Chalcogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/288)
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Publication number: 20020035259Abstract: The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with (derivatised) hydroxyalkyl substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.Type: ApplicationFiled: August 30, 2001Publication date: March 21, 2002Inventors: Emily J. Canada, Christopher S. Galka, Robert P. Gajewski, Neil V. Kirby, Irene M. Morrison, Mary E. Pieczko, Chrislyn M. Carson, Jeannie R. Phillips, Brent J. Rieder, Zhengyu Huang
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Publication number: 20010051726Abstract: 2-Sulfonylpyridine derivatives can be industrially produced efficiently by reacting a sulfonyl cyanide derivative with an &agr;,&bgr;-unsaturated carbonyl compound and a 2-{[(2-pyridyl)methyl]thio}-1H-benzimidazole skeleton can be formed in one step in a good yield by reacting this type of the 2-sulfonylpyridine derivative with a 2-methylthio-1H-benzimidazole derivative in the presence of an organolithium compound.Type: ApplicationFiled: December 7, 2000Publication date: December 13, 2001Applicant: KURARAY CO., LTD.Inventors: Ken-Ichi Koyakumaru, Takashi Sugioka, Tomoya Kuwayama, Goro Asanuma
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Publication number: 20010051732Abstract: A process for preparing a pyridone derivative (4), which comprises reacting the compound (1) with a hypochlorite or a hypobromite or with lead tetraacetate to give the compound (2), and reacting the compound (2) with the compound (3). Said process is preferably especially from the standpoint of safety.Type: ApplicationFiled: May 14, 2001Publication date: December 13, 2001Applicant: SUMITOMO PHARMACEUTICALS COMPANY, LIMITEDInventors: Masami Muraoka, Koji Morishita, Nagisa Aida, Masashi Tanaka, Masatoshi Yuri, Naohito Ohashi
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Patent number: 6310006Abstract: The invention relates to novel compounds of formula I: wherein R, A, B and X have the meaning given in claim 1; and the agronomically acceptable salts or N-oxides thereof, and to herbicidal compositions containing such compounds as active ingredients.Type: GrantFiled: May 13, 1998Date of Patent: October 30, 2001Assignee: American Cyanamid CompanyInventors: Thomas Maier, Stefan Scheiblich, Helmut S. Baltruschat
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Patent number: 6306839Abstract: The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with (derivatised) hydroxyalkyl substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.Type: GrantFiled: September 16, 1999Date of Patent: October 23, 2001Assignee: Dow AgroSciences LLCInventors: Emily J. Canada, Robert P. Gajewski, Christopher S. Galka, Neil V. Kirby, Irene M. Morrison, Jeannie R. Phillips, Mary E. Pieczko, Brent J. Rieder, Chrislyn M. Carson, Zhengyu Huang
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Publication number: 20010008942Abstract: A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.Type: ApplicationFiled: December 21, 2000Publication date: July 19, 2001Inventors: Stephen L. Buchwald, John P. Wolfe, Michael Palucki
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Patent number: 6235909Abstract: This invention is directed to methods for the preparation of [1S-[1a,2b,3b,4a(S*)]]-4-[7-[[-(3-chloro-2-thienyl)methyl]propyl]amino]-3 H-imidazo[4,5-b]pyridin-3-yl]]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide, methods for the preparation of intermediates thereto, and to said intermediates themselves.Type: GrantFiled: July 28, 2000Date of Patent: May 22, 2001Assignee: Aventis Pharmaceuticals Products Inc.Inventors: Herve Garcia, Patrick Leon, Benoit J. Vanasse
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Patent number: 6197964Abstract: The process according to the invention can be illustrated by way of example by the following equation: The monosodium salt of the 3-cyano-2-hydroxy-5-fluoropyrid-6-one (cf. Formula (I)) and/or tautomers thereof are preferably employed in the process according to the invention. The use of a basic catalyst enables significantly lower amounts of chlorinating agent to be employed in the chlorination according to the invention than is necessary, for example, for chlorination of the free dihydroxy compound according to EP-A 333 020. Furthermore, the product 2,6-dichloro-5-fluoronicotinonitrile is obtained in a high purity and high yields after hydrolysis, which is not the case if the conditions according to EP-A 333 020 are applied. Basic catalysts which can be used for the process according to the invention are, for example, organic bases, for example aliphatic and aromatic amines and amides, and also inorganic bases, for example basic compounds of nitrogen and phosphorus and salts thereof.Type: GrantFiled: September 27, 1999Date of Patent: March 6, 2001Assignee: Bayer AktiengesellschaftInventors: Andreas Sattler, Guido Steffan, Bernd Griehsel
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Patent number: 6143894Abstract: This invention is directed to methods for the preparation of [1S-[1a,2b,3b,4a(S*)]]-4-[7-[[1-(3-chloro-2-thienyl) methyl]propyl]amino]-3H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxyc yclopentanecarboxamide, methods for the preparation of intermediates thereto, and to said intermediates themselves.Type: GrantFiled: January 19, 1999Date of Patent: November 7, 2000Assignee: Aventis Pharmaceuticals Products Inc.Inventors: Michael K. O'Brien, Herve Garcia, Patrick Leon, Tory H. Powner, Laurence W. Reilly, Harshavadan C. Shah, Michael D. Thompson, Ching T. Tsuei, Benoit J. Vanasse, Francis L. Walther
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Patent number: 6130226Abstract: Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor .alpha., nuclear factor .kappa.B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.Type: GrantFiled: March 18, 1999Date of Patent: October 10, 2000Assignee: Celgene CorporationInventors: George W. Muller, Mary Shire
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Patent number: 6130335Abstract: N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)be nzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimi din-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.Type: GrantFiled: July 31, 1998Date of Patent: October 10, 2000Assignee: Dow AgroSciences LLCInventors: Timothy C. Johnson, Robert J. Ehr, Timothy P. Martin, Mark A. Pobanz, John C. Van Heertum, Richard K. Mann
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Patent number: 6118002Abstract: The present invention comprises a process for preparing essentially pure 1,2-dihydro-6-alkyl-2-oxo-5-(pyridinyl)-nicotinonitriles from a crude reaction mixture containing the corresponding amide as an impurity. By "essentially pure" is meant a level of purity acceptable for orally administered pharmaceutical products, usually less than 0.1% of any single impurity. At least a stoichiometric amount of an acylating agent is reacted with the crude reaction mixture, and thereafter recovering essentially pure 1,2-dihydro-6-alkyl-2-oxo 5-(pyridinyl)-nicotinonitrile.Type: GrantFiled: March 2, 1999Date of Patent: September 12, 2000Assignee: Wyckoff Chemical Company, Inc.Inventors: James M. VanderRoest, James J. Springer, Richard S. Olsen
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Patent number: 6110871Abstract: The novel cyanopyridines of the general formula (I) ##STR1## (A, B, R.sup.1, R.sup.2, X, m and n are defined in the specification) show selective herbicidal activity.The new compounds can be prepared according to known methods and can be used as herbicides in agriculture and related fields.Type: GrantFiled: July 15, 1999Date of Patent: August 29, 2000Assignee: American Cyanamid CompanyInventors: Thomas Maier, Stefan Scheiblich, Helmut Siegfried Baltruschat
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Patent number: 6022884Abstract: Selected novel substituted pyridine compounds are effective for prophylaxis and treatment of diseases, such as TNF-.alpha., IL-1.beta., IL-6 and/or IL-8 mediated diseases, and other maladies, such as pain and diabetes. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving inflammation, pain, diabetes, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.Type: GrantFiled: November 3, 1998Date of Patent: February 8, 2000Assignee: Amgen Inc.Inventors: Nathan B. Mantlo, Stephen T. Schlachter, John A. Josey
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Patent number: 6015905Abstract: A process for preparing 2-(6-substituted pyrid-2-yloxymethyl)phenyacetates especially useful as intermediates for producing agricultural fungicides. The invention provides a compound having the formula (I): wherein A and D are independently selected from the group comprising halo, hydroxy, halo(C.sub.1-4)alkyl, C.sub.1-4 alkoxy, thio(C.sub.1-4)alkoxy, halo(C.sub.1-4)alkoxy, phenyl, phenoxy, nitro, amino, aclyamino, cyano, carboxy, C.sub.1-4 alkoxycarbonyl and C.sub.1-4 alkylcarbonyloxy, or D is C.sub.1-4 alkyl, and m is 0 or an integer of from 1 to 3. The process comprises treating a compound of formula (II): ##STR1## wherein A, D and m are defined as above and M is a metal atom, with a compound of formula (III): ##STR2## wherein L is a leaving group.Type: GrantFiled: December 2, 1997Date of Patent: January 18, 2000Assignee: Zeneca LimitedInventors: David John Ritchie, Gordon Richard Munns, Julie Forrester, Michael Charles Henry Standen, Paul Anthony Worthington, Raymond Vincent Heavon Jones
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Patent number: 5955615Abstract: Dyestuffs of the formula whereinD is the radical of a carbo- or heterocyclic diazo component,X represents O, NH, NT, NCOT, NCCH.sub.2 T or NSO.sub.2 T,and the other substituents have the meaning given in the description, are preferably suitable, if m=n=l=o, for dyeing and printing hydrophobic synthetic fiber materials and mixtures thereof with naturally occurring fiber materials.Type: GrantFiled: May 18, 1998Date of Patent: September 21, 1999Assignee: Bayer AktiengesellschaftInventor: Rainer Hamprecht
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Patent number: 5942623Abstract: The invention relates to a process for the preparation of 2-(pyrid-2-yloxymethyl)phenylacetates of formula (I) useful as intermediates for agricultural pesticides, which comprises reacting a 2-pyridine of formula (II), wherein L is a leaving group and A, D and m are as defined in the description with a compound MO--CH.sub.2 R where M is a metal atom and R is the residue of a metal salt of phenylacetic acid. It also includes the compounds MO--CH.sub.2 R, a process for their preparation and a "one-pot" process for the preparation of 2-(pyrid-2-yloxymethyl) phenylacetates from 3-isochromanone.Type: GrantFiled: February 19, 1998Date of Patent: August 24, 1999Assignee: ZENECA LimitedInventors: Alfred Glyn Williams, Gordon Richard Munns, Paul Anthony Worthington
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Patent number: 5929245Abstract: The invention concerns naphtholactam derivatives of formula (I), in which: R.sup.1 represents hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl C.sub.5 -C.sub.6 cycloalkcyl or substituted phenyl; R.sup.2 and R.sup.3 represent hydrogen, C.sub.1 -C.sub.8 alkanoyl, optionally substituted benzoyl, optionally substituted C.sub.2 -C.sub.4 alkyl, optionally substituted C.sub.2 -C.sub.4 alkenyl, optionally substituted C.sub.2 -C.sub.4 alkinyl, a halogen, nitro, sulphamoyl, optionally substituted hydroxy, optionally substituted mercapto, C.sub.1 -C.sub.6 alkysulphonyl or optionally substituted phenylsulphonyl; R.sup.4 represents hydrogen or, with R.sup.3, a group of formula (II); R.sup.5 represents hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.6 represents cyano, carbamoyl, C.sub.1 -C.sub.4 mono- or dialkylcarbamoyl carboxyl or C.sub.1 -C.sub.4 alkoxycarbonyl; and R.sup.7 represents substituted C.sub.1 -C.sub.4 alkyl, optionally substituted C.sub.5 -C.sub.13 alkyl or benzoyl.Type: GrantFiled: February 18, 1997Date of Patent: July 27, 1999Assignee: BASF AktiengesellschaftInventors: Clemens Grund, Ernst Schefczik, Gunther Lamm, Roland Merger, Rudiger Sens
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Patent number: 5925596Abstract: Substituted aminomethylphenylsulfonylureas, their preparation, and their use as herbicides and plant growth regulatorsCompounds of the formula (I) and salts thereof ##STR1## where R.sup.1 to R.sup.7 and A are as defined in claim 1 and, inter alia, F.sup.5 is an acyl radical or NR.sup.4 R.sup.5 together are a heterocyclic radical, are useful as herbicides and plant growth regulators. They can be prepared by the methods of known processes, using novel intermediates of the formula (II), (IV), (VI) or (VII) (cf. claim 5).Type: GrantFiled: April 24, 1997Date of Patent: July 20, 1999Assignee: Hoechst-Schering AgrEvo GmbHInventors: Klaus Lorenz, Lothar Willms, Klaus Bauer, Hermann Bieringer, Christopher Rosinger
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Patent number: 5883282Abstract: There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.Type: GrantFiled: May 20, 1997Date of Patent: March 16, 1999Assignee: American Cyanamid CompanyInventors: Alvin Donald Crews, Jr., Philip Mark Harrington, Gary Mitchell Karp, Simon David Gill, Petra Dieterich
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Patent number: 5874615Abstract: The present invention provides an improved method for the preparation of an insecticidal benzoylurea having the structural formula I ##STR1##Type: GrantFiled: March 17, 1998Date of Patent: February 23, 1999Inventors: Pieter Adriaan Verbrugge, Jannetje De Waal
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Patent number: 5852042Abstract: The invention relates to novel substituted N-(4-pyridyl)carboxamides of the formula ##STR1## in which Q is substituted 4-pyridyl, A is hydrogen, alkyl, acyl or aralkyl and Y-Z is an optionally modified hydrocarbon radical or Y is a bond or a bivalent radical and Z is aryl, O-aryl, cycloalkyl, cycloalkenyl or heterocyclyl, all of which are optionally substituted, to processes for their preparation, to intermediates during their preparation, and to their use as pesticides, in particular as insecticides, acaricides and nematicides, and also as fungicides.Type: GrantFiled: September 26, 1995Date of Patent: December 22, 1998Assignee: Hoechst Schering AgrEvo GmbHInventors: Harald Jakobi, Werner Knauf, Ulrich Sanft, Manfred Kern, Dieter Bernd Reuschling, Adolf Heinz Linkies, Werner Bonin
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Patent number: 5811370Abstract: Azamethine dyes of the formula ##STR1## where W is oxygen, sulfur or a radical of the formula --NH--CO--, --NH--COO-- oder --NH--SO.sub.2 --,Z.sup.1 is C.sub.1 -C.sub.4 -alkyl with or without substitution, phenyl or C.sub.1 -C.sub.4 -alkoxy,Z.sup.2 and Z.sup.3 are each hydrogen or C.sub.1 -C.sub.4 -alkyl with or without substitution, provided --CZ.sup.1 Z.sup.2 Z.sup.3 is not linear and is not isopropyl,Z.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,Z.sup.5 and Z.sup.6 are each C.sub.1 -C.sub.10 -alkyl with or without substitution, C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or tolyl, or together with the nitrogen atom joining them together a heterocyclic radical or Z.sup.4 and Z.sup.5 are together a bridge member, andT is a radical of a cyclic acidic--CH compound H.sub.2 T,are useful for thermal transfer.Type: GrantFiled: May 8, 1997Date of Patent: September 22, 1998Assignee: BASF AktiengesellschaftInventors: Rudiger Sens, Andreas Johann Schmidt, Stefan Beckmann, Karl-Heinz Etzbach
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Patent number: 5808080Abstract: The present invention is in the field of medicine, particularly in the treatment of Type II diabetes and obesity. More specifically, the present invention relates to selective .beta.3 adrenergic receptor agonists useful in the treatment of Type II diabetes and obesity.Type: GrantFiled: May 2, 1997Date of Patent: September 15, 1998Assignee: Eli Lilly and CompanyInventors: Michael Gregory Bell, Thomas Alan Crowell, David Andrew Neel, Mark Alan Winter
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Patent number: 5770613Abstract: Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds that are derivatives of pyridine aldehydes, thioaldehyde, acetals, or thioacetals. Such compounds are characterized by the following structure: ##STR1## X.sub.1 is selected from the group consisting of oxygen, sulfur, sulfone, sulfinyl, and --NR-- where R is hydrogen, alkyl, aryl, and aralkyl. R.sub.1 is --Y.sub.n R.sub.6, in which n is an integer between 0 and 10 and each Y.sub.n for n greater than 0 independently is methylene, methine, or quarternary carbon. R.sub.6, for any value of n (i.e.Type: GrantFiled: September 29, 1995Date of Patent: June 23, 1998Assignee: Geron CorporationInventors: Federico C. A. Gaeta, Elaine C. Stracker
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Patent number: 5767278Abstract: Compounds for treating cancer and other diseases involving telomerase activity are characterized by the following structure: ##STR1## Such compounds include those for which X.sub.1 is oxygen, sulfur, sulfone, or sulfinyl, and R.sub.1 is --Y.sub.n R.sub.6, where n is an integer between 0 and 10 and each Y.sub.n independently is methylene, methine, or quaternary carbon. R.sub.6, is alkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl, alkylcarbonyl, arylcarbonyl, heteroalkylcarbonyl, heteroaralkylcarbonyl, aralkylcarbonyl, arninocarbonyl, alkylarninocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylaminocarbonyl, carboxyl, carboxaldehyde, alkoxycarbonyl, aryloxycarbonyl, sulfo, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, or arylsulfinyl. R.sub.6 can also be a linker selected from the group consisting of alkyl, aryl, and heterocycle. R.sub.Type: GrantFiled: October 6, 1995Date of Patent: June 16, 1998Assignee: Geron CorporationInventors: Federico C.A. Gaeta, Elaine C. Stracker
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Patent number: 5763638Abstract: A process for the preparation of nitriles of formula ##STR1## wherein X is CH or N, and R.sub.1 and R.sub.2 are each independently of the other hydrogen, chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, CN, phenyl, phenoxy, dimethylamino, piperidyl, morpholinyl or pyrrolidyl, or R.sub.1 and R.sub.2 together form a fused benzene ring, by reacting an aldehyde of formula ##STR2## with hydroxylaminosulfate in the presence of a tertiary amine base of formula ##STR3## wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen, methyl or ethyl, R.sub.5 is branched C.sub.3 -C.sub.5 alkyl or phenyl, and R.sub.6 and R.sub.7 are methyl or ethyl,in the temperature range from 100.degree. to 160.degree. C., while distilling the released water of reaction off concomittantly at a pressure in the range of 0.02 to 1.5 bar, with subsequent removal of the ammonium salts, and isolating the nitrile so obtained by customary methods.Type: GrantFiled: February 4, 1997Date of Patent: June 9, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Richard Breitschuh
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Patent number: 5760062Abstract: Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds that are derivatives of pyrido?b!thiophenes, pyrido?b!furans, pyridine ethers or pyridine thioethers. Such compounds are characterized by the following structure: ##STR1## X.sub.3 is oxygen or sulfur; and the double dashed lines between X.sub.4 and X.sub.5 indicate an optional double bond, which, when present, forms a fused, bicyclic pyrido?b!furan or pyrido?b!thiophene ring system, depending upon whether X.sub.3 is oxygen or sulfur, respectively. When the double bond is not present, the compound is a monocyclic pyridine ether or thioether, again depending upon whether X.sub.3 is oxygen or sulfur. X.sub.4 is --CH.sub.2 R.sub.21 or --CR.sub.21 --, where R.sub.Type: GrantFiled: April 18, 1995Date of Patent: June 2, 1998Assignee: Geron CorporationInventors: Federico C.A. Gaeta, Adam A. Galan, Michael R. Kozlowski, Karen R. Prowse, Elaine C. Stracker, Patricia A. Peterli-Roth
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Patent number: 5760063Abstract: The subject invention, provides arylhydrazone compounds having the Formula 1: ##STR1## wherein A and B are independently aryl or heteroaryl and A and B independently are substituted with at least one group selected from alkyl, halogen, CN, COOR.sup.7, NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, NO.sub.2, SR.sup.7, SOR.sup.7, SO.sub.2 R.sup.7, NHCOR.sup.7, NHSO.sub.2 R.sup.7, OR.sup.7, hydroxyalkyl, and aminoalkyl. The compounds of this invention are useful for treating a wide variety of bacterial infections, including diseases of the skin, e.g., acne and skin ulcers, gastroenteritis, colitis, meningitis, keratinitis, conjunctivitis, diseases of the urinary and genital tracts, etc.Type: GrantFiled: September 13, 1996Date of Patent: June 2, 1998Assignee: Scriptgen Pharmaceuticals, Inc.Inventors: Kelvin T. Lam, David G. Powers
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Patent number: 5756524Abstract: A compound of formula I ##STR1## X is O or S; A is 6-alkoxy-3-pyridyl optionally substituted by halogen;Y is hydrogen or alkyl;R.sup.3 is alkyl or a metal salt complex thereof. This invention contains fungicidal compositions and are used to combat cytopathogenic fungi.Type: GrantFiled: September 18, 1996Date of Patent: May 26, 1998Assignee: Agrevo UK LimitedInventors: Peter Dominic Riordan, Susan Elizabeth Osbourn, Ian Kenneth Boddy
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Patent number: 5696140Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for ##STR1## where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice for treating asthma, allergy, CNS disorders, or cancer.Type: GrantFiled: October 3, 1996Date of Patent: December 9, 1997Assignee: Leo Pharmaceutical Products Ltd.Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5686470Abstract: A class of substituted pyridyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from hydrido, halo, alkoxy, haloalkoxy, aryl, alkylthio, alkylamino, aralkoxy, azido and allyloxy; wherein R.sup.2 is selected from hydrido, cyano, hydroxyalkyl, haloalkyl, aminoalkyl, aminocarbonyl and alkylcarbonylaminoalkyl; and wherein R.sup.5 and R.sup.6 are one or more radicals independently selected from halo, alkylsulfonyl, aminosulfonyl, alkoxy and alkylthio; provided one of R.sup.5 and R.sup.6 is substituted with alkylsulfonyl, aminosulfonyl, or haloalkylsulfonyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: February 10, 1995Date of Patent: November 11, 1997Inventors: Richard M. Weier, Len F. Lee, Richard A. Partis, Francis J. Koszyk
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Patent number: 5631381Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.Type: GrantFiled: June 28, 1996Date of Patent: May 20, 1997Assignee: Rhone-Poulenc Inc.Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
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Patent number: 5624894Abstract: The invention provides novel peptide derivatives which are designed to deliver pharmacologically active peptides into the central nervous system by sequential metabolism. The peptide is placed in a molecular environment which disguises its peptide nature and provides biolabile, lipophilic functions to penetrate the blood-brain barrier by passive transport. The design incorporates a dihydropyridine-type redox targetor moiety, an amino acid or di- or -tripeptide spacer inserted between the targetor and N-terminal amino acid unit of the peptide and a bulky, lipophilic substituent protecting the C-terminal amino acid unit of the peptide. The dihydropyridine-type targetor undergoes an enzymatically mediated oxidation to a hydrophilic, membrane-impermeable pyridinium salt. That polar targetor-peptide conjugate is trapped behind the lipoidal blood-brain barrier.Type: GrantFiled: April 27, 1995Date of Patent: April 29, 1997Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5625069Abstract: A process of preparing 2-cyano-3,5-dimethyl-4-methoxypyridine. The process includes the steps of: acylating 2-methyl-1-penten-1-alkoxy-3-one to obtain 2-alkoxycarbonyl-3,5-dimethyl-4-pyrone; ammonolyzing 2-alkoxycarbonyl-3,5-dimethyl-4-pyrone to obtain 2-carboxamido-3,5-dimethyl-4(1H)-pyridone; methylating 2-carboxamido-3,5-dimethyl-4(1H)-pyridone to obtain 2-carboxamido-3,5-dimethyl-4-methoxypyridine; and dehydrating said 2-carboxamido-3,5-dimethyl-4-methoxypyridone to obtain 2-cyano-3,5-dimethyl-4-methoxypyridine.Type: GrantFiled: July 22, 1996Date of Patent: April 29, 1997Assignee: Development Center for BiotechnologyInventors: Shan-Yen Chou, Tsai-Mien Huang, Shyh-Fong Chen, Hao Ku
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Patent number: 5594012Abstract: A novel anti-active oxygen agent which comprises as active ingredient an amino acid derivative represented by the following general formula (I): ##STR1## wherein Ar represents a 2-hydroxyphenyl, 2-hydroxy-1-naphthyl or pyridyl group, and one or more of the hydrogen atoms attached to the aromatic ring of these groups may be substituted with a halogen atom, or an alkyl, hydroxyl, hydroxyalkyl, nitro, alkoxyl or carboxyl group; R represents the side chain of an amino acid; X represents --CH.sub.2 --NH-- or --CH.dbd.N--; Y represents a hydrogen atom, --COOR.sup.1, --SO.sub.3 H, --CON(R.sup.2)R.sup.3, --CONHCH(R.sup.5)COOR.sup.4 or --CH.sub.2 OH (where each of R.sup.1 to R.sup.4 represents a hydrogen atom or an alkyl group, and R.sup.5 represents the side chain of an amino acid); and n represents an integer of 0 or 1;or its salt,and which inhibits generation of active oxygen species, has a high safety and can be prepared at relatively low costs.Type: GrantFiled: October 6, 1994Date of Patent: January 14, 1997Assignee: Ajinomoto Co., Inc.Inventors: Manabu Kitazawa, Keiji Iwasaki
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Patent number: 5591833Abstract: Colorants and compositions useful as a fugitive or permanent colorant for a variety of substrates, or as intermediates for their manufacture, and having one or more improved properties of enhanced aqueous washability, compatibility with and non-extractibility from thermoplastic resins, or reactivity with resins having reactive functionality, said composition having the formula C(Z).sub.Type: GrantFiled: August 10, 1993Date of Patent: January 7, 1997Assignee: Milliken Research CorporationInventors: John B. Hines, David J. Moody, Edward W. Kluger
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Patent number: 5587387Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1)compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifiuoromethyl; R.sup.4 is trifiuoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical -Alk-R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy; Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.Type: GrantFiled: May 2, 1995Date of Patent: December 24, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5585327Abstract: 4-substituted pyridyl-3-carbinols of the formula ##STR1## wherein R is hydrogen, or an acyl, alkyl or carbamyl group exhibit desirable preemergent and postemergent herbicidal activity. Also disclosed are herbicidal compositions comprising such compounds and methods of controlling undesirable vegetation employing such compounds. The compounds wherein AR is hydroxyl serve as useful intermediates for the production of the alpha-benzyl substituted compounds as well as exhibiting herbicidal activity.Type: GrantFiled: May 2, 1994Date of Patent: December 17, 1996Assignee: Zeneca LimitedInventors: Hsiao-Ling Chin, Yi-Qiu Wei, Nhan H. Nguyen, Michael P. Ensminger, Linda Willitts, Derek P. Dagarin
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Patent number: 5563160Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for .dbd.N--R.sub.1 where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice as selective serotonin receptor antagonists.Type: GrantFiled: March 15, 1995Date of Patent: October 8, 1996Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5554578Abstract: Oxime ether derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl, Het is pyridyl, quinolyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, quinoxalinyl, isoxazolyl, benzoxazolyl or benzothiazolyl bedeutet, the heterocyclic ring system being unsubstituted or substituted, and X is oxygen or sulfur, their plant-tolerated acid addition salts, metal complexes and N-oxides, and fungicides containing these compounds.Type: GrantFiled: August 8, 1995Date of Patent: September 10, 1996Assignee: BASF AktiengesellschaftInventors: Bernd Wenderoth, Siegbert Brand, Franz Schuetz, Thomas Kuekenhoehner, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5552409Abstract: This invention relates to substituted dihydropyridazinones, pyridazinones and related compounds, of the formula ##STR1## wherein A, Q, D and R.sup.1 are as defined within, compositions containing these compounds and methods of controlling agricultural and mammalian fungal diseases.Type: GrantFiled: March 31, 1994Date of Patent: September 3, 1996Assignee: Rohm and Haas CompanyInventors: Enrique L. Michelotti, Anne R. Egan, Ronald Ross, Jr., Willie J. Wilson
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Patent number: 5548078Abstract: A fungicidal composition for agricultural use, which comprises a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R.sup.3 is lower alkyl or cyclo(lower)alkyl; R.sup.4 and R.sup.5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --OCH.sub.2 --, --SCH.sub.2 -- or --SOCH.sub.2 --.Type: GrantFiled: December 20, 1994Date of Patent: August 20, 1996Assignee: Shionogi Seiyaku Kabushiki KaishaInventors: Yoshio Hayase, Takahiro Kataoka, Hideyuki Takenaka, Mitsuhiro Ichinari, Michio Masuko, Toshio Takahashi, Norihiko Tanimoto
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Patent number: 5516786Abstract: Combating fungi with substituted amine acid derivatives of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cycloalkyl or cycloalkenyl,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen, cycloalkyl or alkyl, orR.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a cycloalkyl ring, andR.sup.6 represents hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, unsubstituted or substituted phenylalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted cycloalkyl, or represents unsubstituted or substituted heterocyclyl or heterocyclylalkyl,orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a heterocyclyl radical, which can contain further hetero atoms.Type: GrantFiled: November 21, 1994Date of Patent: May 14, 1996Assignee: Bayer AktiengesellschaftInventors: Detlef Wollweber, Thomas Seitz, Wilhelm Brandes
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Patent number: 5516776Abstract: A process and intermediates for the enantioselective synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid are disclosed.Type: GrantFiled: September 12, 1994Date of Patent: May 14, 1996Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5512536Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.Type: GrantFiled: November 15, 1994Date of Patent: April 30, 1996Assignee: Rohn and Haas CompanyInventors: Donald E. Korte, Len F. Lee
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Patent number: 5480997Type: GrantFiled: May 12, 1994Date of Patent: January 2, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5470819Abstract: This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests.The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy.Type: GrantFiled: May 9, 1994Date of Patent: November 28, 1995Assignee: Zeneca LimitedInventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Ian Ferguson, Patrick J. Crowley, Michael G. Hutchings
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Patent number: 5466812Abstract: A process for preparing pyridones of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.4 -alkenyl or substituted or unsubstituted phenyl,R.sup.2 is cyano, carbamoyl, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkanoyl, substituted or unsubstituted benzoyl, halogen or nitro,R.sup.3 is hydrogen, andR.sup.4 is substituted or unsubstituted C.sub.1 -C.sub.12 -alkanoyl, C.sub.1 -C.sub.12 -alkoxycarbonyl, substituted carbamoyl, substituted or unsubstituted C.sub.1 -C.sub.12 -alkylsulfonyl, C.sub.5 -C.sub.7 -cycloalkylsulfonyl, substituted or unsubstituted arylsulfonyl or hetarylsulfonyl, substituted or unsubstituted arylcarbonyl or hetarylcarbonyl, or R.sup.3 and R.sup.4 together with the nitrogen atom joining them together are a heterocyclic radical,comprises reacting the carbonyl compounds of the formulae II and III ##STR2## where Y is oxygen or imino and one of the radicals X.sup.1 and X.sup.Type: GrantFiled: June 7, 1994Date of Patent: November 14, 1995Assignee: BASF AktiengesellschaftInventors: Stefan Beckmann, Ernst Schefczik
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Patent number: 5418245Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: March 17, 1994Date of Patent: May 23, 1995Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.Inventors: Alfred P. Spada, Paul E. Persons