Nitrogen Bonded Directly To The Bicyclo Ring System Patents (Class 549/439)
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Patent number: 5189060Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.4 haloalkyl; orR.sub.1 and R.sub.2 taken together are C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy; provided that R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen;R.sub.4 is methyl, ethyl, n-propyl, C.sub.3 -C.sub.7 branched alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.4 alkenyl; or cyclopropyl, optionally substituted by up to 4 methyl groups or up to 2 halogens;R.sub.5 is: ##STR2## R.sub.6 is phenyl, benzyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 alkynyl; R.sub.7, R.sub.8, R.sub.10 and R.sub.11 are each halogen; andR.sub.Type: GrantFiled: November 30, 1990Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: David B. Kanne, Karl J. Fisher, Michael D. Broadhurst
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Patent number: 5141955Abstract: Anti-inflammatory benzylselanobenzamides made from anilines and benzylamines have the formula I ##STR1## are disclosed wherein R is hydrogen, methyl or ethyl;R.sup.1 and R.sup.2 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, amino, dimethylamino or nitro; andR.sup.3 and R.sup.4 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, or nitro and, taken together, represent methylenedioxy; andn is 0.1 or 2.Type: GrantFiled: November 8, 1990Date of Patent: August 25, 1992Assignee: A. Nattermann & Cie. GmbHInventors: Michel Evers, Hartmut Fischer, Jurgen Biedermann, Rolf Terlinden, Sigurd Leyck
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Patent number: 5102905Abstract: The invention concerns heterocyclic nitromethane derivatives of the formula 1 as defined hereinafter (and their non-toxic salts) wherein the heterocyclic moiety Q is thienyl, benzothienyl or dibenzothienyl and may bear a wide variety of optional substituents, together with pharmaceutical compositions containing them. The nitromethane derivatives are inhibitors of the enzyme aldose reductase and are of value in the treatment of certain complications of diabetes and galactosemia.Type: GrantFiled: April 28, 1989Date of Patent: April 7, 1992Assignee: Imperial Chemical Industries PLCInventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey Morris, John Preston
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Patent number: 5070210Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.sub.6 alkenyl; andR.sub.Type: GrantFiled: May 7, 1990Date of Patent: December 3, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cormartie, Karl J. Fisher, William G. Haag, David B. Kanne, Michael R. Leadbetter
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Patent number: 5066657Abstract: A crotonic acid amide derivative represented by formula (I): ##STR1## wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, and X.sub.5, which may be the same or different, each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkyl group, a lower haloalkyl group, a lower haloalkoxy group, a nitro group, a substituted or unsubstituted lower alkanesulfonyl group, a substituted or unsubstituted alkanesulfonyloxy group, a substituted or unsubstituted benzenesulfonyl group, a substituted or unsubstituted benzenesulfonyloxy group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted benzyloxy group, a dialkylamino group, a mono- or di-lower alkanesulfonylamino group, a substituted or unsubstituted lower alkythio group, a --SO.sub.2 R.sub.1 wherein R.sub.1 represents a lower alkyl group or a lower haloalkyl group, a lower alkoxycarbonyloxy group, a substituted or unsubstituted alkoxycarbonyl group, a --CH.dbd.N--OR.sub.Type: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: SDS Biotech K.K.Inventors: Shunji Hayashi, Satoshi Yamanaka, Sayoko Kawaguchi, Teruhiko Ishii, Toshiya Kimata, Naoaki Misu
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Patent number: 5053052Abstract: 2-Substituted para-aminophenols of general formula: ##STR1## where Y denotes oxygen or sulphur and R denotes a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl or C.sub.1 -C.sub.6 haloalkyl or a C.sub.2 -C.sub.6 polyhydroxyalkyl, provided that when Y=O, R is not methyl or ethyl and when Y=S, R is not ethyl; and dye composition containing one or more compounds of formula (I) where Y denotes an oxygen or sulphur atom and R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 haloalkyl or C.sub.2 -C.sub.6 polyhydroxyalkyl.Type: GrantFiled: December 28, 1990Date of Patent: October 1, 1991Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Alain Genet
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Patent number: 5045566Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy; C.sub.1 -C.sub.4 alkylendioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -haloalkenoxy; and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.Type: GrantFiled: April 27, 1989Date of Patent: September 3, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cromartie, Karl J. Fisher, William G. Haag
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Patent number: 4996316Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.Type: GrantFiled: December 24, 1988Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4988730Abstract: The invention relates to novel diphenylpropylamine derivatives of the general formula (I). ##STR1## R.sup.1 stands for hydrogen or a methyl group; R.sup.2 stands for hydrogen, a methyl or n-decyl group;Z means a phenyl group substituted by R.sup.3, R.sup.4 and R.sup.5, whereinR.sup.3 means hydrogen, fluorine, chlorine or bromine, or a nitro, C.sub.1-12 alkyl, C.sub.1-4 alkoxy, phenoxy or benzyloxy group;R.sup.4 and R.sup.5 represent hydrogen, chlorine or a hydroxy, alkoxy, benzyloxy, acetamino or carboxy group; orR.sup.4 and R.sup.5 together form a methylendioxy group;orZ may stand for a 4-methoxynaphtyl or 4-ethoxy-naphthyl group; andR.sup.6 stands for hydrogen or fluorine, with the proviso that each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.6 cannot simultaneously stand for hydrogen, as well as their physiologically acceptable acid addition salts.The invention also relates to a process for the preparation of these compounds and to the pharmaceutical compositions containing these compounds.Type: GrantFiled: July 21, 1989Date of Patent: January 29, 1991Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyar RTInventors: Dezso Korbonits, Pal Kiss, Laszlo Szekeres, Gyula Papp, Gabor Kovacs, Andrea Santane Csutor, Sandor Virag, Eva Udvari, Imre Bata, Katalin Marmarosi nee Kellner, Laszlo Tardos, Peter Kormoczy, Vera Gergely, Zoltan Vargai
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Patent number: 4975456Abstract: Novel N-(substituted-phenyl)-5-(substituted-2,5-dimethylphenoxy)-2,2- dimethylpentanamides which are useful in preventing the intestinal absorption of cholesterol and also increasing high-density lipoprotein (HDL) cholesterol, as well as novel pharmaceutical compositions and methods of use, as well as processes for their manufacture are herein described.Type: GrantFiled: July 13, 1989Date of Patent: December 4, 1990Assignee: Warner-Lambert CompanyInventors: Paul L. Creger, Milton L. Hoefle, Ann Holmes
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Patent number: 4968717Abstract: Compounds of the formula ##STR1## where R.sup.1 to R.sup.7, m, n and p have the meanings stated in the description, and certain derivatives which are p-substituted in the left-hand phenyl ring, are useful for the treatment of disorders.Type: GrantFiled: May 12, 1989Date of Patent: November 6, 1990Assignee: BASF AktiengesellschaftInventors: Liliane Unger, Manfred Raschack, Verena Baldinger, Ferdinand Dengel, Oskar Ehrmann, Hans J. Treiber, Werner Seitz
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Patent number: 4956460Abstract: A process for the preparation of 1-alkyl-3-carboxy-4-cinnolones of formula I ##STR1## wherein R and R.sub.1 are electron donor groups and R.sub.3 is an alkyl group, starting from an amine of formula II ##STR2## which is subjected to the following transformations; (1) diazotation;(2) coupling with a cyanoacetic ester;(3) alkylation of the arylhydrazone obtained in (2);(4) hydrolysis of the ester and conversion into acyl chloride;(5) intramolecular cyclization;(6) hydrolysis of the nitrile residue.Type: GrantFiled: March 23, 1988Date of Patent: September 11, 1990Assignee: Industria Chimica Profarmaco S.p.A.Inventors: Raffaello Fusco, Fulvio L. Piselli, Pier M. Boschi
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Patent number: 4939141Abstract: A (fused) benz(thio)amides of the general ##STR1## (wherein, symbol A represents a single bond or a group of methylene, ethylene, trimethylene, tetramethylene, vinylene, propenylene, butenylene, butadienylene or ethynylene group optionally being substituted by one, two or three of straight or branched alkyl groups(s) of from 1 to 10 carbon atom(s) and/or phenyl group(s);Symbol B represents(i) a heterocyclic ring of from 4 to 8 members containing one, two or three hetero atoms selected from oxygen, nitrogen and/or sulphur atom(s), wherein the ring may optionally be substituted by group(s) of oxo, thioxo and/or hydroxy group(s) with the exclusion of a ring of the formula: ##STR2## Symbol T represents an oxygen atom or a sulphur atom; R.sup.1 represents a group of general formula:(i) ##STR3## (ii) ##STR4## or (iii) ##STR5## or (iv) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 20 carbon atom(s);(wherein R.sup.5 and R.sup.Type: GrantFiled: April 4, 1989Date of Patent: July 3, 1990Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
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Patent number: 4904775Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof and possessing antibacterial activity, and intermediates to compounds of formula I having the formulaType: GrantFiled: May 16, 1988Date of Patent: February 27, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, Peter H. Ermann
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Patent number: 4894472Abstract: The invention relates to new dicyanoethylaryl derivatives and to processes for their preparation. The compounds according to the invention can be used as redox indicators, such as, for example, for the detection of hydrogen peroxide with the aid of peroxidases or peroxidatively active substances.These redox indicators are futhermore suitable for the detection of peroxidases or peroxidatively active compounds, it also being possible to use other peroxides as oxidizing agents.Type: GrantFiled: March 21, 1988Date of Patent: January 16, 1990Assignee: Miles Inc.Inventors: Florin Seng, Klaus Wehling
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Patent number: 4885368Abstract: Novel radical ion salts of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each hydrogen, methyl, ethyl, phenyl, methoxy, ethoxy, fluorine, chlorine or bromine, or R.sup.1 or R.sup.1 and R.sup.3 may furthermore be tert-butyl and/or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 together may in each case form a radical of the formula ##STR2## where z is 0, 1, 2 or 3, and the fused aromatic rings are unsubstituted or monosubstituted or disubstituted by chlorine, bromine, methyl and/or methoxy, M.sup.m.sym. is an m-valent alkali metal, alkaline earth metal, transition metal, tin, lead, thallium, ammonium, phosphonium, arsonium or stibonium ion, k is from 1 to 5, l is from 0.1 to 4, m is from 1 to 3, n is from 0.1 to 4, x is from 0 to 2 and y is from 0 to 6, and k, l, n, x and y may furthermore be non-integral numbers and (l+x)=n.m, are electrically conductive in the crystalline state. A number of the salts are stable at 300.degree. C. and above.Type: GrantFiled: November 23, 1987Date of Patent: December 5, 1989Assignee: BASF AktiengesellschaftInventors: Siegfried Huenig, Alexander Aumueller, Peter Erk
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Patent number: 4873350Abstract: The present invention relates to new diselenobis-benzoic acid amides of primary and secondary amines of the general formula (I): ##STR1## and processes for the treatment of diseases in humans caused by a cell injury.Type: GrantFiled: October 3, 1988Date of Patent: October 10, 1989Assignee: A Nattermann & CIE GmbHInventors: Andre Welter, Harmut Fischer, Leon Christiaens, Albrecht Wendel, Eugen Etschenberg, Norbert Dereu, Peter Kuhl, Eric Graf
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Patent number: 4859783Abstract: 2,2-Difluoro-4-amino-1,3-benzodioxole is useful as an intermediate for the synthesis of 2,2-difluoro-4-(2',4'-dinitro-6'-trifluoromethylanilino)-1,3-benzodioxole of the formula ##STR1## which is suitable as a pesticide. In combination with carriers and further adjuvants, said compound can be employed for controlling pests, in particular phytopathogenic fungi or bacteria, and also insects and acarids.Type: GrantFiled: October 9, 1987Date of Patent: August 22, 1989Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4806604Abstract: The present invention discloses a new class of calcium chelating compounds which have a decreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca.sup.2+ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. However unlike EGTA or BAPTA-like compounds, in which the two halves of the chelator are linked by a simple 1,2-ethanediyl moiety, the compounds of the present invention modify the stereochemical conformation of this linkage by adding bulky substituents or incorporating the linkage into a carbocyclic or heterocyclic ring. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone.Type: GrantFiled: May 13, 1987Date of Patent: February 21, 1989Assignee: Regents of the University of CaliforniaInventors: Roger Yonchien Tsien, Stephen R. Adams
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Patent number: 4789743Abstract: The invention relates to a process for the preparaton of compounds of the formula I by reacting an alkali metal alcoholate with a compound of the formula II in the presence of an aliphatic ester such as methyl formate, and then condensing guanidine with the resulting compound of the formula III.The compound of the formula II can be prepared by reacting the corresponding benzaldehyde with acrylonitrile in the presence of diazabicyclo-2,2,2,-octane.Type: GrantFiled: July 31, 1987Date of Patent: December 6, 1988Assignee: Societe Anonyme: Sanofi Pharma S.A. - Succursale de CarougeInventor: Abram Becker
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Patent number: 4781866Abstract: An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): ##STR1## with H.sub.2 O.sub.2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.Type: GrantFiled: November 24, 1986Date of Patent: November 1, 1988Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, James N. Plampin, Robin C. Stanzione
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Patent number: 4780550Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R hu d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: September 17, 1987Date of Patent: October 25, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4780469Abstract: A (fused) benz(thio)amide of the formula: ##STR1## wherein B represents(i) a carbocyclic ring of from 4 to 8 members being unreplaced or replaced one, two or three of optional carbon atom(s) by oxygen, nitrogen and/or sulphur atom(s) or(ii) a divalent group of the formula: ##STR2## R.sup.1 represents a group of formula: ##STR3## (iv) a straight or branched alkyl, alkenyl, or alkynyl of from 1 to 20 carbon atoms,R.sup.4 represents(i) when B represents a closed ring, a group of the formula: ##STR4## (ii) when B does not represent a ring, a group of formula: ##STR5## with the proviso that compounds of formula: ##STR6## wherein A' is a vinylene or an ethylene group optionally substituted by straight or branched alkyl groups of from 1 to 4 carbon atom(s);R.sup.4' is--(CH.sub.2).sub.n --COOR.sup.8andR.sup.1' is(i) a group of the formula: ##STR7## or (ii) a group of the formula: ##STR8## are excluded, wherein A, R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, U, n, m, p, q, R.sup.5', and R.sup.Type: GrantFiled: August 20, 1985Date of Patent: October 25, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
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Patent number: 4749379Abstract: New nitroaminophenols, the process for preparation thereof and their use in dyeing keratinous fibres, and new intermediate nitroaminobenzenes and their use in dyeing keratinous fibres.The invention relates to a nitroaminophenol of formula: ##STR1## in which Z denotes --CH.sub.2 W, W denoting H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalkoxy(C.sub.1 -C.sub.6)-alkyl and R denotes H, (C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 hy-droxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)-alkoxy(C.sub.1 -C.sub.6)alkyl, and the process for preparation thereof, and the intermediate compound of formula: ##STR2## in which R' denotes C.sub.1 -C.sub.6 hydroxyalkyl, C.sup.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl and the process for preparation thereof.Type: GrantFiled: April 11, 1986Date of Patent: June 7, 1988Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Alain Genet
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Patent number: 4722935Abstract: 2,2-Difluoro-4-(2',4'-dinitro-6'-trifluoromethylanilino)-1,3-benzodioxole of the formula ##STR1## is suitable as a pesticide. In combination with carriers and further adjuvants, said compound can be employed for controlling pests, in particular phytopathogenic fungi or bacteria, and also insects and acarids.Type: GrantFiled: March 25, 1986Date of Patent: February 2, 1988Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4704401Abstract: This invention relates to a method of lowering blood pressure in humans and mammals using 2,6-disubstituted phenyl amidinoureas in which the phenyl ring is additionally substituted by a hydroxy, alkoxy, aralkoxy, alkenyloxy, alkynyloxy, haloacyloxy, or acyloxy group and to novel 2,6-disubstituted phenyl amidinoureas which possess pharmaceutical properties, including blood pressure lowering activity.Type: GrantFiled: December 6, 1984Date of Patent: November 3, 1987Assignee: Rorer Pharmaceutical CorporationInventors: William L. Studt, Richard L. Riley, George H. Douglas
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Patent number: 4693850Abstract: Novel synthetic steps and intermediates leading to guanidines such as the anti-diabetic compound linogliride.Type: GrantFiled: November 26, 1986Date of Patent: September 15, 1987Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, James N. Plampin, Robin C. Stanzione
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Patent number: 4689432Abstract: The present invention discloses a group of calcium chelating compounds which have a descreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca.sup.2+ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone. In a second form, the new compounds are comprised of a BAPTA-like chelator coupled to two 2-nitrobenzyl derivatives, themselves photochemical prcursors of the related 2-nitrosobenzophenones.The present invention also discloses a novel method for preparing 1-hydroxy- or 1-alkoxy-1-(2-nitroaryl)-1-aryl methanes. Methanes of this type are critical to the preparation of, or actually constitute, the photolabile Ca.sup.2+ chelating compounds disclosed and claimed herein.Type: GrantFiled: September 7, 1984Date of Patent: August 25, 1987Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Grzegorz Grynkiewicz, Akwasi Minta
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Patent number: 4686232Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly strains thereof which are resistant to benzimidazole or thiophanate fungicides and/or cyclic imide fungicides.Type: GrantFiled: February 6, 1984Date of Patent: August 11, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Mitsuru Sasaki, Hiroshi Noguchi, Toshiro Kato
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Patent number: 4668787Abstract: Quinazolinone derivatives having an oxy substituent in the 5- and 6-positions are disclosed. The quinazolinone derivatives are useful as cardiovascular agents.Type: GrantFiled: December 20, 1985Date of Patent: May 26, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Stanley C. Bell, Robert Falotico, Charles F. Schwender, Alfonso J. Tobia
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Patent number: 4636523Abstract: Insecticidal compounds of the formula ##STR1## in which A and B are both halogen or hydrogen, or one of A and B is hydrogen, and the other of A and B is halogen; Z and W are independently O or S; the substituted benzofuranyl or benzothienyl group is attached at position 5 or 6; R is halogen; m is 0 to 3; R' is F or CF.sub.3 ; methods for their preparation and formulation, insecticidal compositions, and their use to control insects are disclosed.Type: GrantFiled: January 7, 1986Date of Patent: January 13, 1987Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4617392Abstract: 4-Alkyl-5,6-, 6,7-methylenedioxy-2-1[H]-quinazolinones are prepared from 2,3-methylenedioxyacetophenones. The 4-alkyl-5,6-, 6,7-methylenedioxy-2-1[H]-quinazolinones are active as cardiotonic agents.Type: GrantFiled: September 29, 1983Date of Patent: October 14, 1986Assignee: Ortho Pharmaceutical CorporationInventors: Victor T. Bandurco, Stanley C. Bell, Donald W. Combs, Robert Falotico
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Patent number: 4549992Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aryalkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylaminoalkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused hetero-aryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is a group of the formula ##STR2## wherein X is a branched alkane or cycloalkyl; and where Y is hydroxy their non-toxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.Type: GrantFiled: March 8, 1982Date of Patent: October 29, 1985Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4536587Abstract: A compound of the formula ##STR1## in which R.sup.1 represents a hydrogen or halogen atom or an alkyl radical,R.sup.2 represents a hydrogen or halogen atom,X represents an oxygen or sulphur atom,Y represents a hydrogen or halogen atom or an alkyl or halogenoalkyl radical andA represents an alkylene radical which is substituted by fluorine and optionally additionally substituted by chlorine,which possesses insecticidal activity.Type: GrantFiled: May 12, 1983Date of Patent: August 20, 1985Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Albrecht Marhold, Ingeborg Hammann, Ingomar Krehan, Wilhelm Stendel
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Patent number: 4533676Abstract: A 2,5-dihalogenobenzoyl-(thio)urea of the formula ##STR1## in which X represents sulphur or oxygen,X.sup.1 and X.sup.2 are identical or different and represent fluorine, chlorine, bromine or iodine,R.sup.1 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkoxy and alkylthio,R.sup.2 represents hydrogen, halogen, cyano, nitro or optionally substituted radicals from the series comprising alkyl, alkylthio, alkylsulphonyl, alkoxy, aryloxy, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl and alkoxycarbonylalkylthio,R.sup.1 and R.sup.2 together represent an optionally substituted alkylenedioxy radical or represent --CF.sub.2 --O--CF.sub.2 --O--,R.sup.3 represents hydrogen, halogen, or an optionally substituted alkyl, alkoxy or aryloxy radical, andR.sup.4 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkylthio and alkoxy, with the exception of those cases in which X represents oxygen, X.sup.1 and X.sup.Type: GrantFiled: April 22, 1983Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
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Patent number: 4517130Abstract: An improved process for preparing substituted amino acids and lower alkyl esters thereof, and intermediates therefor, comprising reacting a substituted aniline, HCN and an aldehyde to form a nitrile, converting the nitrile to an imidate salt with a strong acid and an alcohol, hydrolyzing in situ the imidate salt to the ester with addition of water, and optionally converting the ester to the salt or free acid. The acids are useful intermediates in the synthesis of pesticides.Type: GrantFiled: February 17, 1984Date of Patent: May 14, 1985Assignee: Zoecon CorporationInventor: Ted A. Baer
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Patent number: 4511391Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, alkenyl, alkynyl, hydroxy, alkoxy, substituted alkoxy, alkenyloxy, alkynyloxy, alkanoyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;Y and Z are independently selected from methylene, oxygen and sulfur provided that at least one of Y and Z is selected from oxygen and sulfur;R.sup.1 is selected from hydrogen, alkyl, alkenyl alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl;R.sup.4 is selected from hydrogen, halogen, cyano, C.Type: GrantFiled: May 24, 1983Date of Patent: April 16, 1985Assignee: ICI Australia LimitedInventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
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Patent number: 4497740Abstract: New 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine compounds are described having the general formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl or alkenyl radical or the cyclopropylmethyl radical, R.sub.2 is a hydrogen atom, or a lower alkyl or alkenyl radical, n is 0, 1 or 2, R.sub.3 is an optionally substituted furyl, thienyl, pyrrolyl, pyridyl or phenyl radical, R.sub.4 is an optionally substituted furyl, thienyl, pyrrolyl or pyridyl radical, R.sub.5 is a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, hydroxyl, lower alkylthio, nitro, trifluoromethyl, cyano, amino, lower mono- or dialkylamino, lower monoalkanoylamino, lower N-alkyl-N-alkanoylamino or lower alkanoyloxy radical, and R.sub.6 is a hydrogen atom, or a lower alkyl or lower alkoxy radical or R.sub.5 and R.sub.6 together denote a methylenedioxy or ethylenedioxy radical. The compounds have pharmacological, for example, analgesic, properties.Type: GrantFiled: June 8, 1982Date of Patent: February 5, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Horst Zeugner, Dietmar Romer, Hans Liepmann, Wolfgang Milkowski
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Patent number: 4495351Abstract: A method is disclosed for production of 1-alkyl-4(1H)-oxo-cinnolin-3-carboxylic acids. Mesoxalic acid dialkylester-3,4-methylenedioxy-phenylhydrazone is saponified using 1 to 1.5 Mol alkali into the corresponding monoalkylester, which is cyclicized with a Friedel-Crafts catalyst in the presence of a carboxylic acid anhydride into 6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid alkylester, which is alkylated with a C.sub.1 -C.sub.4 alkyl halogenide in the presence of alkali in a suitable solvent, after which the ester is saponified. Small amounts of byproduct alkylated in the 2-position are removed by brief heating and precipitation from alkaline solution, leaving a pure 1-alkyl product. The product is useful for the treatment of urinary tract infections.Type: GrantFiled: December 21, 1982Date of Patent: January 22, 1985Assignee: Veb Arzneimittelwerk DresdenInventors: Hans-Jorg Schmidt, Joachim Franke, Reingard Scheffler, Heinz Tonjes, Gunter Kammann, Gunther Dietz
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Patent number: 4487779Abstract: This invention relates to a method of lowering blood pressure in humans and mammals using 2,6-disubstituted phenyl amidinoureas in which the phenyl ring is additionally substituted by a hydroxy, alkoxy, aralkoxy, alkenyloxy, alkynyloxy, haloacyloxy, or acyloxy group and to novel 2,6-disubstituted phenyl amidinoureas which possess pharmaceutical properties, including blood pressure lowering activity.Type: GrantFiled: July 6, 1981Date of Patent: December 11, 1984Assignee: William H. Rorer, Inc.Inventors: William L. Studt, Richard L. Riley, George H. Douglas
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Patent number: 4477556Abstract: A photopolymerizable coating composition comprising(1) a nongaseous, ethylenically unsaturated, polymerizable compound,(2) a specified acidic o-nitroaromatic compound, and(3) an organic, radiation-sensitive, free-radical generating system which is useful for making a positive or negative polymeric image on a substrate.Type: GrantFiled: August 18, 1982Date of Patent: October 16, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas E. Dueber, William J. Nebe
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Patent number: 4473579Abstract: Tetrasubstituted urea and thiourea compounds useful as antiatherosclerotic agents, compositions thereof and processes for their preparation.Type: GrantFiled: January 26, 1982Date of Patent: September 25, 1984Assignee: American Cyanamid CompanyInventors: Vern G. Devries, Ransom B. Conrow
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Patent number: 4411912Abstract: Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: November 13, 1979Date of Patent: October 25, 1983Assignee: Zoecon CorporationInventors: Clive A. Henrick, Barbara A. Garcia