Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/297)
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Patent number: 4931457Abstract: 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: GrantFiled: June 28, 1989Date of Patent: June 5, 1990Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Richard C. Effland, Joseph T. Klein, Gordon E. Olsen, Larry Davis
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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: 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: 4916229Abstract: 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: GrantFiled: August 26, 1988Date of Patent: April 10, 1990Assignee: Warner-Lambert CompanyInventor: John S. Kiely
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Patent number: 4895842Abstract: 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: GrantFiled: September 29, 1986Date of Patent: January 23, 1990Assignees: Shosuke Okamoto, Showa Denko Kabushiki KaishaInventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Yumi Seki
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Patent number: 4889865Abstract: 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: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4885026Abstract: 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: May 12, 1986Date of Patent: December 5, 1989Assignee: Monsanto CompanyInventors: Len F. Lee, Mark G. Dolson
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Patent number: 4882341Abstract: The invention relates to amino substituted propenoates and their use against fungi.Type: GrantFiled: September 9, 1988Date of Patent: November 21, 1989Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Kay
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Patent number: 4871387Abstract: 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: GrantFiled: December 4, 1986Date of Patent: October 3, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Sasse, Reiner Fischer, Hermann Hagemann, Hans-Joachim Santel, Robert R. Schmidt, Kalus Lurssen
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Patent number: 4866078Abstract: 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: August 27, 1987Date of Patent: September 12, 1989Assignee: Imperial Chemical Industries PLCInventors: Trevor R. Perrior, David J. Tapolczay
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Patent number: 4863938Abstract: 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: GrantFiled: October 31, 1988Date of Patent: September 5, 1989Assignee: Ciba-Geigy CorporationInventors: Georg von Sprecher, Peter Waldmeier
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Patent number: 4863924Abstract: 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: GrantFiled: December 8, 1986Date of Patent: September 5, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Nobutoshi Yamada, Hideo Sugi, Toru Koyanagi, Hiroshi Okada
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Patent number: 4863939Abstract: 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: GrantFiled: July 30, 1987Date of Patent: September 5, 1989Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
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Patent number: 4863936Abstract: Various substituted aminoalkylamino-2-pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.Type: GrantFiled: October 21, 1986Date of Patent: September 5, 1989Assignee: Smith Kline & French Laboratories LimitedInventor: George S. Sach
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Patent number: 4859663Abstract: 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: GrantFiled: December 16, 1986Date of Patent: August 22, 1989Assignee: Hoechst AktiengesellschaftInventors: Wilfried Greve, Ulrich Elben, Karl Rudolph, Ursula Schindler
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Patent number: 4853395Abstract: 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: GrantFiled: November 17, 1987Date of Patent: August 1, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 4851535Abstract: 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: GrantFiled: June 29, 1987Date of Patent: July 25, 1989Assignee: 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
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Patent number: 4849522Abstract: 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: GrantFiled: March 10, 1988Date of Patent: July 18, 1989Assignee: Merrell Dow PharmaceuticalsInventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
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Patent number: 4840953Abstract: 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: GrantFiled: June 15, 1988Date of Patent: June 20, 1989Assignee: Shionogi & Co., Ltd.Inventors: Shigeru Matsutani, Yukio Mizushima, Masami Doteuchi, Yasunobu Ishihara
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Patent number: 4831044Abstract: 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: GrantFiled: October 29, 1987Date of Patent: May 16, 1989Assignee: ICI Americas Inc.Inventors: Don R. Baker, Keith H. Brownell
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Patent number: 4826531Abstract: 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: GrantFiled: April 17, 1987Date of Patent: May 2, 1989Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 4826987Abstract: 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: GrantFiled: February 28, 1986Date of Patent: May 2, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
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Patent number: 4826505Abstract: 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: GrantFiled: February 8, 1988Date of Patent: May 2, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
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Patent number: 4818273Abstract: 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: GrantFiled: December 10, 1986Date of Patent: April 4, 1989Assignee: The Dow Chemical CompanyInventors: William A. Kleschick, Robert J. Ehr, Mark J. Costales, Ben C. Gerwick, III, Richard W. Meikle, deceased, William T. Monte, Pearson, Norman R.
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Patent number: 4818766Abstract: 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: GrantFiled: July 20, 1987Date of Patent: April 4, 1989Assignee: Ciba-Geigy CorporationInventors: Franz Ostermayer, Markus Zimmermann
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Patent number: 4800205Abstract: 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: GrantFiled: October 29, 1987Date of Patent: January 24, 1989Inventors: Don R. Baker, Francis H. Walker, Keith H. Brownell
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Patent number: 4798893Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.Type: GrantFiled: September 21, 1987Date of Patent: January 17, 1989Assignee: McNeilab, Inc.Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
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Patent number: 4797490Abstract: 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: GrantFiled: September 15, 1986Date of Patent: January 10, 1989Assignee: Pfizer Inc.Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
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Patent number: 4792606Abstract: 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: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall
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Patent number: 4791123Abstract: 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: GrantFiled: January 22, 1987Date of Patent: December 13, 1988Assignee: Schering Akt.Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
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Patent number: 4786317Abstract: 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: GrantFiled: September 5, 1986Date of Patent: November 22, 1988Assignee: Celamerck GmbH & Co. KGInventors: Rudolf Mengel, Ludwig Schroder, Werner Stransky, Gerbert Linden, Sigmund Lust
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Patent number: 4783485Abstract: 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: GrantFiled: September 26, 1986Date of Patent: November 8, 1988Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof Van Hes
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Patent number: 4778895Abstract: 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: GrantFiled: April 6, 1987Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventors: Eric Francotte, Peter Ackermann
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Patent number: 4767771Abstract: 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: GrantFiled: April 15, 1987Date of Patent: August 30, 1988Assignee: Stauffer Chemical Co.Inventors: Don R. Baker, Keith H. Brownell
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Patent number: 4762848Abstract: 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: GrantFiled: March 10, 1986Date of Patent: August 9, 1988Assignee: Hoechst AktiengesellschaftInventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
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Patent number: 4762932Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.Type: GrantFiled: June 2, 1986Date of Patent: August 9, 1988Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4761481Abstract: 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: GrantFiled: March 18, 1985Date of Patent: August 2, 1988Assignee: Baxter Travenol Laboratories, Inc.Inventors: Ron L. Hale, Dennis W. Solas
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Patent number: 4759796Abstract: 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: GrantFiled: October 16, 1986Date of Patent: July 26, 1988Assignee: Ciba-Geigy CorporationInventors: Beat Bohner, Hermann Rempfler, Rolf Schurter
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Patent number: 4756739Abstract: 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: GrantFiled: December 19, 1986Date of Patent: July 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Andreas Fuss, Volker Koch
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Patent number: 4748244Abstract: 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: GrantFiled: May 3, 1985Date of Patent: May 31, 1988Assignee: Ciba-Geigy CorporationInventors: Adrian Waldner, Achim Roloff, Daniel Bellus
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Patent number: 4748165Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.Type: GrantFiled: May 11, 1982Date of Patent: May 31, 1988Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4739070Abstract: 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: GrantFiled: April 23, 1986Date of Patent: April 19, 1988Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4738969Abstract: This invention relates to 2-substituted aminopyridone compounds which have histamine H.sub.2 -antagonist activity.Type: GrantFiled: June 19, 1986Date of Patent: April 19, 1988Assignee: Smith Kline & French Laboratories LimitedInventor: Thomas H. Brown
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Patent number: 4732982Abstract: 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: GrantFiled: February 28, 1986Date of Patent: March 22, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 4719303Abstract: A method for the preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethyl-propyl) carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids.Type: GrantFiled: November 21, 1983Date of Patent: January 12, 1988Assignee: American Cyanamid CompanyInventors: William H. Gastrock, Timothy F. Mason, Gregory P. Withers
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Patent number: 4701531Abstract: A process for preparing O-alkylated halopyridinate compounds is described. The process does not require the use of added organic solvents.Type: GrantFiled: December 1, 1986Date of Patent: October 20, 1987Assignee: The Dow Chemical CompanyInventor: Timothy J. Adaway
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Patent number: 4690708Abstract: 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: GrantFiled: July 11, 1984Date of Patent: September 1, 1987Assignee: Rhone-Poulenc AgrochimieInventors: Alain Chene, Guy Borrod
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Patent number: 4665097Abstract: Novel bicyclooxyaryl thioureas are provided together with methods for their preparation and use as the active toxicant in pesticidal compositions.Type: GrantFiled: March 31, 1983Date of Patent: May 12, 1987Assignee: Union Carbide CorporationInventor: Paul A. Cain
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Patent number: 4665073Abstract: 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: GrantFiled: March 14, 1984Date of Patent: May 12, 1987Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman
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Patent number: 4659724Abstract: 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: GrantFiled: April 26, 1985Date of Patent: April 21, 1987Assignee: Union Carbide CorporationInventor: David T. Chou