Two Double Bonds Between Ring Members Of The Five-membered Hetero Ring Patents (Class 548/560)
  • Patent number: 6162918
    Abstract: The invention relates to new and known tricyclic dione derivatives of the general formula ##STR1## and to their salts which are inhibitors of herpes simplex virus thymidine kinase in the treatment and prophylaxis of infections caused by herpes simplex virus.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: December 19, 2000
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Joseph Armstrong Martin, Bradley Stuart Sherborne, Gareth Mark Taylor
  • Patent number: 6156784
    Abstract: Disclosed are compositions containing compounds of the formula (I) below wherein A,B,C,G,Q and R are defined herein. The compounds are useful as phosphotyrosine mimics that, when incorporated into an appropriate molecular structure, inhibit the binding of tyrosine kinase-dependent regulatory proteins to their native phosphotyrosine-containing ligands or receptors. Also disclosed are methods for preparing the compounds of the formula (I).
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: December 5, 2000
    Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventors: Rajashekhar Betageri, Jean-Marie Ferland, Montse Llinas-Brunet, Neil Moss, John R. Proudfoot
  • Patent number: 6133455
    Abstract: There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl)methylamine compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and acarid pests, and may also be used to prepare other pesticidal arylpyrrole compounds.In addition, the present invention provides N-(arylmethylene)-1-chloro-1-(perfluoroalkyl)methylamine compounds which are useful as intermediates in the preparation of arylpyrrole compounds.
    Type: Grant
    Filed: February 9, 1999
    Date of Patent: October 17, 2000
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 6121461
    Abstract: A novel crystalline form of [(R-(R*,R*)]-2-(4-fluorophenyl)-.beta.,.delta.-dihydroxy-5-(1-methylethyl) -3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt designated Form III is characterized by its X-ray powder diffraction and/or solid state NMR is described, as well as methods for the preparation and pharmaceutical composition of the same, which is useful as an agent for treating hyperlipidemia and hypercholesterolemia.
    Type: Grant
    Filed: July 26, 1999
    Date of Patent: September 19, 2000
    Assignee: Warner-Lambert Company
    Inventor: Ann T. McKenzie
  • Patent number: 6077863
    Abstract: The present invention provides a method for the protection of wood, wood products and wooden structures from wood-eating insect attack and infestation which comprises treating said wood, wood product or wooden structure or the soil surrounding said wood, wood product or wooden structure with an insecticidally effective amount of an arylpyrrole compound of formula I.
    Type: Grant
    Filed: August 7, 1998
    Date of Patent: June 20, 2000
    Assignee: American Cyanamid Company
    Inventors: Byron L. Reid, Robert A. Farlow
  • Patent number: 6057342
    Abstract: The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: ##STR1## or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(.dbd.NH)NH.sub.2 and the other H, and J.sup.1 and J.sup.2 may be O or CH.sub.2, which are useful as inhibitors of factor Xa.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: May 2, 2000
    Assignee: Dupont Pharmaceutical Co.
    Inventors: John Matthew Fevig, Donald Joseph Phillip Pinto, Mimi Lifen Quan, Petrus Fredericus Wilhelmus Stouten
  • Patent number: 6022379
    Abstract: Pyrrole derivatives of 1,4-naphthoquinone and of 1,4-dihydroxynaphthalene, dye compositions containing them and the corresponding dyeing process.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: February 8, 2000
    Assignee: L'Oreal
    Inventors: Sylvie Genard, Herve Andrean, Michel Hocquaux
  • Patent number: 6013836
    Abstract: This invention relates to N'-substituted-N,N'-disubstitutedhydrazines of formula I ##STR1## wherein X and X' are independently O, S, or NR; A' and B' are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is alkyl, alkenyl, or aralkyl; and wherein E is a tertiary carbon containing organic radical having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen which are useful as insecticides, compositions containing those compounds, methods of producing the compounds, and methods of their use. More particularly, the invention relates to insect growth regulating compounds and compositions, and methods of using such compounds and compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: January 11, 2000
    Assignee: Rohm and Haas Company
    Inventors: Adam Chi-Tung Hsu, Harold Ernest Aller, Dat Phat Le, Donald Wesley Hamp, Barry Weinstein, Raymond August Murphy
  • Patent number: 6011161
    Abstract: There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoroalkylmethyl)arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and acarid pests, and may also be used to prepare other pesticidal arylpyrrole compounds. In addition, the present invention provides N-(perfluoroalkylmethyl)arylimidoyl chloride compounds which are useful as intermediates in the preparation of arylpyrrole compounds.
    Type: Grant
    Filed: February 9, 1999
    Date of Patent: January 4, 2000
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 6005113
    Abstract: The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-(isoindolyl)methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## that is further substituted by bathochromic substituents that are aryl or heteroaryl moieties further substituted by an additional aryl or heteroaryl, that is itself optionally further substituted by an additional aryl or heteroaryl. These aryl and heteroaryl groups are separated by a covalent bond, or by an ethenyl, butadienyl or hexatrienyl linkage. The dyes of the invention are particularly useful as labels for carriers, particularly polymeric microparticles. The resulting microparticles have a long-wavelength fluorescence emission, and possess utility for tracing flow in biological systems, particularly in tracing blood flow.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: December 21, 1999
    Assignee: Molecular Probes, Inc.
    Inventors: Yexin Wu, Dieter H. Klaubert, Hee Chol Kang, Yu-Zhong Zhang
  • Patent number: 5998459
    Abstract: The invention relates to a pharmaceutical composition comprising a pyrrole derivative of the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate of either of them, as an active ingredient. ##STR1## (wherein R.sup.1 represents hydrogen or alkoxycar91 bonylamino, R.sup.2 represents alkyl, aryl which may be substituted, aromatic heterocyclyl which may be substituted, unsubstituted amino, monoalkylamino, dialkylamino, or cyclic amino which may be substituted; R.sup.3 represents cyano or carbamoyl; R.sup.4 represents hydrogen or alkyl; E represents alkylene; q is equal to 0 or 1, A represents methyl, aryl which may be substituted, or aromatic heterocyclyl which may be substituted). The pharmaceutical composition of the invention is effective for the treatment of pollakiuria or urinary incontinence.
    Type: Grant
    Filed: December 8, 1997
    Date of Patent: December 7, 1999
    Inventors: Masami Tsuda, Mitsushi Tanaka, Ayatsugu Nakamura
  • Patent number: 5942538
    Abstract: The present invention relates to benzamidoxime derivatives represented by the formula ?I!; ##STR1## wherein R.sup.1 is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkenyl or unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, R.sup.2 is phenyl optionally having substituents or heterocycle optionally having substituents X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each independently hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio or the like, and r.sub.1 and r.sub.2 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or the like, having excellent fungicidal activity and being useful as a fungicide for agricultural and horticultural use, and methods for preparation thereof.
    Type: Grant
    Filed: June 26, 1998
    Date of Patent: August 24, 1999
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Isamu Kasahara, Hirohito Ooka, Shinsuke Sano, Hiroyasu Hosokawa, Homare Yamanaka
  • Patent number: 5935990
    Abstract: A class of pyrrolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as described in the specification.
    Type: Grant
    Filed: December 9, 1997
    Date of Patent: August 10, 1999
    Assignee: G.D. Searle & Co.
    Inventors: Ish K. Khanna, Richard M. Weier, Yi Yu
  • Patent number: 5925631
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: July 20, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Cameron Black, Greg Hughes, Erich Grimm, Serge Leger, Petpiboon Prasit, Zhaoyin Wang
  • Patent number: 5925773
    Abstract: There are provided ammonium oxazole intermediates of formula I and amino oxazolium intermediates of formula II, useful in the manufacture of insecticidal arylpyrrole compounds.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: July 20, 1999
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5882393
    Abstract: The invention relates to a dispersing agent or salts thereof, comprising the reaction product of:A one or more polyisocyanates with an average functionality of about 2 to about 5, withB a compound of the type Y--R--X, wherein Y represents a ring structure with at least one nitrogen atom in the ring, R represents a chain of at least three atoms and X has the meaning O--R.sup.1 or N(R.sup.1) (R.sup.2), wherein R.sup.1 is H or a group of the formula R.sup.3 --Z, wherein R.sup.3 represents a chain with at least two atoms and Z represents OH or NH.sub.2, and R.sup.2 represents a group of the formula R.sup.3 --Z, which compound is obtainable through reaction of an acrylate compound or an epoxide compound with a cyclic compound which has at least one group of the structure ##STR1## in the ring.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: March 16, 1999
    Assignee: Efka Chemicals B.V.
    Inventors: Peter Hermann Quednau, Frank Oliver Heinrich Pirrung
  • Patent number: 5824691
    Abstract: Guanidine derivatives of the formula: ##STR1## wherein Y is C--R.sup.1(in which R.sup.1 is hydrogen, lower alkyl, hydroxy, protected hydroxy, etc.,)R.sup.2 is pyrrolyl, tetrazolyl, pyrazolyl, etc.,R.sup.3 is hydrogen, lower alkoxy, hydroxy, protected hydroxy, etc.,Z is C--R.sup.4(in which R.sup.4 is hydrogen, carboxy, protected carboxy, nitro, halogen, hydroxy(lower)alkyl, etc.,), andW is R.sup.12(in which R.sup.12 is hydrogen, lower alkoxy, nitro, hydroxy or protected hydroxy)and pharmaceutically acceptable salts thereof which are useful as a medicament which are useful in inhibiting Na.sup.+ /H.sup.+ exchange in cells and in the prevention of cardiovascular diseases, cerebrovascular diseases, renal diseases, arteriosclerosis and shock.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: October 20, 1998
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Atsushi Kuno, Yoshikazu Inoue, Hisashi Takasugi, Hiroaki Mizuno, Kumi Yamasaki
  • Patent number: 5817691
    Abstract: There are provided arylthio, -sulfinyl and -sulfonyl pyrrole compounds having the structural formula I ##STR1## Further provided are compositions and methods comprising those compounds for the control of insects.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: October 6, 1998
    Assignee: American Cyanamid Company
    Inventors: Keith Douglas Barnes, Robert Eugene Diehl, Susan Hensen Trotto, Yulin Hu
  • Patent number: 5777132
    Abstract: There is provided a single step procedure to prepare 2-aryl-5-perfluoroalkylpyrrole derivatives directly from the perfluoroacetylated Strecker reaction product. Said pyrrole derivatives are insecticidal and also useful as precursors to other insecticidal arylpyrrole compounds.Further provided are amide nitrile intermediates, useful in the preparation of insecticidal arylpyrrole compounds.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: July 7, 1998
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5763610
    Abstract: A composition comprising a nitrogen-containing olefinic compound and a process for using the nitrogen-containing olefinic compound to produce a water-soluble polymer which has applications in a subterranean formation are provided. The nitrogen-containing olefinic compound can be made from an amine and an alkylating agent. The polymer produced can be used in drilling fluids, workover fluids, completion fluids, permeability corrections, water or gas coning prevention, fluid loss prevention, matrix acidizing, fracture acidizing, and combinations of any two or more thereof.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: June 9, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Odd Ivar Eriksen
  • Patent number: 5750726
    Abstract: There is provided a single step procedure to prepare 2-aryl-5-perfluoroalkylpyrrole derivatives directly from the perfluoroacetylated Strecker reaction product. Said pyrrole derivatives are insecticidal and also useful as precursors to other insecticidal arylpyrrole compounds.Further provided are amide nitrile intermediates, useful in the preparation of insecticidal arylpyrrole compounds.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: May 12, 1998
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5723499
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(i): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: March 3, 1998
    Assignee: C.I.R.D. Galderma
    Inventors: Bruno Charpentier, Jean-Michel Bernardon
  • Patent number: 5637600
    Abstract: The present invention relates to pyrrole compounds, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, in particular as anti-psychotic agents.
    Type: Grant
    Filed: August 13, 1996
    Date of Patent: June 10, 1997
    Assignee: SmithKline Beecham p.l.c.
    Inventor: Christopher N. Johnson
  • Patent number: 5587487
    Abstract: The present invention refers to new contrast media particularly suited for X-ray diagnostic procedures of the human and animal body and also to the new compounds of general formulae (I) and (II).
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: December 24, 1996
    Assignee: Dibra S.p.A.
    Inventors: Christoph De Haen, Fulvio Uggeri, Ornella Gazzotti, Marino Brocchetta
  • Patent number: 5573999
    Abstract: .beta.-Substituted cinnamic acid derivatives of the formula 1, ##STR1## where R.sup.1 is alkyl, chlorine or bromine, --X-- is --O--, --S--, ##STR2## m is 0 or 1, --Y is --OR.sup.4, --O--N.dbd.CR.sup.5 R.sup.6, --NR.sup.7 R.sup.8, --N(OR.sup.9)R.sup.10 or --SR.sup.11, where the above-mentioned substituents R.sup.2 to R.sup.11 are alkyl, and R.sup.2, and R.sup.3 and R.sup.5 to R.sup.11 can also be hydrogen,Z is halogen, nitro, cyano, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, alkenyl, aralkenyl, aryloxyalkenyl, arylthioalkenyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylthioalkenyl, alkynyl, arylalkynyl, hetarylalkynyl, aryl, hetaryl, arylazo, acylamino, --OR.sup.12, --SR.sup.13, --SOR.sup.14, --SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22, R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--, N.dbd.CR.sup.27 R.sup.28, --CH.sub.2 --OCOR.sup.39 or --NR.sup.37 R.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: November 12, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Horst Wingert, Wolfgang von Deyn, Wassilios Grammenos, Hartmann Koenig, Harald Rang, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5554633
    Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q is optionally substituted phenyl or benzhydryl; X and Y are each H or together form a group=O; Z is O, S or NR.sup.9, where R.sup.9 is H or C.sub.1-6 alkyl; R.sup.1 represents H or C.sub.1-6 alkyl; R.sup.2 represents C.sub.1-6 alkyl substituted by CONR.sup.7 (CH.sub.2).sub.p R.sup.8 (where R.sup.7 is H or C.sub.1-6 alkyl, R.sup.8 is optionally substituted heteroaryl and p is 0, 1, 2, 3, 4, 5 or 6); R.sup.3 represents H, C.sub.1-6 alkyl or C.sub.2-6 alkynyl; R.sup.4 represents H, C.sub.1-6 alkyl or optionally substitute phenyl; R.sup.5 represents optionally substituted phenyl; R.sup.6 is H or C.sub.1-6 alkyl; and q is 0, 1, 2 or 3; are tachykinin antagonists useful in therapy.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: September 10, 1996
    Assignee: Merck, Sharp & Dohme, Ltd.
    Inventor: Martin R. Teall
  • Patent number: 5525735
    Abstract: Disclosed are methods for synthesizing very large collections of diverse pyrrolidine compounds and derivatives thereof on solid supports and synthetic compound libraries comprising pyrrolidine groups and derivatives thereof prepared by such methods.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: June 11, 1996
    Assignee: AFFYMAX Technologies NV
    Inventors: Mark A. Gallop, Martin A. Murphy
  • Patent number: 5525734
    Abstract: Disclosed are methods for synthesizing very large collections of diverse pyrrolidine compounds on solid supports and synthetic compound libraries comprising pyrrolidine groups prepared by such methods.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: June 11, 1996
    Assignee: Affymax Technologies N.V.
    Inventors: Mark A. Gallop, Martin A. Murphy
  • Patent number: 5523299
    Abstract: Compounds of formula (I), ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl; and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyalkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl; or R.sup.1 and R.sup.2 together form a linking chain-(CH.sub.2).sub.m Op (wherein m is 2 to 4 and p is zero or 1) which chain may be optionally substituted by one or two C.sub.1-4 alkyl groups; and Y represents a group selected from (a) or (b) wherein R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: June 4, 1996
    Assignee: SmithKline Beecham PLC
    Inventors: Geoffrey Stemp, Michael S. Hadley, David J. Nash, Christopher N. Johnson
  • Patent number: 5502213
    Abstract: A process for purifying crude pyrroles obtained in the preparation of pyrroles of the general formula I ##STR1## where R is hydrogen or a C.sub.1 -C.sub.6 -alkyl radical, which comprises treating the mixture containing the crude pyrrole with an acid or an activated carboxylic acid derivative and removing the pyrrole from the mixture by distillation at reduced pressure and at a bottom temperature of up to 160.degree. C.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: March 26, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Pfab, Peter Wahl, Dieter Franz
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5475165
    Abstract: Aryl halide, such as idodobenzene, is reacted with perfluoromethoxycarboxylate, such as CF.sub.3 OCF.sub.2 CO.sub.2 K, in the presence of CuI and an inert aprotic polar solvent to obtain trifluoromethylaryl.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: December 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Keith W. Palmer, Paul R. Resnick
  • Patent number: 5468877
    Abstract: Haloalkylthio, -sulfinyl and -sulfonyl arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: November 21, 1995
    Assignee: American Cyanamid Company
    Inventors: Keith D. Barnes, Victor M. Kamhi, Robert E. Diehl
  • Patent number: 5464858
    Abstract: Inhibitors of nitric oxide formation from arginine useful for treating hypotension, inflammation, stroke and to restore vascular contractile sensitivity to the effects of .alpha..sub.1 adrenergic agonists are physiologically active compounds including N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties or monoalkyl carbon-substituted N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties, having the formula ##STR1## wherein R is (CH.sub.2).sub.y CH.sub.3 or H, R' is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, and R" is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, with y ranging from 0 to 5, and x is 0 or 1 and wherein none or only one of R, R' and R" provides an alkyl substituent on ornithine or lysine moiety, and wherein Q is a heme binding moiety and/or a sulfur-containing binding moiety and Q' is --NH.sub.2 when there is a double bond between the omega carbon and Q and Q' is .dbd.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: November 7, 1995
    Assignee: The Medical College of Wisconsin Research Foundation, Inc.
    Inventors: Owen W. Griffith, Krishnaswamy Narayanan
  • Patent number: 5463079
    Abstract: A process for preparing five-membered nitrogen heterocycles of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 are hydrogen,R.sup.1 is C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -hydroxyalkyl, C.sub.1 -C.sub.10 -aminoalkyl, aryl, C.sub.7 -C.sub.10 -aralkyl and C.sub.7 -C.sub.10 -alkylaryl,R.sup.5 and R.sup.6 are C.sub.1 -C.sub.8 -alkyl,R.sup.2 and R.sup.3 together are oxygen with the proviso that R.sup.8 is hydrogen,R.sup.3 and R.sup.4 and/or R.sup.7 and R.sup.8 or R.sup.4 and R.sup.7 together are a bond,comprises reacting vinyloxiranes of the general formula II ##STR2## where R.sup.5 and R.sup.6 have the abovementioned meanings, with ammonia or primary amines of the general formula IIIR.sup.1 --NH.sub.2 (III),where R.sup.1 has the abovementioned meanings, in the presence of a compound of an element of Group VIIIb or Ib of the Periodic Table, with or without the addition of a Lewis acid, at from 20.degree. to 200.degree. C.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Pinkos, Rolf Fischer
  • Patent number: 5459264
    Abstract: A method for reducing an .alpha.,.beta.-unsaturated ketone of the present invention includes the step of treating the .alpha.,.beta.-unsaturated ketone with a silyl compound in the presence of a Lewis acid and alcohol to selectively reduce the carbonyl group of the .alpha.,.beta.-unsaturated ketone. According to this method, a deoxy-compound can be obtained from the .alpha.,.beta.-unsaturated ketone by selectively reducing the carbonyl group without reducing an .alpha.,.beta.-unsaturated bond.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: October 17, 1995
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Mitsuru Imuta, Makoto Kobayashi, Teruo Iizuka
  • Patent number: 5455260
    Abstract: This invention relates to a class of novel aliphatic amino bis-aryl compounds containing at least four carbon atoms and an amino group either substituted thereon or incorporated therein and is further linked or bridged to two mono- and/or bicyclic rings. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: October 3, 1995
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Robert A. Groneberg, John R. Regan, Kent W. Neuenschwander, Anthony C. Scotese
  • Patent number: 5446170
    Abstract: The present invention provides a process for the manufacture of 2-aryl-5-(perfluoroalkyl)pyrrole-3-carbonitrile comprising the cycloaddition of 5-amino-4-aryl-2-perfluoroalkyl-1,3-oxazole and the appropriate 1,3-dipolarifile. The arylpyrrole-3-carbonitrile product and its derivatives are highly effective insecticidal, acaricidal and nematocidal agents.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: August 29, 1995
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5446054
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: August 29, 1995
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
  • Patent number: 5416222
    Abstract: This invention provides novel pyridonecarboxylic acid derivatives having a quite high antimicrobial activity. The derivatives have the following formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 represent each a hydrogen or C.sub.1 -C.sub.6 alkyl group; R.sup.4 represents an ethyl, 2-fluoroethyl, vinyl, isopropyl, isopropenyl or cyclopropyl group; and X represents CH, C--F, C--Cl or N characterized in that R.sup.2 and R.sup.3 are not hydrogen at the same time.
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: May 16, 1995
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Isao Hayakawa, Shohgo Atarashi
  • Patent number: 5416235
    Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: May 16, 1995
    Assignee: Octel Chemicals Limited
    Inventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
  • Patent number: 5378839
    Abstract: There are provided 1-(substituted)thioalkylpyrrole compounds of formula I ##STR1## the use thereof for the control of insect, acarid and mollusk pests and methods and compositions for the protection of crops from the ravages of said pests.
    Type: Grant
    Filed: January 26, 1994
    Date of Patent: January 3, 1995
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Venkataraman Kameswaran
  • Patent number: 5359090
    Abstract: There is provided a safe and effective means of introducing an alkoxymethyl group onto the ring Nitrogen atom of a wide variety of pyrrole compounds via the reaction of the appropriate pyrrole precursor sequentially with dialkoxymethane, Vilsmeier reagent and a tertiary amine. The product 1-(alkoxymethyl)pyrroles are useful as insecticidal, acaricidal, nematocidal and molluscicidal agents.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: October 25, 1994
    Assignee: American Cyanamid Company
    Inventors: Robert F. Doehner, Jerry M. Barton
  • Patent number: 5310938
    Abstract: This invention relates to methods and compositions for treating, controlling, preventing and protecting warm-blooded animals from infestation and infection by helminths, acarids and arthropod endo- and ectoparasites by administering or applying to the animals a substituted arylpyrrole compound.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: May 10, 1994
    Assignee: American Cyanamid Company
    Inventors: Dale G. Brown, Robert E. Diehl, Donald P. Wright, Jr., Jack K. Siddens, deceased
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5298659
    Abstract: Azomethines can be prepared by the condensation of cycloalkanones and anilines in the presence of acid homogeneous catalysts while the water of reaction is removed azeotropically, the condensation being carried out in a continuous reaction in a column-like reactor to which a temperature profile is applied, the starting materials being fed in in the low-temperature region, and, of the reaction products, the water of reaction to be removed azeotropically being discharged also in the low-temperature region and the azomethine produced being discharged in the high-temperature region.
    Type: Grant
    Filed: January 14, 1993
    Date of Patent: March 29, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Hans-Josef Buysch, Paul Wagner
  • Patent number: 5288776
    Abstract: A composition comprisinga) a chlorinated polymer, andb) at least one compound of formula I ##STR1## wherein X is a group ##STR2## R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.20 alkyl, hydroxy- and/or halogen-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.20 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A.sub.1, which radicals A.sub.1 are each independently of one another selected from the group consisting of C.sub.1 -C.sub.10 alkyl, halogen, hydroxy, methoxy and ethoxy,R.sub.1 and R.sub.2 are further C.sub.7 -C.sub.10 phenylalkyl or C.sub.7 -C.sub.10 phenylalkyl which is substituted in the phenyl moiety by 1 to 3 radicals A.sub.2, which radicals A.sub.2 are each independently of one another selected from the group consisting of C.sub.1 -C.sub.20 alkyl, halogen, hydroxy, methoxy and ethoxy, andR.sub.3 is phenyl or phenyl which is substituted by 1 to 3 radicals A.sub.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: February 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Drewes, Hans-Helmut Friedrich
  • Patent number: 5281719
    Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: January 25, 1994
    Assignee: American Cyanamid Company
    Inventors: Venkataraman Kameswaran, Victor M. Kamhi
  • Patent number: 5278295
    Abstract: A pyrrole polymer membrane having electrical conductivity and liquid crystal properties in the same matrix. The starting pyrrole monomer derivative is illustrated by the formula ##STR1## where R.sub.1 and R.sub.2 are selected so that at least either of them is an electron attractive group. Methods of producing such membranes by a electropolymerization process and by a chemical oxidation process are described.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: January 11, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hirofumi Suzuki, Takehira Kaneko, Nobuo Matsui, Isami Hamamoto, Tetsuya Katoh, Toshiaki Satoh, Fuminiko Nagasaki
  • Patent number: 5274114
    Abstract: This invention relates to the preparation of 3- and/or 4-substituted pyrrolidine catalysts corresponding to formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X.sub.1, X.sub.2, and Y have the meanings described for formula (I) and to use of such catalysts in the polyisocyanate polyaddition process.
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: December 28, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Richard Weider, Uwe Scholz, Andreas Ruckes