At 4- Or 6-position Patents (Class 544/326)
  • Patent number: 4916142
    Abstract: This invention pertains to novel substituted N-heterocyclic-N-(4-piperidinyl)amides useful as analgesics and antagonists of opiolds, wherein the compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein:R is a substituted or unsubstituted unsaturated heterocyclic ring system having 5 to 6 cyclic member atoms containing at least one nitrogen atom, and is preferably selected from the group consisting of pyridinyl, pyrimidinyl, and pyrazinyl;R.sub.1 is selected from the group consisting of unsubstituted or substituted heterocyclic ring systems having 5 cyclic member atoms, lower cyclic alkyl ring systems, lower-alkyl and lower-alkoxy lower-alkyl, and is preferably selected from the group consisting of furanyl lower-alkyl, thienyl lower-alkyl, pyrrolyl lower-alkyl, lower-alkyl, lower-cycloalkyl, and lower-alkoxy lower-alkyl of 2 to 6 carbons;R.sub.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: April 10, 1990
    Assignee: BOC, Inc.
    Inventors: Jerome R. Bagley, H. Kenneth Spencer
  • Patent number: 4908368
    Abstract: Novel heterocyclic compounds shown by the general formula ##STR1## or the pharmaceutically acceptable salts thereof useful as medicament in particular as antagonist of slow reacting substance of anaphylaxis(SRS-A).
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: March 13, 1990
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 4895849
    Abstract: There are disclosed a compound represented by the formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group; R.sub.2 and R.sub.3 each independently represent a halogen atom or a lower alkyl group; R.sub.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: January 23, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Hirosuke Yoshioka, Tokio Obata, Katsutoshi Fujii, Kiyoshi Tsutsumiuchi, Haruo Yoshiya
  • Patent number: 4892946
    Abstract: N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulf onamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenze nesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: January 9, 1990
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: George Levitt
  • Patent number: 4892948
    Abstract: Disclosed are a 2-methyl-4-amino-5-aminomethylpyrimidine carbonate which is a novel compound, a process for preparing the same which comprises subjecting 2-methyl-4-amino-5-aminomethylpyrimidine to reaction with carbon dioxide in a lower aliphatic alcohol, and a simple method of purification of 2-methyl-4-amino-5-aminomethylpyrimidine by using the carbonate thereof.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: January 9, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Keigo Nishihira, Masayoshi Yamashita, Hiroshi Yoshida
  • Patent number: 4874864
    Abstract: Compounds of the formula ##STR1## where HET is a heterocyclic group, n is an integer of 0 to 2 and R.sup.1 is hydrogen or lower alkyl are protease inhibitors use as anti-plasmin and anti-thrombin agents.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: October 17, 1989
    Assignee: Pfizer Inc.
    Inventors: Rodney C. Schnur, Anton F. J. Fliri
  • Patent number: 4868183
    Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2 (.sub.4)-- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heteroaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine-N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl, halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: September 19, 1989
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4845097
    Abstract: Compounds of formula (I): ##STR1## (where R.sup.1 -R.sup.5 are various conventional atoms or groups, m is 2 or 3 and R.sup.6 l is an optionally substituted alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl or heterocyclic-substituted alkyl group or --CH.sub.2 --CH.dbd.NOR.sup.7 where R.sup.7 is hydrogen, alkyl, alkenyl or aralkyl) have insecticidal and acaricidal activities.
    Type: Grant
    Filed: March 14, 1986
    Date of Patent: July 4, 1989
    Assignees: Sankyo Company Limited, UBE Industries Limited
    Inventors: Keigo Matsumoto, Shinji Yokoi, Katsutoshi Fujii
  • Patent number: 4845220
    Abstract: The invention relates to vattable 2-aryl-4,6-diaminopyrimidines of formula ##STR1## wherein A.sub.1 and A.sub.2 are identical or different vattable radicals, andAr is an aryl radical.These pyrimidines are particularly suitable vat dyes for dyeing or printing textile fibres made from natural or regenerated cellulose. They give light- and wetfast orange, red or violet dyeings.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 4, 1989
    Inventor: Hans Altermatt
  • Patent number: 4831139
    Abstract: Process for the preparation of 2-substituted 5-nitroso-4,6-diaminopyrimidines. Malonic dinitrile and amidine are nitrosated in the presence of a nitrite salt, to form the corresponding amidine salt of isonitrosomalononitrile. The latter is converted to the end product in the presence of an aprotic polar solvent by heat treatment in a basic medium.
    Type: Grant
    Filed: September 13, 1988
    Date of Patent: May 16, 1989
    Assignee: Lonza Ltd.
    Inventor: Colm O'Murchu
  • Patent number: 4814338
    Abstract: Disclosed are pyrimidine derivatives represented by general formula ##STR1## wherein Z.sup.1 represents an alkynyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, or an alkynyloxy group which may be substituted with a halogen atom, and Z.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a group of the formula ##STR2## where Z.sup.3 represents a hydrogen atom or a methyl group; or its salt; and processes for preparing same. Also, agricultural or horticultural compositions containing the pyrimidine derivatives as active ingredient are disclosed, which show high controlling activities for cucumber gray mold (Botrytis cinerea), cucumber downey mildew (Pseudoperonospora cubensis), Alternaria sooty spot of Chinese mustard (Alternaria brassicicola), rice blast (Pyricularia oryzae), etc.
    Type: Grant
    Filed: October 29, 1986
    Date of Patent: March 21, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kusano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shin-ichiro Maeno
  • Patent number: 4808621
    Abstract: Certain trans-6-[2-(N-heteroaryl-3,5-disubstituted)pyrazol-4-yl)ethyl]- or ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom which are potent inhibitors of the enzyme 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMG CoA reductase) and are thus useful hypolipidemic or hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of inhibiting the biosynthesis of cholesterol employing such pharmaceutical compositions are also disclosed.
    Type: Grant
    Filed: May 18, 1987
    Date of Patent: February 28, 1989
    Assignee: Warner-Lambert Company
    Inventors: Bruce D. Roth, Drago R. Sliskovic
  • Patent number: 4808588
    Abstract: Compounds of formula (I), or a pharmaceutically acceptable salt thereof: ##STR1## wherein: Het is monocyclic heteroaryl having two adjacent carbon atoms, a and b, depicted in formula (I); p1 R.sub.1 and R.sub.2 are independently selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl and C.sub.1-6 Alkoxy;R.sub.3 is hydroxy, C.sub.1-6 alkoxy, C.sub.3-7 alkenyl-methoxy, phenoxy or phenyl C.sub.1-4 alkoxy in which either phenyl moiety may be substituted by one or two C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halo; CO.sub.2 R.sub.6 wherein R.sub.6 is hydrogen or C.sub.1-6 alkyl, CONR.sub.7 R.sub.8 or SO.sub.2 NR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are independently hydrogen or C.sub.1-6 alkyl or together are C.sub.4-6 polymethylene, NO.sub.2, (CH.sub.2).sub.m OR.sub.9 wherein m is 1 or 2 and R.sub.9 is C.sub.1-6 alkyl or S(O).sub.n R.sub.10 wherein n is 0, 1 or 2 and R.sub.10 is C.sub.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: February 28, 1989
    Assignee: Beecham Group, p.l.c.
    Inventor: Francis D. King
  • Patent number: 4798893
    Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: January 17, 1989
    Assignee: McNeilab, Inc.
    Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
  • Patent number: 4794182
    Abstract: A novel 2-lower alkyl-4-amino-5-substituted iminopyrimidine compound represented by the formula: ##STR1## wherein R is a lower alkyl, and Y is hydroxyl or amino which may be protected or a salt thereof is obtainable by allowing a formylpyrimidine compound represented by the formula: ##STR2## wherein R is a lower alkyl to react with a compound represented by the formula H.sub.2 N--Y, wherein Y is hydroxyl or amino which may be protected, or a salts thereof. The iminopyrimidine compound gives the known pyrimidine compound represented by the formula: ##STR3## wherein R is as defined above in high yield. Therefor, the process is very useful as an industrial production method.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: December 27, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kunio Takanohashi, Toru Yamano, Mitsutaka Tanaka
  • Patent number: 4748165
    Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 31, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4725600
    Abstract: The invention relates to pyrimidine compounds of the formula: ##STR1## wherein the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as herein defined, having activity as a cardiotonic, anti-hypertensive, cerebrovascular vasodilator and anti-platelet aggregation agent.
    Type: Grant
    Filed: July 5, 1985
    Date of Patent: February 16, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Masayoshi Murata, Kiyotaka Ito
  • Patent number: 4723006
    Abstract: New compounds useful as intermediates for biologically-active compounds have the formula I ##STR1## wherein Y is a group having the formula --CH.sub.2 X in which X is F, Cl, or Br, or Y is a group having the formula ##STR2## in which R.sup.2 is F, Cl or Br and R.sup.3 is H, F, Cl, Br or a group having the formula --CR.sup.4 R.sup.5 R.sup.6, in which R.sup.4, R.sup.5 and R.sup.6, independently, are F, Cl or Br; A is H, OH, SH, F, Cl, Br or a group --OR.sup.7 or --SR.sup.7 in which R.sup.7 is C.sub.1 -C.sub.4 straight- or branched chain alkyl, C.sub.2-4 straight- or branched chain alkyl substituted with 1 to 3 F, Cl or Br atoms, or A is a group --NR.sup.8 R.sup.9 in which R.sup.8 and R.sup.9, independently, are H, C.sub.1 -C.sub.4 straight- or branched chain alkyl or C.sub.3 -C.sub.4 alkenyl, or R.sup.8 and R.sup.9 together may form a C.sub.3 -C.sub.7 polymethylene chain, which is optionally interrupted by an oxygen atom; as well as salts of compounds of formula I with acids; provided that: when Y is CH.sub.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: February 2, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert L. Bentley, Brian Tuck
  • Patent number: 4708732
    Abstract: Herbicidal compounds having the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.
    Type: Grant
    Filed: October 24, 1986
    Date of Patent: November 24, 1987
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Carter
  • Patent number: 4683228
    Abstract: A guanidine derivative of the formula I: ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, ring X and D are a variety of radicals defined in the specification and A is a 3-8C alkylene chain which is substituted by a hydroxy radical and into which is optionally inserted, as part of the backbone of the chain, one or two groups selected from oxygen and sulphur atoms and NH and 1-6C N-alkyl radicals; and the pharmaceutically-acceptable acid additions salts thereof. Pharmaceutical compositions and methods of manufacture are also described. The compound of the formula I is a histamine H-2 antagonist and is therefore useful in ulcer therapy.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: July 28, 1987
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Karin M. Kirkland, Derrick M. Mant
  • Patent number: 4678499
    Abstract: Benzenesulfonamide compounds such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4 -oxo-1-phenyl-indeno[1,2-C]-pyrazole-5-sulfonamide and N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl- 4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide, agricultural compositions containing them, and their herbicidal utility are disclosed.
    Type: Grant
    Filed: January 30, 1986
    Date of Patent: July 7, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
  • Patent number: 4657579
    Abstract: The invention provides novel pyrimidine compounds substituted in the 5-position by a chloroacetylamino group which are useful as herbicides. Other objects of the invention are herbicidal compositions comprising such novel compounds and methods of combatting weeds with the aid of said novel compounds.
    Type: Grant
    Filed: March 6, 1985
    Date of Patent: April 14, 1987
    Assignee: Sandoz Ltd.
    Inventors: Karlheinz Milzner, Fred Kuhnen, Karl Seckinger
  • Patent number: 4627872
    Abstract: New herbicidally active 2,4-diamino pyrimidines of the formula ##STR1## wherein R.sup.1 is hydrogen or halogen, R.sup.2 is an optionally halogen-substituted alkyl or is halogen or alkoxy; R.sup.3 is hydrogen or alkyl; Y is oxygen or sulfur; and Z is a branched or unbranched alkylene.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: December 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schwamborn, Engelbert Kuhle, Ludwig Eue, Robert R. Schmidt, Hans-Joachim Santel
  • Patent number: 4610824
    Abstract: Antibacterial activity is exhibited by novel compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: September 9, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Uwe D. Truner
  • Patent number: 4604465
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: August 5, 1986
    Assignees: ICI Americas, Inc., Imperial Chemical Industries, Limited
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4596869
    Abstract: A novel compound, useful as an intermediate in the production of compounds of high antimicrobial activity, of the formula: ##STR1## wherein R.sub.a.sup.1 is hydrogen, amino or a protected amino group,R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or arylthio,R.sup.14 is carboxy or a protected carboxy group,X is lower alkylene or a group of the formula: ##STR2## in which R.sup.6 is hydrogen or an organic residue which may have suitable substituent(s), andZ is N or CH,or a salt thereof.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: June 24, 1986
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takashi Kamiya, Tsutomu Teraji, Yoshiharu Nakai, Kazuo Sakane, Jiro Goto
  • Patent number: 4595539
    Abstract: Certain 2-substituted-2-penem-3-carboxylic acid compounds and pharmaceutically-acceptable salts thereof can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization and addition of an electrophilic sulfur compound followed by halogenation and ring closure. The corresponding desulfurized and halogenated olefinic intermediates are disclosed.
    Type: Grant
    Filed: June 10, 1983
    Date of Patent: June 17, 1986
    Assignee: Pfizer Inc.
    Inventor: Ernest S. Hamanaka
  • Patent number: 4592978
    Abstract: N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]-2-methoxycarbonylbenzenesul fonamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenze nesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: December 22, 1982
    Date of Patent: June 3, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4587047
    Abstract: Antibacterial activity is exhibited by .beta.-lactams having a ##STR1## substituent in the 1-position and an acylamino substituent in the 3-position wherein Z is oxygen or sulfur, and R is alkyl, alkenyl, alkynyl, substituted alkyl, phenyl, substituted phenyl, a 5,6 or 7-membered heterocycle (R.sub.c), phenylalkyl, (substituted phenyl)alkyl, R.sub.c -alkyl or --NR.sub.a R.sub.b wherein R.sub.a and R.sub.b are the same or different and each is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, phenylalkyl, or (substituted phenyl)alkyl or one of R.sub.a and R.sub.b is hydrogen, alkyl, phenyl, substituted phenyl, phenylalkyl or (substituted phenyl)alkyl and the other is amino, alkanoylamino, arylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkylamino, dialkylamino, phenylamino, (substituted phenyl)amino, hydroxy, cyano, alkoxy, phenyloxy, (substituted phenyl)oxy, phenylalkoxy, (substituted phenyl)alkoxy, R.sub.c, R.sub.c -alkyl, R.sub.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: May 6, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Hermann Breuer, William A. Slusarchyk, Theodor Denzel, Uwe D. Treuner
  • Patent number: 4587051
    Abstract: A compound having the formula ##STR1## can be prepared by heating an anion having the formula ##STR2## with a cation having the formula ##STR3## or a cation having the formula ##STR4##
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: May 6, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: William H. Koster
  • Patent number: 4584295
    Abstract: Heterocyclic compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X are as defined hereinafter, process for their preparation, as well as pesticidal compositions containing these compounds as the active ingredient and methods for using the pesticidal compositions for the control of pests are described.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 22, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Christoph Luthy
  • Patent number: 4576749
    Abstract: Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituent and a 1-substituent of the formula ##STR1## (or a salt or ester thereof).
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: March 18, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, William H. Koster, William A. Slusarchyk
  • Patent number: 4565864
    Abstract: Imidazo[1,2,-c]pyrimidines which are bronchodilators. Pharmacological methods of using these compounds, pharmaceutical compositions containing these compounds, and synthetic intermediates for preparing these compounds are also described.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: January 21, 1986
    Assignee: Riker Laboratories, Inc.
    Inventor: James J. Wade
  • Patent number: 4547511
    Abstract: This invention relates to novel heterocyclic carboxamides which increase the activity of the immune system and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds and methods of treatment therewith.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: October 15, 1985
    Assignee: Aktiebolaget Leo
    Inventors: Edgar Eriksoo, Eva B. Sandberg, Lars J. T. Stalhandske
  • Patent number: 4544401
    Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: October 1, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4539403
    Abstract: There is disclosed a process for the preparation of a 2-alkyl-4-amino-5-aminomethylpyrimidine, which comprises subjecting a 2-alkyl-4-amino-5-formylpyrimidine to catalytic reaction with hydrogen and ammonia in the presence of a reduction catalyst.According to the process of this invention, the desired product can be obtained in much higher yield as compared with the processes known to the art.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: September 3, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue, Kiyosi Oomori
  • Patent number: 4536579
    Abstract: 1,2,4-Triazolo[4,3-c]pyrimidines substituted at the 5 or 7 position through a nitrogen atom which is part of a heterocyclic ring have been found to have potent bronchodilator activity and to be useful synthetic intermediates in the preparation of 1,2,4-triazolo[1,5-c]pyrimidines. Methods for inducing bronchodilation, pharmaceutical compositions, and synthetic processes and intermediates are also described.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: August 20, 1985
    Assignee: Riker Laboratories, Inc.
    Inventor: James J. Wade
  • Patent number: 4536577
    Abstract: Disclosed is a process for preparing 2-alkyl-4-amino-5-aminomethylpyrimidine comprising (i) a first step of reacting 2-alkyl-4-amino-5-formylpyrimidine with ammonia in an inert solvent in the presence of at least one compound selected from heteropolyacids, isopolyacids, oxyacids and salts thereof containing molybdenum or tungsten, and (ii) a second step of reacting the reaction product in the first step catalytically with ammonia and hydrogen in an inert solvent in the presence of a reducing catalyst together with or without a hydroxide of an alkali metal or alkaline earth metal.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: August 20, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Yoshida, Sadao Niida
  • Patent number: 4535080
    Abstract: Compounds are disclosed as useful as drugs or as intermediates for the manufacture of drugs, the compounds having the formula: ##STR1## in which X is hydrogen, chlorine, alkyl, alkoxy or alkylthio having 1 to 3 carbon atoms, R.sub.2 is hydrogen or alkyl having 1 to 3 carbon atoms, Y.sub.2 is chlorine and Y.sub.1 is chlorine or ##STR2## in which R.sub.1 is hydrogen, straight or branched chain alkyl having 1 to 7 carbon atoms, cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 4 to 8 carbon atoms, or Y.sub.2 and Y.sub.1 are both OH. Also disclosed are methods for preparation of the compounds.
    Type: Grant
    Filed: August 24, 1983
    Date of Patent: August 13, 1985
    Assignee: Pharmuka Laboratoires
    Inventors: Francois Audiau, Claude G. A. Gueremy, Gerard R. Le Fur
  • Patent number: 4505910
    Abstract: Herein is disclosed amino-pyrimidine derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for increasing cardiac contractility in a mammal.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: March 19, 1985
    Assignee: American Home Products Corporation
    Inventor: Jehan F. Bagli
  • Patent number: 4503050
    Abstract: Imidazo[1,2-c]pyrimidines which are bronchodilators. Pharmacological methods of using these compounds, pharmaceutical compositions containing these compounds, and synthetic intermediates for preparing these compounds are also described.
    Type: Grant
    Filed: June 2, 1983
    Date of Patent: March 5, 1985
    Assignee: Riker Laboratories, Inc.
    Inventor: James J. Wade
  • Patent number: 4492792
    Abstract: A process for preparing a 4-amino-5-dialkoxymethylpyrimidine derivative of the formula: ##STR1## which comprises reacting a propanenitrile derivative represented by the formula (I) or the novel compound represented by formula (II): ##STR2## with an amidine of the formula: ##STR3## wherein R.sup.1 to R.sup.6 are as defined in the specification. Also disclosed is a process for making the novel compounds of formula (II).
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: January 8, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue
  • Patent number: 4482558
    Abstract: Compounds of the general formula ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R is naphthyl, biphenylyl, phenyl or substituted phenyl; and R.sup.1 is ##STR2## where X is O or S, R.sup.2 is H, or C.sub.1 -C.sub.4 alkyl and R.sup.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, optionally mono- or disubstituted phenyl, benzyl or Het and Het is pyridyl, pyrimidinyl or pyrazinyl; said substituents being halo, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxy, or R.sup.2 and R.sup.3 taken together complete a 1-pyrrolidinyl or piperidino ring; methods for their use in combatting fungal infections in plants and animals, including humans; pharmaceutical and agricultural compositions containing them and intermediates useful in their preparation.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: November 13, 1984
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4464374
    Abstract: The invention relates to a guanidine derivative of the formula: ##STR1## in which W is a 2-6C alkylene chain optionally substituted by 1 or 2 1-4C alkyls; E is O, S, SO, SO.sub.2 or NR.sup.3 in which R.sup.3 is H or 1-6C alkyl; R.sup.1 is H or a straight chain 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls; or R.sup.1 and R.sup.3 are joined to form a morpholine, pyrrolidine, piperidine or piperazine ring; X, P, Y, Q and R.sup.2 are as defined in the specification, and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing process, pharmaceutical compositions and intermediates are also described. The compounds of the formula I are histamine H-2 antagonists.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: August 7, 1984
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman, Derrick F. Jones, Keith Oldham
  • Patent number: 4450162
    Abstract: New 4-anilinopyrimidine derivatives of formula (I): ##STR1## (wherein: R.sup.1 and R.sup.2 are the same or different and each represents a C.sub.1 -C.sub.6 alkyl group or R.sup.1 and R.sup.2 together represent a C.sub.3 -C.sub.5 alkylene group;R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group;n is 0, 1 or 2; andR.sup.4 represents a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group, a halogen atom, a nitro group, a C.sub.1 -C.sub.6 alkanesulphonyl group, a cyano group, a carboxy group or a C.sub.2 -C.sub.7 alkoxycarbonyl group and, when n is 2, the two groups represented by R.sup.4 may be the same or different or they may together represent a methylenedioxy group)and pharmaceutically acceptable acid addition salts thereof have been found to have strong antidepressant activity, with low toxicity and very few side-effects.
    Type: Grant
    Filed: June 2, 1982
    Date of Patent: May 22, 1984
    Assignees: Sankyo Company, Limited, Ube Industries Limited
    Inventors: Toshiharu Kamioka, Isao Nakayama, Takeo Honda, Takashi Kobayashi, Tokio Obata, Katsutoshi Fujii, Mikio Kojima, Yuji Akiyoshi
  • Patent number: 4435402
    Abstract: Compounds having the formula (I) ##STR1## [wherein: R.sup.1 and R.sup.2 are each alkyl or halogen, or they are trimethylene or tetramethylene; R.sup.3 is hydrogen or alkyl; A is alkylene; and R.sup.4 is optionally substituted phenyloxy or benzyloxy substituted with at least one alkyl, halogen, alkoxy, alkylthio, alkenyl, trifluoromethyl or nitro; optionally substituted phenyl substituted with one or two halogen atoms, alkyl or alkoxy; furyl or thienyl] and their salts.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: March 6, 1984
    Assignees: Sankyo Company, Limited, Ube Industries, Limited
    Inventors: Hideakira Tsuji, Shinjiro Yamamoto, Kazuto Nakagami, Takeo Honda, Katsutoshi Fujii, Takashi Kobayashi, Tokio Obata, Mikio Kojima, Yuji Akiyoshi
  • Patent number: 4435206
    Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: March 6, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4434167
    Abstract: Pyrimidyl thioureas of the formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 individually represent hydrogen, halogen, a linear or branched alkoxy group, or a linear or branched alkyl group, said groups having 1 to 8 carbon atoms, and their pharmaceutically acceptable salts. These compounds are useful for the treatment of hyperlipidemia and hypertension.Compositions containing these compounds as well as methods of use and preparation thereof are also disclosed.
    Type: Grant
    Filed: April 24, 1981
    Date of Patent: February 28, 1984
    Assignee: Beiersdorf Aktiengesellschaft
    Inventor: Wolfgang Stenzel
  • Patent number: 4423219
    Abstract: Improved processes for producing purine derivatives, such as 9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine, which are useful as anticoccidial agents, and new arylazopyrimidine compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen, C.sub.1-3 alkyl, allyl or dihalobenzyl, and when either one of R.sup.1 and R.sup.2 is hydrogen, the other is other than hydrogen, and R.sup.3 is aryl, and acid addition salts thereof, which are useful as intermediates for production of the purine derivatives.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: December 27, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kin-ichi Imai, Mitsuhiko Mano