Patents by Inventor Robert W. Lang

Robert W. Lang has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5149717
    Abstract: Substituted alkanophenones of general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is phenyl that is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterified or amidated carboxy, or is lower alkyl that is unsubstituted, substituted by fluoro and chloro or substituted by free esterified or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties and can be used as anti-allergic active ingredients in medicaments.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: September 22, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas von Sprecher, Andreas Beck, Bruno Schaub, Robert W. Lang
  • Patent number: 5108482
    Abstract: The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth.The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I ##STR1## wherein A is --COOR.sub.1, --COSR.sub.1, --COO.sup..crclbar. M.sup..sym., --CONR.sub.2 R.sub.3 or --COCl; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl; R.sub.2 and R.sub.3 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.7 cycloalkyl; or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C.sub.1 14 C.sub.4 alkyl; and M.sup..sym.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: April 28, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert W. Lang, Urs Muller
  • Patent number: 5032606
    Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: July 16, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
  • Patent number: 5003074
    Abstract: Compounds of formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, alkyl or aryl, m and n are 0 or 1, and A is a divalent organic radical which, with (CR.sup.1 R.sup.2).sub.m NF--SO.sub.2 (CR.sup.3 R.sup.4).sub.n groups, forms a 5- to 8-membered ring, are admirably suitable fluorinating agents for fluorinating carbon atoms, especially as stereospecific fluorinating agents, when the compounds contain a chiral carbon atom and are in optically active form. The compounds of formula I are prepared by reacting the corresponding silated sulfonamides, wherein the NF group is replaced by an N-SiR.sup.7 R.sup.8 R.sup.9 group and R.sup.7, R.sup.8 R.sup.9 are each independently C.sub.1 -C.sub.12 alkyl, cyclopentyl, cyclohexyl, benzyl or phenyl, with a fluorinating agent.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: March 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Thomas Allmendinger, Edmond Differding, Robert W. Lang
  • Patent number: 4914196
    Abstract: Compounds of the formulae I and Ia ##STR1## in which R.sup.1 is a group which can be transferred to carbonyl or imine compounds, for example alkyl, allyl, vinyl or the radical of an enol or enamine, R.sup.2 is, for example, cyclopentadienyl, R.sup.3 is the radical of an optically active sugar or sugar derivative, Me is Ti, Zr or Hf, x is 0, 1 or 2 and y is 0, 1, 2 or 3, M.sup..sym. is Li.sup..sym., Na.sup..sym., K.sup..sym., MgY.sup..sym., ZnY.sup..sym., CdY.sup..sym., HgY, CuY.sup..sym. or quaternary ammonium, Y being halogen, are suitable for use as chiral reactants for compounds containing aldehyde, keto and/or N-substituted imine groups.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: April 3, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Riediker, Robert W. Lang, Rudolf Duthaler, Peter Herold, Konrad Oertle, Guido Bold
  • Patent number: 4892962
    Abstract: The reaction of allyl bromo- or chloro-difluoroacetates with monochlorisilanes in the presence of zinc with heating gives silyl esters of .alpha.,.alpha.-difluoro-.gamma.,.delta.-pentenoic acids. The free acids, from which acid derivatives can be prepared by conventional methods, are obtained by hydrolysis. The pentenoic acids and pentenoic acid derivatives are suitable for the preparation of polymers and copolymers, from which metal-organic polymers and copolymers having catalytic properties are obtainable.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: January 9, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4886879
    Abstract: Zinc compounds of formula IICF.sub.3 CCl.sub.2 ZnCl.cndot.yL (II)wherein y is 1 or 2 and L is a solvent ligand selected from the group of the N-disubstituted acid amides, N-substituted lactams and the organic sulfoxides, are suitable for reaction with CO.sub.2, COS or SO.sub.2 to give, after working up, the acids of formula ICF.sub.3 CCl.sub.2 --X (I)wherein X is --CO.sub.2 H, --CSOH or --SO.sub.2 H, in good yield.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert W. Lang, Bernd Klingert
  • Patent number: 4868202
    Abstract: Novel 3-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sup.1 is cyano, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sup.2 is vinyl or a group --CH.sub.2 --CH.sub.2 --X, in which X is chlorine or bromine, or is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylsulfonyl, 4-bromophenylsulfonyl or 4-methylphenylsulfonyl, R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, and n is zero, one or two, have valuable microbicidal properties for controlling phytopathogenic plant pests, particularly phytopathogenic fungi.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: September 19, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Robert W. Lang
  • Patent number: 4847258
    Abstract: The invention relates to novel N-benzoyl-N,-4-(5-phenylpyrimid-2-yloxy)phenylureas of formula ##STR1## wherein X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio,X.sub.2 is halogen, methyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio,Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,Z is methyl, halomethyl containing 1 to 3 halogen atoms or pentafluoroethyl; andR.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or C.sub.1 -C.sub.3 alkoxy,to the preparation thereof and to intermediates for the synthesis of these compounds, as well as to compositions containing them for use in pest control, especially for controlling representatives of the order Acarina that attack plants and animals and for controlling insects. The novel compounds exhibit especially pronounced activity against plant-destructive mites.
    Type: Grant
    Filed: August 17, 1987
    Date of Patent: July 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Elmar Sturm, Robert W. Lang, Odd Kristiansen
  • Patent number: 4826965
    Abstract: Compounds of the forulae I and Ia ##STR1## in which R.sup.1 is a group which can be transferred to carbonyl or imine compounds, for example alkyl, allyl, vinyl or the radical of an enol or enamine, R.sup.2 is, for example, cyclopentadienyl, R.sup.3 is the radical of an optically active sugar or sugar derivative, Me is Ti, Zr or Hf, x is 0, 1 or 2 and y is 0, 1, 2 or 3, M.sym. is Li.sym., Na.sym., K.sym., MgY.sym., ZnY.sym., CdY.sym., HgY, CuY.sym. or quaternary ammonium, Y being halogen, are suitable for use as chiral reactants for compounds containing aldehyde, keto and/or N-substituted imine groups.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: May 2, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Riediker, Robert W. Lang, Rudolf Duthaler, Peter Herold, Konrad Oertle, Guido Bold
  • Patent number: 4822919
    Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, andn is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.
    Type: Grant
    Filed: August 26, 1987
    Date of Patent: April 18, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Robert W. Lang
  • Patent number: 4820726
    Abstract: 4-Acylresorcinol esthers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: April 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
  • Patent number: 4808572
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: a is an integer of from 1 to 7,R.sup.o represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted at the terminal carbon atom by a free or acylated hydroxy group, by a halogen atom having an atomic number of at most 17, or by methoxy, or represents C.sub.1-3 -perfluoroalkyl,R.sup.2 represents an optionally unsaturated aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene or alternatively, if R.sup.1 represents a halogenated radical and/or B represents phenylene or ethylene, a single bond or vinylene,B represents a single bond, ethynylene or phenylene,R.sup.3 represents hydroxy, C.sub.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: February 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Werner Breitenstein, Andreas von Sprecher, Robert W. Lang, Konrad Oertle
  • Patent number: 4785004
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
  • Patent number: 4759881
    Abstract: Zinc compounds of formula IICF.sub.3 CCl.sub.2 ZnCl.yL (II)wherein y is 1 or 2 and L is a solvent ligand selected from the group of the N-disubstituted acid amides, N-substituted lactams and the organic sulfoxides, are suitable for reaction with CO.sub.2, COS or SO.sub.2 to give, after working up, the acids of formula ICF.sub.3 CCl.sub.2 --X (I)wherein X is --CO.sub.2 H, --CSOH or --SO.sub.2 H, in good yield.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: July 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert W. Lang, Bernd Klingert
  • Patent number: 4734516
    Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4705801
    Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and n is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.
    Type: Grant
    Filed: October 7, 1985
    Date of Patent: November 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Robert W. Lang
  • Patent number: 4692536
    Abstract: The reaction of dimethylformamide, R.sup.1 R.sup.2 R.sup.3 SiX and RY in the presence of zinc or the reaction of dimethylformamide, R.sup.1 R.sup.2 R.sup.3 SiX and a zinc compound RZnY.yL affords hemiaminals of formula I ##STR1## R is e.g. polyhalogenated alkyl containing at least one fluorine atom; R.sup.1, R.sup.2 and R.sup.3 are e.g. alkyl; L is a ligand; X is chlorine or bromine; Y is chlorine, bromine or iodine and y is 1 or 2.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: September 8, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4670604
    Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: June 2, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk