Halogen Attached Directly To The Diazine Ring By Nonionic Bonding Patents (Class 544/313)
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Patent number: 5840892Abstract: 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: GrantFiled: April 8, 1997Date of Patent: November 24, 1998Assignee: Lonza AGInventors: Yves Bessard, Gerhard Stucky
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Patent number: 5817664Abstract: 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: GrantFiled: June 6, 1995Date of Patent: October 6, 1998Assignee: Glaxo Wellcome Inc.Inventors: Thomas Spector, David J. T. Porter, Saad G. Rahim
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Patent number: 5767100Abstract: 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: GrantFiled: March 13, 1996Date of Patent: June 16, 1998Assignee: Gilead Sciences, Inc.Inventors: Petr Alexander, Ernest J. Prisbe
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Patent number: 5753635Abstract: 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: GrantFiled: August 16, 1996Date of Patent: May 19, 1998Assignee: Berlex Laboratories, Inc.Inventors: Brad O. Buckman, Raju Mohan, Michael M. Morrissey
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Patent number: 5747500Abstract: 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: GrantFiled: June 18, 1996Date of Patent: May 5, 1998Assignee: Korea Research Institute of Chemical TechnologyInventors: Jong-Chan Son, III-Young Lee, Byung-II Bae, Jeong-Sik Han, Joong-Kwon Choi, Yung-Bok Chae
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Patent number: 5728833Abstract: 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: GrantFiled: August 4, 1994Date of Patent: March 17, 1998Assignee: Zeneca LimitedInventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Alison Mary Smith, Roger Salmon, Harjinder Singh Bansal
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Patent number: 5726128Abstract: 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: GrantFiled: September 8, 1995Date of Patent: March 10, 1998Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hisashi Kanno, Yoshikazu Kubota, Tsutomu Sato, Masato Arahira
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Patent number: 5723412Abstract: 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: GrantFiled: July 13, 1995Date of Patent: March 3, 1998Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hisashi Kanno, Yoshikazu Kubota, Tsutomu Sato, Masato Arahira
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Patent number: 5723473Abstract: 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: GrantFiled: April 11, 1995Date of Patent: March 3, 1998Assignee: Zeneca LimitedInventor: Brian Leslie Pilkington
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Patent number: 5719132Abstract: 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: GrantFiled: June 27, 1996Date of Patent: February 17, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Pin-Fang Lin, Yi-Fei Gong
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Patent number: 5714606Abstract: The invention relates to pyrrolidine monomeric units and to oligomers which are joined via phosphate linkages, including phosphorothioate, phosphodiester and phosphoramidate linkages.Type: GrantFiled: August 15, 1996Date of Patent: February 3, 1998Assignee: ISIS Pharmaceuticals, Inc.Inventors: Oscar L. Acevedo, Normand Hebert
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Patent number: 5714437Abstract: 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: GrantFiled: August 30, 1995Date of Patent: February 3, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Minoru Takano, Masayuki Enomoto, Kazuo Saito, Satoru Kizawa
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Patent number: 5707995Abstract: 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: GrantFiled: July 24, 1995Date of Patent: January 13, 1998Assignee: American Cyanamid CompanyInventors: David Munro, Royston Davis, Janet Anne Day, Jacqueline Anne Wilkin, William W. Wood
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Patent number: 5693771Abstract: 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: GrantFiled: March 13, 1996Date of Patent: December 2, 1997Assignee: Gilead Sciences, Inc.Inventors: Petr Alexander, Ernest J. Prisbe
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Patent number: 5688778Abstract: 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: GrantFiled: February 17, 1995Date of Patent: November 18, 1997Assignees: 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
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Patent number: 5681794Abstract: 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: GrantFiled: September 30, 1994Date of Patent: October 28, 1997Assignee: Bayer AktiengesellschaftInventors: Roland Andree, Mark-Wilhelm Drewes, Albrecht Marhold, Hans-Joachim Santel, Markus Dollinger
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Patent number: 5610300Abstract: 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: GrantFiled: June 6, 1995Date of Patent: March 11, 1997Assignee: Ciba-Geigy CorporationInventors: Karl-Heinz Altmann, Ren e Imwinkelried, Albert Eschenmoser
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Patent number: 5602077Abstract: 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: GrantFiled: July 13, 1994Date of Patent: February 11, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Kofi S. Amuti, Wonpyo Hong, Joseph E. Semple
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Patent number: 5599770Abstract: 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: GrantFiled: June 21, 1995Date of Patent: February 4, 1997Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshikazu Kubota, Hisashi Kanno, Tsutomu Sato, Masato Arahira
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Patent number: 5599771Abstract: 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: GrantFiled: December 16, 1994Date of Patent: February 4, 1997Assignee: Ciba-Geigy CorporationInventor: Jean Wenger
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Patent number: 5593945Abstract: 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: GrantFiled: August 11, 1994Date of Patent: January 14, 1997Assignee: Bayer AktiengesellschaftInventors: Roland Andree, Mark-Wilhelm Drewes, Albrecht Marhold, Hans-Joachim Santel, Markus Dollinger
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Patent number: 5550132Abstract: 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: GrantFiled: June 22, 1994Date of Patent: August 27, 1996Assignees: 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
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Patent number: 5539116Abstract: 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: GrantFiled: February 10, 1993Date of Patent: July 23, 1996Assignee: Emory UniversityInventors: Dennis C. Liotta, Woo-Baeg Choi
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Patent number: 5525724Abstract: 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: GrantFiled: February 27, 1995Date of Patent: June 11, 1996Assignee: Huels AktiengesellschaftInventor: Artur Hunds
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Patent number: 5519139Abstract: 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: GrantFiled: May 23, 1995Date of Patent: May 21, 1996Assignee: Shionogi & Co., Ltd.Inventors: Toshikazu Ohtsuka, Moriyasu Masui, Takami Takeda, Michio Masuko, Katsuaki Ohba
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Patent number: 5519134Abstract: 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: GrantFiled: January 11, 1994Date of Patent: May 21, 1996Assignee: Isis Pharmaceuticals, Inc.Inventors: Oscar L. Acevedo, Normand Hebert
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Patent number: 5512678Abstract: 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: GrantFiled: April 29, 1994Date of Patent: April 30, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: James R. McCarthy, Donald P. Matthews, Jeffrey S. Sabol
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Patent number: 5486610Abstract: 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: GrantFiled: March 17, 1994Date of Patent: January 23, 1996Assignee: Uniroyal Chemical Company, Inc.Inventors: Richard J. Strunk, Allyn R. Bell
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Patent number: 5480992Abstract: 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: GrantFiled: September 16, 1993Date of Patent: January 2, 1996Assignee: Eli Lilly and CompanyInventors: Larry W. Hertel, Charles D. Jones, Julian S. Kroin, Thomas E. Mabry
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Patent number: 5470975Abstract: 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: GrantFiled: January 11, 1994Date of Patent: November 28, 1995Assignee: E.R. Squibb & Sons, Inc.Inventor: Karnail Atwal
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Patent number: 5461060Abstract: 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: GrantFiled: September 3, 1993Date of Patent: October 24, 1995Assignee: Mitsubishi Kasei CorporationInventors: Tadashi Miyasaka, Hiromichi Tanaka, Erik D. A. De Clercq, Masanori Baba, Richard T. Walker, Masaru Ubasawa
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Patent number: 5461152Abstract: 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: GrantFiled: June 28, 1993Date of Patent: October 24, 1995Assignee: Ciba-Geigy CorporationInventors: Karl-Heinz Altmann, Rene Imwinkelried, Albert Eschenmoser
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Patent number: 5449663Abstract: 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: GrantFiled: June 11, 1993Date of Patent: September 12, 1995Inventor: Haim I. Bicher
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Patent number: 5439874Abstract: 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: GrantFiled: July 21, 1993Date of Patent: August 8, 1995Assignee: Bayer AktiengesellschaftInventors: Mark W. Drewes, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5424275Abstract: 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: GrantFiled: October 14, 1993Date of Patent: June 13, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsunori Hiratsuka, Toru Uekawa, Naonori Hirata, Kazuo Saito, Hiroyuki Yogai
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Patent number: 5414096Type: GrantFiled: February 22, 1994Date of Patent: May 9, 1995Assignee: Bristol-Myers Squibb Co.Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
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Patent number: 5414000Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is a substituted purinyl group including pharmaceutically acceptable salts are useful as antiviral agents.Type: GrantFiled: February 22, 1994Date of Patent: May 9, 1995Assignee: Bristol-Myers Squibb Co.Inventors: Joseph A. Tino, Gregory S. Bisacchi, Saleem Ahmad
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Patent number: 5411964Abstract: 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: GrantFiled: March 15, 1993Date of Patent: May 2, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Koichi Niimura, Takako Kawabe, Takao Ando, Kenichi Saito
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Patent number: 5401711Abstract: 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: GrantFiled: February 1, 1993Date of Patent: March 28, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Sato, Koichiro Kaku, Shigehiko Tachikawa
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Patent number: 5380701Abstract: 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: GrantFiled: October 12, 1993Date of Patent: January 10, 1995Assignee: Ciba-Geigy CorporationInventors: Paul Winternitz, Martin Zeller
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Patent number: 5378711Abstract: .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: GrantFiled: December 28, 1992Date of Patent: January 3, 1995Assignee: BASF AktiengesellschaftInventors: Franz Schuetz, Thomas Kuekenhoehner, Jochen Wild, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5371062Abstract: 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: GrantFiled: April 1, 1993Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Roland Andreee, Mark W. Drewes, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5356863Abstract: 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: GrantFiled: October 21, 1993Date of Patent: October 18, 1994Assignee: 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
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Patent number: 5352787Abstract: 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: GrantFiled: July 2, 1993Date of Patent: October 4, 1994Assignee: Bayer AktiengesellschaftInventors: Peter Andres, Albrecht Marhold
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Patent number: 5346880Abstract: 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: GrantFiled: April 6, 1993Date of Patent: September 13, 1994Assignee: Nihon Bayer Agrochem K.K.Inventors: Toshio Goto, Yoshinori Kitagawa, Hidenori Hayakawa, Katsuhiko Shibuya, Ryo Watanabe
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Patent number: 5340816Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts.Type: GrantFiled: January 15, 1993Date of Patent: August 23, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, William A. Slusarchyk
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Patent number: 5336663Abstract: 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: GrantFiled: November 4, 1992Date of Patent: August 9, 1994Assignee: Ciba-Geigy CorporationInventors: Jean Wenger, Paul Winternitz, Martin Zeller
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Patent number: 5332814Abstract: 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: GrantFiled: October 30, 1992Date of Patent: July 26, 1994Assignee: Ciba-Geigy CorporationInventor: Heinz Moser
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Patent number: 5330989Abstract: 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: GrantFiled: September 11, 1992Date of Patent: July 19, 1994Assignee: American Home Products CorporationInventors: Richard M. Soll, William A. Kinney
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Patent number: 5324854Abstract: 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: GrantFiled: December 7, 1992Date of Patent: June 28, 1994Assignee: Uniroyal Chemical Company, Inc.Inventors: Richard J. Strunk, Allyn R. Bell