Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/297)
  • Patent number: 4931457
    Abstract: There are described compounds of the formula ##STR1## where R is hydrogen, loweralkyl, arylloweralkyl or loweralkylcarbonyl;X is O or NR.sub.1, R.sub.1 being hydrogen, loweralkyl or loweralkylcarbonyl; andY is hydrogen, loweralkyl, loweralkoxy, halogen or trifluoromethyl;which compounds are useful as topical antiinflammatory agents for the treatment of skin disorders.
    Type: Grant
    Filed: June 28, 1989
    Date of Patent: June 5, 1990
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Richard C. Effland, Joseph T. Klein, Gordon E. Olsen, Larry Davis
  • Patent number: 4921867
    Abstract: 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: Grant
    Filed: February 9, 1988
    Date of Patent: May 1, 1990
    Assignee: Glaxo Group Limited
    Inventor: Lawrence H. C. Lunts
  • Patent number: 4920225
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: April 24, 1990
    Assignee: Laboratoires Syntex S.A.
    Inventor: Gilles Genain
  • Patent number: 4916229
    Abstract: The present invention covers a novel process for preparing substituted naphthyridines which are useful as intermediates in the production of certain antibacterial agents such as enoxacin. Also covered are novel intermediates in the process and methods for preparing them.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: April 10, 1990
    Assignee: Warner-Lambert Company
    Inventor: John S. Kiely
  • Patent number: 4895842
    Abstract: A phenylalanine derivative having the formula (I): ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen provided that both R.sup.1 and R.sup.2 are not hydrogen at the same time;C.sub.1 -C.sub.8 alkyl which may be substituted with hydroxy, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkoxy, carbamoyl, sulfamoyl, pyridyl, or phenyl which may further be substituted with nitro, C.sub.1 -C.sub.4 alkoxy, or halogen;C.sub.6 -C.sub.8 cycloalkyl which may be substituted with hydroxy, C.sub.1 -C.sub.4 alkoxy, hydroxylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or C.sub.1 -C.sub.4 alkyl;phenyl which may be substituted with halogen, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkylcarbonyl, phenylcarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl, sulfamoyl, amidino, pyridylcarbonyl, or C.sub.1 -C.sub.6 alkyl which may further be substituted with C.sub.1 -C.sub.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: January 23, 1990
    Assignees: Shosuke Okamoto, Showa Denko Kabushiki Kaisha
    Inventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Yumi Seki
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4885026
    Abstract: 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: Grant
    Filed: May 12, 1986
    Date of Patent: December 5, 1989
    Assignee: Monsanto Company
    Inventors: Len F. Lee, Mark G. Dolson
  • Patent number: 4882341
    Abstract: The invention relates to amino substituted propenoates and their use against fungi.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Ian T. Kay
  • Patent number: 4871387
    Abstract: New pyri(mi)dyl-oxy- or -thio-benzoic acid derivatives of the formula ##STR1## are taught which have herbicidal and plant growth regulating activity. In the formula Z can be Ch or N, X is oxygen or sulphur, A is oxygen, sulphur, a radical R.sup.5 --N.dbd.or a radical R.sup.6 O--N.dbd.and B is oxygen, sulphur, a radical ##STR2## with the proviso that at least one of the radicals R.sup.1, R.sup.2 or R.sup.3 represents alkyl or a part of a 3- to 6-membered fused carbocyclic ring.
    Type: Grant
    Filed: December 4, 1986
    Date of Patent: October 3, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Sasse, Reiner Fischer, Hermann Hagemann, Hans-Joachim Santel, Robert R. Schmidt, Kalus Lurssen
  • Patent number: 4866078
    Abstract: 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: Grant
    Filed: August 27, 1987
    Date of Patent: September 12, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Trevor R. Perrior, David J. Tapolczay
  • Patent number: 4863938
    Abstract: Pyridine derivatives of the formula ##STR1## their tautomers and their salts, in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n have the meanings given in the claims, can be used as active ingredients in medicaments and are manufactured in a manner known per se.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: September 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg von Sprecher, Peter Waldmeier
  • Patent number: 4863924
    Abstract: An N-benzoyl urea compound having the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom or a nitro group, n is an integer of from 1 to 3, and Q is ##STR2## wherein Y.sub.1 is an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Y.sub.2 is a hydrogen atom, a halogen atom, a nitro group, an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Z is a hydrogen atom, a halogen atom, a trifluoromethyl group or a nitro group, and each of A and B is .dbd.CH-- or a nitrogen atom, provided that one of A and B is .dbd.CH-- and the other is a nitrogen atom, with the provisos (1) that when Q is ##STR3## where when X is a hydrogen atom and Y.sub.1 is an alkyl group, Z is not a hydrogen atom, a halogen atom nor a trifluoromethyl group, and (2) that when Q is ##STR4## wherein A is a nitrogen atom and Y.sub.1 is a trifluoromethyl group, Y.sub.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: September 5, 1989
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Nobutoshi Yamada, Hideo Sugi, Toru Koyanagi, Hiroshi Okada
  • Patent number: 4863939
    Abstract: The growth of livestock is promoted by the new compounds of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, halogen, halogenoalkyl, hydroxyl, cyano, alkoxycarbonyl, aminocarbonyl, mono- and dialkylaminocarbonyl, alkoxy, halogenoalkoxy, halogenoalkylthio or NHSO.sub.2 -alkyl,R.sup.2 represents hydrogen, hydroxyl, alkoxy or the --NR.sup.11 R.sup.12 radical,R.sup.3 represents the radicals mentioned in the case of R.sup.1R.sup.4 represents hydroxyl, acyloxy or alkoxy,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen or alkyl,R.sup.7 represents hydrogen or alkyl,R.sup.8 represents hydrogen or alkyl,X represents C.sub.1 -C.sub.10 -alkylene or a direct bond,Y represents oxygen or a direct bond,R.sup.9 represents hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by hydroxyl, alkoxy, acyloxy or the --NR.sup.13 R.sup.14 radical, or represents the COR.sup.15 radical or the O--Z--R.sup.16 radical,Z represents C.sub.1 -C.sub.10 -alkylene, C.sub.1 -C.sub.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: September 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
  • Patent number: 4863936
    Abstract: Various substituted aminoalkylamino-2-pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: October 21, 1986
    Date of Patent: September 5, 1989
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George S. Sach
  • Patent number: 4859663
    Abstract: Multiply substituted pyridine 1-oxides of the formula I ##STR1## in which R.sup.1 and R.sup.2 are, in each case, identical or different and represent alkyl having 1 to 6 carbon atoms,R.sup.3 denotes hydrogen, andR.sup.4 denotes mercaptoalkyl having up to 4 carbon atoms, orR.sup.3 and R.sup.4 form, together with the nitrogen atom in the 4-position, a five- to seven-membered saturated heterocyclic ring which has up to 2 heteroatoms, the second heteroatom being oxygen, sulfur which can carry up to two oxygen atoms, or nitrogen in the form of the NR.sup.6 group, in which R.sup.
    Type: Grant
    Filed: December 16, 1986
    Date of Patent: August 22, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilfried Greve, Ulrich Elben, Karl Rudolph, Ursula Schindler
  • Patent number: 4853395
    Abstract: Novel 5-acyl-2-(1H)pyridinones 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: Grant
    Filed: November 17, 1987
    Date of Patent: August 1, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
  • Patent number: 4851535
    Abstract: This invention relates to a process for industrially producing a 1-substituted aryl-1,4-dihydro-4-oxonaphthyridine derivative and a salt thereof which are useful as an antibacterial agent, and also to intermediates therefor and processes for producing the intermediates.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: July 25, 1989
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Yozo Todo, Tetsuo Yamafuji, Katsuyuki Nagumo, Isao Kitayama, Hideyoshi Nagaki, Mikako Miyajima, Yoshinori Konishi, Hirokazu Narita, Shuntaro Takano, Isamu Saikawa
  • Patent number: 4849522
    Abstract: This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: July 18, 1989
    Assignee: Merrell Dow Pharmaceuticals
    Inventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
  • Patent number: 4840953
    Abstract: 9-(Substituted thio)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives of the formula: ##STR1## wherein n is 0 or 1, R is --COR.sup.1, --CONR.sup.4 R.sup.5 or --CH.sub.2 R.sup.6, R.sup.1 is C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allythio, styryl, phenoxymethyl, thienylmethyl, C.sub.6 -C.sub.10 aryl optionally substituted, benzyl optionally substituted or 5- or 6-membered heterocyclic group optionally substituted, R.sup.2 and R.sup.3 each is hydrogen, C.sub.1 -C.sub.5 alkyl, carboxy, C.sub.2 -C.sub.5 alkoxycarbonyl or benzyloxycarbonyl optionally substituted, R.sup.4 and R.sup.5 each is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl or phenyl optionally substituted, and R.sup.8 is pyridyl or phenyl optionally substituted) being useful as antiulcer agents are provided through several routes.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: June 20, 1989
    Assignee: Shionogi & Co., Ltd.
    Inventors: Shigeru Matsutani, Yukio Mizushima, Masami Doteuchi, Yasunobu Ishihara
  • Patent number: 4831044
    Abstract: Novel fungicidal pyridyl cyclopropane carboxamidines having the general structural formula ##STR1## and tautomers thereof wherein R is selected from the group consisting of hydrogen, pyridyl, substituted pyridyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.6 alkyl, acyl, carbamoyl, sulfonyl and cyano;R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.2 -C.sub.3 alkenyloxy;R.sub.2 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl;R.sub.3 is selected from the group consisting of hydrogen, alkyl, aryl or arylalkyl;and fungicidally acceptable organic and inorganic salts thereof.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: May 16, 1989
    Assignee: ICI Americas Inc.
    Inventors: Don R. Baker, Keith H. Brownell
  • Patent number: 4826531
    Abstract: 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 or --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: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4826987
    Abstract: The present invention relates to compounds of formula I ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: May 2, 1989
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 4826505
    Abstract: A monoazo pyridone compound of the following formula, ##STR1## wherein X is a member selected from hydrogen, halogeno, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or cyano, and R is alkyl, alkenyl, cycloalkyl, phenyl or anilino, with the provisos that X is a member selected from those defined above except for hydrogen, chloro, methyl and methoxy when R is ethyl, and X is a member selected from those defined above except for alkyl when R is iso-butyl, which is stable under dyeing conditions, and useful for dyeing hydrophobic fiber materials to give dyed products of a deep, fast and brilliant color of greenish yellow to orange.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
  • Patent number: 4818273
    Abstract: Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salts are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: April 4, 1989
    Assignee: The Dow Chemical Company
    Inventors: William A. Kleschick, Robert J. Ehr, Mark J. Costales, Ben C. Gerwick, III, Richard W. Meikle, deceased, William T. Monte, Pearson, Norman R.
  • Patent number: 4818766
    Abstract: The invention relates to novel 1,4-dihydropyridine-3-carboxylic acid phenoxyaliphatylphenyleneoxyalkyl esters of the formula ##STR1## in which Ac represents an acyl group, X represents oxy or optionally substituted imino, A represents a divalent aliphatic hydrocarbon radical interrupted by a group --X.sub.1 --Ph--X.sub.2 -- in which at least one of the radicals X.sub.1 and X.sub.2 represents oxy and a radical X.sub.1 or X.sub.2 that is other than oxy represents a direct bond, and Ph represents an optionally substituted phenylene radical, and R represents an optionally substituted phenyl, pyridyl or 1-oxidopyridyl, (1,3-dioxa)indanyl or benzofurazanyl radical, R.sub.1 represents an optionally substituted phenyl or indolyl radical, R.sub.2 represents an aliphatic hydrocarbon radical and R.sub.3 represents an aliphatic radical, cyano or amino, and acid addition salts thereof.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: April 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Franz Ostermayer, Markus Zimmermann
  • Patent number: 4800205
    Abstract: Novel fungicidal pyridyl sulfenyl carbamates having the formula ##STR1## wherein R is selected from the group consisting of haloalkyl, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, alkanoyl, alkylamino, arylamino, arylalkylamino and substituted pyridylcarbamoyl;R.sub.1 is C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy or halomethoxy; alkenyloxy; and halogen;R.sub.2 is C.sub.1 -C.sub.3 alkyl;X is oxygen or sulfur; andY is oxygen or sulfurand fungicidally acceptable organic and inorganic salts thereof which are highly effective fungicides for use both as preventive and curative fungicides are disclosed herein.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: January 24, 1989
    Inventors: Don R. Baker, Francis H. Walker, Keith H. Brownell
  • Patent number: 4798893
    Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: January 17, 1989
    Assignee: McNeilab, Inc.
    Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
  • Patent number: 4797490
    Abstract: 6-Fluoro-7-pyridylquinolone carboxylic esters and acids having antibacterial activity are prepared by coupling of a 2-fluorophenyl-metallic compound with a pyridyl bromide or iodide in the presence of a transition metal catalyst, nitrating and hydrogenating the pyridyl-2-fluorophenyl compound formed, introducing a substituent on the nitrogen of the amine formed, and cyclizing after reacting with a dialkyl or dibenzyl ethoxymethylene malonate to form a 6-fluoro-7-pyridyl-1,4-dihydroquinol-4-one 3-carboxylate, and hydrolyzing to the corresponding acid.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: January 10, 1989
    Assignee: Pfizer Inc.
    Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
  • Patent number: 4792606
    Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: December 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hermann-Dieter Krall
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4786317
    Abstract: Compounds of the formula ##STR1## wherein W and X, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Y is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Z is fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms, chloro-substituted alkyl of 1 to 4 carbon atoms, --COOH or --COO-(alkyl of 1 to 4 carbon atoms); andn is 0 or 1;and, when Z is COOH, salts thereof, especially their alkali metal salts. The compunds as well as the salts are useful as selective herbicides.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: November 22, 1988
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Rudolf Mengel, Ludwig Schroder, Werner Stransky, Gerbert Linden, Sigmund Lust
  • Patent number: 4783485
    Abstract: The invention relates to new benzoylurea compounds having insecticidal and acaricidal activity, of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom or represents 1 or 2 halogen atoms;Ar is a para-phenylene group or a para-pyridylene group, which groups may be substituted with 1 or 2 substituents selected from the group consisting of chlorine, methyl and trifluoromethyl;B is an oxygen atom or represents a group having the formula ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: November 8, 1988
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof Van Hes
  • Patent number: 4778895
    Abstract: The invention relates to enantiomers of 1-(6-phenoxy-2-pyridyl)ethanols of the formula ##STR1## wherein * is (+) or (-) and X and Y are each independently of the other hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.2 -C.sub.5 alkynyl.The invention also relates to the preparation of these enantiomers and to their use for the preparation of biocidal compounds.
    Type: Grant
    Filed: April 6, 1987
    Date of Patent: October 18, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Eric Francotte, Peter Ackermann
  • Patent number: 4767771
    Abstract: Novel fungicidal pyridyl imidates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 14 C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are --Cl, --Br, --F and --NO.sub.2, furfuryl pyridyl, C.sub.1 -C.sub.6 alkyl substituted phosphorus, and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring, R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.2 is selected from the group consisting of methyl and hydrogen, and X is S or O; and fungicidally accepable organic and inorganic salts thereof.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: August 30, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Don R. Baker, Keith H. Brownell
  • Patent number: 4762848
    Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4762932
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: August 9, 1988
    Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4761481
    Abstract: It is disclosed that aryl-substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl] pyridines in which the aryl groups are substituted with one or more electron-releasing groups are an advantageous ligand for forming fluorescent chelates with rare earth metals. The pyridine moieties can be linked to target molecules, especially biologically active target molecules to provide fluorescent tagging for use in fluoroassay techniques. The pyridine moieties are disclosed as tetraacids, as salts and as esters. Preparation processes and precursors including the corresponding aryl-substituted 2,6-dicarboxypyridines as acids, salts and esters, are disclosed as well.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: August 2, 1988
    Assignee: Baxter Travenol Laboratories, Inc.
    Inventors: Ron L. Hale, Dennis W. Solas
  • Patent number: 4759796
    Abstract: 2-Phenoxypropionic acid cyanamides of the formula ##STR1## have a useful selective herbicidal activity against weeds, preferably grass weeds, in crops of useful plants.In this formulaR is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C.sub.2 -C.sub.4 alkoxyalkyl, andT is a radical ##STR2## wherein A is oxygen or sulfur,X is fluorine, chlorine, bromine, iodine or trifluoromethyl,Y is hydrogen, fluorine, chlorine, bromine or trifluoromethyl, andZ is nitrogen or the methine bridge.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: July 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat Bohner, Hermann Rempfler, Rolf Schurter
  • Patent number: 4756739
    Abstract: The compounds of the formula I ##STR1## in which A denotes N or N.fwdarw.O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R.sup.1 denotes hydrogen, halogen, amino, --NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N--, Y.sup.1 Y.sup.2 C.dbd.N--, Y.sup.3 NH-- or ##STR2## K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH.sub.2, (R.sup.1).sub.n denotes at least one radical of the formula ##STR3## or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Fuss, Volker Koch
  • Patent number: 4748244
    Abstract: The invention relates to a process for the preparation of pyridine-2,3-dicarboxylic acid derivatives of formula ##STR1## which process comprises reacting a hydrazone of formula II ##STR2## with a maleic acid derivative of formula III ##STR3## to give a 1-amino-1,4-dihydropyridine-2,3-dicarboxylic acid derivative of formula IV ##STR4## and subsequently removing R.sub.9 R.sub.10 NH. In the above formulae, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.9, R.sub.10 and X are as defined in claim 1. The pyridine-2,3-dicarboxylic acid derivatives of formula I are intermediates for the preparation of herbicidal compounds.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: May 31, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Adrian Waldner, Achim Roloff, Daniel Bellus
  • Patent number: 4748165
    Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 31, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4739070
    Abstract: 2- and 4-(Dichloromethyl)pyridines containing electron withdrawing substituents on the ring are prepared by the reaction of the corresponding 2- or 4-halopyridines with excess chloroform in the presence of a strong base in a medium containing a dipolar aprotic solvent or a phase transfer catalyst. 3-Chloro-5-(trifluoromethyl)-2-(dichloromethyl)pyridine, for example, is prepared by the reaction of 2,3-dichloro-5-(trifluoromethyl)pyridine with chloroform in the presence of sodium hydroxide and N-methylpyrrolidone. Substituted 2-(dichloromethyl)pyridines are useful as agricultural pesticides and as intermediates for the preparation of agricultural pesticides.
    Type: Grant
    Filed: April 23, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4738969
    Abstract: This invention relates to 2-substituted aminopyridone compounds which have histamine H.sub.2 -antagonist activity.
    Type: Grant
    Filed: June 19, 1986
    Date of Patent: April 19, 1988
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: Thomas H. Brown
  • Patent number: 4732982
    Abstract: This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: March 22, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
  • Patent number: 4719303
    Abstract: A method for the preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethyl-propyl) carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: January 12, 1988
    Assignee: American Cyanamid Company
    Inventors: William H. Gastrock, Timothy F. Mason, Gregory P. Withers
  • Patent number: 4701531
    Abstract: A process for preparing O-alkylated halopyridinate compounds is described. The process does not require the use of added organic solvents.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: October 20, 1987
    Assignee: The Dow Chemical Company
    Inventor: Timothy J. Adaway
  • Patent number: 4690708
    Abstract: A herbicide of the formula: ##STR1## in which: Z is N or CX',W, Y, Y', X, Z' and X' represent H, a halogen atom, NO.sub.2, CN or a polyhalogenoalkyl, alkyl or alkoxy group,R.sup.2 represents H, halogen, substituted alkyl, allyl, propargyl, CN, NR.sup.4 R.sup.5, C(X.sup.2)R.sup.7, C(X.sup.2)X.sup.3 R.sup.8, C(X.sup.2)NR.sup.4 R.sup.5, SO.sub.2 F, SO.sub.2 OR.sup.8, SO.sub.2 NR.sup.4 R.sup.5 or P(X.sup.2)R.sup.9 R.sup.10,R.sup.1 is halogen, X.sup.2 R.sup.3 or NR.sup.4 R.sup.5,R.sup.3 is optionally substituted alkyl or is allyl or propargyl,R.sup.4, R.sup.7 and R.sup.8 represent H, alkyl, cycloalkyl, phenyl, allyl, propargyl or the like,R.sup.5 represents R.sup.4, a cation or OR.sup.6, R.sup.6 being H, a cation or alkyl,X.sup.2 and X.sup.3 are O or S,R.sup.9 and R.sup.10 are H, alkyl, OH, OM or R.sup.1, andM is a cation.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: September 1, 1987
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Alain Chene, Guy Borrod
  • Patent number: 4665097
    Abstract: Novel bicyclooxyaryl thioureas are provided together with methods for their preparation and use as the active toxicant in pesticidal compositions.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: May 12, 1987
    Assignee: Union Carbide Corporation
    Inventor: Paul A. Cain
  • Patent number: 4665073
    Abstract: The invention relates to guanidine 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 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-15C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: May 12, 1987
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4659724
    Abstract: Novel pyridyloxyaryl benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in insecticidal compositions.
    Type: Grant
    Filed: April 26, 1985
    Date of Patent: April 21, 1987
    Assignee: Union Carbide Corporation
    Inventor: David T. Chou