Carbonyl In Substituent Q Patents (Class 564/88)
  • Patent number: 6538016
    Abstract: The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R1 is C1-C12alkyl, C1-C12alkyl substituted with C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1-C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or C3-C6alkynyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl; C2-C12alkynyl; C1-C12haloalkyl; or a group NR12R13 wherein R12 and R13 are each independently of the other hydrogen or C1-C6-alkyl, or together are tetra- or penta-methylene; R2 and R3 are each independently hydrogen; C1-C8alkyl; C1-C8alkyl substituted with hydroxy, mercapto, C1-C4alkoxy or C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8cycloalkyl-C1-C4alkyl; or the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring; R4, R5, R6 and R7 are each independently hydrogen or C1-C4al
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: March 25, 2003
    Assignee: Syngenta Participations AG
    Inventors: Martin Zeller, André Jeanguenat, Clemens Lamberth
  • Patent number: 6538159
    Abstract: The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R1 is C1-C12alkyl, C1-C12alkyl substituted with C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1-C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or C3-C6alkenyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl; C2-C12alkynyl; C1-C12haloalkyl; or a group NR12R13 wherein R12 and R13 are each independently of the other hydrogen or C1-C6-alkyl, or together are tetra- or penta-methylene; R2 and R3 are each independently hydrogen; C1-C8alkyl; C1-C8alkyl substituted with hydroxy, mercapto, C1-C4alkoxy or C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8cycloalkyl-C1-C4alkyl; or the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring; R4, R5, R6 and R7 are each independently hydrogen or C1-C4alk
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: March 25, 2003
    Assignee: Syngenta Participations AG
    Inventors: Martin Zeller, André Jeanguenat, Clemens Lamberth
  • Patent number: 6506937
    Abstract: Benzenesulfonylureas and -thioureas of the formula I where R(1) is H or (fluoro)methyl, R(2) is H, Hal or (fluoro) (mercapto)alk(oxy)yl, E is O or S; Y is —[CR(3)2]n—, where R(3)=H or alkyl and n=1-4, X is H, Hal or alkyl and Z is Hal, NO3 or alk(yl)oxy, are described. The compounds I are used for treatment of disturbances in cardiac rhythm and prevention of sudden cardiac death caused by arrhythmia, and can therefore be used an antiarrhythmics. They are particularly suitable for those cases where arrhythmias are a consequence of a narrowing of a coronary vessel, such as angina pectoris or acute cardiac infarction.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: January 14, 2003
    Inventors: Heinrich Englert, Dieter Mania, Jens Hartung, Heinz Gögelein, Joachim Kaiser, Wolfgang Linz, David Wettlaufer
  • Patent number: 6489365
    Abstract: Compounds of the formula which is explained more fully in the specification, may be prepared by conventional methods and used therapeutically in conventional galenic preparations.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: December 3, 2002
    Assignee: Boehringer Ingelheim KG
    Inventors: Ralf Anderskewitz, Kurt Schromm, Ernst-Otto Renth, Frank Himmelsbach, Franz Birke, Armin Fugner
  • Patent number: 6482860
    Abstract: The invention provides methods and compositions relating to novel pentafluorophenylsulfonamide derivatives and analogs and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, vascular restenosis, microbial infections, and psoriasis, or as lead compounds for the development of such agents.
    Type: Grant
    Filed: July 18, 1997
    Date of Patent: November 19, 2002
    Assignee: Tularik Inc.
    Inventors: John A. Flygare, Julio Cesar Medina, Bei Shan, David Louis Clark, Terry J. Rosen
  • Publication number: 20020016491
    Abstract: A method of selectively controlling undesirable vegetation in crops by using a postemergent application of an herbicidally effective amount of a metal chelate of a 2-(substituted benzoyl)-1,3-cyclohexanedione compound to the locus of such undesirable vegetation.
    Type: Application
    Filed: May 28, 1999
    Publication date: February 7, 2002
    Inventors: HERBERT B. SCHER, JINLING CHEN
  • Patent number: 6335467
    Abstract: Benzenesulfonylureas and -thioureas of the formula I where R(1) in N or (fluoro)methyl, R(2) is H, Hal or (fluoro)(mercapto)alk(oxy)yl, E is O or S, Y is —[CR(3)2]n—, where R(3)=H or alkyl and n=1-4, X is H, Hal or alkyl and Z is Hal, NO2 or alk(yl)oxy, are described. The compounds I are used for treatment of disturbances in cardiac rhythm and prevention of sudden cardiac death caused by arrhythmia, and can therefore be used as antiarrhythmics. They are particularly suitable for those cases where arrhythmias are a consequence of a narrowing of a coronary vessel, such as angina pectoris or acute cardiac infarction.
    Type: Grant
    Filed: January 24, 2000
    Date of Patent: January 1, 2002
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinrich Englert, Dieter Mania, Jens Hartung, Heinz Gögelein, Joachim Kaiser, Wolfgang Linz, David Wettlauper
  • Patent number: 6333337
    Abstract: Compounds useful as potassium channel inhibitors and especially useful for the treatment of cardiac arrhythmias and cell proliferative disorders are described.
    Type: Grant
    Filed: January 13, 1999
    Date of Patent: December 25, 2001
    Assignee: ICAgen, Inc.
    Inventors: Michael F. Gross, Neil A. Castle
  • Patent number: 6221914
    Abstract: The present invention is directed to compounds which are capable of inhibiting the activity of tryptase. Such compounds are useful in the treatment or prevention of inflammatory disease, particularly those disease states which are mediated by mast cell activation. Also encompassed by the invention are formulations comprising the noted compounds, processes for preparing such compounds and methods for treating or preventing an inflammatory disease.
    Type: Grant
    Filed: October 27, 1998
    Date of Patent: April 24, 2001
    Assignee: Array Biopharma Inc.
    Inventors: Laurence E. Burgess, James P. Rizzi
  • Patent number: 6214882
    Abstract: Benzenesulphonamide compounds of general formula (I), wherein R1 is a hydrogen or halogen atom such as chlorine or fluorine, or a straight or branched C1-4 alkyl or C1-4 alkoxy group, each of R2, R3 and R4, which are the same or different, is a hydrogen atom or a straight, branched or cyclic C1-4 alkyl group, and R1 is a hydrogen atom or a C1-2 alkyl, C1-2 fluoroalkyl or C1-2 perfluoroalkyl group, in the form of enantiomers, diastereoisomers or mixtures thereof, including racemic mixtures, as well as pharmaceutically acceptable acid addition salts thereof, are provided for therapeutical use.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: April 10, 2001
    Assignee: Synthelabo
    Inventors: Thomas Purcell, Christophe Philippo
  • Patent number: 6204387
    Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: March 20, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Ian W. Davies, Linda Gerena, Michel Journet, Robert D. Larsen, Philip J. Pye, Kai Rossen
  • Patent number: 6096930
    Abstract: The present invention relates to novel cyclohexane-1-3-dione derivatives of formula (1) useful as herbicides and plant-growth regulants, ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, nitro, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 sulfamoyl, and N, N-di(C.sub.1 -C.sub.6 alkyl)sulfamoyl group; (X)n represents the number of X substituents which may be substituted on benzene ring, wherein n is 1, 2 or 3. Also, cyclohexyl moiety, one of the substituents on benzofuran ring, is substituted at C-4, C-5, C-6 or C-7 position on benzene ring; R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl group; R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl and C.sub.2 -C.sub.6 alkynyl group; R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: August 1, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Eung Kul Ryu, Kyoung Mahn Kim, Jae Nyoung Kim, Jin Seog Kim
  • Patent number: 6090981
    Abstract: Benzenesulfonylureas and -thioureas of the formula I ##STR1## where R(1) is H or (fluoro)methyl, R(2) is H, Hal or (fluoro)(mercapto)alk(ozy)yl, E is O or S; Y is --[CR(3).sub.2 ].sub.n --, where R(3)=H or alkyl and n=1-4, X is H, Hal or alkyl and Z in Hal, NO.sub.2 or alk(yl)oxy, are described.The compounds I are used for treatment of disturbances in cardiac rhythm and prevention of sudden cardiac death caused by arrhythmia, and can therefore be used as antiarrhythmics. They are particularly suitable for those cases where arrhythmias are a consequence of a narrowing of a coronary vessel, such as angina pectoris or acute cardiac infarction.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: July 18, 2000
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinrich Englert, Dieter Mania, Jens Hartung, Heinz Gogelein, Joachim Kaiser, Wolfgang Linz, David W. Laufer
  • Patent number: 6083987
    Abstract: A phenylenediamine derivative or a salt thereof in accordance with the present invention is expressed by the following formula 1: ##STR1## wherein A represents a group expressed by --CO--, --CH.sub.2 CO--, --CS--, or --SO.sub.2 --; Y represents a carbon atom or nitrogen atom; R.sub.1 represents a lower alkyl group; R.sub.2 represents a hydrogen, lower alkyl, alkenyl, benzyl, or benzoyl group; and each of R.sub.3 and R.sub.4 represents an alkyl group having 1-10 carbon atoms. The phenylenediamine derivative above mentioned, as a radical scavenger, has antioxidant effect and lipid peroxidation inhibitory activity so as to be available for inhibiting brain infarction or brain edema.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: July 4, 2000
    Assignee: Shiseido Co., Ltd.
    Inventors: Chikao Nishino, Kazuyuki Miyazawa, Hideo Kanno
  • Patent number: 5968978
    Abstract: Compounds of the formula I ##STR1## in which the symbols have the meanings indicated in the claims, have outstanding antiarrhythmic properties. They exhibit a cardioprotective component. They can inhibit or greatly decrease, in a preventive manner, the pathophysiological processes in the formation of ischemically induced damage, in particular in the elicitation of ischemically induced cardiac arrhythmias. Moreover, they have a strong inhibitory action on the proliferation of cells.
    Type: Grant
    Filed: September 21, 1998
    Date of Patent: October 19, 1999
    Assignee: Hoechst Marion Roussel Deutschland
    Inventors: Heinz-Werner Kleemann, Jan-Robert Schwark, Sabine Faber, Hans Jochen Lang, Andreas Weichert, Hans-Willi Jansen
  • Patent number: 5945450
    Abstract: Naphthalene derivatives represented by formula ?I!: ##STR1## (wherein A is a hydrogen atom, a hydroxy group, a C.sub.7 -C.sub.11 aralkyloxy group, or an alkoxy group composed of an oxy group and a C.sub.1 -C.sub.12 aliphatic or alicyclic, saturated or unsaturated hydrocarbon group where the allyl may be substituted with a C.sub.6 -C.sub.10 allyloxy group; Q represents O, S, CH.sub.2, O--CH.sub.2, S--CH.sub.2, CO, or CHOR.sup.1 ; L represents CO, CR.sup.2 R.sup.3 CO, CH.sub.2 CH.sub.2 CO, or CH.dbd.CHCO; D represents a hydrogen atom, NO.sub.2, NH.sub.2, CO.sub.2 R.sup.4, or a group having the following formula ?II!: ##STR2## (wherein G represents. a hydrogen atom, OH, SO.sub.2 NH.sub.2, CO.sub.2 R.sup.6, CN, or a tetrazol-5-yl group); E represents a hydrogen atom, OH, SO.sub.2 NH.sub.2, CO.sub.2 R.sup.5, CN, or a tetrazol-5-yl group; M represents a hydrogen atom, a C.sub.1 -C.sub.4 lower alkyl group, a nitro group, or a halogen atom; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: August 31, 1999
    Assignee: Teijin Limited
    Inventors: Kazuya Takenouchi, Katsushi Takahashi, Masaichi Hasegawa, Takahiro Takeuchi, Keiji Komoriya
  • Patent number: 5872280
    Abstract: The invention relates to benzoic acid derivatives being leukotriene antagonists. The compounds therefore are suitable as active ingredients in medicaments particularly in medicaments for the treatment of respiratory diseases.
    Type: Grant
    Filed: November 13, 1996
    Date of Patent: February 16, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Trevor Smyth Abram, Nigel James Cuthbert, Hilary Patricia Francis, Phillip John Gardiner, Peter Norman, Stephen Richard Tudhope
  • Patent number: 5767291
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: June 16, 1998
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Yves Ducharme, Jacques Yves Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 5744641
    Abstract: 4-Sulfonyl- or 4-sulfinylbenzoylguanidines of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.6 and n have the meanings indicated, and their physiologically acceptable salts exhibit antiarrhythmic properties and, act as inhibitors of the cellular Na.sup.+ /H.sup.+ antiporter.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: April 28, 1998
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Klaus-Otto Minck, Norbert Beier
  • Patent number: 5741794
    Abstract: Compounds of formula (I), wherein: A represents: a) a --VR.sup.6 group wherein v is --C(.dbd.O), --C(.dbd.O)O--, --CH.sub.2 O--, --CH.sub.2 OC(.dbd.O)--, --C(.dbd.S)--, --CH.sub.2 OC(.dbd.O)NH--, --C(.dbd.S)O--, --CH.sub.2 S--, --C(.dbd.O)NHSO.sub.2 --, --SO.sub.2 NHC(.dbd.O)-- or --CH.sub.2 OSiPh.sub.2 --; b) a --CH.sub.2 NR.sup.9 R.sup.10 group or a --CONR.sup.9 R.sup.10 group wherein each of R.sup.9 and R.sup.10 is independently hydrogen, -alkyl-, -alkenyl-, -alkynyl, -cycloalkyl, -cycloalkenyl, pyridyl (any of which may optionally be substituted) or a group --D as defined above or R.sup.9 and R.sup.10 together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic ring; c) a group Y where Y is a 5- or 6-membered optionally substituted heterocyclic ring containing one or more heteroatoms selected from nitrogen, oxygen and sulphur; or d) a group --CH.sub.2 Y or --C(.dbd.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: April 21, 1998
    Assignee: British Biotech Pharmaceuticals Limited
    Inventors: Stephen Arthur Bowles, Christopher David Floyd, Andrew Miller, Mark Whittaker, Lars Michael Wood
  • Patent number: 5733909
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: March 31, 1998
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Cameron Black, Mario Girard, Daniel Guay, Zhaoyin Wang
  • Patent number: 5670544
    Abstract: There are described benzoylguanidines of the formula I ##STR1## where R(1) is hydrogen, Hal, --NO.sub.2, --CN, --CF.sub.3, R(4)--SO.sub.m or R(5)R(6)N--SO.sub.2 --, where m is zero to 2, R(4) and R(5) are alk(en)yl or --C.sub.n H.sub.2n --R(7), n is zero to 4, where R(5) also has the meaning of H,R(6) is H or (C.sub.1 -C.sub.4)-alkyl, where R(5) and R(6) together can be 4 or 5 methylene groups,R(2) is --SR(10), --OR(10), --NRH(10), --NR(10)R(11), --CHR(10)R(12), ##STR2## where R(10) and R(11) are identical or different and are--?CHR(16)!.sub.s --(CH.sub.2).sub.p --(CHOH).sub.q --(CH.sub.2).sub.r --(CH.sub.2 OH).sub.t --R(21) or --(CH.sub.2).sub.p --O--(CH.sub.2 --CH.sub.2 O).sub.q --R(21)R(12) and R(13) are hydrogen or alkyl or, together with the carbon atom carrying them, form a cycloalkyl,R(14) is H, (cyclo)alkyl or --C.sub.n H.sub.2n --R(15),R(3) is defined as R(1), or is alkyl, hydrogen or --X--R(22) where X is oxygen, S or NR(16),and their pharmaceutically tolerable salts.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: September 23, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Weichert, Hans-Jochen Lang, Heinz-Werner Kleemann, Wolfgang Scholz, Udo Albus
  • Patent number: 5650533
    Abstract: The invention relates to 4-substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meaning defined in the description which possess valuable herbicidal properties.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 22, 1997
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventors: David Alan Roberts, Susan Mary Cramp, Derek Ian Wallis, Jean-Paul Bulot
  • Patent number: 5631394
    Abstract: This invention provides a compound having the formula R.sup.1 --Y.sup.1 --CHZ.sup.1 --CH(NY.sup.2 Y.sup.3)--CH.sub.2 --Z.sup.2, wherein: R.sup.1 is a straight-chained alkyl, alkenyl or alkynyl group having from 8 to 19 carbon atoms in the aliphatic chain; Y.sup.1 is --CH.dbd.CH--, --C.tbd.C-- or --CH(OH)CH(OH)--; Z.sup.1 is OH or a conversion-inhibiting group; Z.sup.2 is a conversion-inhibiting group; Y.sup.2 is H, a phenyl group, an alkyl-substituted phenyl group having from 1 to about 6 carbons in the alkyl chain, or an alkyl chain having from 1 to 6 carbons; Y.sup.3 is H or a group having the formula --C(O)R.sup.2 or --S(O).sub.2 R.sup.2 ; R.sup.2 is a straight-chained alkyl, alkenyl or alkynyl group having from 1 to 23 carbon atoms in the chain; and when Z.sup.2 is an amino, R.sup.2 is an aliphatic chain having from 1 to 9 or from 19 to 23 carbon atoms in the aliphatic chain.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: May 20, 1997
    Assignee: The Liposome Company, Inc.
    Inventors: Yong Wei, Eric Mayhew, Imran Ahmad, Andrew S. Janoff
  • Patent number: 5624959
    Abstract: (1) Naphthyloxyaetic acid represented by the compound of the formula (I): ##STR1## and non-toxic salts thereof, (2) process for the preparation of the compounds represented by the compound of the formula (I) described hereinbefore,(3) PGE.sub.2 antagonist or agonist containing the compound represented by the compound of the formula (I) as the active ingredient.The compounds represented by the compounds of the formula (I) can be adapted to medicines which possess an inhibitory effect of uterine contraction, an analgesic action, an inhibitory effect of digestive peristalsis, a sleep-inducing effect as PGE.sub.2 antagonists, and an uterine contractile activity, a promoting effect of digestive peristalsis, a suppressive effect of gastric acid secretion, hypotensive activity as PGE.sub.2 agonists. The compounds bind to PGE.sub.2 receptor and have an activity of antagonist or agonist against the action thereof.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: April 29, 1997
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Yuuki Nagao, Takayuki Maruyama, Nobuyuki Hamanaka
  • Patent number: 5618975
    Abstract: Biphenyl derivatives and processes for the preparation of biphenyl derivatives are described. A compound of formula (I) is disclosed ##STR1## in which the substituent X is --CHO or --CH(OR.sup.1)OR.sup.2, where R.sup.1 and R.sup.2 independently of one another are (C.sub.1 -C.sub.6)-alkyl or R.sup.1 and R.sup.2 together are an alkylene group (--CH.sub.2).sub.n --, where n is 2, 3 4 or 5 and R is --F, --Cl, --NO.sub.2, --(CH.sub.2).sub.m --COOR.sup.3, --(CH.sub.2).sub.m --CONHR.sup.3, --(CH.sub.2).sub.m --CN, --SO.sub.2 NH--COOR.sup.3, --SO.sub.2 NH--CO--NHR.sup.3, --SO.sub.2 NH--SO.sub.2 --R.sup.3, --NHSO.sub.2 R.sup.3, ##STR2## --PO.sub.3 R.sup.3, --NH--SO.sub.2 --CF.sub.3, --SO.sub.2 NR.sup.4 where R.sup.3 is hydrogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.6)cycloalkyl, or (C.sub.1 -C.sub.6)-alkyl-(C.sub.3 -C.sub.6)cycloalkyl and R.sup.4 is a group .dbd.C--N(CH.sub.3).sub.2, and m is 0, 1, 2, 3, or 4.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: April 8, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Adalbert Wagner, Neerja Bhatnagar, Jean Buendia, Christine Griffoul
  • Patent number: 5616797
    Abstract: An electrophotographic toner having polymeric binder and a charge control agent selected from the group consisting of sulfonamides having the general structure: ##STR1## and metal salts thereof. T.sup.1 is independently selected from H, alkyl having from 1 to 20 carbons, cycloalkyl having from 3 to 18 carbons, and aromatic and heteroaromatic ring systems having a solitary ring or 2 to 3 linked or fused rings. R.sup.1 is O, S, N--H, N--R.sup.5, or N--L--R.sup.5 ; where L is a linking group selected from: ##STR2## and R.sup.5 is independently selected from alkyl having from 1 to 20 carbons, cycloalkyl having from 3 to 18 carbons, and aromatic and heteroaromatic ring systems having a solitary ring or 2 to 3 linked or fused rings. L.sup.1 and L.sup.2 are each independently a direct link or divalent alkyl or fluoroalkyl having from 1 to 20 carbons. R.sup.a and R.sup.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: April 1, 1997
    Assignee: Eastman Kodak Company
    Inventors: John C. Wilson, Peter S. Alexandrovich, Steven M. Bonser
  • Patent number: 5610320
    Abstract: Sulfonamide compounds of the formula or pharmacologically acceptable salts thereof: ##STR1## wherein: R.sup.1 is a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, nitro group, phenoxy group, cyano group, acetyl group, amino group or a protected amino group; R.sup.2 and R.sup.3 may be the same or different from each other and each is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group; R.sup.4 and R.sup.7 may be the same or different from each other and each is a hydrogen atom or a lower alkyl group; R.sup.5 and R.sup.6 may be the same or different from each other and each is a hydrogen atom, halogen atom, lower alkoxy group, amino group or amino group substituted with a lower alkyl or a phenyl group; A is .dbd.CH--; B is .dbd.CH--; and E is selected from the group consisting of ##STR2## in which Q is an oxygen atom or a sulfur atom; and R.sup.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: March 11, 1997
    Assignee: Eisai Co., Ltd.
    Inventors: Hiroshi Yoshino, Norihiro Ueda, Hirovuki Sugumi, Jun Niijima, Yoshihiko Kotake, Toshimi Okada, Nozomu Koyanagi, Tatsuo Watanabe, Makoto Asada, Kentaro Yoshimatsu, Atsumi Iijima, Takeshi Nagasu, Kappei Tsukahara, Kyosuke Kitoh
  • Patent number: 5545838
    Abstract: Compounds of the formula ##STR1## wherein Z is SO or SO.sub.2 possess renin inhibition activity and are useful in treating hypertension and other diseases where the reduction of the levels of circulating angiotensin II are beneficial.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: August 13, 1996
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Michael A. Poss
  • Patent number: 5536752
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: July 16, 1996
    Assignee: Merck Frosst Canada Inc.
    Inventors: Yves Ducharme, Jacques Y. Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 5523464
    Abstract: The present invention relates to benzenesulfonamide derivatives represented by Formula (I): ##STR1## in which R.sup.1 and R.sup.2 independently represent hydrogen or lower alkanoyl; and R.sup.3 and R.sup.4 independently represent hydrogen, lower alkyl, cycloalkyl, substituted or unsubstituted polycycloalkyl, substituted aryl, or a substituted or unsubstituted heterocyclic group, or R.sup.3 and R.sup.4 are combined together with the adjacent nitrogen atom to form a substituted or unsubstituted aliphatic heterocyclic group, or a pharmaceutically acceptable salt thereof. The derivatives are useful as therapeutic agents for osteoporosis.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: June 4, 1996
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Iwao Kinoshita, Haruki Takai, Nobuo Kosaka, Katsura Sugawara, Akio Ishii, Hiroyuki Ishida, Katsushige Gomi
  • Patent number: 5463081
    Abstract: The invention relates to novel intermediates for the preparation of a certain group of novel phenylsulfonylurea herbicides, which herbicides are particularly advantageous for use in crop protection. The novel intermediate compounds are of the formula II ##STR1## and of the formula VI, ##STR2## as defined in the specification and claims. The intermediate compounds may be used to prepare herbicidal and plant growth regulating compounds of the formula I or salts thereof: ##STR3## as defined in the specification. The herbicides so obtained are particularly suitable for selectively controlling weeds.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Oswald Ort, Klaus Bauer, Hermann Bieringer
  • Patent number: 5463104
    Abstract: Succinoylamino hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: October 31, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
  • Patent number: 5451677
    Abstract: Substituted phenylsulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted alkyl epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: September 19, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Michael H. Fisher, Robert J. Mathvink, Hyun O. Ok, Emma R. Parmee, Ann E. Weber
  • Patent number: 5391825
    Abstract: Pharmaceutical compositions are provided for the treatment of disorders in a subject, such as hypertension, congestive heart failure, angina pectoris, lower urinary tract dysfunction and prostatic hypertrophy. The compositions when administered to a subject produce an .alpha.-adrenergic blocking action and contain as an active ingredient sulfamoyl-substituted phenethylamine derivatives, such as optically active 5-2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl-2-methoxybenzenesulfonam ide, and a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: December 28, 1993
    Date of Patent: February 21, 1995
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kunihiro Niigata, Takashi Fujikura
  • Patent number: 5210257
    Abstract: Novel aryl ethers, containing both a carboxylic acid and a sulfonic acid functionality; and a process for making them are described. These difunctional aryl compounds comprise:i) a carboxylic acid group or its derivative,ii) a first aromatic group bonded to the carboxylic acid or its derivative,iii) a second aromatic group linked to the first aromatic group by a non-electron-withdrawing moiety,iv) a third aromatic group linked to the second aromatic group by a non-electron-withdrawing moiety, andv) a sulfonyl group or its derivative bonded to the third aromatic group.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventor: William J. Harris
  • Patent number: 5152826
    Abstract: An herbicide 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.n -- wherein n 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.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.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; orR.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; orR.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: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5086060
    Abstract: The effects of acne and psoriasis are relived by applying either topically or by oral adminstration, a compound having the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently selected from the group consisting of H, Cl, straight or branched alkyl of 1 to 10 carbon atoms, NO.sub.2, COOR.sub.6, CN, OR.sub.6, NR.sub.6 R.sub.7, NR.sub.6 C(.dbd.S)NR.sub.7 R.sub.8, NF.sub.6 COR.sub.7, SO.sub.2 NR.sub.6 R.sub.7, CH(CH.sub.3)COOH, CONR.sub.6 R.sub.7, COR.sub.6, OCONR.sub.6 R.sub.7, NR.sub.6 COONR.sub.7, R.sub.9 OR.sub.6, NR.sub.6 SO.sub.2 R.sub.7, Si(CH.sub.3).sub.3, and NR.sub.6 CONR.sub.7 R.sub.8,R.sub.3 together with R.sub.4 forms a benzo ring or taken together with R.sub.2 forms a benzo or tetrahydrobenzo ring or together with R.sub.2 and R.sub.1 forms a: ##STR2## moiety or together with R.sub.2 forms a ##STR3## moiety or R.sub.2 together with R.sub.1 forms a benzo ring or R.sub.2 together with R.sub.3 forms a ##STR4## moiety, or R.sub.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: February 4, 1992
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Xina Nair, Gerard J. Gendimenico, F. Christopher Zusi, R. Thomas Swann
  • Patent number: 5047420
    Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 10, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
  • Patent number: 5030631
    Abstract: Novel tricyclic arylsulfonamides useful for treating hypertension and bronchoconstiction, as well as to their pharmaceutical compositions and methods for using the same.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 9, 1991
    Assignee: Schering Corporation
    Inventor: Barr E. Bauer
  • Patent number: 5002972
    Abstract: Pharmaceutical compounds and compositions for injectable use in the treatment of thromboxane A.sub.2 mediating diseases, comprising a pharmaceutical carrier and a pharmacologically effective amount of a compound of the formula: ##STR1## wherein R.sup.1 is carboxyl or 5-tetrazolyl; R.sup.2 is hydrogen, methyl, hydroxy, chloro, or bromo; or a pharmaceutically acceptable ester or salt thereof, together with one or more non-toxic pharmaceutically acceptable carriers; and methods for treating thromboxane A.sub.2 mediating diseases.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: March 26, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Takaharu Matsuura
  • Patent number: 4997473
    Abstract: Compunds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, nitro, C.sub.1 C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or C.sub.1 C.sub.2 alkylsulfonyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.2 alkyl; and R.sup.4 and R.sup.5 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.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.3 C(O)- wherein R.sup.3 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.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: March 5, 1991
    Assignee: ICI Americas Inc.
    Inventor: Nhan H. Nguyen
  • Patent number: 4994612
    Abstract: Dihydropyridine derivatives of the formula ##STR1## wherein the symbols R and R.sup.1 to R.sup.6 have the significance given in claim 1, have a pronounced calcium-antagonist activity and can accordingly be used as medicaments, especially in the control or prevention of angina pectoris, ischemia, high blood pressure and/or migraine.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: February 19, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Roland Jaunin, Henri Ramuz
  • Patent number: 4992563
    Abstract: This invention relates to several intermediates useful in preparing thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-1.alpha ., 4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha., 7a.alpha.-4.alpha.,7.alpha.-methano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: February 12, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4948809
    Abstract: The present invention provides sulphonylphenylalkylamines of the general formula: ##STR1## wherein R.sub.1 is an alkyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3-7 carbon atoms or an aralkyl, aralkenyl or aryl radical, the aryl moiety, in each case, being optionally substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.16 acyl or azide, R.sub.2 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical or an aralkyl or aralkenyl radical, the aryl moiety, in each case, optionally being substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: August 14, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ernst-Christian Witte, Hans-Peter Wolff, Karlheinz Stegmeier, Johannes Pill
  • Patent number: 4946981
    Abstract: Compounds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro, S(O).sub.n R wherein R is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.2 through R.sup.8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: August 7, 1990
    Assignee: ICI Americas Inc.
    Inventors: Charles G. Carter, David L. Lee, William J. Michaely, Gary W. Kraatz
  • Patent number: 4943655
    Abstract: Process for preparing 2-alkyl-5-haloacetylbenzenesulfonamide represented by the general formula (1), ##STR1## (wherein R.sup.1 is an alkyl group having 1 to 5 carbon atoms; and X is a chlorine atom, bromine atom or iodine atom), characterized by halogenating a 5-acetyl-2-alkylbenzenesulfonamide represented by the general formula (2), ##STR2## (wherein R.sup.1 is the same as defined above) in a lower alcohol represented by the general formula (3),R.sup.4 --OH(wherein R.sup.4 is an alkyl group having 1 to 5 carbon atoms).
    Type: Grant
    Filed: March 24, 1989
    Date of Patent: July 24, 1990
    Assignee: Seitetsu Kagaku Co., Ltd.
    Inventors: Kunioki Kato, Masao Kawamura, Hiroshi Goda, Kiyoshi Sawada, Kazuhiro Hamatani
  • Patent number: 4912262
    Abstract: According to the present invention there is provided process for preparing a compound of formula (I): ##STR1## or a salt, acylate or sulphonate derivative thereof; wherein R.sup.1 is an optionally substituted aryl group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a wherein R.sup.a is C.sub.1-4 alkyl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the carbon atom to which they are attached form a C.sub.3-6 cycloalkyl ring, provided that at least R.sub.2 and R.sup.3 or R.sup.4 and R.sup.5 are not both hydrogen and that not more than two of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a ; which process comprises reacting a compound of formula (II): ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in relation to formula (I) with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: March 27, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Glynn Mitchell
  • Patent number: 4908467
    Abstract: N-Phenylsulfonyl-B'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## wherein A is 3,3,3-trifluoropropyl or 3,3-difluorobutyl,R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, --CO--R.sup.6, --NR.sup.7 R.sup.8, --CO--NR.sup.9 R.sup.10 or --SO.sub.2 --NR.sup.11 R.sup.12,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl or C.sub.1 -C.sub.4 -alkylsulfonyl,R.sup.3 and R.sup.4 independently of one another are each hydrogen, halogen C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkoxy or --NR.sup.12 R.sup.13,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sup.6 is C.sub.1 -C.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Konrad Oertle
  • Patent number: 4902787
    Abstract: A method of producing a UV lightfast disperse dyestuff comprising selecting a disperse dyestuff having predetermined chromophoric groups, selecting a photostabilizer compound, designing a hybrid disperse dye molecular structure which contains the chromophoric groups of the selected disperse dyestuff and also contains the molecular structural features of the selected photostabilizer compound, and synthesizing the thus designed hybrid disperse dyestuff molecule. Such a method produces a hybrid dye molecule which is a UV lightfast analog of a disperse dyestuff having predetermined chromophoric groups, said hybrid dye molecule containing in its molecular structure the chromophoric groups of the selected disperse dyestuff and also containing the molecular structural features of a photostabilizer compound.
    Type: Grant
    Filed: April 21, 1988
    Date of Patent: February 20, 1990
    Assignee: North Carolina State University
    Inventor: Harold S. Freeman