Halogen Attached Directly To The Diazine Ring By Nonionic Bonding Patents (Class 544/313)
  • Patent number: 5840892
    Abstract: A novel process for the preparation of substituted pyrimidine derivatives of the general formula: ##STR1## in which a halopyrimidine is reacted in the presence of a sulfinate with a compound selected from the series: ##STR2## The compounds of the general formula I are precursors of, for example, compounds with herbicidal activity.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: November 24, 1998
    Assignee: Lonza AG
    Inventors: Yves Bessard, Gerhard Stucky
  • Patent number: 5817664
    Abstract: The present invention relates to a group of 5-substituted uracil derivatives which are inactivators of uracil reductase and which are particularily useful in cancer chemotherapy, especially in combination with antimetabolite antineoplastic agents such as 5-fluorouracil (5-FU).
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 6, 1998
    Assignee: Glaxo Wellcome Inc.
    Inventors: Thomas Spector, David J. T. Porter, Saad G. Rahim
  • Patent number: 5767100
    Abstract: In accordance with this invention novel compounds are provided that are selected from saturated and unsaturated pyrans and furans substituted with at least a phosphonate group and a heterocyclic base. These compounds are useful as antiinfectives, flame retardants, diagnostic oligonucleotides and immunogens.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: June 16, 1998
    Assignee: Gilead Sciences, Inc.
    Inventors: Petr Alexander, Ernest J. Prisbe
  • Patent number: 5753635
    Abstract: This invention is directed to purine derivatives of the following formulae: ##STR1## wherein Z.sup.1 is --O--, --N(R.sup.10)-- or --CH.sub.2 O--;Z.sup.2 is --O--, --N(R.sup.10)-- or --OCH.sub.2 --;R.sup.1 and R.sup.4 are each independently hydrogen, halo, alkyl, --OR.sup.10, --C(O)OR.sup.10, --C(O)N(R.sup.10)R.sup.11, --N(R.sup.10)R.sup.11, --N(R.sup.10)C(O)R.sup.10, or --N(H)S(O).sub.2 R.sup.13 ;R.sup.2 is --C(NH)NH.sub.2, --C(NH)N(H)OR.sup.10, --C(NH)N(H)C(O)OR.sup.13, --C(NH)N(H)C(O)R.sup.10, --C(NH)N(H)S(O).sub.2 R.sup.13, or --C(NH)N(H)C(O)N(H)R.sup.10 ;R.sup.3 is halo, alkyl, haloalkyl, haloalkoxy, ureido, cyano, guanidino, --OR.sup.10, --C(NH)NH.sub.2, --C(NH)N(H)OR.sup.10, --C(O)N(R.sup.10)R.sup.11, --R.sup.12 --C(O)N(R.sup.10)R.sup.11, --CH(OH)C(O)N(R.sup.10)R.sup.11, --N(R.sup.10)R.sup.11, --R.sup.12 --N(R.sup.10)R.sup.11, --C(O)OR.sup.10, --R.sup.12 --C(O)OR.sup.10, --N(R.sup.10)C(O)R.sup.
    Type: Grant
    Filed: August 16, 1996
    Date of Patent: May 19, 1998
    Assignee: Berlex Laboratories, Inc.
    Inventors: Brad O. Buckman, Raju Mohan, Michael M. Morrissey
  • Patent number: 5747500
    Abstract: Novel 2,4-pyrimidinedione compounds, and pharmaceutically acceptable salts thereof which possess good antiviral activities, and specifically represented by the following formula(I): ##STR1## wherein: R.sup.1 represents an unsubstituted or substituted allyl group represented by CH.sub.2 CH.dbd.CR.sup.5 R.sup.6 or an unsubstituted or substituted propargyl group represented by CH.sub.2 C.tbd.CR.sup.7 wherein R.sup.5, R.sup.6 and R.sup.7 are each independently a hydrogen atom; a methyl group optionally substituted with a halogen atom, or a C.sub.1-10 carbonyloxy, hydroxy, azido, cyano, optionally substituted amino, optionally substituted phosphonyl, optionally substituted phenyl, C.sub.3-10 heteroaryl, C.sub.1-3 alkoxy or benzyloxy radical; a C.sub.2-10 alkyl or alkenyl group; a cyclopropyl group; an optionally substituted phenyl group; a C.sub.3-10 heteroaryl group; a C.sub.1-10 ester group; or an optionally substituted C.sub.1-10 alkylamide group;R.sup.2 represents a halogen atom, an optionally substituted C.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: May 5, 1998
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Jong-Chan Son, III-Young Lee, Byung-II Bae, Jeong-Sik Han, Joong-Kwon Choi, Yung-Bok Chae
  • Patent number: 5728833
    Abstract: A process for the preparation of a compound of formula (I):HetSCH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 (I)wherein Het is an optionally substituted 5- or 6-membered heterocyclic ring, which comprises reacting a compound of formula (II):HetSH (II)with a compound of formula (III):CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 L (III)wherein L is chlorine or bromine or a group --OSO2R.sup.a wherein R.sup.a is a C1-4 alkyl group or a phenyl group optionally substituted by a C1-4 alkyl group.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: March 17, 1998
    Assignee: Zeneca Limited
    Inventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Alison Mary Smith, Roger Salmon, Harjinder Singh Bansal
  • Patent number: 5726128
    Abstract: 1. A benzyloxypyrimidine derivative of the formula (I): ##STR1## wherein R.sup.1 represents hydrogen, a 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.3 -C.sub.5 alkenyloxy, C.sub.1 -C.sub.4 alkylthio, or cyano;each X, which may be identical or different if n is greater than 1, represents a 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, or C.sub.1 -C.sub.4 haloalkyl;each Y, which may be identical or different if m is greater than 1, represents a halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 haloalkoxy;G represents O or S; andn and m each independently represent an integer of 0 to 5.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: March 10, 1998
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisashi Kanno, Yoshikazu Kubota, Tsutomu Sato, Masato Arahira
  • Patent number: 5723412
    Abstract: A 2-benzyloxy-4-phenoxypyrimidine derivative represented by the formula (I): ##STR1## wherein R.sup.1 represents hydrogen, a 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.3 -C.sub.5 alkenyloxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, cyano, or phenyl;each X, which may be identical or different if n is greater than 1, represents a halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or C.sub.1 -C.sub.4 alkoxy;each Y, which may be identical or different if m is greater than 1, represents a 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 C.sub.1 -C.sub.4 haloalkylthio; andn and m each independently represent an integer of 0 to 5, which is useful as a herbicide.
    Type: Grant
    Filed: July 13, 1995
    Date of Patent: March 3, 1998
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisashi Kanno, Yoshikazu Kubota, Tsutomu Sato, Masato Arahira
  • Patent number: 5723473
    Abstract: A fungicidal compound of formula (I): ##STR1## wherein A is hydrogen, halogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; and one of R.sup.1 and R.sup.2 is optionally substituted isoquinoline while the other is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halogen or cyano.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: March 3, 1998
    Assignee: Zeneca Limited
    Inventor: Brian Leslie Pilkington
  • Patent number: 5719132
    Abstract: The present invention is directed to the use of pharmaceutical compositions containing anti-retroviral effective amounts of (a) d4T and (b) 5-fluorouracil or a prodrug, or salt thereof.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: February 17, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Pin-Fang Lin, Yi-Fei Gong
  • Patent number: 5714606
    Abstract: The invention relates to pyrrolidine monomeric units and to oligomers which are joined via phosphate linkages, including phosphorothioate, phosphodiester and phosphoramidate linkages.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: February 3, 1998
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Oscar L. Acevedo, Normand Hebert
  • Patent number: 5714437
    Abstract: Novel compounds of the formula ?1! are disclosed, wherein X is hydrogen, fluorine or chlorine; Y is fluorine, chlorine or bromine; R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.2 and Q are various groups. Also disclosed are herbicidal compositions containing these compounds as active ingredients and methods for controlling unfavorable weeds by application of these compounds.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: February 3, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Minoru Takano, Masayuki Enomoto, Kazuo Saito, Satoru Kizawa
  • Patent number: 5707995
    Abstract: Compounds of formula (I) in which X.sup.1 and X.sup.2 each represents oxygen; S(O).sub.n, n being 0, 1 or 2; or CO, CH.sub.2 or NR, R being hydrogen or alkyl; R.sup.1 and R.sup.10 are each hydrogen or halogen; R.sup.2 and R.sup.9 are each hydrogen, halogen, cyano, nitro, alkyl, halo-alkyl, alkoxy, alkylthio, amino, mono- or di-alkylamino, alkoxyalkyl, haloalkoxyalkyl or alkoxycarbonyl; R.sup.3 and R.sup.8 are each hydrogen, chlorine, alkyl, haloalkyl, haloalkenyl, halo-alkynyl, haloalkoxy, haloalkoxycarbenyl, haloalkylthio, haloalkoxyalkyl, haloalkylsulphinyl, or haloalkylsulphonyl, nitro or cyano; R.sup.4 and R.sup.7 are each hydrogen, halogen, alkyl or alkoxy; R.sup.5 is hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulphonyl or phenyl; and R.sup.6 is hydrogen or, when R.sup.5 is hydrogen, alkyl; provided that either each phenyl is unsubstituted or at least one of R.sup.3 and R.sup.8 is not hydrogen, have useful pesticidal activity.
    Type: Grant
    Filed: July 24, 1995
    Date of Patent: January 13, 1998
    Assignee: American Cyanamid Company
    Inventors: David Munro, Royston Davis, Janet Anne Day, Jacqueline Anne Wilkin, William W. Wood
  • Patent number: 5693771
    Abstract: In accordance with this invention novel compounds are provided that are selected from saturated and unsaturated pyrans and furans substituted with at least a phosphonate group and a heterocyclic base. These compounds are useful as antiinfectives, flame retardants, diagnostic oligonucleotides and immunogens.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: December 2, 1997
    Assignee: Gilead Sciences, Inc.
    Inventors: Petr Alexander, Ernest J. Prisbe
  • Patent number: 5688778
    Abstract: Provided are compounds of the following formulae:A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl;B is a purine or pyrimidine base.optionally R is taken together with X' to complete a cyclic phosphonate having the formula ##STR2## A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR3## wherein X and X' are the same or different and are hydrogen or alkyl, the dashed line is an optional bond,Y and Z are the same or different and are hydrogen, hydroxyl or alkyl or Y+Z are taken together to form an epoxide or cyclopropyl, andB is a purine or pyrimidine base.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: November 18, 1997
    Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.
    Inventors: Choung Un Kim, John C. Martin, Bing Uh Luh, Peter F. Misco
  • Patent number: 5681794
    Abstract: The invention relates to new N-cyanoaryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Z have the meanings given in the description,to a plurality of processes for their preparation, to their use as herbicides and to novel intermediates.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 28, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Mark-Wilhelm Drewes, Albrecht Marhold, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5610300
    Abstract: Compounds of the formulae I and Ia and their racemates ##STR1## in which A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --, R.sub.1 is hydrogen or a protective group, R.sub.2 is hydrogen or a protective group or a radical forming a phosphorus-containing nucleotide bridge group and B is a purine or pyrimidine radical or an analogue thereof, can be used as antiviral active ingredients or for the preparation of biologically active oligonucleotides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 11, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl-Heinz Altmann, Ren e Imwinkelried, Albert Eschenmoser
  • Patent number: 5602077
    Abstract: A method is disclosed for controlling the growth of undesired vegetation in a plantation crop by applying to the locus of the crop an effective amount of a compound of formula I ##STR1## and A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, Y and Z are as defined in the disclosure. Also disclosed are novel substituted heterocyclic compounds and their agriculturally suitable compositions which are generally useful as herbicides, as well as methods of their use as general or selective preemergent or postemergent herbicides, or as plant growth regulants.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: February 11, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Kofi S. Amuti, Wonpyo Hong, Joseph E. Semple
  • Patent number: 5599770
    Abstract: A herbicidal composition comprising a herbicidally effective amount of a 2-benzyloxypyrimidine derivative represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are each independently H, a halogen, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.5 alkynyloxy, C.sub.1 -C.sub.4 alkylthio, or phenyl;n is an integer of 0 to 5; andeach X which may be identical or different if n is greater than 1, is a 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 alkylthio, C.sub.7 -C.sub.9 aralkyloxy, phenyl, hydroxymethyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or nitro, andan adjuvant.
    Type: Grant
    Filed: June 21, 1995
    Date of Patent: February 4, 1997
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshikazu Kubota, Hisashi Kanno, Tsutomu Sato, Masato Arahira
  • Patent number: 5599771
    Abstract: 3-Aryluracil derivatives of formula I ##STR1## wherein W is a group of the formula ##STR2## wherein the bond to the ring nitrogen atom is made via the carbon atom; wherein R.sub.1 to R.sub.9 are as defined in claim 1, are suitable as active ingredients in weed control compositions.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: February 4, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean Wenger
  • Patent number: 5593945
    Abstract: The invention relates to new N-cyanoaryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Z have the meanings given in the description,to a plurality of processes for their preparation, to their use as herbicides and to novel intermediates.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: January 14, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Mark-Wilhelm Drewes, Albrecht Marhold, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5550132
    Abstract: Novel hydroxyalkylammonium-pyrimidine of the formula ##STR1## and nucleoside derivatives have been found to be useful as inhibitors of inflammatory cytokines. They can be used, inter alia, in the therapy of septic shock, cachexia, rheumatoid arthritis, inflammatory bowel disease, multiple sclerosis and AIDS. The compounds are typically prepared by reaction of an iodo substituted nucleoside with the appropriately substituted hydroxyalkylamine.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: August 27, 1996
    Assignees: University of North Carolina, Macronex, Inc.
    Inventors: Bradley J. Benson, Xiannong Chen, George J. Cianciolo, Jose-Luis Diaz, Khalid S. Ishaq, Susan L. Morris-Natschke, Ronald J. Uhing, Henry Wong
  • Patent number: 5539116
    Abstract: The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: July 23, 1996
    Assignee: Emory University
    Inventors: Dennis C. Liotta, Woo-Baeg Choi
  • Patent number: 5525724
    Abstract: A process for the preparation of chloropyrimidines of the formula ##STR1## in which the substituents may be alkyl, cycloalkyl, aryl or radicals containing heteroatoms, but in which at least one of the substituents R.sup.1 to R.sup.4 must be Cl, which involves:reacting a hydroxy-pyrimidine or its tautomeric keto form with phosphoryl chloride in the presence of an amine or amine hydrochloride;recovering phosphoryl chloride after the reaction by adding phosphorus pentachloride and distilling the phosphoryl chloride; andseparating the chloropyrimidine from the amine hydrochloride by addition of a solvent which will dissolve the chloropyrimidine but not the amine hydrochloride and removing the amine hydrochloride.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: June 11, 1996
    Assignee: Huels Aktiengesellschaft
    Inventor: Artur Hunds
  • Patent number: 5519139
    Abstract: There is disclosed a novel 4-aminopyrimidine derivative containing an optionally esterified carboxyl group at the 5-position which has potent fungicidal activity as well as insecticidal and miticidal activity. The compound is useful as agricultural fungicides, insecticides and miticides.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: May 21, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toshikazu Ohtsuka, Moriyasu Masui, Takami Takeda, Michio Masuko, Katsuaki Ohba
  • Patent number: 5519134
    Abstract: Novel pyrrolidine monomers bearing various functional groups are used to prepare oligomeric structures. The pyrrolidine monomers can be joined via standard phosphate linkages including phosphodiester and phosphorothioate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen-bonding.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: May 21, 1996
    Assignee: Isis Pharmaceuticals, Inc.
    Inventors: Oscar L. Acevedo, Normand Hebert
  • Patent number: 5512678
    Abstract: The present invention provides novel 5-(1-fluorovinyl)-1H-pyrimidine-2,4-dione derivatives which are useful as antineoplastic agents by themselves or in conjunctive therapy with the antineoplastic agent 5-fluorouracil.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: April 30, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: James R. McCarthy, Donald P. Matthews, Jeffrey S. Sabol
  • Patent number: 5486610
    Abstract: Pyrimidinylbenzenesulfonyl chloride compounds of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 haloalkyl;X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxy, or halogen;Y is hydrogen or halogen;R.sup.3 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl; andR.sup.4 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.The compounds are useful as intermediates in the preparation of herbicides.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: January 23, 1996
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Richard J. Strunk, Allyn R. Bell
  • Patent number: 5480992
    Abstract: Anomeric 2,2-difluororibosyl azide and amine intermediates which are useful for the preparation of 2'-deoxynucleosides, and processes thereto, are provided. Processes for preparing 2'-deoxynucleosides also are provided.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: January 2, 1996
    Assignee: Eli Lilly and Company
    Inventors: Larry W. Hertel, Charles D. Jones, Julian S. Kroin, Thomas E. Mabry
  • Patent number: 5470975
    Abstract: Novel A-II receptor antagonists have the formula ##STR1## and its isomer ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined herein.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: November 28, 1995
    Assignee: E.R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5461060
    Abstract: The disclosure concerns pyrimidine derivatives represented by the following general formulas [I] and [I'] and having antiviral activity, particularly antiretroviral activity such as anti-HIV activity: ##STR1## and pharmaceutical compositions having antiviral activity and comprising the above-described derivative(s) as an active ingredient.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: October 24, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tadashi Miyasaka, Hiromichi Tanaka, Erik D. A. De Clercq, Masanori Baba, Richard T. Walker, Masaru Ubasawa
  • Patent number: 5461152
    Abstract: Compounds of the formulae I and Ia and their racemates ##STR1## in which A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --, R.sub.1 is hydrogen or a protective group, R.sub.2 is hydrogen or a protective group or a radical forming a phosphorus-containing nucleotide bridge group and B is a purine or pyrimidine radical or an analogue thereof, can be used as antiviral active ingredients or for the preparation of biologically active oligonucleotides.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: October 24, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl-Heinz Altmann, Rene Imwinkelried, Albert Eschenmoser
  • Patent number: 5449663
    Abstract: Anti-cancer compositions containing chiral monosaccharides and methods of their use are disclosed herein. The compositions, exhibiting cytostatic and cytotoxic properties with regard to neoplastic cells are formulated using the L-isomeric form of monosaccharides. A preferred embodiment of the invention employs the L-isomeric form of glucose with a pharmaceutically acceptable carrier. The compositions may be used alone or as an adjunct to other forms of cancer therapy. They are useful in combination with all major forms of cancer therapy including surgery, biological and chemical therapies, radiation therapy, and hyperthermia. In addition to increasing the mortality rate of neoplastic cells, these compositions can reduce the metastatic potential of the tumor, and slow the growth of the malignancy.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: September 12, 1995
    Inventor: Haim I. Bicher
  • Patent number: 5439874
    Abstract: The invention relates to novel substituted bicyclo[3.1.0]hexanes of the formula ##STR1## in which R.sup.1 represents, e. g., hydroxyl or alkoxy,R.sup.2 to R.sup.8 represent, e. g., hydrogen or alkyl,R.sup.9 and R.sup.10 represent, e.g., methyl or methoxy,X represents, e.g., oxygen,Y represents, e.g., oxygen or sulphur andZ represents, e.g., CH or N,as well as salts of the free acid (R.sup.1 =OH) and their further functional derivatives, and furthermore to processes and novel intermediates for their preparation, and to their use as herbicides.In addition, a novel process is described for preparing certain 2-keto-bicyclo[3.1.0]hexanes, which are required as intermediates, starting from correspondingly substituted .alpha.,.beta.-unsaturated carbonyl compounds (of the methacrolein type) and .beta.-keto acid esters (of the acetoacetic acid ester type).
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: August 8, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mark W. Drewes, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5424275
    Abstract: Novel biphenyl derivatives represented by the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X.sup.1, X.sup.2, X.sup.3 and Y are as defined hereinafter.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: June 13, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Toru Uekawa, Naonori Hirata, Kazuo Saito, Hiroyuki Yogai
  • Patent number: 5414096
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 9, 1995
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
  • Patent number: 5414000
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is a substituted purinyl group including pharmaceutically acceptable salts are useful as antiviral agents.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 9, 1995
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
  • Patent number: 5411964
    Abstract: A phenylalanine-glycine compound of formula (I): ##STR1## wherein R represents a residue of an antitumor substance, or a salt or ester thereof, a process for preparation thereof, and a pharmaceutical composition containing the same are described. The novel conjugate of the phenylalanine-glycine compound and the antitumor substance exhibits superior antitumor activity in comparison with the case wherein an antitumor substance is administered alone or as a mixture with phenylalanine.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: May 2, 1995
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Koichi Niimura, Takako Kawabe, Takao Ando, Kenichi Saito
  • Patent number: 5401711
    Abstract: The present invention provides a herbicidal composition containing a novel pyrimidine derivative having the formula (1), ##STR1## wherein R.sup.1 is a trifluoromethanesulfonyioxy group, an ethenyl group which may be substituted, or an ethynyl group which may be substituted; R.sup.2 is a hydrogen atom, an alkyl group, 2-trimethylsilyl ethyl group; R.sup.3 and R.sup.4 are the same or different, and are a methoxy group or a halogen atom; X is an oxygen atom or a sulfur atom; and Z is a methine group; or its salt, as an active ingredient.The pyrimidine derivative of the present invention exhibits an excellent herbicidal effect against noxious weeds which grow in paddy fields, upland fields and non-agricultural fields.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: March 28, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Sato, Koichiro Kaku, Shigehiko Tachikawa
  • Patent number: 5380701
    Abstract: The invention relates to 3-aryluracils of formula I ##STR1## wherein W is a group of formula ##STR2## in which the linkage to the ring nitrogen atom is through the carbon atom: R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 - or C.sub.4 alkenyl or C.sub.3 - or C.sub.4 alkynyl;R.sub.2 is halogen or cyano;R.sub.3 is hydrogen or fluoro;R.sub.4 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 C.sub.4 haloalkyl;R.sub.6 to R.sub.9 are each independently of one another hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.4 haloalkyl or phenyl; orR.sub.6 and R.sub.7 or R.sub.8 and R.sub.9, together with the linking carbon atom, form a 3-, 4-, 5- or 6-membered ring which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups; or R.sub.7 and R.sub.9, together with the linking carbon atoms, form a 3-, 4-, 5- or 6-membered ring which may be substituted by one or more C.sub.1 -C.sub.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: January 10, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Winternitz, Martin Zeller
  • Patent number: 5378711
    Abstract: .alpha.-Arylacrylates substituted by a heterocyclic radical and of the general formula I ##STR1## where R.sup.1 is alkoxy or alkylthio, R.sup.2 is alkyl, Het is quinolyl, which is unsubstituted or substituted, A is oxygen and n is 1, and their plant-tolerated acid addition salts and metal complexes, and the N-oxides of the heterocyclic compounds, and fungicides containing these compounds.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: January 3, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Thomas Kuekenhoehner, Jochen Wild, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5371062
    Abstract: The present invention relates to new substituted azines, of the general formula (I) ##STR1## in which n, Q.sup.1, Q.sup.2, Q.sup.3, R.sup.1, R.sup.2, R.sup.3, X, Y and Z have the meanings given in the description, to a plurality of processes for their preparation, and to their use as herbicides.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: December 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andreee, Mark W. Drewes, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5356863
    Abstract: The present invention relates to an uracil derivative represented by the formula (1): ##STR1## in which R.sup.1 represents hydrogen, alkyl or haloalkyl; R.sup.2 represents haloalkyl; R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxymethyl, halogen or nitro; R.sup.4 represents hydrogen or halogen; R.sup.5 represents hydrogen, halogen, nitro or cyano; X represents oxygen or sulfur: provided that the case where both of Da and Db represent hydrogen is excluded and a herbicide containing the same. The compound can be safely applied to important crops and shows high effect against many weeds in a low amount.
    Type: Grant
    Filed: October 21, 1993
    Date of Patent: October 18, 1994
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Jun Satow, Kenzou Fukuda, Kaoru Itoh, Hiroshi Kita, Yasuo Kawamura, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe, Toshiharu Endo, Kimihiro Ishikawa
  • Patent number: 5352787
    Abstract: 5-Trifluoromethyl-uracil is obtained by chlorinating thymine under mild conditions, further chlorinating the resulting 2,4-dichloro-5-methyl-pyrimidine under drastic conditions to give 2,4-dichloro-5-trichloromethylpyrimidine, reacting the latter with a fluorinating agent to give 2,4-fluorinated and/or -chlorinated 5- trifluoromethylpyrimidines and subjecting these to hydrolysis. The novel chemical compounds 2,4-dichloro- 5-trichloromethylpyrimidine and 2,4-difluoro-5-trifluoromethylpyrimidine are obtained in the course of this process.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: October 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • Patent number: 5346880
    Abstract: This invention relates to novel pyrimidinylthioalkane derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are defined in the specification and A represents hydroxy, and B represents hydrogen or A and B together form a carbonyl group, a process for their production and a method of using said derivatives to combat unwanted plant growth.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: September 13, 1994
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Toshio Goto, Yoshinori Kitagawa, Hidenori Hayakawa, Katsuhiko Shibuya, Ryo Watanabe
  • Patent number: 5340816
    Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: August 23, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, William A. Slusarchyk
  • Patent number: 5336663
    Abstract: 3-Aryluracil derivatives of the formula I ##STR1## in which --W-- is the group ##STR2## where the ring nitrogen atom is bonded via the C atom; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 alkenyl or C.sub.4 alkenyl or C.sub.3 alkynyl or C.sub.4 alkynyl;R.sub.2 is halogen or cyano;R.sub.3 is hydrogen or halogen;R.sub.4 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; or R.sub.4 and R.sub.5 together are --(CH.sub.2).sub.n --;n is the number 3 or 4;R.sub.13 is C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl or C.sub.4 alkynyl or C.sub.3 alkynyl or C.sub.4 alkynyl; andQ is one of the groups a) to e): ##STR3## where R.sub.6 to R.sub.12 are substituents, m is 3, 4 or 5, X is oxygen or sulfur and t is 2, 3 or 4, and if R.sub.1 is hydrogen, the agrochemically acceptable salts of compounds of the formula I. the compounds of formula I have herbicidal properties and are suitable as the active ingredient in a herbicide.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: August 9, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean Wenger, Paul Winternitz, Martin Zeller
  • Patent number: 5332814
    Abstract: Process for the preparation of racemic compounds of the formula I ##STR1## or enantiomers thereof, in which B is the radical of a nucleic base from the series comprising purine, a purine analogue or a pyridine analogue, and R is H or a protective group R.sub.1, by reactinga) a compound of the formula II or enantiomer thereof ##STR2## with a compound of the formulae X--CO--X, X--CS--X, X--SO--X, X--SO.sub.2 --X, R.sub.2 --NCO, R.sub.3 R.sub.4 N--C(O)--R.sub.5, X.sub.2 P--R.sub.6 or X.sub.2 P(O)--R.sub.6, in which X is a leaving group, R.sub.2 is, for example, C.sub.1 -C.sub.18 alkyl, R.sub.3 and R.sub.4 are, for example, H or C.sub.1 -C.sub.18 alkyl, R.sub.5 is, for example, H or C.sub.1 -C.sub.12 alkyl, and R.sub.6 is, for example, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, to give a compound of the formula III or enantiomers thereof ##STR3## in which Y is the groups --C(O)--, --C(S)--, --SO--, --SO.sub.2 --, R.sub.2 NH--CH.dbd., R.sub.3 R.sub.4 N--CR.sub.5 .dbd., R.sub.6 P.dbd. and R.sub.6 (O)P.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: July 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Heinz Moser
  • Patent number: 5330989
    Abstract: Biphenyl derivatives of cyclobutene-1,2-dione of formula 1 are angiotensin II antagonists and are useful for the treatment of hypertension and congestive heart failure ##STR1## wherein: Y is O, NR.sup.7, NCOR.sup.7 ; or R.sup.5 and Y taken together represent a linking chain of N.dbd.CR.sup.8 N; or R.sup.5 and Y taken together represent a linking chain of (CR.sup.9 R.sup.10).sub.n CON where n=1,2,3,4, or 5;X is N, CR.sup.7 ;Z is N, CR.sup.7 ;R.sup.1 is H, alkyl, benzyl, alkoxyalkyl, phenyl;R.sup.2 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.3 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.4 is H, NR.sup.7 R.sup.8, OR.sup.1, CN, F, Cl, I, Br, perfluoroalkyl, alkyl, phenyl, alkoxy, alkyl-OH, alkoxyalkyl, --(CH.sub.2).sub.n CO.sub.2 R.sup.1, --(CH.sub.2).sub.n CONR.sup.7 R.sup.8 where n=1, 2, 3, 4, or 5;R.sup.5, R.sup.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: July 19, 1994
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, William A. Kinney
  • Patent number: 5324854
    Abstract: Compounds having the formula: ##STR1## wherein X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxy or halogen;Y is hydrogen, halogen, or C.sub.1 -C.sub.4 dialkylamino;R.sup.1 is C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl or C.sub.3 -C.sub.8 alkoxy;R.sup.2 is C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, halo substituted C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.4 alkoxy, cyano C.sub.1 -C.sub.4 alkyl, alkoxyalkyl, phenyl, aralkyl, C.sub.1 -C.sub.4 acyl, C.sub.1 -C.sub.4 carbalkoxyalkyl, C.sub.1 -C.sub.4 carbalkoxyalkyl substituted by C.sub.1 -C.sub.4 alkyl, phenylmethyl or methylthioethyl, dialkylaminoethyl, or tetrahydrofuranylmethyl;R.sup.1 and R.sup.2 taken together form a C.sub.3 -C.sub.8 membered heterocyclic ring containing one or more heteroatoms.The compounds are useful as intermediates for making herbicides.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: June 28, 1994
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Richard J. Strunk, Allyn R. Bell