Nitrogen Bonded Directly To The Bicyclo Ring System Patents (Class 549/439)
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Patent number: 6605626Abstract: This application relates to a compound of formula I (or a prodrug thereof or a pharmaceutically acceptable salt of the compound or prodrug thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.Type: GrantFiled: September 21, 2001Date of Patent: August 12, 2003Assignee: Eli Lilly and CompanyInventors: Douglas Wade Beight, Trelia Joyce Craft, Jeffry Bernard Franciskovich, Theodore Goodson Jr., Steven Edward Hall, David Kent Herron, Valentine Joseph Klimkowski, Jeffrey Alan Kyle, John Joseph Masters, David Mendel, Guy Milot, Jason Scott Sawyer, Robert Theodore Shuman, Gerald Floyd Smith, Anne Louise Tebbe, Jennifer Marie Tinsley, Leonard Crayton Weir, James Howard Wikel, Michael Robert Wiley, Ying Kwong Yee
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Patent number: 6596863Abstract: Process for producing a nitroetheneamine derivative or its stereoisomer, its tautomer or a salt thereof comprising reacting a compound of the formula with a compound of the formula R6—CH2NO2 to obtain a compound of the formula and reacting the resulting compound with a compound of the formulaType: GrantFiled: April 29, 2002Date of Patent: July 22, 2003Assignee: Ishihara Sangyo Kaisha, Ltd.Inventors: Fuminori Kato, Keizo Miyata, Hirohiko Kimura, Kazuhiro Yamamoto, Hiroyuki Ikegami, Hiromi Takeo
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Patent number: 6518291Abstract: The present invention relates to a novel class of compounds which are IMPDH inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting IMPDH enzyme activity and consequently, may be advantageously used as therapeutic agents for IMPDH mediated processes. This invention also relates to methods for inhibiting the activity of IMPDH using the compounds of this invention and related compounds.Type: GrantFiled: September 14, 1999Date of Patent: February 11, 2003Assignee: Vertex Pharmaceuticals, IncorporatedInventors: Jeffrey O. Saunders, David M. Armistead, Michael C. Badia, Randy S. Bethiel, Catherine A. Frank, Doug Naegele, Perry M. Novak, David A. Pearlman, Steven M. Ronkin
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Patent number: 6512140Abstract: A process for the preparation of highly pure 1-(mercaptomethyl)-cyclopropaneacetic acid is described. Treatment of 1-(hydroxymethyl)-cyclopropaneacetonitrile with an acid provides the corresponding imino ester and/or halo-amide, which when reacted with thiourea provide the corresponding amide-isothiuronium salt. Hydrolysis of the amide-isothiuronium salt followed by an in situ oxidation allows the facile isolation and purification of 1-[1 -(carboxymethyl)-cyclopropanemethyldisulfanylmethyl]-cyclopropaneacetic acid (also known as 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide). Reduction of the 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide under mild conditions provides the 1-(mercaptomethyl)-cyclopropaneacetic acid with high purity.Type: GrantFiled: April 15, 2002Date of Patent: January 28, 2003Assignee: Delmar Chemicals Inc.Inventors: Lu Wei Liu, Yuan Wang, Hérika Marrugo, Sylvain Harper, David D. C. Quan, Zhihong (Nancy) Zhou, Gregory Bydlinski
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Patent number: 6451792Abstract: A medical composition containing, as an active constituent, a nitroetheneamine derivative represented by the formula (I): wherein the substituents are as defined in the disclosure, its stereoisomers, its tautomers or a salt thereof.Type: GrantFiled: March 20, 2001Date of Patent: September 17, 2002Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Fuminori Kato, Keizo Miyata, Hirohiko Kimura, Kazuhiro Yamamoto, Hiroyuki Ikegami, Hiromi Takeo
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Patent number: 6448412Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the Cn fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by 3He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.Type: GrantFiled: October 30, 2000Date of Patent: September 10, 2002Assignee: Sphere Biosystems, Inc.Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
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Patent number: 6448295Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N-fused-phenyl-N-benzyl aminoalcohols.Type: GrantFiled: November 14, 2001Date of Patent: September 10, 2002Assignee: G.D. Searle & Co.Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
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Patent number: 6399628Abstract: Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.Type: GrantFiled: March 12, 1999Date of Patent: June 4, 2002Assignees: Athena Neurosciences, Inc., Eli Lilly & CompanyInventors: James E. Audia, Beverly K. Folmer, Varghese John, Lee H. Latimer, Jeffrey S. Nissen, Jon K. Reel, Eugene D. Thorsett, Celia A. Whitesitt
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Patent number: 6399785Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the Cn fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by 3He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.Type: GrantFiled: October 30, 2000Date of Patent: June 4, 2002Assignee: C-Sixty, Inc.Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
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Patent number: 6388131Abstract: The invention provides compounds, compositions and methods relating to novel electrophilic aromatic derivatives and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, psoriasis, vascular restenosis, infections, atherosclerosis and hypercholesterolemia, or as lead compounds for the development of such agents.Type: GrantFiled: May 31, 2001Date of Patent: May 14, 2002Assignee: Tularik, Inc.Inventors: Julio Cesar Medina, David Louis Clark, John A. Flygare, Terry J. Rosen, Bei Shan
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Patent number: 6362205Abstract: Described are substituted cyanoenamines of formula I wherein Z, R1, R2 and R3 are defined in the description, compositions thereof and methods for preparing these compounds. These compounds are useful in the treatment of diseases of the central nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinologic system.Type: GrantFiled: March 16, 2001Date of Patent: March 26, 2002Assignee: Novo Nordisk A/SInventors: John Bondo Hansen, Tina Moller Tagmose, John Patrick Mogensen, Florencio Zaragoza Dorwald, Anker Steen Jorgensen
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Publication number: 20020019440Abstract: The invention concerns aryloxypropanolamnine derivatives having at least an anti-diabetic and anti-fat activity and their methods of preparation and applications, particularly as human and veterinary medicine and animal food additive. These derivatives comply with the general formula (I) in which R2 represents one of the following groups: —CH2—, —CH2—CH2, —CH(CH3)—CH2—C(CH3)—CH—, —C(CH3)2—CH2— or a bond; Q represents: (i) a phenyl radical 3,4-substituted alkylene dioxy determining with the phenyl radical, a non-substituted benaodioxane unit, a non-substituted benzodioxol unit, or a 2-substituted benzodioxol unit, (ii) a phenyl radical 3 and/or 4-substituted, by a O—(CH2)x—COOR5 group, (iii) a condensed polycyclic hydrocarbon comprising at least two condensed cycles, (iv) a cyclic hydrocarbon system, optionally cross-linked, and constituting a cycloalkane comprising 1, 2 or 3 cycles.Type: ApplicationFiled: August 23, 2001Publication date: February 14, 2002Applicant: VIRBAC SAInventors: Archimbault Philippe, Leclerc Gerard, Strosberg Arthur Donny, Pietri-Rouxel France
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Patent number: 6313122Abstract: This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.Type: GrantFiled: March 20, 2000Date of Patent: November 6, 2001Assignee: Eli Lilly and CompanyInventors: Douglas Wade Beight, Trelia Joyce Craft, Jeffry Bernard Franciskovich, Theodore Goodson, Jr., Steven Edward Hall, David Kent Herron, Valentine Joseph Klimkowski, Jeffrey Alan Kyle, John Joseph Masters, David Mendel, Guy Milot, Jason Scott Sawyer, Robert Theodore Shuman, Gerald Floyd Smith, Anne Louise Tebbe, Jennifer Marie Tinsley, Leonard Crayton Weir, James Howard Wikel, Michael Robert Wiley, Ying Kwong Yee
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Patent number: 6310080Abstract: Selected amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically inhibiting retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.Type: GrantFiled: December 1, 1999Date of Patent: October 30, 2001Assignee: G. D. Searle & Co.Inventors: Daniel P Getman, Gary A. DeCrescenzo, John N. Freskos, Michael L. Vazquez, James A. Sikorski, Balekudru Devadas, Srinivasan Nagarajan, David L. Brown, Joseph J. McDonald
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Patent number: 6284923Abstract: The invention provides compounds, compositions and methods relating to novel electrophilic aromatic derivatives and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, psoriasis, vascular restenosis, infections, atherosclerosis and hypercholesterolemia, or as lead compounds for the development of such agents.Type: GrantFiled: August 22, 1997Date of Patent: September 4, 2001Assignee: Tularik INCInventors: Julio Cesar Medina, David Louis Clark, John A. Flygare, Terry J. Rosen, Bei Shan
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Patent number: 6271399Abstract: Indane and indene compounds are described which are endothelin receptor antagonists.Type: GrantFiled: June 2, 1995Date of Patent: August 7, 2001Assignee: SmithKline Beecham CorporationInventors: Russell Donovan Cousins, John Duncan Elliott, Maria Amparo Lago, Jack Dale Leber, Catherine Elizabeth Peishoff
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Patent number: 6214870Abstract: The present invention relates to dioxocyclopentyl hydroxamide derivatives of the formula wherein X, Z and Q are as defined in the specification, and to pharmaceutical compositions and methods of treatment thereof.Type: GrantFiled: March 28, 2000Date of Patent: April 10, 2001Assignee: Pfizer IncInventors: Kim F. McClure, Ralph P. Robinson
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Patent number: 6162926Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the C.sub.n fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by .sup.3 He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.Type: GrantFiled: November 13, 1997Date of Patent: December 19, 2000Assignee: Sphere Biosystems, Inc.Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
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Patent number: 6017918Abstract: The present invention provides compounds having the Formula I ##STR1## The present invention also provides methods of treating atherosclerosis, coronary heart disease, and restenosis using the compounds of Formula I, and pharmaceutical compositions comprising the compounds of Formula I.Type: GrantFiled: July 26, 1999Date of Patent: January 25, 2000Assignee: Warner-Lambert CompanyInventors: Helen Tsenwhei Lee, Mark Alan Massa, William Chester Patt, Bruce David Roth
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5948909Abstract: The invention relates to a method for the stereoselective preparation of a hetero-bicyclic alcohol enantiomer, characterized in that a substantially pure enantiomer of the general formula ##STR1## is prepared from a compound of the general formula ##STR2## wherein the variable are as defined as in claim 1. The method comprises the following successive reaction steps:(i) reaction with a substantially enantiomerically pure compound of the general formula ##STR3## wherein Z, R.sub.3 and R.sub.4 are defined as in claim 1; (ii) subjection of the compound formed to a deprotection/ring-closure reaction;(iii) optionally deprotection of the hydroxy group of the ring-closed product.The invention further relates to enantiomerically pure intermediates, the preparation of these intermediates and the preparation of a starting compound.Type: GrantFiled: January 22, 1997Date of Patent: September 7, 1999Assignee: Duphar International Research B.V.Inventors: Nicolaas Buizer, Chris G. Kruse, Klara M. Schenk, Belal Shadid
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Patent number: 5912365Abstract: Novel derivatives of 1R- or 1S-2-azabicyclo?2.2.1!heptane with the general formula (I) or (I'), preparation and their application. ##STR1## In the general formulas (I) and (I'), R represents a hydrogen atom or a group with the formula ##STR2## respectively, in which R.sub.1 represents an alkyl group containing 1-4 carbon atoms and Ar represents an optionally substituted phenyl or a- or b-naphthyl group.Type: GrantFiled: August 19, 1997Date of Patent: June 15, 1999Assignee: Rhone-Poulenc Rorer SAInventors: Denis Largeau, Patrick Leon
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Patent number: 5847123Abstract: Imide compounds having a propioloyl group or pharmaceutically acceptable salts thereof which exhibit potent activities to inhibit the production of Interleukin 1-.beta. and also the production of Tumor Necrosis Factor .alpha.. These imide compounds are useful as a prophylactic or therapeutic agent for inhibiting the production of Interleukin 1-.beta. and the production of Tumor Necrosis Factor .alpha., typically for such diseases as chronic rheumatism, sepsis, ulcerative colitis, Crohn's disease and many other related diseases in which Interleukin 1-.beta. and/or Tumor Necrosis Factor .alpha. would participate.Type: GrantFiled: July 1, 1997Date of Patent: December 8, 1998Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Shinji Yokoyama, Noriyoshi Sueda, Hiroaki Yamada, Ryotaro Kojima, Koichi Katsuyama
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Patent number: 5780592Abstract: A composition comprising lipoproteins and a compound of the formula I ##STR1## stereoisomeric form or salt thereof, suitable for the treatment of immunological disorders, cancer or in transplantation.Type: GrantFiled: December 10, 1996Date of Patent: July 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Stefan Mullner, Axel Hofmann, Karin Saar, Hans-Ulrich Schorlemmer, Robert Bartlett
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Patent number: 5777137Abstract: Disclosed are novel pancratistatins and methods for their total asymmetric synthesis. In particular embodiments, processes for the total asymmetric synthesis of (+)-pancratistatin, (-)-pancratistatin, (+)-7-deoxypancratistatin, (-)-7-deoxypancratistatin, truncated pancratistatins, and related derivatives are provided.Type: GrantFiled: November 1, 1995Date of Patent: July 7, 1998Assignee: University of FloridaInventors: Tomas Hudkicky, Kurt Konigsberger, Sherita D. McLamore, Rakesh Maurya
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Patent number: 5777162Abstract: Described herein are compounds of Formula (XX) and Formula (XXIV), shown below, and processes of making same. ##STR1## wherein p is 0 ##STR2## wherein p is 1, and Y is chlorine or bromine.Type: GrantFiled: November 12, 1996Date of Patent: July 7, 1998Assignee: Zeneca LimitedInventors: Ian Richard Matthews, Christopher Richard Ayles Godfrey, John Martin Clough
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Patent number: 5739166Abstract: A class of terphenyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and halo; or wherein R.sup.2 and R.sup.3 together form --OCH.sub.2 O--; wherein each of R.sup.6 through R.sup.8 is independently selected from hydrido, lower alkyl, halo, lower alkoxy, lower haloalkyl, and lower dialkylamino; or wherein R.sup.6 and R.sup.7 together form --OCH.sub.2 O; and wherein R.sup.12 is selected from lower alkylsulfonyl and aminosulfonyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: November 29, 1994Date of Patent: April 14, 1998Assignee: G.D. Searle & Co.Inventors: David B. Reitz, Jinglin Li, Monica B. Norton
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Patent number: 5670665Abstract: According to the invention, a new process for the preparation of fluorine-substituted aminobenzodioxoles and -benzodioxanes of the formula (I) ##STR1## in which n represents an integer 1 or 2, has been found, in which fluorine-substituted nitro-halogeno-benzodioxoles and -benzodioxanes, which are likewise new, are hydrogenated. The novel intermediates are obtained from fluorine-substituted benzodioxoles and benzodioxanes by halogenation and subsequent nitration. The amino compounds are important starting materials for highly active biocides.Type: GrantFiled: June 17, 1996Date of Patent: September 23, 1997Assignee: Bayer AktiengesellschaftInventors: Peter Andres, Albrecht Marhold
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Patent number: 5665155Abstract: The invention relates to a coating material comprising polyorganosiloxanes with ester and/or epoxide groups, linked to silicon atoms over carbon atoms, for modifying the surface of finely divided particles, such as pigments and fillers, or of glass fibers.Type: GrantFiled: January 31, 1996Date of Patent: September 9, 1997Assignee: Th. Goldschmidt AG.Inventors: Werner Hohner, Dietmar Schaefer
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Patent number: 5663368Abstract: This invention relates to novel diastereomeric acid addition salts of homochiral hydroxylamines, to processes for obtaining such, to processes for the conversion thereof to the corresponding homochiral hydroxylamines, to certain novel homochiral hydroxylamines and the processes for using these as intermediates.Type: GrantFiled: April 11, 1996Date of Patent: September 2, 1997Assignee: Smithkline Beecham CorporationInventors: Joseph R. Flisak, Stephen Torey Ross
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Patent number: 5554772Abstract: N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives, their N-oxide forms and pharmaceutically acceptable salts having gastrointestinal motility stimulating properties, compositions containing these compounds as active ingredient and methods of treating warm-blooded animals suffering from the decreased peristalsis of the gastrointestinal system.Type: GrantFiled: April 3, 1995Date of Patent: September 10, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Frans M. A. Van den Keybus
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Patent number: 5536853Abstract: Compounds of Formula 1 bind opioid receptors: ##STR1## wherein X and Y are each independently ##STR2##Type: GrantFiled: April 11, 1994Date of Patent: July 16, 1996Assignee: Chiron CorporationInventors: David C. Spellmeyer, Walter H. Moos, Eric J. Martin, Ronald N. Zuckermann, Gregory Stauber, Kevin R. Shoemaker, Dane Goff
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Patent number: 5480871Abstract: Compounds of the formula: ##STR1## are useful for treating conditions modulated by .alpha..sub.1 -adrenergic receptors.Type: GrantFiled: May 12, 1995Date of Patent: January 2, 1996Assignee: Chiron CorporationInventors: David C. Spellmeyer, Walter H. Moos, Eric J. Martin, Ronald N. Zuckermann, Gregory Stauber
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Patent number: 5459149Abstract: The present Application discloses pesticidally active compounds of formula (I):Q(CH.sub.2).sub.a (O).sub.b Q.sup.1 CR.sup.2 =CR.sup.3 CR.sup.4 =CR.sup.5 CXNR.sup.1 R.sup.xor a salt or propesticide thereof, wherein Q is an optionally substituted aromatic monocyclic or fused bicyclic ring system in which at least one ring is aromatic, or Q is a dihalovinyl group or a group R.sup.6 --C=C--where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halo or hydrogen; Q.sup.1 is a 1,2-cyclopropyl ring optionally substituted by one or more groups selected from C.sub.1-3 alkyl, halo, C.sub.1-3 haloalkyl, C.sub.2-3 alkynyl, or cyano; or Q.sup.1 is (CH.sub.2).sub.7 ; a=0 or 1; b=0 or 1; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; X is oxygen or sulphur;R.sup.1 is phenyl optionally substituted by 1-5 substituents chosen from: a) C.sub.1-4 alkyl, C.sub.Type: GrantFiled: September 20, 1994Date of Patent: October 17, 1995Assignee: Roussel UclafInventors: John E. Robinson, George S. Cockerill
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Patent number: 5447916Abstract: Compounds of the formula: ##STR1## are useful for treating conditions modulated by .alpha..sub.1 -adrenergic receptors.Type: GrantFiled: July 30, 1993Date of Patent: September 5, 1995Assignee: Chiron CorporationInventors: David C. Spellmeyer, Walter H. Moos, Eric J. Martin, Ronald N. Zuckermann, Gregory Stauber
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Patent number: 5420273Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.Type: GrantFiled: December 23, 1993Date of Patent: May 30, 1995Assignee: Hoffman-La Roche Inc.Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
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Patent number: 5420309Abstract: Novel fluorinated 1,3-benzo- and 1,3-pyrido-dioxoles of formula (I): ##STR1## in which A is C-R.sup.4 or N,X is hydrogen, fluorine, chlorine or bromine andR.sup.1 to R.sup.4 can be identical to or different from one another and are each hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogeno-C.sub.1 -C.sub.6 -alkyl, C.sub.6 -C.sub.10 -aryl, CHO, COOH, COCl, CN, OH, NCO, COO--C.sub.1 -C.sub.6 -alkyl, NO.sub.2, NH.sub.2, NH--C.sub.1 -C.sub.6 -alkyl, N(C.sub.1 -C.sub.6 -alkyl).sub.2, SO.sub.2 Cl, SO.sub.3 H, SO.sub.3 Na or SO.sub.3 K,it also being possible for two adjacent radicals from the series R.sup.1 to R.sup.4 together to be an optionally substituted --CH.dbd.CH--CH.dbd.CH-- bridge, processes for their preparation and their use for the preparation of plant protection agents.Type: GrantFiled: October 29, 1993Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5416112Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of ##STR2## Z.sub.1 and Z.sub.2 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN and alkyl of 1 to 3 carbon atoms, R.sub.3 is hydrogen or alkyl of 1 to 3 carbon atoms, m is an integer from 0 to 6, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are individually selected from the group consisting of hydrogen, halogen, --CN, --NO.sub.2, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.10, --(CH.sub.2).sub.n --CX.sub.3, --O--(CH.sub.2).sub.n CX.sub.3 and --S--(CH.sub.2).sub.n --CX.sub.3, R.sub.Type: GrantFiled: June 6, 1994Date of Patent: May 16, 1995Assignee: Roussel UclafInventor: Elizabeth A. Kuo
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Patent number: 5395952Abstract: A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hetero atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 --group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 --groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.Type: GrantFiled: January 10, 1994Date of Patent: March 7, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Masayuki Enomoto, Junya Takahashi, Tomoyuki Kusaba, Masayo Sugano, Rei Matsunaga, Masahiro Tamaki
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Patent number: 5384423Abstract: A compound selected from the group consisting of all tautomeric forms of a cycloalkyl-propanamide of the formula ##STR1## wherein R.sub.1 is cycloalkyl of 3 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, azido, --CN, alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, --(CH.sub.2).sub.m --CF.sub.3, --O--(CH.sub.2).sub.m --CF.sub.3, --S--(CH.sub.2).sub.m --CF.sub.3, m is an integer from 0 to 3, --CF.sub.2 --Hal, --OCF.sub.2 --Hal, ##STR2## n is an integer from 1 to 3, Hal, Hal.sub.1, and Hal.sub.2 and Hal.sub.3 are individually halogen, and --COR', R' is --OH or alkyl or alkoxy of 1 to 3 carbon atoms or R.sub.4 and R.sub.5 together are --O--CH.sub.2 --O-- and their non-toxic, pharmaceutically acceptable basic salts having anti-inflammatory activity.Type: GrantFiled: April 22, 1993Date of Patent: January 24, 1995Assignee: Roussel-UclafInventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully
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Patent number: 5378727Abstract: Novel substituted heterocyclic derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.Type: GrantFiled: July 19, 1993Date of Patent: January 3, 1995Assignee: G. D. Searle & Co.Inventors: Philippe R. Bovy, Joseph G. Rico, Thomas E. Rogers, Foe S. Tjoeng, Jeffery A. Zablocki
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Patent number: 5356924Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a halogen atom or an alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, alkenoxy, cyano or nitro group; R.sub.3 and R.sub.4 each independently represents a hydrogen atom or an alkyl group; R.sub.5 represents a hydrogen atom, or an alkyl, alkoxy or alkoxycarbonylalkyl group; X and Y each independently represents an oxygen or sulphur atom or a group N--R, in which R is a hydrogen atom or an alkyl group; n is 0-3; r is 0 or 1; m is 0-4; and A or B represents a group of the general formula: ##STR2## wherein R.sub.6 represents a hydrogen or halogen atom, or an alkyl group; and R.sub.7 represents a halogen atom or an alkyl group; the other of A and B being a hydrogen atom or as for R.sub.1 or R.sub.2, have useful pesticidal activity.Type: GrantFiled: February 22, 1993Date of Patent: October 18, 1994Assignee: Shell Research LimitedInventors: Martin Anderson, Antony G. Brinnand, Roger E. Woodall
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Patent number: 5310682Abstract: Compounds containing .alpha.-discarbonyl groups are rendered capable of fluorescent emission by conjugation with carboxylic acid-terminated ortho-diaminoaryl reagents. The carboxylic acid groups serve as ionizable moieties which facilitate the conjugation reaction, and are retained in the conjugation product to enable, or enhance the ability of, the conjugated compounds to be separated in chromatographic and electromigration separation processes, notably electrophoresis. Ortho-dinitro derivatives of the reagents are also disclosed, these derivatives offering the advantage of stability as well as the ability to be used directly in the reaction in the presence of a reducing agent.Type: GrantFiled: June 17, 1992Date of Patent: May 10, 1994Assignee: Indiana University FoundationInventors: Milos V. Novotny, Osamu Shirota, Donald Wiesler
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Patent number: 5308865Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of ##STR2## R.sub.13, R.sub.14 and R.sub.15 are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 3 carbon atoms, n is an integer from 1 to 3, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4 R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, alkylcarbonyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, ##STR3## m is 0, 1, 2 or 3, n is 1, 2 or 3; Hal, Hal.sub.1, Hal.sub.2 and Hal.sub.3 are individually halogen and ##STR4## R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are individually any of the groups defined above for R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 or R.sub.4 and R.sub.5 together form --O--CH.sub.Type: GrantFiled: January 6, 1993Date of Patent: May 3, 1994Assignee: Roussel UclafInventors: Robert R. Bartlett, David P. Kay, Elizabeth A. Kuo, Rudolf Schleyerbach, Wilfried Schwab
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Patent number: 5298661Abstract: Charge transporting materials having general formula (I): ##STR1## R.sup.1 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; an aralkyl group; a nitro group; an unsubstituted or substituted aryl group; a halogen; an amino group; an unsubstituted or substituted dialkylamino group; R.sup.2 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; or a halogen; R.sup.3 represents hydrogen; an alkyl group having 1 to 4 carbon atoms; an alkoxyl group having 1 to 4 carbon atoms; a halogen; a dialkylamino group; an amino group; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; a methylenedioxy group; an aralkyl group; or an unsubstituted or substituted aryl group; R.sup.Type: GrantFiled: June 18, 1993Date of Patent: March 29, 1994Assignee: Ricoh Company, Ltd.Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
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Patent number: 5281725Abstract: New 2,2-dihalogeno-benzo[1,3]dioxoles substituted in the 4-position, of the general formula (I) ##STR1## in which R represents fluorine, chlorine, bromine or nitro andHal represents chlorine or fluorine, and their use as starting substances for the synthesis of highly active compounds, for example in the field of plant protection and pharmaceuticals.The compounds of the formula (I) can be prepared by analogous processes, for example by chlorination from corresponding benzo[1,3]dioxoles substituted in the 4-position, and these substances according to the invention can be further reacted with hydrogen fluoride to give substances to which the invention likewise relates.Type: GrantFiled: September 28, 1992Date of Patent: January 25, 1994Assignee: Bayer AktiengesellschaftInventors: Peter Andres, Albrecht Marhold
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Patent number: 5273997Abstract: The invention provides compounds of general formula ##STR1## wherein m is 0 or 1; each of R.sup.1 and R.sup.2, and R.sup.3 and R.sup.4 if present, independently represents a hydrogen or halogen atom or an optionally substituted alkyl, cycloalkyl or aryl group, or R.sup.1 and R.sup.2 together or R.sup.3 and R.sup.4 together represent an optionally substituted alkylene chain; X represents a cyano group, a group --COOH or a salt, ester or amido derivative thereof; Y represents an alkyl group or a halogen atom; and n represents 0, 1, 2 or 3; a process for their preparation; compositions containing such compounds and their use as fungicides.Type: GrantFiled: June 12, 1992Date of Patent: December 28, 1993Assignee: Shell Research LimitedInventors: Thomas W. Naisby, William W. Wood, Werner E. J. Simon
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Patent number: 5270343Abstract: The present Application discloses pesticidally active compounds of formula (I):Q(CH.sub.2).sub.a (O).sub.b Q.sup.1 CR.sup.2 .dbd.CR.sup.2 .dbd.CR.sup.3 CR.sup.4 .dbd.CR.sup.5 CXNR.sup.1 R.sup.xor a salt or propesticide thereof, wherein Q is an optionally substituted aromatic monocyclic or fused bicyclic ring system in which at least one ring is aromatic, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halo or hydrogen; Q.sup.1 is a 1,2-cyclopropyl ring optionally substituted by one or more groups selected from C.sub.1-3 alkyl, halo, C.sub.1-3 haloalkyl, C.sub.2-3 alkynyl, or cyano; or is (CH.sub.2).sub.7 ;a=0 or 1; b= 0 or 1;R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl;X is oxygen or sulphur;R.sup.1 is phenyl optionally substituted by 1-5 substituents chosen from:a) C.sub.1-4 alkyl, C.Type: GrantFiled: June 15, 1992Date of Patent: December 14, 1993Assignee: Roussel UclafInventors: John E. Robinson, George S. Cockerill
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Patent number: 5260460Abstract: According to the invention, a new process for the preparation of fluorine-substituted aminobenzodioxoles and -benzodioxanes of the formula (I) ##STR1## in which n represents an integer 1 or 2, has been found, in which fluorine-substituted nitrohalogeno-benzodioxoles and -benzodioxanes, which are likewise new, are hydrogenated. The novel intermediates are obtained from fluorine-substituted benzodioxoles and benzodioxanes by halogenation and subsequent nitration. The amino compounds are important starting materials for highly active biocides.Type: GrantFiled: September 28, 1992Date of Patent: November 9, 1993Assignee: Bayer AktiengesellschaftInventors: Peter Andres, Albrecht Marhold
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Patent number: 5240960Abstract: A compound selected from the group consisting of all tautomeric forms of a cycloalky-propanamide of the formula ##STR1## wherein R.sub.1 is cycloalkyl of 3 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, azido, --CN, alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, --(CH.sub.2).sub.m --CF.sub.3, --O--(CH.sub.2).sub.m --CF.sub.3, --S--(CH.sub.2).sub.m --CF.sub.3, m is an integer from 0 to 3, --CF.sub.2 --Hal, --OCF.sub.2 --Hal, ##STR2## n is an integer from 1 to 3, Hal, Hal.sub.1, Hal.sub.2 and Hal.sub.3 are individually halogen, and --COR', R' is --OH or alkyl or alkoxy of 1 to 3 carbon atoms or R.sub.4 and R.sub.5 together are --O--CH.sub.2 --O-- and their non-toxic, pharmaceutically acceptable basic salts having anti-inflammatory activity.Type: GrantFiled: October 30, 1991Date of Patent: August 31, 1993Assignee: Roussel UclafInventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully