a temperature below the dew point of water but above the dew point of the methyl isocyanate.
    Type: Grant
    Filed: February 11, 1986
    Date of Patent: October 6, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles T. Blaisdell, Walter J. Cordes, George E. Heinsohn, John F. Kook, John R. Kosak
  • Patent number: 4668806
    Abstract: Reacting an alkali metal cyanate salt with dimethyl sulfate in acetonitrile, heating in a steady stream of nitrogen and thereafter immediately bubbling the formed methyl isocyanate into a solution of an appropriate oxime or phenol to form an N-methylcarbamate.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 26, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph J. Mrowca
  • Patent number: 4659845
    Abstract: Process for the production of N-methylcarbamates: ##STR1## (wherein RO- is the radical of a substituted phenol or of a naphthol), wherein:in a first reaction step methylamine and diphenyl carbonate are reacted with each other, operating in the liquid phase and as a continuous process, in order to form phenol and phenyl-N-methylurethane;in a second reaction step phenyl-N-methylurethane, within the related reaction mixture outcoming from the first step, is thermally continuously decomposed, to yield a gaseous stream containing methyl isocyanate, from which the components different than methyl isocyanate are condensed off;in a third step the methyl isocyanate stream, outcoming from the second step, after an optional preliminary condensation, is continuously fed and contacted with a solution of a substituted phenol or of a naphthol in an inert organic solvent, containing a basic catalyst, to form N-methylcarbamate (I);N-methylcarbamate (I) is finally recovered from the reaction mixture outcoming from the third st
    Type: Grant
    Filed: May 7, 1985
    Date of Patent: April 21, 1987
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Franco Rivetti, Franco Mizia, Guido Garone, Ugo Romano
  • Patent number: 4605667
    Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: August 12, 1986
    Assignee: Union Carbide Corporation
    Inventors: Chennupati K. Rao, Themistocles D. D'Silva
  • Patent number: 4595769
    Abstract: Carbamate-sulfenyl-carbamoyl fluoride compounds are valuable insecticidal compositions and are also useful intermediates in the production of bis-carbamate compounds.
    Type: Grant
    Filed: April 20, 1984
    Date of Patent: June 17, 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: 4532256
    Abstract: N-Methyl-carbamic acid esters of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted 2,3-dihydrobenzofuranyl, phenyl, naphthyl or ##STR2## R.sub.2 is hydroxyl, halogen, --OR.sub.1, C.sub.1 -C.sub.10 -alkoxy, C.sub.2 -C.sub.10 -alkenyloxy, C.sub.1 -C.sub.10 -dialkylamino or ##STR3## R.sub.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.3 -alkenyl, R.sub.4 is C.sub.1 -C.sub.6 -alkyl, --SR.sub.5, ##STR4## R.sub.5 is C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.3 -alkenyl, R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.6 -alkyl, andn is zero or 1.A process for producing these compounds and their use for combating pests are described.
    Type: Grant
    Filed: December 12, 1983
    Date of Patent: July 30, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Jozef Drabek
  • Patent number: 4491671
    Abstract: The present invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formulaR.sup.1 --N(CO--OR.sup.2).sub.2 (I)whereinR.sup.1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; andR.sup.2 is an optionally substituted aryl radical, which are useful as intermediates for the production of known herbicides, which process comprises reacting a primary amine of the formulaR.sup.1 --NH.sub.2 (II)with a carbonic acid aryl ester halide of the formulaX--CO--OR.sup.2 (III)wherein X is a halogen atom, at a temperature between 100.degree. and 300.degree. C.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: January 1, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • 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: 4474808
    Abstract: N-Sulphenylated biuret-N"-carboxylic acid esters of the general formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an optionally substituted aliphatic, cycloaliphatic, aromatic or araliphatic radical,R.sup.3 represents a hydrogen atom or an optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical andR.sup.4 represents a trihalogenomethyl radical,are obtained by the reaction of an acyl isocyanate of the general formula ##STR2## with a sulphenamide of the general formula ##STR3## if appropriate in the presence of a diluent. The compounds of the formula (I) are new. They can be used as pest-combating agents which are microbicides, especially fungicides or bactericides.
    Type: Grant
    Filed: November 3, 1982
    Date of Patent: October 2, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Engelbert Kuhle, Paul Reinecke, Karl-Heinz Kuck
  • Patent number: 4451406
    Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical,and a process for their preparation characterized in that a carbamic acid aryl ester of the general formula:R.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.
    Type: Grant
    Filed: August 5, 1983
    Date of Patent: May 29, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • Patent number: 4447635
    Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical, and a process for their preparation characterized in that a carbamic acid aryl ester of the general formulaR.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: May 8, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • Patent number: 4430341
    Abstract: Water soluble quaternary ammonium salt compounds exhibit outstanding insecticidal and miticidal activity coupled with reduced mammalian toxicity and acceptable phytotoxicity.
    Type: Grant
    Filed: August 24, 1977
    Date of Patent: February 7, 1984
    Assignee: Union Carbide Corporation
    Inventor: Barbara W. Kaplan
  • 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: 4399148
    Abstract: This invention relates to novel hydroxyarylalkyleneaminoaryl carbamate compounds and derivatives thereof and to their preparation. This invention is also directed to insecticidal compositions comprising an acceptable carrier and an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention as well as to a method of controlling insects by subjecting them to an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention.
    Type: Grant
    Filed: March 25, 1981
    Date of Patent: August 16, 1983
    Assignee: Union Carbide Corporation
    Inventor: Charles A. Wilson, II
  • 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: 4390710
    Abstract: Aromatic esters of carbamic acid derivatives, e.g., p-chlorophenyl-N-methyl carbamate, are prepared by reaction of the corresponding aromatic alcohol, e.g., p-chlorophenol, and monoisocyanate, e.g., methyl isocyanate, in the presence of a catalytic amount of a combination of a 4-aminopyridine catalyst, e.g., 4-dimethylaminopyridine, and pyridine or methyl substituted pyridines. The product is substantially pure, having less than 0.80 weight percent allophanate ester by-product, e.g., p-chlorophenyl-N,N'-dimethyl allophanate, and less than 0.50 weight percent unreacted aromatic alcohol, e.g., p-chlorophenol. The reaction is readily controlled and characterized by the substantial absence of reflux. The product can be retained in the liquid state at reaction temperature for extended periods of time without significantly increasing the level of allophanate ester by-product.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: June 28, 1983
    Assignee: PPG Industries, Inc.
    Inventor: James A. Manner
  • Patent number: 4387058
    Abstract: Novel phenyl and naphthyl esters of 2-(1-oxo-alkoxy)ethyl carbamic acids are prepared. The compounds are useful as pharmacological and agricultural agents.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: June 7, 1983
    Assignee: The Dow Chemical Company
    Inventor: Chester E. Pawloski
  • Patent number: 4386101
    Abstract: Unsymmetrical bis-carbamates of the formula ##STR1## wherein R.sub.1 is a phenyl, dihydrobenzofuranyl, naphthyl, pyrimidyl, pyrazolyl, triazolyl, quinolinyl or tetrahydroquinolinyl group, andR.sub.2 is a benzyl group,processes for producing them and their use for combating pests are described.
    Type: Grant
    Filed: November 9, 1981
    Date of Patent: May 31, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Manfred Boger
  • Patent number: 4378371
    Abstract: Fungicidally active N-alkyl-carbamic acid 1,1,2-trimethyl-5-substituted-indan-4-yl esters of the formula ##STR1## in which R.sup.1 is an alkyl group,R.sup.2 is an alkyl or aralkyl group,R.sup.3 is a hydrogen atom, an alkyl group or a halogen atom, andR.sup.4 is a hydrogen atom, an alkyl group, a halogen atom, or an alkoxy or alkylmercapto group.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: March 29, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Peuker, Detlef Grotkopp, Karlfried Wedemeyer, Wilhelm Brandes
  • Patent number: 4348331
    Abstract: This invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formulaR.sup.1 --N(CO--OR.sup.2).sub.2 (I)whereinR.sup.1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical, andR.sup.2 is an optionally substituted aryl radical,which can be used as intermediates for the production of known herbicides, which process comprises reacting an amine salt of the formulaR.sup.1 --NH.sub.2.HX.sup.1 (II)wherein X.sup.1 is a halogen, with a carbonic acid aryl ester halide of the formulaR.sup.2 --O--CO--X.sup.2 (III)wherein X.sup.2 is halogen, at a temperature from 100.degree. C. to 300.degree. C.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: September 7, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore, Engelbert Kuhle
  • 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: 4339592
    Abstract: A urethane is produced by reacting an organic nitro compound with carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst and a co-catalyst. This reaction is conducted in the liquid phase at elevated temperature and pressure. The catalyst employed is an element and/or compound of an element from the group of noble metals of the 8th Secondary Group of the Periodic Table. The co-catalyst used is formed from (1) a component taken from the group consisting of iron oxychloride, a mixture of iron compounds containing iron oxychloride and oxide-chloride combinations and (2) metallic iron or an iron alloy in finely divided or high surface form. The oxides which may be used in the oxide-chloride combinations of co-catalyst component (1) are the oxides and/or oxide hydrates of tetravalent tin, trivalent chromium, hexavalent molybdenum, hexavalent tungsten, pentavalent vanadium, divalent iron and trivalent iron.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: July 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Robert Becker, Christian Rasp, Gunter Stammann, Johann Grolig
  • Patent number: 4333949
    Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: June 8, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Elmar Sturm, Robert Nyfeler