At 4- Or 6-position Patents (Class 544/326)
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Patent number: 4916142Abstract: 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: GrantFiled: June 6, 1989Date of Patent: April 10, 1990Assignee: BOC, Inc.Inventors: Jerome R. Bagley, H. Kenneth Spencer
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Patent number: 4908368Abstract: 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: GrantFiled: June 7, 1989Date of Patent: March 13, 1990Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
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Patent number: 4895849Abstract: 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: GrantFiled: October 5, 1987Date of Patent: January 23, 1990Assignee: Ube Industries, Ltd.Inventors: Hirosuke Yoshioka, Tokio Obata, Katsutoshi Fujii, Kiyoshi Tsutsumiuchi, Haruo Yoshiya
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Patent number: 4892946Abstract: 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: GrantFiled: November 24, 1980Date of Patent: January 9, 1990Assignee: E. I. Du Pont De Nemours and CompanyInventor: George Levitt
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Patent number: 4892948Abstract: 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: GrantFiled: April 26, 1988Date of Patent: January 9, 1990Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Masayoshi Yamashita, Hiroshi Yoshida
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Patent number: 4874864Abstract: 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: GrantFiled: May 24, 1988Date of Patent: October 17, 1989Assignee: Pfizer Inc.Inventors: Rodney C. Schnur, Anton F. J. Fliri
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Patent number: 4868183Abstract: 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: GrantFiled: July 20, 1987Date of Patent: September 19, 1989Assignee: Otsuka Pharmaceutical Factory, Inc.Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
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Patent number: 4863945Abstract: 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: GrantFiled: December 10, 1987Date of Patent: September 5, 1989Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
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Phenoxyalkylaminopyrimidine derivatives and insecticidal and acaricidal compositions containing them
Patent number: 4845097Abstract: 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: GrantFiled: March 14, 1986Date of Patent: July 4, 1989Assignees: Sankyo Company Limited, UBE Industries LimitedInventors: Keigo Matsumoto, Shinji Yokoi, Katsutoshi Fujii -
Patent number: 4845220Abstract: 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: GrantFiled: December 30, 1987Date of Patent: July 4, 1989Inventor: Hans Altermatt
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Patent number: 4831139Abstract: 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: GrantFiled: September 13, 1988Date of Patent: May 16, 1989Assignee: Lonza Ltd.Inventor: Colm O'Murchu
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Patent number: 4814338Abstract: 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: GrantFiled: October 29, 1986Date of Patent: March 21, 1989Assignees: 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
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Patent number: 4808621Abstract: 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: GrantFiled: May 18, 1987Date of Patent: February 28, 1989Assignee: Warner-Lambert CompanyInventors: Bruce D. Roth, Drago R. Sliskovic
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Patent number: 4808588Abstract: 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: GrantFiled: July 30, 1987Date of Patent: February 28, 1989Assignee: Beecham Group, p.l.c.Inventor: Francis D. King
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Patent number: 4798893Abstract: 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: GrantFiled: September 21, 1987Date of Patent: January 17, 1989Assignee: McNeilab, Inc.Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
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Patent number: 4794182Abstract: 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: GrantFiled: July 14, 1987Date of Patent: December 27, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Kunio Takanohashi, Toru Yamano, Mitsutaka Tanaka
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Patent number: 4748165Abstract: 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: GrantFiled: May 11, 1982Date of Patent: May 31, 1988Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4725600Abstract: 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: GrantFiled: July 5, 1985Date of Patent: February 16, 1988Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Masayoshi Murata, Kiyotaka Ito
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Patent number: 4723006Abstract: 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: GrantFiled: January 21, 1986Date of Patent: February 2, 1988Assignee: Ciba-Geigy CorporationInventors: Robert L. Bentley, Brian Tuck
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Patent number: 4708732Abstract: 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: GrantFiled: October 24, 1986Date of Patent: November 24, 1987Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4683228Abstract: 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: GrantFiled: January 22, 1985Date of Patent: July 28, 1987Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Karin M. Kirkland, Derrick M. Mant
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Patent number: 4678499Abstract: 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: GrantFiled: January 30, 1986Date of Patent: July 7, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
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Patent number: 4657579Abstract: 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: GrantFiled: March 6, 1985Date of Patent: April 14, 1987Assignee: Sandoz Ltd.Inventors: Karlheinz Milzner, Fred Kuhnen, Karl Seckinger
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Patent number: 4627872Abstract: 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: GrantFiled: December 5, 1985Date of Patent: December 9, 1986Assignee: Bayer AktiengesellschaftInventors: Michael Schwamborn, Engelbert Kuhle, Ludwig Eue, Robert R. Schmidt, Hans-Joachim Santel
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Patent number: 4610824Abstract: Antibacterial activity is exhibited by novel compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: October 9, 1984Date of Patent: September 9, 1986Assignee: E. R. Squibb & Sons, Inc.Inventor: Uwe D. Truner
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Patent number: 4604465Abstract: 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: GrantFiled: September 21, 1982Date of Patent: August 5, 1986Assignees: ICI Americas, Inc., Imperial Chemical Industries, LimitedInventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4596869Abstract: 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: GrantFiled: September 19, 1985Date of Patent: June 24, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Tsutomu Teraji, Yoshiharu Nakai, Kazuo Sakane, Jiro Goto
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Patent number: 4595539Abstract: 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: GrantFiled: June 10, 1983Date of Patent: June 17, 1986Assignee: Pfizer Inc.Inventor: Ernest S. Hamanaka
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Patent number: 4592978Abstract: 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: GrantFiled: December 22, 1982Date of Patent: June 3, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4587047Abstract: 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: GrantFiled: April 1, 1982Date of Patent: May 6, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Hermann Breuer, William A. Slusarchyk, Theodor Denzel, Uwe D. Treuner
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Patent number: 4587051Abstract: 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: GrantFiled: May 21, 1984Date of Patent: May 6, 1986Assignee: E. R. Squibb & Sons, Inc.Inventor: William H. Koster
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Patent number: 4584295Abstract: 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: GrantFiled: December 27, 1983Date of Patent: April 22, 1986Assignee: Hoffmann-La Roche Inc.Inventor: Christoph Luthy
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Patent number: 4576749Abstract: 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: GrantFiled: April 13, 1984Date of Patent: March 18, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, William H. Koster, William A. Slusarchyk
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Patent number: 4565864Abstract: 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: GrantFiled: December 17, 1984Date of Patent: January 21, 1986Assignee: Riker Laboratories, Inc.Inventor: James J. Wade
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Patent number: 4547511Abstract: 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: GrantFiled: February 22, 1982Date of Patent: October 15, 1985Assignee: Aktiebolaget LeoInventors: Edgar Eriksoo, Eva B. Sandberg, Lars J. T. Stalhandske
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Patent number: 4544401Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.Type: GrantFiled: January 22, 1981Date of Patent: October 1, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4539403Abstract: 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: GrantFiled: January 26, 1983Date of Patent: September 3, 1985Assignee: UBE Industries, Ltd.Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue, Kiyosi Oomori
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Patent number: 4536579Abstract: 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: GrantFiled: February 24, 1984Date of Patent: August 20, 1985Assignee: Riker Laboratories, Inc.Inventor: James J. Wade
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Patent number: 4536577Abstract: 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: GrantFiled: March 26, 1984Date of Patent: August 20, 1985Assignee: Ube Industries, Ltd.Inventors: Hiroshi Yoshida, Sadao Niida
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Patent number: 4535080Abstract: 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: GrantFiled: August 24, 1983Date of Patent: August 13, 1985Assignee: Pharmuka LaboratoiresInventors: Francois Audiau, Claude G. A. Gueremy, Gerard R. Le Fur
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Patent number: 4505910Abstract: 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: GrantFiled: June 30, 1983Date of Patent: March 19, 1985Assignee: American Home Products CorporationInventor: Jehan F. Bagli
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Patent number: 4503050Abstract: 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: GrantFiled: June 2, 1983Date of Patent: March 5, 1985Assignee: Riker Laboratories, Inc.Inventor: James J. Wade
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Patent number: 4492792Abstract: 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: GrantFiled: January 26, 1983Date of Patent: January 8, 1985Assignee: Ube Industries, Ltd.Inventors: Kozo Fujii, Keigo Nishihira, Hiroyuki Sawada, Shuji Tanaka, Mamoru Nakai, Hiroshi Yoshida, Teruhiko Inoue
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Patent number: 4482558Abstract: 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: GrantFiled: June 3, 1983Date of Patent: November 13, 1984Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4464374Abstract: 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: GrantFiled: July 23, 1981Date of Patent: August 7, 1984Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman, Derrick F. Jones, Keith Oldham
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Patent number: 4450162Abstract: 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: GrantFiled: June 2, 1982Date of Patent: May 22, 1984Assignees: Sankyo Company, Limited, Ube Industries LimitedInventors: Toshiharu Kamioka, Isao Nakayama, Takeo Honda, Takashi Kobayashi, Tokio Obata, Katsutoshi Fujii, Mikio Kojima, Yuji Akiyoshi
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Patent number: 4435402Abstract: 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: GrantFiled: January 22, 1982Date of Patent: March 6, 1984Assignees: Sankyo Company, Limited, Ube Industries, LimitedInventors: Hideakira Tsuji, Shinjiro Yamamoto, Kazuto Nakagami, Takeo Honda, Katsutoshi Fujii, Takashi Kobayashi, Tokio Obata, Mikio Kojima, Yuji Akiyoshi
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Patent number: 4435206Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.Type: GrantFiled: January 22, 1981Date of Patent: March 6, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4434167Abstract: 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: GrantFiled: April 24, 1981Date of Patent: February 28, 1984Assignee: Beiersdorf AktiengesellschaftInventor: Wolfgang Stenzel
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Patent number: 4423219Abstract: 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: GrantFiled: November 4, 1981Date of Patent: December 27, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Kin-ichi Imai, Mitsuhiko Mano