Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/298)
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Patent number: 5118696Abstract: Novel 5-acyl-2-(1H)pyrdinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-pentanedione in an inert organic solvent.Type: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 5114465Abstract: 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 5-(haloalkyl) carboxamide or 5-(haloalkyl)carbamate substitution, useful as herbicides and herbicide intermediates.Type: GrantFiled: June 17, 1991Date of Patent: May 19, 1992Assignee: Monsanto CompanyInventors: Robert D. Bryant, Shridhar G. Hegde, Len F. Lee
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Patent number: 5112386Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur, A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 --S(O).sub.n R.sup.3 groups; any two of the groups, A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.Type: GrantFiled: December 30, 1988Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventors: Anthony Vivienne, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 5103009Abstract: A method for the preparation of o-carboxyl imidazolinone compounds including oxidizing the appropriate 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}benzoic acid intermediate with a brominating agent. Compounds useful as intermediates in the oxidation method and methods for preparing them are disclosed.Type: GrantFiled: June 14, 1991Date of Patent: April 7, 1992Assignee: American Cyanamid CompanyInventor: Robert F. Doehner, Jr.
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5089168Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: May 16, 1989Date of Patent: February 18, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 5084466Abstract: Novel carboxamides and sulfonamides are described having of the formulaR.sup.1 --A--(W).sub.a --X--(CH.sub.2).sub.b --(Y).sub.c --B--Z--COOR (I),in which R.sup.1, A, W, X, Y, B, Z, R, a, b and c are as provided in the description. These compounds are useful in the treatment of thromboses, apoplexy, myocardial infarct, inflammations, arteriosclerosis as well as in the treatment and prevention of tumors. These novel compounds are prepared by eliminating the protective groups in corresponding compounds with protected amidino or guanidino groups.Type: GrantFiled: January 16, 1990Date of Patent: January 28, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Albrecht Edenhofer, Marcel Muller, Arnold Trzeciak, Thomas Weller
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Patent number: 5084204Abstract: Naphthylacetylenes of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --C.tbd.C--A.sup.3 --(Z.sup.2 --A.sup.4).sub.n --R.sup.2 Iin which R.sup.1, A.sup.1, Z.sup.1, m, A.sup.2, A.sup.3, Z.sup.2, A.sup.4, n and R.sup.2 have the meanings described herein, are suitable as components of liquid crystal phases.Type: GrantFiled: November 10, 1988Date of Patent: January 28, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Georg Weber
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Patent number: 5082853Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.Type: GrantFiled: April 4, 1990Date of Patent: January 21, 1992Inventor: Nicholas S. Bodor
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Patent number: 5079366Abstract: The invention provides novel amino acids and peptides containing them which comprise a dihydropyridine.revreaction.pyridinium salt-type redox system and which provide site-specific and sustained delivery of pharmacologically active peptides to the brain. These new amino acids contain a redox system appended directly or via an alkylene bridge to the carbon atom adjacent to the carboxyl carbon and may be incorporated into a peptide chain at a variety of positions, including non-terminal positions.Type: GrantFiled: October 4, 1989Date of Patent: January 7, 1992Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5079361Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.Type: GrantFiled: September 9, 1988Date of Patent: January 7, 1992Assignee: Celltech LimitedInventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
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Patent number: 5071860Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.Type: GrantFiled: March 7, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
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Patent number: 5068337Abstract: The invention concerns compounds of formula ##STR1## or salts thereof; wherein Ar is an optionally substituted aryl radical;R represents hydrogen or an optionally substituted alkyl or aralkyl group;R.sup.1 and R.sup.2 are the same or different and are selected from hydrogen and saturated or unsaturated, cyclic or acyclic aliphatic hydrocarbon residues optionally substituted by one or more groups selected from halogen, OH, carboxy, CN, alkoxy, alkylthio, aryloxy, alkoxycarbonyl, amino, substituted amino, and optionally substituted aryl;A represents a group of formula --XR.sup.3 whereinX is (i) a group of formula --(CHR.sup.6).sub.p --Y--(CHR.sup.7).sub.q --or (ii) a group of formula --(CHR.sup.6).sub.r --O--(CHR.sup.7).sub.qin which formulae: Y represents --S--, NR.sup.8 or a direct bond, p and q each represent 0, 1 or 2 providing that p and q do not both represent 0, 1 or 2 and the other is zero; R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen or lower alkyl, and R.sup.Type: GrantFiled: November 13, 1986Date of Patent: November 26, 1991Assignee: John Wyeth & Brother LimitedInventors: John L. Archibald, Terence J. Ward, Albert Opalko
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Patent number: 5049571Abstract: There are disclosed novel 1-nitro-2,2-diaminoethylene derivatives of formula I ##STR1## wherein X is chlorine, fluorine, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkyl; unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkoxy, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkylthio, unsubstituted or halogen-substituted alkylsulfinyl, unsubstituted or halogen-substituted alkylsulfonyl; or also nitro, cyano, thiocyanato, C.sub.3 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 haloalkynyl, hydroxy, C.sub.1 -C.sub.5 alkoxycarbonyl, amino, C.sub.1 -C.sub.4 dialkylamino, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkylcarbamoyl or C.sub.1 -C.sub.5 alkylcarbonyloxy,n is an integer from 0 to 4,R.sub.1 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.7 cycloalkyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl,R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, benzyl or pyridinylmethyl, or R.sub.2 and R.sub.Type: GrantFiled: January 24, 1990Date of Patent: September 17, 1991Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 5047410Abstract: New pharmacologically active amidino and guanidino derivatives which are 5-HT.sub.3 receptor antagonists useful as antiemetic, gastric prokinetic and antimigrainic agents of the following general formula (I) ##STR1## , wherein the substituents are defined hereinbelow, which compounds are 5-HT.sub.3 receptor antagonists useful as antiemetic gastric prokinetic and antimigraine agents, inter alia.Type: GrantFiled: July 12, 1989Date of Patent: September 10, 1991Assignee: Istituto de Angeli S.p.A.Inventors: Arturo Donetti, Marco Turconi, Massimo Nicola, Rosamaria Micheletti
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Patent number: 5039807Abstract: A compound of formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are independently selected from hydrogen, halogen, lower alkyl optionally substituted by halogen, lower alkoxy optionally substituted by halogen and lower alkenyl optionally substituted by halogen;R.sup.3 is halogen, amino, mono- or di(lower alkyl)-amino, lower alkyl substituted by halogen, lower alkoxy optionally substituted by halogen and lower alkenyl optionally substituted by halogen provided that R.sup.3 is not monochloro or monobromo-methyl;R.sup.6 is oxygen or sulphur;R.sup.7 and R.sup.10 are independently selected from hydrogen, halogen, lower alkyl optionally substituted by halogen, lower alkoxy optionally substituted by halogen, and lower thioalkoxy optionally substituted by halogen; andR.sup.Type: GrantFiled: March 22, 1989Date of Patent: August 13, 1991Assignee: Imperial Chemical Industries PLCInventors: Trevor R. Perrior, David J. Tapolczay
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Patent number: 5019153Abstract: Disclosed are pyridine herbicides characterized by substitution with a fluorine-containing methyl group at the 2- or 6-position, a carboxylic acid-derived group at the 3-position, and a halogen or a substituted nitrogen-containing group at the 5-position.Type: GrantFiled: December 1, 1989Date of Patent: May 28, 1991Assignee: Monsanto CompanyInventors: Len F. Lee, Mark G. Dolson
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Patent number: 5008276Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 5008391Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.Type: GrantFiled: July 7, 1989Date of Patent: April 16, 1991Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5002694Abstract: Nitrogen-containing heterocyclic compounds of the formula II ##STR1## wherein R.sup.1 and R.sup.2 in each case denote an alkyl group having 1 to 15 C atoms, wherein one or more CH.sub.2 groups may also be replaced by a grouping selected from the group comprising --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --CH.dbd.CH--, --CH--halogen and --CHCN--, or else by a combination of two suitable groupings, two heteroatoms not being directly linked to each other,m denotes 0 or 1,Ar denotes 1,4-phenylene, 4,4'-biphenylyl or 2,6-naphthylene, wherein one or more CH groups are in each case replaced by N,Z denotes --C--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CHCN--, --CHCNCH.sub.2 --, --CH.dbd.CH or a single bond, andA denotes unsubstituted 1,4-cyclonexylene or 11,4-cyclohexylene substituted in position 1 or position 4 by CN,with the proviso that if A=unsubstituted 1,4-cyclonexylene, Z denotes --CHCNCH.sub.2 -- or --CH.sub.2 CHCN-- and/or at least one CH.sub.Type: GrantFiled: May 13, 1987Date of Patent: March 26, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble
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Patent number: 5001137Abstract: A novel pyridine compound of the formula ##STR1## wherein each symbol is as defined in the specification, or a salt thereof which exhibit inhibitory activity or prolylendopeptidase and a pharmaceutical use thereof are disclosed.Type: GrantFiled: September 14, 1989Date of Patent: March 19, 1991Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Takanori Oe, Yuji Ono, Kazuyuki Kawasaki, Tohru Nakajima
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Patent number: 4996218Abstract: Compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof, which have .beta..sub.2 -adrenoreceptor stimulant activity. They may be used in the treatment of diseases associated with reversible airways obstruction, such as asthma and chronic bronchitis.In preferred embodiments, Q represents a chlorine atom or a trifluoromethyl group, X represents a C.sub.3-4 alkylene chain, Y a C.sub.1-5 alkylene chain, R, R.sup.1 and R.sup.2 are each preferably a hydrogen atom or a methyl group and Het represents a pyrimidinyl pyrazinyl, triazinyl, thiazolyl, quinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl or pyridyl group.Type: GrantFiled: August 10, 1988Date of Patent: February 26, 1991Assignee: Glaxo Group LimitedInventor: Lawrence H. C. Lunts
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Patent number: 4990620Abstract: R.sup.2 is halogen,R.sup.3 is alkyl,R.sup.4 is C.sub.1-3 -alkyl,R.sup.5 is hydrogen or C.sub.1-2 -alkyl,R.sup.6 is C.sub.1-3 -alkyl, andHal is halogen.The process is new as are intermediates II, IV and V. The products are known intermediates.Type: GrantFiled: January 24, 1990Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach
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Patent number: 4987232Abstract: 2-chloropyridine 3-carboxylic acid esters are prepared by cyclization of 1,3-butadiene derivatives in the presence of hydrogen chloride.Type: GrantFiled: December 5, 1989Date of Patent: January 22, 1991Assignee: Shell Internationale Research Maatschappij, B.V.Inventor: Ludwig Schroder
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Patent number: 4978801Abstract: Aromatic aldehydes are more efficiently produced by reacting carbon monoxide/hydrogen admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous based and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the CO/H.sub.2 ratio is less than 1.Type: GrantFiled: April 28, 1987Date of Patent: December 18, 1990Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4973429Abstract: A material in the form of a film is described which contains, in an orientated arrangement which does not display point symmetry, compounds of formula I ##STR1## wherein X is .dbd.CH-- or .dbd.N--, R.sup.1 is C.sub.12 -C.sub.30 -alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 -alkyl, R.sup.3 is --NO.sub.2, --CN, --CF.sub.3, --COCF.sub.3, --SO.sub.2 CH.sub.3 or --SO.sub.2 CF.sub.3, R.sup.4 is hydrogen or is defined in the same way as R.sup.3, R.sup.5 is hydrogen or --NR.sup.6 R.sup.7 and R.sup.6 and R.sup.7 independently of one another are hydrogen or C.sub.1 -C.sub.30 -alkyl, it also being possible for any of the alkyl radicals to be partially fluorinated or perfluorinated.The compounds of formula I can be arranged in Langmuir-Blodgett layer systems. Such systems can be used for example for the manufacture of opto-electronic units.Type: GrantFiled: February 15, 1989Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventors: Gero Decher, Bernd Tieke, Christian Bosshard, Peter Gunter
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Patent number: 4969949Abstract: A pyrimidine derivative of the formula: ##STR1## wherein each of R.sup.1 and R.sup.2 which may be the same or different is an alkyl group, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a ring.Type: GrantFiled: March 21, 1989Date of Patent: November 13, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Shigematsu, Shoji Kusano, Takayoshi Takehi, Takeshige Miyazawa, Yasufumi Toyokawa
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4968796Abstract: Disclosed is a process for the preparation of a sulphonylisothiourea of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, and Z are as defined herein, which comprises reacting a sulphonic acid amide of the formulaR.sup.1 --SO.sub.2 --NH.sub.2, (II)or a metal salt thereof, with an N-heteroaryl-iminodithiocarbonic acid S,S-diester of the formula ##STR2## at a temperature between about 20.degree. C. and 200.degree. C. Intermediates and a process for their preparation are also disclosed.Type: GrantFiled: August 17, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventor: Hans-Jochem Riebel
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Patent number: 4968803Abstract: The present invention relates to a process for the preparation of hydroxypyridine based compounds. The process comprises the step of: in water, reacting a pyridine based compound with the proviso that the second position on the nitrogen ring is unsubstituted and the fourth position in the nitrogen ring is not substituted with halogen, with elemental fluorine at a temperature of about -25.degree. to about +30.degree. C. for a time sufficient to form a 2-hydroxypyridine based compound.The resulting 2-hydroxypyridine or quinoline carboxylic acids and esters are useful as herbicide and pharmaceutical intermediates.Type: GrantFiled: April 10, 1989Date of Patent: November 6, 1990Assignee: Allied-Signal Inc.Inventors: Michael Van Der Puy, David Nalewajek, Gene Wicks
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Patent number: 4966902Abstract: Compounds of the formula (I) and their stereoisomers ##STR1## wherein A, B, C' and D independently of one another denote CH or N, in which at least one of the symbols A, B, C' or D must correspond to a nitrogen atom,X denotes CH.sub.2 or oxygen,R.sup.1 denotes a radical bonded to a carbon atom from the series comprising H, trialkylsilyl, halogen, nitro, cyano, alkenyl, alkynyl, amino, cycloalkyl, phenyl, phenxy, alkoxy, alkenyloxy, alkynyloxy, hydroxycarbonyl, alkylthio, cycloalkyloxy, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkoxyalkyl, alkylthioalkyl, alkoxyalkoxy, halogenoalkoxyalkoxy, alkenyloxyalkoxy, halogenoalkenyloxy, alkoxyalkylthio, alkylthioalkoxy, alkylthioalkylthio, halogenoalkoxycarbonyl, halogenoalkenyloxycarbonyl or dialkylamino or two radicals R.sup.1 when they are positioned ortho to one another together denote a methylenedioxy, ethylenedioxy or alkylene radical,R.sup.2 and R.sup.Type: GrantFiled: April 13, 1988Date of Patent: October 30, 1990Assignee: Hoechst AktiengesellschaftInventors: Hans H. Schubert, Gerhard Salbeck, Hans-Peter Krause, Walter Luders, Werner Knauf, Anna Waltersdorfer, Manfred Kern
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Patent number: 4964896Abstract: This invention relates to compounds of the formula: ##STR1## wherein R.sub.1 is an optionally substituted alkyl or alkenyl group; at least one of R.sub.2, R.sub.5 and R.sub.6 is ##STR2## wherein (1) when R.sub.2 is ##STR3## R.sub.5 is a hydrogen atom, an alkyl group or a halogen atom and R.sub.6 is a hydrogen atom or an alkyl group,(2) when R.sub.5 is ##STR4## R.sub.2 is an alkyl group and R.sub.6 is a hydrogen atom or an alkyl group,(3) when R.sub.6 is ##STR5## R.sub.2 is an optionally substituted (C.sub.1 -C.sub.6) alkyl or a (C.sub.3 -C.sub.6) alkenyl group and R.sub.5 is a hydrogen atom, a (C.sub.1 -C.sub.6) alkyl group or a halogen atom, and(4) when R.sub.2 and R.sub.6 are both independently ##STR6## R.sub.5 is hydrogen atom or an alkyl group; Y is a hydrogen atom or an alkyl group; X is a hydrogen atom, a halogen atom, a trihalomethyl group and the like; and n is an integer from 1 to 3; or the agronomically acceptable alkali metal or acid addition salts thereof.Type: GrantFiled: August 15, 1988Date of Patent: October 23, 1990Assignee: Monsanto CompanyInventor: Glenn R. Carlson
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Patent number: 4963682Abstract: A dihydropyridine.rarw..fwdarw. pyridinium salt type of redox, or chemical, delivery system for the site-specific and/or site-enhanced delivery of a radionuclide to the brain is provided. A chelating agent capable of chelating with a radionuclide and having a primary, secondary or tertiary amino function can be converted to the corresponding analogue in which said function is replaced with a dihydropyridine.rarw. .fwdarw. pyridinium salt redox system and then complexed with a radionuclide to provide a new radiopharmaceutical that, in its lipoidal dihydropyridine form, penetrates the blood-brain barrier ("BBB") and allows increased levels of radionuclide concentration in the brain, particularly since oxidation of the dihydropyridine moiety in vivo to the ionic pyridinium salt retards elimination from the brain while elimination from the general circulation is accelerated.This radionuclide delivery system is well suited for use in scintigraphy and similar radiographic techniques.Type: GrantFiled: August 21, 1987Date of Patent: October 16, 1990Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 4962113Abstract: Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group;R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group;l is 0 or 1;R.sup.5 is a phenylene group or an alkylene group which may be substituted;R.sup.11 is an alkyl group or aryl group;X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3;U is a group of the formula: ##STR4## wherein R.sup.Type: GrantFiled: July 26, 1988Date of Patent: October 9, 1990Assignee: Takeda Chemical Industries, LtdInventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
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Patent number: 4960896Abstract: A process for the preparation of 5-halo-2-hydroxynicotinic acids having the formula: ##STR1## wherein X is chlorine or bromine, Y and Z are selected from hydrogen, loweralkyl or loweralkyl, is described wherein a corresponding 2-hydroxynicotinic acid is halogenated with alkali-metal hypohalite in a strongly alkaline solution pH 12 and above. Certain aspects of the isolation of the product are directed to avoiding replacement of the carboxy group with halogen.Type: GrantFiled: November 13, 1987Date of Patent: October 2, 1990Assignee: A. H. Robins Company, Inc.Inventor: Young S. Lo
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Patent number: 4946497Abstract: A compound of the formula (I) ##STR1## or a salt thereof, wherein R is hydrogen atom, or a group of --(CH.sub.2).sub.n --R.sub.1 wherein n is an integer from 1 to 3 and R.sub.1 is hydrogen atom, hydroxy group, a lower alkoxy group, mercapto group, a lower alkylthio group, amino group, a di-lower alkylamino group, a C.sub.3-11 alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a 5- or 6-membered heterocyclic group, or a phenyl group which may be substituted by one or two substituents of a halogen, a lower alkyl or a lower alkoxy;R.sub.2 and R.sub.7 are the same, a C.sub.1-11 alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a lower alkoxyalkyl group, an aralkyl group whose nucleus may be substituted by one or two substituents of a halogen, a lower alkyl or a lower alkoxy, or a halalkyl group;R.sub.3, R.sub.4 and R.sub.Type: GrantFiled: November 22, 1988Date of Patent: August 7, 1990Assignee: Daicel Chemical Industries Ltd.Inventors: Yukihisa Goto, Kazuhisa Masamoto, Hiroshi Yagihara, Yasuo Morishima, Hirokazu Osabe
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Patent number: 4943314Abstract: A compound of the formula (I) ##STR1## or a salt thereof, wherein R is hydrogen atom, phenyl group which may be substituted freely or a group of --(CH.sub.2).sub.n --R.sub.1 wherein n is an interger from 1 to 3 and R.sub.1 is hydrogen atom, hydroxy group, lower alkoxy group, mercapto group, lower alkylthio group, amino group, di-lower alkylamino group, C.sub.3-11 alkyl group, lower alkenyl group, lower alkynyl group, cycloalkyl group, 5- or 6-membered heterocyclic group, or phenyl group which may be substituted by one or two substituents of halogen, lower alkyl or lower alkoxy;R.sub.2 and R.sub.7 are different, hydrogen atom, C.sub.1-11 alkyl group, lower alkenyl group, lower alkylyl group, cycloalkyl group, lower alkoxyalkyl group, lower alkylthioalkyl group, phenyl group which may be substituted freely, aralkyl group whose nucleus may be subsituted by one or two substituents of halogen, lower alkyl or lower alkoxy or haloalkyl group or 5- or 6-membered heterocyclic group;R.sub.3, R.sub.4 and R.sub.Type: GrantFiled: March 3, 1989Date of Patent: July 24, 1990Assignee: Daicel Chemical Industries, Ltd.Inventors: Yukihisa Goto, Kazuhisa Masamoto, Hiroshi Yagihara, Yasuo Morishima, Hirokazu Osabe
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Patent number: 4942240Abstract: Aromatic aldehydes are more rapidly produced by reacting hydrogen/carbon monoxide admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous base and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the concentration of said tertiary nitrogenous base, expressed in moles per liter of reaction mixture, is maintained at a value of at least two moles/liter over the course of the reaction.Type: GrantFiled: April 28, 1987Date of Patent: July 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4939160Abstract: Hydropyridine derivatives of the formula ##STR1## in which R.sub.1 represents carboxy, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl, R.sub.2 represents hydrogen, an optionally etherified or acylated hydroxy group or an optionally acylated amino group, and R.sub.3 represents a radical of the formula R- (Ia), R-alk.sub.1 - (Ib) or R'=alk.sub.2 - (Ic) in which R represents a benzocycloalkenyl radical having a total of from 8 to 12 ring carbon atoms which is bonded via a saturated carbon atom and which is unsubstituted or is mono- or poly-substituted in the benzo moiety by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, lower alkyl and/or by trifluoromethyl, and/or substituted in the .alpha.Type: GrantFiled: December 9, 1988Date of Patent: July 3, 1990Assignee: Ciba-Geigy CorporationInventors: Georg von Sprecher, Wolfgang Frostl, Armin Zust
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Patent number: 4936904Abstract: The present invention relates to N-alkyl-2-aryl-4-oxonicotinates, N-alkyl-5-aryl-4-oxonicotinates, N-alkyl-6-aryl-4-oxonicotinates and N-alkyl-2,6-diaryl-4-oxonicotinates and their use as plant hybridization agents especially useful in wheat, barley and corn. These compounds are particularly active as chemical gametocides and possess a high degree of male/female selectivity. Moreover, these compounds are relatively noninjurious to both corn and wheat crops. The fact that these chemicals possess a high degree of male sterility without affecting female fertility makes them very useful as chemical gametocides.Type: GrantFiled: December 2, 1987Date of Patent: June 26, 1990Inventor: Glenn R. Carlson
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Patent number: 4936905Abstract: Disclosed herein are substituted pyridine-3-monocarboxylate compounds in which a substituent is bonded to the pyridine ring at the 5-position through an oxygen atom.Type: GrantFiled: April 22, 1988Date of Patent: June 26, 1990Assignee: Monsanto CompanyInventors: Maria L. Miller, Len F. Lee, Mark G. Dolson
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Patent number: 4931452Abstract: Substituted N-cyanomethyl-2-pyridinones were prepared by the reaction of alkali metal substituted-2-pyridinates with monohaloacetonitriles and found to possess insecticidal properties. The alkali metal substituted-2-pyridinates can be preformed or prepared from the corresponding 2-halopyridines or 2-pyridinols in the reaction medium. N-cyanomethyl-3-fluoro-5-(trifluoromethyl)-2-pyridinone, for example, was prepared from 2,3-difluoro-5-(trifluoromethyl)pyridine and found to control aster leafhoppers both on contact and systemically.Type: GrantFiled: August 24, 1988Date of Patent: June 5, 1990Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, James E. Dripps, Gregory A. Bradfisch, Susan Wollowitz, Ingrid L. Knox
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Patent number: 4925590Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.Type: GrantFiled: March 9, 1989Date of Patent: May 15, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
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Pyridine compounds useful for therapy or prophylaxis of a disease associated with airway obstruction
Patent number: 4921867Abstract: Compounds of formula (I) ##STR1## wherein X and Y each represent a bond or an alkylene, alkenylene or alkynylene chain;R.sup.1 and R.sup.2 each represent a hydrogen atom or a lower alkyl group; andPy represents a pyridyl group having one or two substituents. The compounds have a stimulant action at beta.sub.2 -adrenoreceptors. The compounds may be used in the treatment of diseases associated with reversible airway obstruction such as asthma and chronic bronchitis.Type: GrantFiled: February 9, 1988Date of Patent: May 1, 1990Assignee: Glaxo Group LimitedInventor: Lawrence H. C. Lunts -
Patent number: 4920224Abstract: Variously substituted trans-3-[3-(3-hydroxypiperid-2-yl)-2-oxopropyl]quinazolin-4(3H)-ones, a method of controlling or preventing coccidiosis in poultry therewith, intermediates therefor, and a process for the preparation of certain intermediates therefor.Type: GrantFiled: March 13, 1989Date of Patent: April 24, 1990Assignee: Pfizer Inc.Inventor: Edward A. Glazer
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Patent number: 4920225Abstract: Optically active compounds of formula 1 ##STR1## wherein R.sub.1 is H or lower alkyl;R.sub.2 and R.sub.6 are each independently lower alkyl, aryl, or arylalkyl;R.sub.3 is CN, NO.sub.2, CO.sub.2 R.sub.5, CONHR.sub.5, SO.sub.2 R.sub.5, or P(O)(OR.sub.5).sub.2, where R.sub.5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl;R.sub.4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO.sub.2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF.sub.3, OCH.sub.2 F, or OCF.sub.3 ;are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.Type: GrantFiled: December 22, 1986Date of Patent: April 24, 1990Assignee: Laboratoires Syntex S.A.Inventor: Gilles Genain
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Patent number: 4920230Abstract: Nitrogen-containing heteroaromatic compounds having an alkoxy group can be produced by reacting nitrogen-containing heteroaromatic compounds having a nitro group with alcohol or alcoholate in the presence of a phase transfer catalyst and a base.Type: GrantFiled: June 21, 1988Date of Patent: April 24, 1990Assignee: Takeda Chemical Industries, Ltd.Inventor: Masayasu Kato
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Patent number: 4913837Abstract: Heterocyclic compounds of the formula IR.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.n -R.sup.2Iwherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are defined in claim 1, can be used as components of liquid-crystalline phases.Type: GrantFiled: September 1, 1987Date of Patent: April 3, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: George W. Gray, Kenneth J. Toyne, David Lacey, Michael P. Burrow, Rudolf Eidenschink, Andreas Wachtler, Georg Weber
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Patent number: 4902796Abstract: 2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a halo-aromatic compound and an unsaturated compound in the prosence of a palladium catalyst. The products are chemical intermediates for the preparation of antineo-plastic agents.A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.Type: GrantFiled: August 8, 1988Date of Patent: February 20, 1990Assignee: The Trustees of Princeton UniversityInventors: Edward C. Taylor, George S. K. Wong
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Patent number: 4900749Abstract: Novel isoprenoidamine compounds (I) which show antiulcer activity are provided.Type: GrantFiled: March 10, 1986Date of Patent: February 13, 1990Assignee: Shionogi & Co., Ltd.Inventors: Saichi Matsumoto, Masami Doteuchi, Takuji Mizui, Kentaro Hirai