Plural Rings In Acid Moiety Patents (Class 560/27)
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Patent number: 6265590Abstract: Protected amino acid derivatives of general formula (I) and methods for the prepatation of the derivatives are provided.Type: GrantFiled: July 12, 1999Date of Patent: July 24, 2001Assignee: Hyundai Pharm, Ind. Co., Ltd.Inventors: Vladimir V. Samukov, Aydar N. Sabirov, Pavel I. Pozdnyakov, Hack-Joo Kim, Young-Deug Kim
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Patent number: 6265432Abstract: Fluorine-substituted biphenyl butyric acid compounds and derivatives are described as well as acid methods for the preparation and pharmaceutical compositions of same, which are useful as inhibitors of matrix metalloproteinases, particularly gelatinase A, stromelysin-1, and collagenase-3, and for the treatment of atherosclerotic plaque rupture, aortic aneurism, heart failure, restenosis, periodontal disease, corneal ulceration, treatment of bums, decubital ulcers, wound healing, cancer, inflammation, pain, arthritis, osteoporosis, multiple sclerosis, renal disease, and other autoimmune or inflammatory disorders dependent upon tissue invasion by leukocytes or other activated migrating cells, acute and chronic neurodegenerative disorders including stroke, head trauma, spinal cord injury, Alzheimer's disease, amyotrophic lateral sclerosis, cerebral amyloid angiopathy, AIDS, Parkinson's disease, Huntington's disease, prion diseases, myasthenia gravis, and Duchenne's muscular dystrophy.Type: GrantFiled: February 11, 2000Date of Patent: July 24, 2001Assignee: Warner-LambertInventors: Claude Forsey Purchase, Jr., Bruce David Roth, Gerald Paul Schielke, Lary Craswell Walker, Andrew David White
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Patent number: 6242609Abstract: A method for manufacturing a color coupler used in a silver halide photographic light-sensitive material using an ammonium trihalide. Said method for manufacturing the color coupler comprising the following step: a step for halogenating a coupling position of a four equivalent coupler using a halogenating agent, wherein said halogenating agent is said ammonium trihalide.Type: GrantFiled: April 7, 1999Date of Patent: June 5, 2001Assignee: Konica CorporationInventor: Fumio Ishii
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Patent number: 6232339Abstract: Phenylcarbamates of the formula I where: R1 is C1-C4-alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl and C1-C4-alkoxy; m is 0, 1 or 2, where the radicals R2 may be different if m is 2; R3 is hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl; R4, R5 and R6 are each as defined in claim 1, and salts thereof, a process and intermediates for preparing these compounds and compositions comprising them for controlling animal pests and harmful fungi are described.Type: GrantFiled: July 21, 1999Date of Patent: May 15, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Gypser, Thomas Grote, Hubert Sauter, Herbert Bayer, Oliver Cullmann, Markus Gewehr, Wassilios Grammenos, Bernd Müller, Arne Ptock, Eberhard Ammermann, Gisela Lorenz, Siegfried Strathmann, Volker Harries, Franz Röhl
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Patent number: 6197798Abstract: Compounds of the formula I wherein R2—C, R3—C, R4—C or R5—C may be replaced by N; and wherein n is 1, 2 or 3; R1 is aryl, cycloalkyl or heterocyclyl; R2, R3, R4 and R5 are independently hydrogen, optionally substituted alkyl, halo, amino, substituted amino, trifluoromethyl, cyano, carboxyl, alkoxycarbonyl, aralkoxycarbonyl, (alkyl, aryl or aralkyl)-thio, (alkyl, aryl or aralkyl)-oxy, acyloxy, (alkyl, aryl or aralkyl)-aminocarbonyloxy; or any two of R2, R3, R4 and R5 at adjacent positions are alkylenedioxy; R6 is hydrogen, optionally substituted alkyl, amino, substituted amino, acylamino, wherein Ra is hydrogen or optionally substituted alkyl, Rb and Rc are independently hydrogen, optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; or Rb and Rc together represent lower alkylene or lower alkylene interrupted by O, S, or N—(H, alkyl or aralkyl); Rd is optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; and Re is opType: GrantFiled: July 20, 1999Date of Patent: March 6, 2001Assignee: Novartis AGInventors: Cynthia A. Fink, Gary M. Ksander, Paivi J. Kukkola, Eli M. Wallace, Mahavir Prashad
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Patent number: 6184410Abstract: Carbodiimides based on 1,3-bis(1-methyl-1-isocyanatoethyl)benzene contain from 12 to 40% by weight of ethylene oxide units [—CH2—CH2—O—], based on the weight of the carbodiimides.Type: GrantFiled: April 22, 1999Date of Patent: February 6, 2001Assignee: BASF AktiengesellschaftInventors: Heinz Bollmann, Karl Häberle, Nicolas Kokel, Raina Thärigen
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Patent number: 6166243Abstract: Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C.sub.1 -C.sub.4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C.sub.1 -C.sub.4 alkoxy carbonyl; and R is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C.sub.3 -C.sub.Type: GrantFiled: November 1, 1999Date of Patent: December 26, 2000Assignee: CK Witco CorporationInventors: Haihong Jin, Joseph A. Feiccabrino
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Patent number: 6143917Abstract: A process for producing an aryl carbamate of a high purity at a high yield by reacting a diaryl carbonate with an amine compound having one or more hydrogen atoms bonded to the N position in the presence of carboxylic acid(s) of the following general formulae (I): R.sup.1 --COOH and/or (II): R.sup.2 --COOH (wherein R.sup.1 represents an alkyl or cycloalkyl group having an .alpha.-positioned carbon atom bonded to only one hydrogen atom, an alkyl group having an .alpha.-positioned carbon atom bonded to no hydrogen atom, or an aryl or heterocyclic group, and R.sup.2 represents an alkyl group having an .alpha.-positioned carbon atom bonded to two or more hydrogen atoms).Type: GrantFiled: October 13, 1998Date of Patent: November 7, 2000Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Ryoji Sugise, Kohichi Kashiwagi, Tsunao Matsuura
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Patent number: 6127414Abstract: There is provided pharmaceutically useful compounds of formula I, ##STR1## wherein Ar.sup.1, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have meanings given in the description, which are useful as antagonists of neuropeptide Y and in particular in the treatment of cardiovascular diseases, for example vasoconstriction.Type: GrantFiled: October 26, 1998Date of Patent: October 3, 2000Assignee: Astra AktiebolagInventors: Nils-.ANG.ke Bergman, Thomas D'Ambra, Garry M Pilling
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Patent number: 6124345Abstract: The present invention relates to carbomoylcarboxamide oximes of the formula (I): ##STR1## or salts thereof, processes for preparing the carbomoylcarboxamide oximes, compositions containing the carbomoylcarboxamide oximes and processes for controlling harmful fungi with an effective amount of the carbomoylcarboxamide oximes.Type: GrantFiled: November 24, 1998Date of Patent: September 26, 2000Assignee: BASF AktiengesellschaftInventors: Frank Wetterich, Karl Eicken, Reinhard Kirstgen, Eberhard Ammermann, Gisela Lorenz, Siegfried Strathmann
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Patent number: 6121268Abstract: Compounds with fungicidal properties having formula I ##STR1## where m and n are 0 or 1 provided that m+n is 1; X is hydrogen, halo, (C.sub.1 -C.sub.4)alkyl, or (C.sub.1 -C.sub.4)alkoxy; R is an optionally-substituted alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aryl, aralkyl, or heterocyclic group; R.sub.1 and R.sub.2 are hydrogen, optionally-substituted alkyl, cycloalkyl, cyano, carboxy alkyl, or aryl; at least one of R.sub.1 and R.sub.2 is hydrogen; and R.sub.3 is alkyl or haloalkyl.Type: GrantFiled: November 23, 1998Date of Patent: September 19, 2000Assignee: Rohm and Haas CompanyInventors: Ronald Ross, Ted Tsutomo Fujimoto, Edward Michael Szapacs, Steven Howard Shaber
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Patent number: 6120699Abstract: The present invention provides a liquid methylene bis(phenylisocyanate) composition including a high concentration of methylene bis(phenylisocyanate) which has an improved storage stability. The invention further provides a method of making the liquid methylene bis(phenylisocyanate) compositions of the present invention.Type: GrantFiled: September 21, 1998Date of Patent: September 19, 2000Assignee: BASF CorporationInventors: Thirumurti Narayan, Anthony Lunato, Jon S. Speier, David D. Peters, Cynthia Loop, Filip Nevejans
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Patent number: 6114325Abstract: A 1,2-di-substituted benzene-carboxamide derivative or a salt thereof expressed by the following Formula (I); ##STR1## wherein each of A and B is R.sup.1 or --(CH.sub.2)n-NR.sup.2 R.sup.3, wherein when A is R.sup.1, B is --(CH.sub.2)n-NR.sup.2 R.sup.3 and when A is --(CH.sub.2)n-NR.sup.2 R.sup.3, B is R.sup.1 ; Z is --O--, --OCO--, --OCONR.sup.6 -- or --NR.sup.6 --; R.sup.1 is a hydrocarbon group of C.sub.10-30 ; R.sup.2 and R.sup.3 individually represent a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, or together represent a heterocyclic ring having 3-7 members; when A is --(CH.sub.2)n-NR.sup.2 R.sup.3, R.sup.2 may be a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, and R.sup.3 and R.sup.5 together may represent a heterocyclic ring of 6 or 7 members including two nitrogen atoms; when --Z--B is --OCONR.sup.6 --(CH.sub.2)n-NR.sup.2 R.sup.3 or --NR.sup.6 --(CH.sub.2)n-NR.sup.2 R.sup.3, R.sup.Type: GrantFiled: October 22, 1998Date of Patent: September 5, 2000Assignee: Shiseido Co., Ltd.Inventors: Hirotada Fukunishi, Kenichi Umishio, Masahiro Tajima, Koji Kobayashi
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Patent number: 6114569Abstract: An efficient method for the preparation of a compound of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, also known as DMP-266, a reverse transcriptase inhibitor is achieved using a cyclization reaction of the amino alcohol intermediate with an alkyl or aryl chloroformate and a base.Type: GrantFiled: January 4, 1999Date of Patent: September 5, 2000Assignee: Merck & Co., Inc.Inventors: Lisa F. Frey, Edward J. J. Grabowski, Richard D. Tillyer
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Patent number: 6114381Abstract: Compounds, compositions and methods of treatment are described to control brain damage associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of a .beta.-phenyl-.alpha.-aminopropionic acid N phenyl amide compound as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites. Compounds of most interest are those of the formula ##STR1## wherein each of R.sup.1 and R.sup.5 is independently selected from hydrido, fluoro, chloro, bromo, methyl and ethyl; wherein R.sup.3 is selected from hydroxy, methoxy, ethoxy, methoxycarbonyloxy, ethoxycarbonyloxy, (2-methylpropoxy)carbonyloxy and (2-propenyloxy) carbonyloxy; wherein each of R.sup.6, R.sup.7 and R.sup.8 is hydrido; wherein each of R.sup.9 and R.sup.10 is independently selected from hydrido, methyl and ethyl; wherein R.sup.Type: GrantFiled: October 13, 1998Date of Patent: September 5, 2000Assignee: G. D. Searle & Co.Inventors: Barnett S. Pitzele, Nizal S. Chandrakumar, Michael Clare
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Patent number: 6114550Abstract: A .beta.-phenylisoserine derivative of general formula (I): ##STR1## in the form of a salt or an ester, in which Ar represent an aryl radical, R represents a phenyl or naphthyl or a O--R.sub.1 radical and G.sub.1 represents --CH.sub.2 --Ph radical; and a method of using the same for making taxane derivatives.Type: GrantFiled: November 10, 1997Date of Patent: September 5, 2000Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Noel Denis, Andrew-Elliot Greene, Alice Kanazawa
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Patent number: 6114380Abstract: This invention relates to novel difluoro statone analogs, to the processes and intermediates useful for their preparation and to their use as anti-viral agents.Type: GrantFiled: September 8, 1997Date of Patent: September 5, 2000Assignee: Merrell Pharmaceuticals Inc.Inventors: Daniel Schirlin, Viviane Van Dorsselaer, Celine Tarnus
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Patent number: 6093843Abstract: Compounds having the formula: ##STR1## wherein R is hydrogen or CO.sub.2 CH(CH.sub.3).sub.2, useful as intermediates in the preparation of the miticide bifenazate, methods for their preparation, and methods for the preparation of bifenazate.Type: GrantFiled: October 6, 1999Date of Patent: July 25, 2000Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Co./CIE.Inventors: Gaik-Lean Chee, Sheldon Bernard Park, Mark Archiel Dekeyser
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Patent number: 6080839Abstract: The invention relates to a novel labeling reactant, suitable for labeling of a biospecific binding reactant using solid-phase synthesis. The invention further concerns new labeling methods. The novel labeling reactant has the formula (I) ##STR1## wherein -A- is a bivalent aromatic structure capable of absorbing light or energy and transferring the excitation energy to a lanthanide ion after the product made by the said solid-phase synthesis has been released from the used solid support, deprotected and converted to a lanthanide chelate;-G- is a bridge replacing a hydrogen atom in A;R is a protected amino acid residue --CH(NHX)COOH, where X is a transient protecting group, or its active ester, where said ester is e.g. an N-hydroxysuccinimido, p-nitrophenol or pentafluorophenol ester; andR' is --COOR'" where R'" is an alkyl of 1 to 4 carbon atoms, phenyl or benzyl, which phenyl or benzyl can be substituted or unsubstituted.Type: GrantFiled: June 25, 1998Date of Patent: June 27, 2000Assignee: Wallac OyInventors: Harri Takalo, Jari Hovinen, Veli-Matti Mukkala, Paivi Liitti, Heikki Mikola
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Patent number: 6072060Abstract: An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process incudes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, cephalomanninne and various analogs, including photoaffinity labeling candidates.Type: GrantFiled: February 19, 1999Date of Patent: June 6, 2000Assignee: Bryn Mawr CollegeInventors: Charles S. Swindell, Nancy Krauss
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Patent number: 6072072Abstract: The present invention provides a chemically modified form of hemoglobin that is stabilized and can efficiently bind and release oxygen. In addition the chemically modified hemoglobin may be polymerized to increase its molecular weight and increase its stability so that it will have a longer half life in the circulatory system and may be used as a stable oxygen transport mediator which is useful as the basis of a blood substitute.Type: GrantFiled: March 22, 1999Date of Patent: June 6, 2000Assignee: Montefiore Medical CenterInventors: Iraj Lalezari, Parviz Lalezari
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Patent number: 6063963Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.The method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: August 4, 1997Date of Patent: May 16, 2000Assignee: Pharm-Eco Laboratories, Inc.Inventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 6054457Abstract: This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc, and represented by general formula (I): ##STR1## wherein R.sup.1 is aryl optionally substituted with lower alkoxy, etc., R.sup.2 is lower alkyl, etc.,R.sup.3 is hydrogen, etc.,R.sup.4 is lower alkoxy, etc.,R.sup.5 is hydrogen, etc.,A is NH, etc.,E is ##STR2## etc., X is --CH.dbd.CH--, --CH.dbd.N--, or S, andY is CH or N,and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.Type: GrantFiled: December 9, 1997Date of Patent: April 25, 2000Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hiroyuki Setoi, Takehiko Ohkawa, Tatsuya Zenkoh, Hitoshi Sawada, Kentaro Sato, Hirokazu Tanaka
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Patent number: 6043284Abstract: The present invention is concerned with diaryl compounds of formula (I) and their use in medical therapy, particularly in the prophylaxis or treatment of a clinical condition for which an ACAT inhibitor is indicated, such as hyperlipidaema or atherosclerosis. The invention also relates to pharmaceutical compositions and processes for the preparation of compounds according to the invention.Type: GrantFiled: February 5, 1998Date of Patent: March 28, 2000Assignee: Glaxo Wellcome Inc.Inventors: Richard James Arrowsmith, John Gordon Dann, Karl Witold Franzmann, Simon Teanby Hodgson, Peter John Wates
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Patent number: 6043247Abstract: The present invention relates to novel substituted acrylic acids, to methods for their preparation, compositions containing them, and their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention also relates to modulation of the activity of molecules with phospho-tyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganisms, eukaryotic cells, whole animals and human beings.Type: GrantFiled: April 16, 1997Date of Patent: March 28, 2000Assignee: Novo Nordisk A/SInventors: Henrik Sune Andersen, Niels Peter Hundahl M.o slashed.ller, Peter Madsen
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Patent number: 6034131Abstract: A diphenyl ether of the formula I, ##STR1## or a salt or N-oxide thereof wherein Q is C(CO.sub.2 CH.sub.3).dbd.CHCH.sub.3, C(CONH.sub.2).dbd.CHOCH.sub.3, C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3, C(CONHCH.sub.3).dbd.NOCH.sub.3 or N(OCH.sub.3)--CO.sub.2 CH.sub.3 ;n is 0 or 1;R.sup.1 is hydrogen or a carbon bonded organic radical;R.sup.2 is hydrogen or an organic radical bonded via C, O, S or N;x is 0, 1 or 2;R.sup.3 is cyano, nitro, halogen or an organic radical bonded via C, O, S or N; ory is 0, 1, 2 or 3;R.sup.4 is cyano, halogen, alkyl, haloalkyl or alkoxy,intermediates and processes for its preparation, and its use.Type: GrantFiled: September 3, 1998Date of Patent: March 7, 2000Assignee: BASF AktiengesellschaftInventors: Klaus Oberdorf, Wassilios Grammenos, Hubert Sauter, Thomas Grote, Bernd Muller, Reinhard Kirstgen, Herbert Bayer, Arne Ptock, Michael Rack, Albrecht Harreus, Franz Rohl, Eberhard Ammermann, Volker Harries, Gisela Lorenz, Siegfried Strathmann
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Patent number: 6031124Abstract: The subject invention pertains to compounds of the formula Y.sup.1 Y.sup.2 N--(CH.sub.2).sub.4 --CH.dbd.C(Ph)--X wherein Y.sup.1 and Y.sup.2 are independently H or a removable blocking group, or Y.sup.1 and Y.sup.2 together are a removable divalent blocking group; and X is COOCH.sub.3 or a group convertible thereto. Such a compound may be cyclised, by Michael addition, to give methylphenidate, if necessary after removing blocking group(s) and converting X to COOCH.sub.3. The subject invention also pertains to methods for preparing compounds of the invention.Type: GrantFiled: September 25, 1998Date of Patent: February 29, 2000Assignee: Medeva Europe LimitedInventors: Martin Edward Fox, Jane Marie Paul
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Patent number: 6028112Abstract: There is provided novel spirocyclopropyl fluorene derivatives having the general Formula I ##STR1## wherein R, R.sup.1 and X are as defined herein which are useful as melatonergic agents.Type: GrantFiled: July 31, 1998Date of Patent: February 22, 2000Assignee: Bristol-Myers Squibb CompanyInventors: Karen L. Leboulluec, Katherine S. Takaki
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Patent number: 6028093Abstract: Fungicidal mixtures, comprisinga) a carbamate of the formula I ##STR1## where T is CH or N, n is 0, 1 or 2 and R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, it being possible for the radicals R to be different when n is 2, and/orb) an oxime ether of the formula II, ##STR2## where the substituents have the following meanings: X is oxygen or amino;Y is CH or N;Z is oxygen, sulfur, amino or C.sub.1 -C.sub.4 -alkylaminoR' is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -haloalkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -haloalkynyl, C.sub.3 -C.sub.6 -cycloalkyl-methyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: 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 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio; andc) a carbamate of the formula III(CH.sub.3).sub.2 N--CH.sub.2 CH.sub.2 CH.sub.Type: GrantFiled: October 21, 1998Date of Patent: February 22, 2000Assignee: BASF AktiengesellschaftInventors: Bernd Muller, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz, Siegfried Strathmann, Klaus Schelberger, Maria Scherer, Dietrich Mappes, Joachim Leyendecker, Herbert Bayer, Ruth Muller
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Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its conversion to C-13 sidechain of taxanes
Patent number: 6025516Abstract: The present invention provides an efficient route to the C-13 side chain of the anti-cancer drug paclitaxel (TAXOL) and its analogs. The process includes the resolution of racemic erythro 2-hydroxy-3-amino-3-phenylpropionamide by diastereomeric crystallization and its conversion via various intermediates to the threo-ethylester and threo-methylester isomers.Type: GrantFiled: October 14, 1998Date of Patent: February 15, 2000Assignee: Chiragene, Inc.Inventors: Sowmianarayanan Ramaswamy, Venkat G. Reddy, Yalin Luo -
Patent number: 6025517Abstract: A synthesis of fluoxetine is disclosed. The process begins with benzoylacetonitrile, which is reduced, optionally in the presence of a chiral ligand, to produce the corresponding aminoalcohol, and the amine is carbamoylated without isolation. The alcohol is deprotonated and reacted with 4-chloro- or 4-fluoro benzotrifluoride or with 4-trifluoromethylphenol to provide a carbamate of fluoxetine. The carbamate is reduced with a hydride or with borane to provide fluoxetine free base. The process may be employed for the synthesis of individual enantiomers of fluoxetine.Type: GrantFiled: August 3, 1998Date of Patent: February 15, 2000Assignee: Sepracor Inc.Inventors: James Wallace Hilborn, Alex Roger Jurgens
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Patent number: 6013827Abstract: This invention relates to componds of formula I ##STR1## which are useful as PDE IV inhibitors and for treating diseases related thereto.Type: GrantFiled: July 11, 1996Date of Patent: January 11, 2000Assignee: SmithKline Beecham CorporationInventors: Joseph Bordas-Nagy, Peter Gorycki, Kevin Scott Webb
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Patent number: 5994558Abstract: The invention provides methods for preparing a 2-isoxazoline compound represented by formula (1) and a 2,5-diamino-1,6-diphenyl-3-hydroxyhexane compound obtainable by reducing the 2-isoxazoline compound and represented by formula (6): ##STR1## wherein Ph is phenyl; and each of R.sup.1 and R.sup.2 independently represents hydrogen, acyl, alkyloxycarbonyl, arylalkyloxycarbonyl, aryloxycarbonyl, alkylaminocarbonyl, arylalkylaminocarbonyl, arylaminocarbonyl, alkyl, arylalkyl, aryl, alkylsulfonyl, acylalkylsulfonyl, or arylsulfonyl, or R.sup.1 and R.sup.2 are linked to each other to form divalent acyl. These compounds are useful as intermediates in the synthesis of medicines such as retrovirus protease inhibitors including human immunodeficiency virus (HIV) protease inhibitors.Type: GrantFiled: November 24, 1997Date of Patent: November 30, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Murai, Masahiro Nishikawa, Yoichiro Ueda, Ichiro Takase
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Patent number: 5990171Abstract: The invention concerns hydrazonoacetic acid amides of general formula (I), a process for producing them, and the use of the said amides as pesticides. In the formula shown, the following meanings apply: A stands for a simple bond or optionally substituted alkylene; Q stands for oxygen or sulphur, R.sup.1 stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl; R.sup.2 stands for hydrogen or optionally substituted alkyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl; R.sup.3 and R.sup.4 are identical or different and each stand for hydrogen or optionally substituted alkyl or cycloalkyl; R.sup.2 and R.sup.3 together with the nitrogen atom to which they are bound form an optionally substituted heterocyclyl ring; R.sup.5 stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl.Type: GrantFiled: September 25, 1997Date of Patent: November 23, 1999Assignee: Bayer AktiengesellschaftInventors: Thomas Seitz, Klaus Stenzel
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Patent number: 5985919Abstract: (Het)aryloxy-, -thio- and -aminocrotonates of the formula I ##STR1## where the substituents have the following meanings: U is oxygen, sulfur or amino;V is oxygen, sulfur, amino or alkylamino;X, Y and Z independently of one another are .dbd.N-- or .dbd.CR.sup.3 --;R.sup.1 and R.sup.2 independently of one another are alkyl;R.sup.3 is hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio; andR.sup.4 is an organic radical which is bonded to the skeleton directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group,process for their preparation, and their use.Type: GrantFiled: October 30, 1997Date of Patent: November 16, 1999Assignee: BASF AktiengesellschaftInventors: Thomas Grote, Reinhard Kirstgen, Bernd Muller, Hubert Sauter, Albrecht Harreus, Hartmann Konig, Eberhard Ammermann, Gisela Lorenz, Siegfried Strathmann, Franz Rohl
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Patent number: 5977074Abstract: This invention relates to compounds and pharmaceutical compositions, and methods for inhibiting or preventing the amyloid protein deposits in the brain which are associated with Alzheimer's disease and aged Down's syndrome patients. More particularly, it relates to the treatment of Alzheimer's disease.Type: GrantFiled: March 28, 1996Date of Patent: November 2, 1999Assignee: Merrell Pharmaceuticals, Inc.Inventors: Barbara Cordell, Daniel Schirlin, Norton P. Peet, Jeffrey N. Higaki, Viviane Van Dorsselaer, Michael R. Angelastro
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Patent number: 5977170Abstract: This invention relates to the treatment of atherosclerosis via raising the level of HDL cholesterol by administration of a compound of the formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl or --(CH.sub.2).sub.0-6 Ph where Ph is optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH;R.sub.4 and R.sub.5 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or --(CH.sub.2).sub.0-6 Ar.sup.1 where Ar.sup.1 is phenyl, naphthyl, furanyl, pyridinyl or thenyl and Ar.sup.1 can be optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, trifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH; andAr is phenyl, naphthyl, furanyl, pyridinyl or thienyl or Ar is optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.Type: GrantFiled: June 11, 1998Date of Patent: November 2, 1999Assignee: American Home Products CorporationInventors: Thomas Joseph Commons, Susan Christman
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Patent number: 5968975Abstract: This invention relates to the treatment of atherosclerosis via raising the level of HDL cholesterol by administration of a compound of the formula ##STR1## wherein: R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl or --(CH.sub.2).sub.0-6 Ph where Ph is phenyl optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH;R.sup.4 and R.sup.5 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or --(CH.sub.2).sub.0-6 Ar.sup.1 where Ar.sup.1 is phenyl, naphthyl, furanyl, pyridinyl or thienyl and Ar.sup.1 can be optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, trifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH; andAr is phenyl, naphthyl, furanyl, pyridinyl or thienyl or Ar is optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.Type: GrantFiled: June 11, 1998Date of Patent: October 19, 1999Assignee: American Home Products CorporationInventors: Thomas Joseph Commons, Susan Christman
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Patent number: 5962651Abstract: The present invention provides a chemically modified form of hemoglobin that is stabilized and can efficiently bind and release oxygen. In addition the chemically modified hemoglobin may be polymerized to increase its molecular weight and increase its stability so that it will have a longer half life in the circulatory system and may be used as a stable oxygen transport mediator which is useful as the basis of a blood substitute.Type: GrantFiled: July 31, 1997Date of Patent: October 5, 1999Assignee: Montefiore Medical CenterInventors: Iraj Lalezari, Parviz Lalezari
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Patent number: 5962487Abstract: Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.Type: GrantFiled: December 16, 1997Date of Patent: October 5, 1999Assignee: Agouron Pharmaceuticals, Inc.Inventors: Stephen E. Webber, Peter S. Dragovich, Thomas J. Prins, Ethel S. Littlefield, Joseph T. Marakovits, Robert E. Babine
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Patent number: 5955501Abstract: Compounds having anti-inflammatory and other activities are disclosed. The compounds are derived from phorboids of the diterpene- and benzolactam-classes.Type: GrantFiled: June 7, 1995Date of Patent: September 21, 1999Assignee: Procyon Pharmaceuticals, Inc.Inventors: Paul E. Driedger, James Quick
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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: 5948778Abstract: This invention relates to novel statone antiviral analogs, to the processes and intermediates useful for their preparation and to their use as antiviral agents.Type: GrantFiled: May 19, 1998Date of Patent: September 7, 1999Assignee: Merrel Pharmaceuticals Inc.Inventors: Viviane Van Dorsselaer, Daniel Schirlin, Celine Tarnus
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Patent number: 5945543Abstract: A process for preparing .alpha.-(N,N-dialkylamino) carboxamides of the formula I ##STR1## where the substituents have the stated meanings, comprises reacting the corresponding free acids with primary or secondary amines in the presence of anhydrides of an alkanephosphonic acid.Type: GrantFiled: January 20, 1998Date of Patent: August 31, 1999Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Thomas Zierke
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Patent number: 5939554Abstract: A method for preparing a diarylalanine compound is provided. The method includes reacting a diarylaminopropanediol with a reducing agent to form a diarylaminopropanol compound and/or contacting a serine ester derivative with an aryl metal reagent to form diarylaminopropanediol. A diarylmethyloxazolidinone compound is also provided.Type: GrantFiled: April 17, 1997Date of Patent: August 17, 1999Assignee: NDSU Research FoundationInventors: Mukund P. Sibi, Prasad K. Despande, Anthony J. LaLoggia
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Patent number: 5932586Abstract: This invention relates to ortho substituted phenyl compounds as inhibitors of prostaglandin synthase, to pharmaceutical compositions comprising such compounds and to methods of using such compounds as antiinflammatory and antipyretic agents.Type: GrantFiled: November 19, 1996Date of Patent: August 3, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Douglas Guy Batt, Donald Joseph Phillip Pinto, Michael James Orwat, Joseph James Petraitis, William John Pitts
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Patent number: 5922864Abstract: An efficient method for the preparation of a compound of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl- 1,4-dihydro-2H-3, 1-benzoxazin-2-one, also known as DMP-266, a reverse transcriptase inhibitor is achieved using a cyclization reaction of the amino alcohol intermediate with an alkyl or aryl chloroformate and a base.Type: GrantFiled: February 3, 1998Date of Patent: July 13, 1999Assignee: Merck & Co., Inc.Inventors: Lisa F. Frey, Richard D. Tillyer, Edward J. J. Grabowski
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Patent number: 5914425Abstract: The invention relates to novel modifications of the compound 2-amino-4-(4-fluorobenzylamino)-1-ethoxy-carbonylaminobenzene of the formula I ##STR1## processes for their preparation and their use in pharmaceutical compositions.Type: GrantFiled: January 9, 1998Date of Patent: June 22, 1999Assignee: ASTA Medica AktiengesellschaftInventors: Peter Meisel, Karl-Friedrich Landgraf, Jurgen Schafer, Wilfried Thiel, Matthias Rischer, Alfred Olbrich, Bernhard Kutscher
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Patent number: 5886046Abstract: This invention relates to chemical compounds that contain adjacent carbonyl groups, which effectively inhibit the biological, chemical, and/or physical properties of enzymes and other medicinally-significant proteins. In particular, the invention relates to dicarbonyl compounds that are capable of acting as enzyme inhibitors, including irreversible inhibitors of HIV-1 protease.Type: GrantFiled: January 19, 1996Date of Patent: March 23, 1999Assignee: The Trustees of the University of PennsylvaniaInventors: Ralph F. Hirschmann, Amos B. Smith, III, Paul Sprengeler, Wenqing Yao, Paul Anderson
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Patent number: 5874465Abstract: Compounds having the structural formula: ##STR1## wherein: R is C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkyl, C.sub.7 -C.sub.9 aralkyl, or nitroso; R' is C.sub.1 -C.sub.4 alkyl; and R" is C.sub.1 -C.sub.4 alkyl. These compounds exhibit insecticidal and miticidal activity.Type: GrantFiled: October 24, 1996Date of Patent: February 23, 1999Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Co./CIE.Inventors: Mark Achiel Dekeyser, Paul Thomas McDonald