Substituent Q Contains Benzene Ring Patents (Class 564/161)
  • Patent number: 5621133
    Abstract: Novel compounds having the formula ##STR1## and the pharmaceutically acceptable salts, esters and amides thereof, whereinA is --O--, --S-- or --CR.sup.2 R.sup.8 --;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, X and Y are specifically defined; andup to one combination of (a) R.sup.2 and R.sup.5, (b) R.sup.5 and R.sup.6, (c) R.sup.5 and R.sup.7, (d) R.sup.6 and R.sup.7, and (e) R.sup.7 and Y, taken together with the atoms to which they are attached, may form a ring, the compounds being useful for treating dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of cognitive impairment, attention deficit disorder, and substance abuse and other addictive behavior disorders.Also disclosed are intermediates and processes useful in the preparation of the above compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 15, 1997
    Inventors: Michael P. DeNinno, Richard J. Perner
  • Patent number: 5616711
    Abstract: A method of producing an aminobutene derivative of formula (I) by allowing a butenol derivative of formula (II) to react with an amide derivative of formula (III) is disclosed. The aminobutene derivative of formula (I) can be deprotected to produce an aminobutene derivative of formula (I-1) or an aminobutene derivative of formula (I-2): ##STR1## The aminobutene derivative of formula (I-A) can also be deprotected to produce the aminobutene derivative of formula (I-B). Any or all of the above aminobutene derivatives are useful as intermediates for producing anti-ulcer drugs, and anti-ulcer drugs having an inhibitory effect on gastric acid secretion based on the antagonism against histamine H.sub.2 receptor.
    Type: Grant
    Filed: August 6, 1993
    Date of Patent: April 1, 1997
    Assignee: Fujirebio Inc.
    Inventors: Hiroshi Ikawa, Hajime Matsumoto, Masakatsu Matsumoto, Yasuo Sekine, Masato Nishimura, Akihiko Hosoda
  • Patent number: 5614648
    Abstract: A method of producing an antioxidant containing derivatives of an organic compound, and in particular, an antioxidant glyceride derivative, comprises reacting a first compound with a second medium. By this reaction, a product is formed whereby an active component of the first compound, e.g., an antioxidant moiety, is covalently incorporated into the second medium.The second medium comprises glyceride derivatives, silicones, fluorocarbons and alkoxylates containing reactive groups such as hydroxy, amino, carboxyl, ester, or amides.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: March 25, 1997
    Inventors: George H. Greene, Robert Miller, James L. Williams, James C. Phillips, Jerry F. Stults, Jan P. E. Tellings
  • Patent number: 5612479
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: March 18, 1997
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5607953
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: March 4, 1997
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5599975
    Abstract: A compound selected from those of formula (I): ##STR1## wherein A, X, Y, Z, R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.This compound or its physiologically tolerable salts may be used therapeutically as platelet anti-aggregation agent.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: February 4, 1997
    Assignee: Adir Et Compagnie
    Inventors: Ren e Gree, Ali M. Hachem, Danielle Gree, Yves Le Floc'h, Yves Rolland, Serge Simonet, Tony Verbeuren
  • Patent number: 5599967
    Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification have retinoid-like biological activity.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: February 4, 1997
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Richard L. Beard, Alan T. Johnson, Min Teng, Tae K. Song, Roshantha A. Chandraratna
  • Patent number: 5591884
    Abstract: Novel compounds having the formula ##STR1## and the pharmaceutically acceptable salts, esters and amides thereof, whereinA is --O--, --S-- or --CR.sup.2 R.sup.8 --;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, X and Y are specifically defined; andup to one combination of (a) R.sup.2 and R.sup.5, (b) R.sup.5 and R.sup.6, (c) R.sup.5 and R.sup.7, (d) R.sup.6 and R.sup.7, and (e) R.sup.7 and Y, taken together with the atoms to which they are attached, may form a ring, the compounds being useful for treating dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of cognitive impairment, attention deficit disorder, and substance abuse and other addictive behavior disorders.Also disclosed are intermediates and processes useful in the preparation of the above compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: January 7, 1997
    Assignee: Abbott Laboratories
    Inventors: Michael P. DeNinno, Richard J. Perner
  • Patent number: 5567734
    Abstract: Phenyl-substituted alkylcarboguanidides carrying perfluoroalkyl groups, of the formula I ##STR1## are described where R(A) and R(B) are H, Hal, CN, OR(6), alkyl, O.sub.r -perfluoroalkyl or NR(7)R(8); R(6) is hydrogen, (cyclo)alk(en)yl, perfluoroalkyl, phenyl or benzyl; R(7) and R(8) are defined as R(6); X is 1-3; R(1) is H, alkyl or --O.sub.0-1 (CH.sub.2)O.sub.0-1 perfluoroalkyl; R(2), R(3), R(4) and R(5) are defined as R(1), with the condition, however, that R(1), R(2), R(3), R(4) and R(5) are not simultaneously hydrogen and that R(1), R(2), R(3), R(4) and R(5) can only be alkyl when at least one of the substituents R(A) or R(B) contains a O.sub.r (CH.sub.2).sub.a C.sub.b F.sub.2b+1 group; as are the pharmaceutically acceptable salts thereof. Methods of preparation of compounds of formula I are also described.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: October 22, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jan-Robert Schwark, Heinz-Werner Kleemann, Hans-Jochen Lang, Andreas Weichert, Wolfgang Scholz, Udo Albus
  • Patent number: 5534653
    Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.5 R.sup.6, whereR.sup.5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.6 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: July 9, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert Gotz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5527945
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: June 18, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5523458
    Abstract: Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: June 4, 1996
    Assignee: Takasago International Corporation
    Inventors: Tetsuro Yamasaki, Hidenori Kumobayashi, Noboru Sayo, Toshiyuki Murayama, Noboru Sano, Takero Ishizaki
  • Patent number: 5516931
    Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected comprises signal, release, and reactivity groups. A class of release tag compounds that are cleaved to release as signal groups very stable electrophoric ketones which are sufficiently volatile for determination in the gas phase of an analytical reaction mixture is disclosed.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: May 14, 1996
    Assignee: Northeastern University
    Inventors: Roger W. Giese, Samy Abdel-Baky, Linxiao Xu
  • Patent number: 5492917
    Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
  • Patent number: 5481005
    Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: January 2, 1996
    Assignee: Sanofi
    Inventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
  • Patent number: 5476863
    Abstract: A glycerin derivative having the following formula (I) or (I') and a pharmacologically acceptable salt thereof are useful to treat diseases caused by the platelet activating factor.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: December 19, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Kazuo Okano, Osamu Asano, Naoyuki Shimomura, Tetsuya Kawahara, Shinya Abe, Shuhei Miyazawa, Mitsuaki Miyamoto, Hiroyuki Yoshimura, Koukichi Harada, Junsaku Nagaoka, Tsutomu Kawata, Tsutomu Yoshimura, Hiromasa Suzuki, Shigeru Souda, Yoshimasa Machida, Kouichi Katayama, Isao Yamatsu
  • Patent number: 5476944
    Abstract: The present invention relates to derivatives of cyclic phenolic thioethers of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, which are inhibitors or stimulators of superoxide generation, and which may also inhibit cyclooxygenase and/or 5-lipoxygenase, to pharmaceutical compositions containing one or more of these compounds in combination with a pharmaceutically-acceptable carrier, and to medical methods of treatment employing these compounds.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: December 19, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Partis, Richard A. Mueller, Francis J. Koszyk, Richard M. Weier
  • Patent number: 5464821
    Abstract: Small peptidic compounds containing a small and branched chained amino acid residue, pharmaceutical compositions containing at least one such compound active against glaucoma and intraocular hypertension and a method for treating glaucoma and intraocular hypertension.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: November 7, 1995
    Assignee: Carlbiotech, Ltd.
    Inventors: Aasmul-Olsen Stig, Fred Widmer, Kailash K. Gauri
  • Patent number: 5463125
    Abstract: New anticonvulsant compounds include (.+-.)-2-hydroxy-2-phenylbutyramide and (.+-.)-3-hydroxy-3-phenylpentamide. These homologues of (.+-.)-4-hydroxy-4-phenylhexanamide have anticonvulsant activity as well as unexpected properties, particularly low neurotoxicity and pharmacological differences. The invention further provides methods for the synthesis of (.+-.)-2-hydroxy-2-phenylbutyramide and (.+-.)-3-hydroxy-3-phenylpentamide as exemplified in the examples.
    Type: Grant
    Filed: June 3, 1993
    Date of Patent: October 31, 1995
    Inventors: Guillermo C. Sandoval, Sergio E. M. Toledo, Martha T. Z. Garcia
  • Patent number: 5442060
    Abstract: Carboxamide derivatives of the following general formula (I): ##STR1## (wherein R.sup.1 and R.sup.2 are C.sub.1 -C.sub.3 alkyl group or both taken together C.sub.1 -C.sub.3 alkylene group,R.sup.3 is hydrogen atom, dialkylamino group, etc.,R.sup.4 is hydrogen atom, C.sub.1 -C.sub.10 alkyl group,R.sup.5 is C.sub.1 -C.sub.10 alkyl group,m, n, q are an integer from 0-3,p is 0, 1,A ring is ##STR2## B ring is 5 or 6 membered nitrogen containing aromatic ring, are provided, which are useful as medicinals for treating hyperlipemia or atherosclerosis.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: August 15, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Tadashi Shirasaka, Kazuo Suzuki, Hiroko Suzuki, Masao Taniguchi, Shinya Inoue
  • Patent number: 5434188
    Abstract: 1-Ether and 1-thioether-naphthalene-2-carboxamides are described, methods of manufacture therefor and their use as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases, and their utility in inhibiting the activation of human immunodeficiency virus (HIV), latent in infected humans.
    Type: Grant
    Filed: March 7, 1994
    Date of Patent: July 18, 1995
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Sony S. Khatana, James B. Kramer, Paul C. Unangst
  • Patent number: 5405873
    Abstract: There are provided substituted acetamide derivatives represented by general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, n and Z are defined in the specification. The substituted acetamide derivatives strongly inhibit acylcoenzyme A cholesterol acyltransferase (ACTA) and are expected to be effective for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: April 11, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshikazu Iwasawa, Hiromi Hattori, Yasufumi Nagata, Akiko Shimizu, Yoshio Sawasaki
  • Patent number: 5403853
    Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: April 4, 1995
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane
  • Patent number: 5395846
    Abstract: This invention relates to a class of novel amino bi- and tri-carbocyclic alkane compounds having bis-aryl substitution which exhibit squalene synthase inhibition properties. The bi- and tri-carbocyclic alkane ring contains an amino group and the ring is further linked or bridged to two mono- and/or bicyclic rings. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
    Type: Grant
    Filed: June 25, 1993
    Date of Patent: March 7, 1995
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Robert L. Morris, Kent W. Neuenschwander, Keith S. Learn, Anthony C. Scotese
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5391819
    Abstract: Disclosed herein is a process of making chiral 2-aryl-1,4-butanediamine derivatives useful as neurokinin-A antagonists of Formula 7 ##STR1##
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: February 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Paul E. Finke, Jeffrey J. Hale, Malcolm Maccoss, Sander G. Mills
  • Patent number: 5373023
    Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: December 13, 1994
    Assignee: SYNTHELABO
    Inventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
  • Patent number: 5369108
    Abstract: The present invention provides the compound having the structure: ##STR1## wherein each of R.sub.1 and R.sub.2 are independently the same as or different from each other; when R.sub.1 and R.sub.2 are the same, each is a substituted or unsubstituted arylamino, cycloalkylamino, pyridineamino, piperidino, 9-purine-6-amine, or thiozoleamino group; when R.sub.1 and R.sub.2 are different, R.sub.1 =R.sub.3 --N--R.sub.4, wherein each of R.sub.3 and R.sub.4 are independently the same as or different from each other and are a hydrogen atom, a hydroxyl group, a substituted or unsubstituted, branched or unbranched alkyl, alkenyl, cycloalkyl, aryl, alkyloxy, aryloxy, arylalkyloxy, or pyridine group, or R.sub.3 and R.sub.4 bond together to form a piperidine group and R.sub.2 is a hydroxylamino, hydroxyl, amino, alkylamino, dialkylamino or alkyloxy group; and n is an integer from about 4 to about 8.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 29, 1994
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia
    Inventors: Ronald Breslow, Paul A. Marks, Richard A. Rifkind, Branko Jursic
  • Patent number: 5360924
    Abstract: Process for preparing aromatic olefins of the formula (1) ##STR1## in which R.sup.1 -R.sup.3 are hydrogen, alkyl (C.sub.1 -C.sub.8) , alkoxy-(C.sub.1 -C.sub.5), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO, --COalkyl(C.sub.1 -C.sub.4) , --COphenyl, --COOalkyl (C.sub.1 -C.sub.4) , --OCOalkyl(C.sub.1 -C.sub.4), --NHCOalkyl(C.sub.1 -C.sub.4) , --CF.sub.3, --NH.sub.2, --NH--alkyl(C.sub.1 -C.sub.4) or --N(alkyl(C.sub.1 -C.sub.4)).sub.2 and R.sup.4 is hydrogen, alkyl(C.sub.1 -C.sub.8), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO or --OCOalkyl (C.sub.1 -C.sub.4) , and X is, inter alia, alkenyl(C.sub.2 -C.sub.12) or cycloalkenyl(C.sub.4 -C.sub.8) or the group ##STR2## in which R.sup.5 and R.sup.6 are, independently of one another, hydrogen or methyl, and Y is --phenyl, --CN, --COOH, --COOalkyl(C.sub.1 -C.sub.12), --COOphenyl, ##STR3## --CON (phenyl).sub.2, --COalkyl(C.sub.1 -C.sub.12), --COphenyl, --Oalkyl(C.sub.1 -C.sub.12) , --Ophenyl or the radical ##STR4## in which R.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: November 1, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Hartmut Fischer, Heinz Strutz
  • Patent number: 5342835
    Abstract: Compounds of formula ##STR1## in which: CYCLE surrounded by a semicircle represents, with the two carbon atoms to which the semicircle is linked, a carbon-containing, optionally heterocyclic, ring containing at least one ethylenic or aromatic bond between the two carbon atoms which carry the --C(Z).dbd.Y group and the phenyl group, Y is oxygen or sulphur, Z is NR.sub.1 R.sub.2, R.sub.1 and R.sub.2, each represents optionally substituted alkyl, alkoxy or cycloalkyl; alkenyl or alkynyl; or --NR.sub.1 R.sub.2 represents saturated or unsaturated heterocyclyl;R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: August 30, 1994
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
  • Patent number: 5340827
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: August 23, 1994
    Assignee: Celltech, Limited
    Inventors: Nigel R. A. Beeley, Thomas A. Millican
  • Patent number: 5320776
    Abstract: A novel antiferroelectric liquid crystal compound is disclosed which is represented by the following formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from C.sub.3 -C.sub.18 alkyl groups, respectively, Rf is a lower fluoroalkyl group, X is a group selected from the group consisting of --O--, --COO--, --OOC--, and --CO--, or a single bond, (A) and (B) each is independently a group selected from the group consisting of phenyl, biphenyl, and naphthalene group which may be substituted with a halogen atom, and C having an asterisk indicates an asymmetric carbon atom.
    Type: Grant
    Filed: May 19, 1993
    Date of Patent: June 14, 1994
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Toru Ohde
  • Patent number: 5312958
    Abstract: A process for the production of a compound of general formula ##STR1## wherein R represents cyano, carboxy which may be esterified or amidated or tetrazolyl which may be substituted, comprising brominating the corresponding methyl compound with a brominating agent such as N -bromoacetamide, N-bromophtalimide, N-bromosuccinimide and so on in a halogenated hydrocarbon solvent in the presence of an azobis compound.
    Type: Grant
    Filed: January 26, 1993
    Date of Patent: May 17, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Syuji Suenaga, Hitoshi Kawaguchi, Takeshi Kato
  • Patent number: 5302742
    Abstract: N-acylated p-amino-phenols can be prepared by catalytical hydrogenation of the underlying aromatic nitro compounds in a reaction medium of aqueous sulfuric acid in the sense of a Bamberger type reaction at elevated temperature, optionally in the presence of a water-miscible organic solvent, and subsequent reaction of this reaction mixture with an acid chloride, optionally in the presence of an acid binder and optionally in the presence of a diluent.
    Type: Grant
    Filed: May 5, 1993
    Date of Patent: April 12, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Landscheidt, Alexander Klausener, Heinz-Ulrich Blank
  • Patent number: 5302595
    Abstract: Compounds of the formula I ##STR1## wherein X, Y and v are as defined below, novel intermediates used in their synthesis, and the pharmaceutically acceptable salts of such compounds and intermediates. The compounds of formula I and the novel intermediates used in their synthesis are muscarinic receptor antagonists that are selected for smooth muscle muscarinic sites and are useful in the prevention and treatment of diseases associated with altered motility or tone of smooth muscle, such as irritable bowel syndrome, diverticular disease, urinary incontinence, aesophageal achalasia, and chronic obstructive airways disease.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: April 12, 1994
    Assignee: Pfizer Inc.
    Inventors: Peter E. Cross, Alexander R. MacKenzie
  • Patent number: 5300676
    Abstract: Fluorine-substituted .alpha.-(5-aryloxy-naphthalen-1-yl-oxy)-propionic derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, as defined herein, are useful as herbicides. Processes and intermediates for their preparation are also disclosed.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: April 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Michael Haug, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 5298647
    Abstract: Aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, selected from the group consisting of ##STR1## whose variable substituents are as defined in the specification, e.g. ##STR2## are useful as photoprotective agents or tanning accelerators.
    Type: Grant
    Filed: December 14, 1987
    Date of Patent: March 29, 1994
    Inventors: Dominique Robert, Louis Jung
  • Patent number: 5254584
    Abstract: Certain N-acetonylbenzamides exhibit low phytotoxicity and are useful for control of a wide range of fungi, including phytopathogenic fungi of the classes Oomycetes, Ascomycetes, Deuteromycetes and Basidiomycetes.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: October 19, 1993
    Assignee: Rohm and Haas Company
    Inventors: Enrique L. Michelotti, Robert R. Raney, David H. Young
  • Patent number: 5254714
    Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventor: Merrikh Ramezanian
  • Patent number: 5248781
    Abstract: Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: September 28, 1993
    Assignee: The Trustees of Princeton University
    Inventor: Alexander McKillop
  • Patent number: 5236956
    Abstract: The invention concerns compounds having the formula I ##STR1## wherein Ar is a phenyl or benzyl group which is optionally substituted with hydroxy or alkoxy;R.sup.1 is hydrogen, lower alkyl, lower alkoxy, hydroxy;R.sup.2 is hydrogen, lower alkyl;R.sup.3 is NR.sup.4 R.sup.5, whereinR.sup.4 and R.sup.5 which can be the same or different, are lower alkyl, or wherein R.sup.4 and R.sup.5, when taken together, form a ring with the nitrogen atom, whereby said ring optionally is substituted with lower alkyl;n is 0 or 1;m is 2 or 3 andtheir salts with physiologically acceptable acids and when the compounds can be in form of optical isomers, the racemic mixture and the individual isomers, for the treatment of disorders of the urinary bladder.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: August 17, 1993
    Assignee: Kabi Pharmacia Aktiebolag
    Inventors: Christer Sjogren, Rene Mollberg, Sten Kelfve
  • Patent number: 5229424
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is a monocylcic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, 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, halogen or hydrogen; 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; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: July 20, 1993
    Assignee: The Wellcome Foundation Limited
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5225444
    Abstract: The compounds of this invention are anilides represented by the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR2## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio, sulfinyl or sulfonyl; Alk is straight or branched chain lower alkylene; R.sub.3 is hydrogen or lower alkyl; and R.sub.4 is phenyl or substituted phenyl. The compounds of the present invention are useful in the treatment of inflammation, allergy and hypersensitivity reactions and other disorders of the immune system.
    Type: Grant
    Filed: August 27, 1991
    Date of Patent: July 6, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis, James R. Deason
  • Patent number: 5220048
    Abstract: Benzocyclobutene-1,2-dichlorides, -bromides and -iodides which are substituted in the benzene ring are accessible in good yields and short reaction times by reacting substituted 1,2-(dichloromethyl or dibromomethyl)-benzenes with NaI in acetonitrile as the solvent. They can be used together with dienophils, for example 1,4-quinones, in Diels-Alder reactions.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: June 15, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Marcus Baumann, Walter Fischer, Vratislav Kvita, Carl W. Mayer
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5202356
    Abstract: The present Application discloses pesticidally active compounds of the formula (I):Q Q.sup.1 CR.sup.2 =CR.sup.3 CR.sup.4 =CR.sup.5 C (.dbd.X) NHR.sup.1or a salt thereof, wherein Q is an monocyclic aromatic ring. or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each optionally substituted, 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, halogen 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, alkynyl, or cyano; 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; and R.sup.1 is selected from hydrogen and C.sub.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: April 13, 1993
    Assignee: The Wellcome Foundation Limited
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinston
  • Patent number: 5190741
    Type: Grant
    Filed: August 6, 1991
    Date of Patent: March 2, 1993
    Assignees: Institut National de la Sante et de la Recherche Medicale (INSERM), Cis Bio International
    Inventors: Marie-France Moreau, Josette Michelot, Annie J. Veyre, Jean-Claude Madelmont, Denise Godeneche, Pierre Lebarre, Daniel Parry, Gaston Meyniel
  • Patent number: 5180737
    Abstract: Compound of the formula (I):Q.sup.1 Q(CR.sup.2 .dbd.CR.sup.3).sub.a (CR.sup.4 .dbd.CF)(CR.sup.5 .dbd.CR.sup.6).sub.b C(.dbd.O)NHR.sup.1 (1)or a salt thereof, wherein Q.sup.1 is a phenyl ring or a fused bicyclic ring system containing 9 or 10 ring carbon atoms at least one ring being aromatic, or Q.sup.1 is a dihalovinyl group; Q is an alkyl chain containing 1 to 12 carbon atoms and optionally containing one or two oxygen atoms and/or an unsaturated group --CR.sup.7 .dbd.CR.sup.8 --, or --C.dbd.C--, wherein R.sup.7 and R.sup.8 are selected from hydrogen or halo; a is 0 or 1; b is 0 or 1; the sum of a and b is 0 or 1; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different, and are independently selected from hydrogen, halo and C.sub.1-4 alkyl; R.sup.1 is selected from hydrogen and C.sub.1-6 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy are disclosed which have pesticidal activity.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: January 19, 1993
    Assignee: Roussel Uclaf
    Inventor: Robert J. Blade
  • Patent number: 5167696
    Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: December 1, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
  • Patent number: 5166434
    Abstract: A process is disclosed for preparing aromatic-substituted unsaturated amides. The process comprises treating a compound of the formula ##STR1## where Ar is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 linear or branched alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched or the group ##STR2## where Ar' is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched; and R and R' are the same or different and are hydrogen or C.sub.1 to C.sub.12 linear or branched alkyl and can also be phenyl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: November 24, 1992
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo