Five-membered Alicyclic Ring Patents (Class 568/330)
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Patent number: 6384284Abstract: A description is given of diphenyl compounds of formula wherein R is a camphor or hydantoin derivative; and R1 is hydrogen; or C1-C5alkyl. These compounds are suitable as light stabilizers in cosmetic, pharmaceutical and veterinary formulations.Type: GrantFiled: March 29, 2001Date of Patent: May 7, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Rudolf Zink, Dieter Reinehr, Helmut Luther, Bernd Herzog
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Patent number: 6310114Abstract: Compact and preferably cellular polyurethane elastomers are produced by reacting a) polyhydroxyl compounds having molecular weights of from 800 to 6000 and, if desired, b) chain extenders and/or crosslinkers having molecular weights of up to 800 [lacuna] c) naphthylene 1,5-diisocyanate and at least one additional aromatic diisocyanate selected from the group consisting of tolylene diisocyanate, diphenylmethane diisocyanate, 3,3′-dimethylbiphenyl diisocyanate, 1,2-diphenylethane diisocyanate and phenylene diisocyanate, and/or aliphatic diisocyanate having from 4 to 12 carbon atoms and/or cycloaliphatic diisocyanate having from 6 to 18 carbon atoms, where the formative components (a), (c) and, if used, (b) are preferably reacted by the prepolymer method, in the presence or absence of d) catalysts, e) blowing agents and f) additives. Isocyanate prepolymers suitable for this purpose are also described.Type: GrantFiled: August 21, 1998Date of Patent: October 30, 2001Assignee: BASF AktiengesellschaftInventors: Manfred Genz, Walter Haselhorst, Torsten Jeschke, Ute Nichau, Heinz Bollmann, Michael Strauss, Wolfgang Scholz, Rüdiger Voelkel, Hartmut Peuker, Gerhard Hellmann
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Patent number: 6300376Abstract: Indane dimer compounds and their pharmaceutical use particularly to achieve smooth muscle relaxing activity and/or mast cell stabilizing activity and/or anti-inflammatory activity are described.Type: GrantFiled: June 8, 1998Date of Patent: October 9, 2001Assignee: Venantius LimitedInventors: John Walsh, Neil Frankish, Helen Sheridan, Ronan Farrell, William Byrne
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Patent number: 6287749Abstract: Biradical initiators and methods using the same are disclosed. Polymerization of compositions which include the compounds of the invention may be activated by irradiating the composition with radiation.Type: GrantFiled: May 4, 1998Date of Patent: September 11, 2001Assignees: First Chemical Corporation, Univ. of Southern MississippiInventors: Rajamani Nagarajan, Joseph Stanton Bowers, Jr., Charles E. Hoyle, E. Sonny Jönsson, John R. I. Eubanks
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Patent number: 6251833Abstract: The present invention relates to novel 2-aryl-3-hydroxy-&Dgr;2-cyclopentene-1-one derivatives of the formula (I) in which A, B, D1, D2, G, W, X, Y and Z are each as defined in the description, to processes for their preparation and to their use as herbicides and pesticides.Type: GrantFiled: August 31, 1999Date of Patent: June 26, 2001Inventors: Christoph Erdelen, Ulrike Wachendorff-Neumann, Reiner Fischer, Alan Graff, Norbert Mencke, Andreas Turberg
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Patent number: 6239135Abstract: A series of aryl piperazine compounds of the formula: or the pharmaceutically acceptable salts thereof, are effective pharmaceuticals for the treatment of conditions related to or affected by the serotonin 1A receptor; the compounds are particularly effective antagonists at that receptor, and are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal.Type: GrantFiled: December 9, 1998Date of Patent: May 29, 2001Assignee: Eli Lilly and CompanyInventors: Daniel Timothy Kohlman, Yao-Chang Xu
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Patent number: 6172118Abstract: This invention relates to ketones, alcohols and amines represented by the likes of of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylcyclobutan-1-one. They are useful as PDE 4 antagonists.Type: GrantFiled: April 8, 1999Date of Patent: January 9, 2001Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Cornelia J. Forster
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Patent number: 6150374Abstract: The invention relates to novel substituted cycloalkenes of the formula (I), ##STR1## to a plurality of processes for their preparation, and to novel intermediates and a plurality of processes for their preparation.Type: GrantFiled: September 29, 1997Date of Patent: November 21, 2000Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Peter Gerdes, Ralf Tiemann, Stefan Dutzmann, Klaus Stenzel
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Patent number: 6133481Abstract: Improved low density polyurethane foams are prepared from an isocyanate-terminated prepolymer having an NCO content of more than about 31 to about 33.5% by weight comprising:(a) a polyphenylene polymethylene polyisocyanate comprising(i) about 30 to about 100% by weight of diphenylmethane diisocyanate and(ii) the remainder selected from the group consisting essentially of higher homologues of polyphenylene polymethylene polyisocyanate, isocyanate-containing ester groups, urea groups, biuret groups, aliphatic groups, carbodiimide groups, isocyanurate groups, uretdione groups and urethane groups; and(b) a polyoxyalkylene polyol having an oxyethylene content of about 30 to about 90%, a molecular weight of about 1000 to about 12000 and a functionality of about 2 to about 8.Type: GrantFiled: February 10, 1998Date of Patent: October 17, 2000Inventors: Sachchida Nand Singh, Michael John Cartmell, James Holloway
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Patent number: 6127189Abstract: The invention includes compositions comprising and methods of using 1,2-indanedione derivatives for detecting an amine compound such as an amino acid. Methods of detecting and recording the pattern of a fingerprint on a surface are also included, as are a kit for detecting an amine compound such as a constituent of a fingerprint. The invention further includes a device for developing a fingerprint and a method of making 1,2-indanedione derivatives.Type: GrantFiled: November 7, 1997Date of Patent: October 3, 2000Assignee: The Trustees of the University of PennsylvaniaInventors: Madeleine M. Joullie, Diane Hauze, Olga Petrovskaia
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Patent number: 6127579Abstract: A method of manufacturing the useful substance 1-indanone from easily obtainable materials consists of reacting an indanyl ether represented by the generic formula ##STR1## under basic conditions to give a novel substance which is the indenyl ether derivative represented by the generic formula ##STR2## and hydrolyzing this to give the 1-indanone represented by the generic formula ##STR3##Type: GrantFiled: July 1, 1999Date of Patent: October 3, 2000Assignee: Ichikawa Gosei Chemical Co., Ltd.Inventors: Shigeru Nakano, Noriko Yoneta, Takashi Tate
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Patent number: 6127445Abstract: The present invention relates to anionic photoinitiator compounds, compositions containing them, and methods of using them having the structure: ##STR1## wherein X and Y are independently selected from the group consisting of a direct single bond and --C(.dbd.O)--, wherein at least one of X and Y is --C(.dbd.O)--;R.sup.1 and R.sup.2 are independently selected from the group consisting of H and substituted phenyl, wherein both R.sup.1 and R.sup.2 are not H;and wherein neither --X--R.sup.1 nor --Y--R.sup.2 is --C(.dbd.O)H. The anionic photoinitiators have improved storage stability, without loss of photosensitivity, even when stored with polymerizable or crosslinkable monomer, oligomer, or crosslinkable polymer species.Type: GrantFiled: November 3, 1998Date of Patent: October 3, 2000Assignee: The University of Georgia Research Foundation, Inc.Inventors: Charles R. Kutal, Yoshikazu Yamaguchi
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Patent number: 6118017Abstract: This invention relates to ketones, alcohols and amines and acids represented by the likes of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylcyanoclobutan-1-one. They are useful as PDE 4 antngionists.Type: GrantFiled: April 8, 1999Date of Patent: September 12, 2000Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Cornelia J. Forster
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Patent number: 6048877Abstract: Tetralone derivatives of the formula ##STR1## where R.sup.1 is halo, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, (aryl)alkenyl, (aryl)alkynyl, alkoxy, O-alkenyl, O-aryl, O-alkyl(heterocyclo), COO-alkyl,alkanoyl, CO-amino, CO-substituted amino, alkyl-CO-amino, alkyl-CO-substituted amino, NHCO-alkyl, NHCO-aryl, NHCO-alkyl(heterocyclo), N(alkyl)CO-alkyl, N(alkyl)CO-aryl, N(alkyl)CO-heterocyclo, N(alkyl)CO-alkyl(heterocyclo);R.sup.2 is hydrogen, alkyl, halo, aryl, alkoxy, amino, substituted amino;R.sup.3 is oxo, hydroxy, alkoxy, O--COalkyl, --O--COaryl, --O--COheterocyclo, NOH, NO-alkyl, N-amino, N-substituted amino, N-NHCONHalkyl, N-NHSO.sub.2 alkyl, N-NHSO.sub.2 aryl, amino, substituted amino, NHCO-alkyl, NHCO-aryl, NHCO-heterocyclo, spiroheterocyclo;R.sup.4 is hydrogen, alkyl, alkyl(COalkyl), alkyl(COOalkyl); orR.sup.3 and R.sup.4 taken together with the atoms to which they are attached form a five- to seven-membered ring which can contain up to three heteroatoms selected from oxygen, nitrogen and sulfur;R.sup.Type: GrantFiled: January 20, 1998Date of Patent: April 11, 2000Assignee: Bristol-Myers Squibb CompanyInventors: Saleem Ahmad, Philip D. Stein, Francis N. Ferrara, Karnail S. Atwal
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Patent number: 5908944Abstract: This invention describes a new methylation or ethylation agent containing trimethyl aluminum or dimethyl zinc or triethyl aluminum as methyl or ethyl source, which additionally contains catalytic amounts of one or more copper(I) and/or copper(II) compounds as well as a process for the 1,4-addition of a methyl or ethyl group to an .alpha.,.beta.-unsaturated or an .alpha.,.beta.-double unsaturated ketone or an .alpha.,.beta.-unsaturated aldehyde using the agent according to the invention.By using only catalytic amounts of copper and a CKW (chlorinatedhydrocarbon)-free reaction medium, the new methylation/ethylation agent/process is distinguished by its environmental compatibility and it is, for example, suitable for the production of initial products for the synthesis of biologically effective compounds.Type: GrantFiled: September 30, 1994Date of Patent: June 1, 1999Assignee: Schering AktiengesellschaftInventors: Jurgen Westermann, Klaus Nickisch
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Patent number: 5861421Abstract: This invention relates to derivatives of 4,4-(disubstituted)cyclohexan-1-ones and related compounds which are useful for treating allergic and inflammatory diseases.Type: GrantFiled: June 23, 1997Date of Patent: January 19, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5840661Abstract: The present invention relates to novel 2-aryl-3-hydroxy-cyclopent-2-en-1-one derivatives of the formula (I) ##STR1## in which X represents halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Y represents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Z represents halogen, nitro, cyano, alkyl, alkoxy or halogenoalkoxy andA, B, D.sup.1, D.sup.2, G and n have the meaning given in the description,several processes for their preparation and their use as compositions for controlling pests and as herbicides.Type: GrantFiled: December 31, 1996Date of Patent: November 24, 1998Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Jacques Dumas, Thomas Bretschneider, Christoph Erdelen, Ulrike Wachendorff-Neumann, Hans-Joachim Santel, Markus Dollinger, Andreas Turberg, Norbert Mencke
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Patent number: 5665773Abstract: Disclosed is the use of cloprostenol and fluprostenol analogues for the treatment of glaucoma and ocular hypertension. Also disclosed are ophthalmic compositions comprising said compounds.Type: GrantFiled: December 18, 1996Date of Patent: September 9, 1997Assignee: Alcon Laboratories, Inc.Inventors: Peter G. Klimko, John E. Bishop, Verney L. Sallee, Paul W. Zinke
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Patent number: 5639918Abstract: (Benzylidene)-azolylmethylcycloalkane or -alkene of formula ##STR1## in which: A and A.sub.1 are hydrocarbon chains of 1 to 3 carbon atoms,R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrocarbon radicals,X is halogen,Y is H or halogen,n=1, 2 or 3,W is --CH.dbd. or --N.dbd..Use as a fungicide.Type: GrantFiled: September 26, 1994Date of Patent: June 17, 1997Assignee: Rhone-Poulenc AgrochimieInventors: Jean Hutt, Jacques Mugnier, Alfred Greiner, Regis Pepin
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Patent number: 5466721Abstract: Provided are compounds having the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from the group consisting of a hydrogen atom, an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group, provided that R.sup.1 and R.sup.2 may together form a divalent radical selected from the group consisting of an aliphatic radical and hetero-aliphatic group;each R.sup.3 is independently selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group;R.sup.4 is selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group; andn is an integer from 0 to 5.Also provided are polymerizable compositions containing such compounds and a method of coating a substrate which uses such polymerizable compositions.Type: GrantFiled: June 13, 1994Date of Patent: November 14, 1995Assignee: Henkel CorporationInventor: Paul E. Share
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Patent number: 5380900Abstract: Disclosed herein is an .alpha.-methylene-cyclopentanone derivative represented by the formula [I] below which is useful as an intermediate for pharmaceuticals and insecticides, especially prostaglandins. Also disclosed herein is a process for producing the derivative advantageously on an industrial scale. ##STR1## where X denotes (.alpha.-OZ, .beta.-H) or (.alpha.-H, .beta.-OZ), with Z representing a protecting group for the hydroxyl group; U denotes (.alpha.-H, .beta.-R.sup.1) or (.beta.-R.sup.1, .alpha.-H); R.sup.1 denotes ##STR2## where R.sup.2 denotes a protected hydroxyl group, a substituted or unsubstituted C.sub.1-15 alkyl group, a substituted or unsubstituted C.sub.2-15 alkenyl group, a substituted or unsubstituted C.sub.2-15 alkynyl group, or a substituted or unsubstituted C.sub.6-15 aryl group; Z' denotes a protecting group for the hydroxyl group; and k is 0 or 1).Type: GrantFiled: February 12, 1992Date of Patent: January 10, 1995Assignee: Nissan Chemical Industries, LimitedInventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5362915Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: R.sub.1 is --CH.sub.3 or --CH.sub.2 CH.sub.3 unsubstituted or substituted by 1 to 3 fluorines;X is O or S(O).sub.s where s=0 to 2;R.sub.2 is C.sub.4 -C.sub.6 cyclic alkyl, optionally substituted by one to three methyl groups or one ethyl group; --CH.sub.2 -cyclopentyl, --CH.sub.2 -cyclopropyl, 3-tetrahydrofuranyl, C.sub.1-7 alkyl, CH.sub.3 or CH.sub.2 CH.sub.3 substituted by one to three fluorines;--(CH.sub.2).sub.n COO(CH.sub.2).sub.g CH.sub.3, or (CH.sub.2).sub.n O(CH.sub.2).sub.g CH.sub.3, wherein n is 2 to 4 and g is 0 to 2;R.sub.3 represents a moiety of formula (a); ##STR2## wherein R.sub.4 and R.sub.5 each represent hydrogen or R.sub.4 and R.sub.5 together represent a bond;B represents >C.dbd.O, >C.dbd.S or >CH--R.sub.6 wherein R.sub.6 represents H, OH, C.sub.1-6 alkoxy or C.sub.Type: GrantFiled: October 2, 1992Date of Patent: November 8, 1994Assignees: SmithKline Beecham Pharma GmbH, SmithKline Beecham CorporationInventors: Harald Maschler, Siegfried B. Christensen, IV
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Patent number: 5254708Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: October 19, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5248830Abstract: Disclosed are intermediates and a process of making an anticholesterolemic compound of the formula ##STR1## the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Type: GrantFiled: June 23, 1992Date of Patent: September 28, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: John Ullrich, John R. Regan
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Patent number: 5231208Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: July 27, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5159118Abstract: Disclosed herein are an azole derivative represented by the formula(I): ##STR1## wherein R.sup.1 and R.sup.2 respectively represent a (C.sub.1 -C.sub.5) alkyl group or a hydrogen atom; X represents a halogen atom, a (C.sub.1 -C.sub.5) alkyl group or a phenyl group; n represents an integer of from 0 to 2 and A represents a nitrogen atom or a CH, provided that R.sup.1 is not a hydrogen atom when R.sup.2 is a hydrogen atom, a process for producing the azole derivative represented by the formula(I), and an agricultural and horticultural composition containing the azole derivative represented by the formula(I).Type: GrantFiled: April 25, 1991Date of Patent: October 27, 1992Assignee: Kureha Kagaku Kabushiki KaishaInventors: Satoru Kumazawa, Susumu Shimizu, Hiroyuki Enari, Atsushi Ito, Susumu Ikeda, Nobuo Sato, Toshihide Saishoji
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Patent number: 5149711Abstract: A 2-cyclopentenone derivative represented by the following formula ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 10 carbon atoms which may be substituted by a substituted or unsubstituted phenyl or phenoxy group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and each represents a hydrogen atom or a lower alkanoyl group, and the wavy line shows that the bonded state of the double bond is E or Z.This compound is useful for treating, for instance, malignant tumors.Type: GrantFiled: March 7, 1989Date of Patent: September 22, 1992Assignee: Teijin LimitedInventors: Atsuo Hazato, Seizi Kurozumi
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Patent number: 5146001Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formual (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.Type: GrantFiled: June 3, 1991Date of Patent: September 8, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
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Patent number: 4981872Abstract: Prostaglandin derivatives having an oxo group at specified positions in the .alpha. side chain have a variety of physiological effects, notably a strong anti-ulcer activity accompanied by a limited ability to inhibit blood platelet aggregation.Type: GrantFiled: January 15, 1988Date of Patent: January 1, 1991Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Keiichi Tabata, Nobuyoshi Iwata
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Patent number: 4929613Abstract: The novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
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Patent number: 4929740Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower akoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.Type: GrantFiled: July 11, 1988Date of Patent: May 29, 1990Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4918236Abstract: A compound of the formula ##STR1## wherein R is 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 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 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.Type: GrantFiled: June 9, 1986Date of Patent: April 17, 1990Assignee: ICI Americas Inc.Inventors: Christopher G. Knudsen, William J. Michaely
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Patent number: 4871756Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.Type: GrantFiled: February 17, 1987Date of Patent: October 3, 1989Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
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Patent number: 4829091Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordane with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: May 27, 1987Date of Patent: May 9, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr
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Patent number: 4778904Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower alkoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.Type: GrantFiled: January 9, 1987Date of Patent: October 18, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4767447Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 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.Type: GrantFiled: September 12, 1986Date of Patent: August 30, 1988Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4755511Abstract: This invention relates to tricyclic pyridazinone compounds, pharmaceutical compositions containing the compounds, and a method of stimulating cardiac activity in a mammal by administering an effective amount of the compound. A compound of the invention is 7-carboxamido-4,4a-dihydro-4a-methyl-[5H]-indeno[1,2-c]-pyridazin-3[2H]-on e.Type: GrantFiled: September 22, 1987Date of Patent: July 5, 1988Assignee: Smith Kline & French Laboratories LimitedInventor: Brian H. Warrington
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Patent number: 4713392Abstract: A compound of formula IIR.sub.A CH.sub.2 COCHDR.sub.bin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 -- in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy or C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached jointly represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 cycloalkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [IR, cis]2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropane carboxylic ester is signficantly insecticidal.Type: GrantFiled: May 10, 1985Date of Patent: December 15, 1987Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
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4-hydroxy-2-cyclopentenone, process for production thereof, pharmaceutical composition comprising it
Patent number: 4711895Abstract: A 4-hydroxy-2-cyclopentenone represented by the following formula (I) ##STR1## wherein X represents a hydrogen or halogen atom, A represents a hydrogen atom and B represents a hydroxyl group, or A and B are bonded to each other to represent a bond, R.sup.1 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a protective group for a hydroxyl group, provided that R.sup.2 is not a 2-octenyl, 8-acetoxy-2-octenyl or 2,5-octadienyl group. The compounds of formula (I) in which A is hydrogen and B is hydroxyl group are prepared by subjecting a 5-unsubstituted cyclopentenone and an aldehyde to aldol condensation reaction. The compounds of formula (I) in which A and B form a bond is prepared by subjecting the compounds of the formula (I) in which A is hydrogen and B is hydroxyl group to dehydration.Type: GrantFiled: October 22, 1985Date of Patent: December 8, 1987Assignee: Teijin LimitedInventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori -
Patent number: 4696944Abstract: A compound of formula I ##STR1## in which formula: R.sub.a represents hydrogen or a C.sub.1 -C.sub.6 alkyl group, and R.sub.c represents a C.sub.1 -C.sub.6 alkyl group;R.sub.b represents a phenyl group, optionally substituted by a C.sub.1 -C.sub.6 alkyl group or halogen, a group of formula --CH.dbd.CR.sub.d R.sub.e in which R.sub.d and R.sub.e, which may be identical or different represent hydrogen or C.sub.1 -C.sub.6 alkyl groups or a group of formula --CH.dbd.NOR.sub.f in which R.sub.f represents hydrogen or a C.sub.1 -C.sub.6 alkyl group andRCOO represents a residue of an acid RCO.sub.2 H, which acid, or an ester-forming derivative of which acid, on reaction with .alpha.-cyano-3-phenoxybenzyl alcohol or an ester forming derivative thereof, gives rise to an .alpha.-cyano-3-phenoxybenzyl ester having pesticidal properties.Type: GrantFiled: March 14, 1985Date of Patent: September 29, 1987Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
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Patent number: 4696766Abstract: (2R*,3S*)-(E)-3-Methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol possesses a very intense creamy, woody, musk, sandalwood odor and is a valuable ingredient for use in fragrance compositions for its musk and sandalwood-like qualities. This odorant is more intense than any of the campholenic aldehyde derivatives that have been previously reported.Type: GrantFiled: March 19, 1986Date of Patent: September 29, 1987Assignee: Givaudan CorporationInventor: Richard E. Naipawer
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Patent number: 4692447Abstract: The tricyclic dihydropyridazinone derivatives having formula I ##STR1## are endowed with interesting hypotensive, vasodilating, antiaggregant, antithrombotic and cytoprotective properties and are therefore useful in human or veterinary medicine.Type: GrantFiled: July 22, 1985Date of Patent: September 8, 1987Assignee: Boehringer Biochemia Robin, S.p.A.Inventors: Giorgio Cignarella, Carmelo A. Gandolfi, Odoardo Tofanetti, Piervitto Cipolla, Sergio Tognella
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Patent number: 4681621Abstract: Compounds of the formula ##STR1## wherein R is halogen, preferably chlorine or bromine; C.sub.1 -C.sub.4 alkoxy, preferably methoxy; nitro; cyano; --S(O).sub.n R' wherein n is the integer 0, 1 or 2, preferably 2 and R' is C.sub.1 -C.sub.4 alkyl, preferably methyl; or R is C.sub.1 -C.sub.4 alkyl or methyl and most preferably R is chlorine, bromine, methoxy, nitro, methyl or CF.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; and 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) OCF.sub.3 ; (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.Type: GrantFiled: December 3, 1985Date of Patent: July 21, 1987Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4625066Abstract: Novel substituted acetylene-ketones of the formulaR.sup.2 --C.tbd.C--CO--R.sup.1 (I)in whichR.sup.1 represents optionally substituted cycloalkyl with 4 to 7 carbon atoms or the groupings ##STR1## or represents optionally substituted aryl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.2 represents alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl or optionally substituted aralkyl;R.sup.3 represents halogen;R.sup.4 represents hydrogen or halogen;R.sup.5 represents alkyl with more than 1 carbon atom, alkenyl, alkinyl or the CHO group or a derivative thereof, or represents methyl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.6 represents cyano, optionally substituted aryl or the groupings --XR.sup.7 or --CONR.sup.8 R.sup.9 ;R.sup.Type: GrantFiled: November 29, 1984Date of Patent: November 25, 1986Assignee: Bayer AktiengesellschaftInventor: Hans-Ludwig Elbe
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Patent number: 4587357Abstract: A process for direct preparation of enantiomers of a substituted fluorenyloxyacetic acid is disclosed. The acetic acid derivative is useful for treating brain edema.Type: GrantFiled: October 1, 1984Date of Patent: May 6, 1986Assignee: Merck & Co., Inc.Inventor: Apurba Bhattacharya
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Patent number: 4582843Abstract: Triazolyl-alkanones or triazolyl-alkanols of the formula ##STR1## in which R.sup.1 is alkyl, cycloalkyl, aryl or substituted aryl, andR.sup.2 is hydrogen, alkyl, cycloalkyl, aryl or substituted aryl, orR.sup.1 and R.sup.2 are joined to form an aliphatic ring, andA is a keto group or a CH(OH) group,or a salt thereof which possess fungicidal, microbicidal and plant-growth regulating properties.Type: GrantFiled: August 10, 1981Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Helmut Timmler, Wolfgang Kramer, Karl H. Buchel, Helmut Kaspers, Wilhelm Brandes
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Patent number: 4529813Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: March 14, 1980Date of Patent: July 16, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4503256Abstract: Novel compounds of general formula I ##STR1## wherein R is a branched or unbranched alkyl, cycloalkyl, or aralkyl group, which group optionally contains or is substituted by a halogen or oxygen function, the oxygen function optionally being in the form of an alcohol or ether moiety;R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, is hydrogen, an alkyl, acyl, or benzoyl group, which group optionally contains or is substituted by a halogen or oxygen function;R.sub.4 is hydrogen, an alkyl, alkenyl preferably being an allyl or prenyl group, or aralkyl group which group optionally contains or is substituted by an alkyl, aryl, halogen or oxygen function;R.sub.5 is hydrogen, an alkyl, aralkyl, acyl, or aryl group, which group optionally contains or is substituted by an alkyl, aryl, halogen, or oxygen function;except that R.sub.4 and R.sub.5 are not both hydrogen;and except for the compounds when R.sub.Type: GrantFiled: June 21, 1982Date of Patent: March 5, 1985Assignee: Noristan LimitedInventors: Theunis G. Fourie, Theodor G. Dekker, Friedrich O. Snyckers, Cornelis J. van der Schyf
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Patent number: 4500737Abstract: Novel substituted cycloalkanediones and their use for the control of weeds.Type: GrantFiled: March 2, 1984Date of Patent: February 19, 1985Assignee: Zoecon CorporationInventor: Clive A. Henrick
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Patent number: 4477684Abstract: The present invention provides a process for the preparation of 11.alpha.-alkylprostaglandin E compounds from corresponding prostaglandin A compounds via reaction with alkyllithium complexes, and novel 11-deoxy-11.alpha.-alkylprostaglandin E compounds useful for the same pharmacological purposes as the natural PGE compounds, e.g., antiulcer and antisecretory effects.Type: GrantFiled: June 23, 1982Date of Patent: October 16, 1984Assignee: The Upjohn CompanyInventor: Gordon L. Bundy