Aldehyde Or Ketone Patents (Class 562/459)
  • Patent number: 5716624
    Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: February 10, 1998
    Assignee: C.I.R.D. Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5710277
    Abstract: An improved process for the preparation of R(+)1,2,3,6-tetrahydro-4-phenyl-1-?(3-phenyl-3-cyclohexen-1-yl)methyl!pyri dine by a novel synthesis is described where 5-oxo-3-phenyl-3-cyclohexene-carboxylic acid is converted in five operations to the desired product, as well as processes for the resolution of 5-oxo-3-phenyl-3-cyclohexenecarboxylic acid using cinchonidine to afford (S)5-oxo-3-phenyl-3-cyclohexenecarboylic acid or .alpha.-chymotrypsin to selectively hydrolyze n-butyl 5-oxo-3-phenyl-3-cycohexenecarboxylate to afford (S)5-oxo-3-phenyl-3-cyclohexenecarboxylic acid as well as other valuable intermediates used in the processes.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: January 20, 1998
    Assignee: Warner-Lambert Company
    Inventors: Donald Eugene Butler, Jodette Gailey, Tung Van Le, William John Smith, III, David Juergen Wustrow
  • Patent number: 5670692
    Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.
    Type: Grant
    Filed: August 27, 1996
    Date of Patent: September 23, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 5663412
    Abstract: The present invention relates to substantially pure piperidine derivative compounds of the formulae: ##STR1## wherein R.sub.1 is hydrogen or hydroxy;R.sub.2 is hydrogen;or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ;R.sub.3 is --COOH or --COOR.sub.4 ;R.sub.4 has 1 to 6 carbon atoms;A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents.A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: September 2, 1997
    Assignee: Albany Molecular Research, Inc.
    Inventor: Thomas E. D'Ambra
  • Patent number: 5650533
    Abstract: The invention relates to 4-substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meaning defined in the description which possess valuable herbicidal properties.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 22, 1997
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventors: David Alan Roberts, Susan Mary Cramp, Derek Ian Wallis, Jean-Paul Bulot
  • Patent number: 5508309
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--;wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole;wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons;wherein p and q are integers from 0 to 20;wherein n is 0 or 1; andwherein m is 0, 1, 2, or 3.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: April 16, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5491257
    Abstract: The present invention provides a compound which has a fluoroalkyl group, a lipophilic group (an alkyl group) and a hydrophilic group in the same molecule.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: February 13, 1996
    Assignee: Daikin Industries, Ltd.
    Inventor: Norio Yoshino
  • Patent number: 5475132
    Abstract: 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 or 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: May 27, 1994
    Date of Patent: December 12, 1995
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
  • Patent number: 5466880
    Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4 -dichlorophenyl)-3,4-1(2H)- naphthalenone in a highly-optically pure form is disclosed. The process involved starts from the known 4-(3,4-dichlorophenyl)-4-ketobutanoic acid and proceeds through such intermediates as (1) isopropyl or tert.- butyl 4-(3,4 -dichlorophenyl)-4-ketobutanoate, (2) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-hydroxybutanoate, (3) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl-(4R)-sulfonyloxybutanoate, (4) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-phenylbutanoate to finally yield the desired (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro -1(2H)-naphthalenone compound in a highly-optically pure form. The latter compound, which is a (4S)-enantiomer per se, has utility as an intermediate that ultimately leads to pure cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal eneamine (sertraline), which is a known antidepressant agent. The aforementioned isopropyl and tert.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: November 14, 1995
    Assignee: Pfizer Inc.
    Inventor: George J. Quallich
  • Patent number: 5453443
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of the PLA.sub.2 s enzymes. These compounds are useful as anti-allergic, anti-asthmatic, they are also useful in treating various inflammatory diseases such as rheumatoid arthritis, osteoarthritis, bursitis, psoriasis; immunoinflammatory disorders such as contact dermatitis, irritable bowel disease and the like.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: September 26, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Helene Perrier, Petpiboon Prasit, Ian Street, Zhaoyin Wang
  • Patent number: 5436369
    Abstract: Certain novel alicyclic compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: July 25, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventors: Joanne J. Bronson, Katharine M. Greene, Muzammil M. Mansuri, Stanley V. D'Andrea, F. Ivy Carroll, Anita Lewin
  • Patent number: 5430047
    Abstract: Neurotensin antagonists are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as antipsychotic agents and as agents to treat Parkinson's disease and gastrointestinal disorders.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: July 4, 1995
    Assignee: Warner-Lambert Company
    Inventors: Stephen J. Johnson, Suzanne R. Kesten, Lawrence D. Wise, David J. Wustrow
  • Patent number: 5403952
    Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: April 4, 1995
    Assignee: Merck & Co., Inc.
    Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
  • Patent number: 5378728
    Abstract: Compound of the formula ##STR1## where R is CH.sub.3 (CH.sub.2).sub.m, A and B are hydrogen, a bond or --(CH.sub.2).sub.n,X is ##STR2## m is 0, 1 , 2 or 3, n is 1 , 2, or 3, R.sub.1 is hydrogen or lower alkyl, andY is --OH, --OR.sub.2 or --NR.sub.3 R.sub.4where R.sub.2, R.sub.3 and R.sub.4 are hydrogen or unsubstituted or substituted alkyl, aryl and aralkyl substituents.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: January 3, 1995
    Assignee: Sandoz Ltd.
    Inventors: Jeffrey Nadelson, William R. J. Simpson, Robert C. Anderson, Joginder S. Bajwa
  • Patent number: 5360927
    Abstract: A process for the preparation of monohydrated sodium phenylpyruvate comprises reacting benzaldehyde with the stoichiometric quantity of hydantoin in the aqueous medium in the presence of a catalytic quantity of a primary or secondary amine at high temperature, treating the reaction mixture with an excess of sodium hydroxide at high temperature, adding sodium chloride to the sodium hydroxide-treated solution, acidifying the so obtained solution with concentrated hydrochloric acid, and washing the formed precipitate with methanol.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: November 1, 1994
    Assignee: Development Center for Biotechnology
    Inventors: Jin-Tann Chen, Same-Ting Chen, Hsin Tsai
  • Patent number: 5356919
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--; wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole; wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation; wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons; wherein p and q are integers from 0 to 20; wherein n is 0 or 1; and wherein m is 0, 1, 2, or 3.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: October 18, 1994
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5350872
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: September 27, 1994
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5338881
    Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and a phosphorus pentoxide. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: August 16, 1994
    Assignee: Eastman Chemical Company
    Inventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
  • Patent number: 5304672
    Abstract: A method for the preparation of compounds of the formula ##STR1## wherein X represents a group of the formula OR.sub.1 or NR.sub.1 R.sub.2, wherein R.sub.1 and R.sub.2 independently represent H or an organic group that forms a stable covalent bond with the N or 0 of said X; Y is H or an organic group that forms a stable ester with the adjacent COO group; R is an alkyl or aryl group optionally substituted with one or more stable organic substituents; each R.sub.3 independently represents a stable organic group; and n is an integer from 0 to 3;the method using new intermediates of the formula ##STR2## wherein R.sub.3 and Y have the foregoing meanings;W is either F or Cl; andR.sub.9 is a hydrocarbon such as a C.sub.1 -C.sub.4 alkyl or alkenyl group.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: April 19, 1994
    Assignees: Orsan, Orsem
    Inventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
  • Patent number: 5288750
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: February 22, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Pentti Pohto, Paivi A. Aho, Reijo J. Backstrom, Erkki J. Honkanen, Inge-Britt Y. Linden, Erkki A. O. Nissinen
  • Patent number: 5280045
    Abstract: The subject invention involves compositions comprising 4-(3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl)-4-oxobutanamide, or 4-(3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl)-4-oxobutanoic acid and pharmaceutically-acceptable salts thereof, and a pharmaceutically-acceptable carrier. The subject invention also involves methods for treating diseases characterized by inflammation and/or pain, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals by administration of a safe and effective amount of this compound to the human or lower animal in need of such treatment.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: January 18, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Roy L. M. Dobson, Kenneth R. Wehmeyer, Steven P. Sirko, Benjamin F. Floyd
  • Patent number: 5194625
    Abstract: A compound of the formula:AN/xSwherein A represents an amino acid, N represents an .alpha.-keto acid, S represents a lower alcohol or acetone; and x ranges from 0.1 to 3.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: March 16, 1993
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toshiya Tanabe, Shin-ichi Kishimoto
  • Patent number: 5183891
    Abstract: A method for the preparation of compounds of the formula ##STR1## wherein X represents a group of the formula OR.sub.1 or NR.sub.1 R.sub.2, wherein R.sub.1 and R.sub.2 independently represent H or an organic group that forms a stable covalent bond with the N or O of said X; Y is H or an organic group that forms a stable ester with the adjacent COO group; R is an alkyl or aryl group optionally substituted with one or more stable organic substituents; each R.sub.3 independently represents a stable organic group; and n is an integer from 0 to 3;the method using new intermediates of the formula ##STR2## wherein R.sub.3 and Y have the foregoing meanings; W is either F or Cl;and R.sub.9 is a hydrocarbon such as a C.sub.1 -C.sub.4 alkyl or alkenyl group.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: February 2, 1993
    Assignees: Orsan, Orsem
    Inventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
  • Patent number: 5177204
    Abstract: This relates to substances represented by formula (I), wherein X stands for represented by either OR in which R is an alkyl of 1 to 4 carbon atoms, or NHR in which is an alkyl of 1 to 4 carbon atoms, or a (CH.sub.2).sub.n NR.sub.2 group wherein n is 2 or 3 while R.sup. is an methyl or an ethyl group; eventually X may represent morpholinyl. Also considered are salts of 4-(2,4-difluorbiphenylyl)-2-methyl-4-oxobutanoic acid with appropriate inorganic or organic bases represented by formula (II) wherein B.sup.+ is either an alkaline metal cation, alkaline earth metal cation, cyclohexylamine cation, or lysine cation. Said substances are characterized by antiinflamatory properties comparable to (and greater than) the initial acid while simultaneously said modifications of their physico-chemical properties broaden the posibilities of their therapeutic application.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: January 5, 1993
    Assignee: Vyzkumng, USTAV pro farmacii a biochemii, Statni podnik
    Inventors: Miroslav Kuchar, Marie Poppova, Jaroslava Grimova, Eva Maturova
  • Patent number: 5147892
    Abstract: Benzyl ketones of the formula ##STR1## where X is CH or N,Y is O or NR.sup.4,R.sup.1, R.sup.2 are H or alkyl,R.sup.3 is halogen, cyano, nitro, alkyl, cycloalkyl, alkoxy, haloalkyl, arylalkyl, arylalkoxy, aryloxy or aryl, and the aryl groups in turn may be substituted,R.sup.4 is OH, alkoxy or arylalkoxy andR.sup.5 is H, methyl, halogen or methoxy,and fungicides containing these compounds.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: September 15, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Hubert Sauter, Franz Roehl, Reinhard Doetzer, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5142095
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5086067
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: February 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5041610
    Abstract: Ring-opened resorcyclic acid lactone derivatives of the formla ##STR1## wherein X is ethylene or ethenylene; Y and Z, which may be the same or different, are methylene, hydroxymethylene or carbonyl; R.sub.1 is hydrogen or lower alkyl of from 1 to about 6 carbon atoms; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which may be the same or different, are hydrogen, hydroxyl, halogen, nitro, amino or a radical selected from the group consisting of --R', --OR', --COOR' and --OCOR' wherein R' is lower alkyl of from 1 to about 6 carbon atoms, lower cycloalkyl of from 3 to about 8 carbon atom, alkenyl of from 2 to about 6 carbon atoms, substituted or unsubstituted aryl of from 6 to about 8 carbon atoms, or substituted or unsubstituted aralkyl wherein the alkyl portion contains from 1 to about 6 carbon atoms and the aryl portion contains from 6 to about 8 carbon atoms. These compounds are useful as growth-promotants in food-producing animals.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 20, 1991
    Assignee: International Minerals & Chemical Corp.
    Inventor: Keith A. Drengler
  • Patent number: 5028738
    Abstract: There is a process for producing 2-oxo-3-aromatic carboxylic acid derivatives which comprises reacting aromatic pyruvic acid derivatives with electrophilic compounds in the presence of bases in a protic solvent. According to this process, 2-oxo-3-aromatic carboxylic acid derivatives which can be easily converted to aromatic amino acid derivatives or 2-aromatic carboxylic acid derivatives as important synthetic intermediates of medicines and agricultural chemicals can be produced in good yields with high selectivity.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: July 2, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Kenji Hirai, Kazumi Nakamura, Atsuko Fujita
  • Patent number: 5004754
    Abstract: The invention relates to a biofungicidal composition characterized by its capacity to arrest the growth and/or destroy the cell wall of pathogenic fungi, comprises a composition of a compound of the formula I ##STR1## wherein R.sub.1 is selected from the group consisting of ##STR2## and R.sub.2 is --H or --OH and mixtures thereof in association with an inert carrier, and to a method for arresting the growth and/or destroying the cell wall of pathogenic fungi by applying thereto a biofungicidal amount of the composition of a compound of formula I in association with an inert carrier.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: April 2, 1991
    Assignee: Universite Laval
    Inventors: J. Andre Fortin, Kelvin K. Ogilvie, Youla S. Tsantrizos, Harry H. Kope
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 4956490
    Abstract: There is disclosed a continuous, non-isolation process for preparing benzylpyruvic acids and benzylpyruvic esters. The benzylpyruvic acids and esters obtained are useful as intermediates to prepare carboxyalkyl dipeptide compounds which are used as angiotension converting enzyme (ACE) inhibitors to treat hypertension.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: September 11, 1990
    Assignee: Merck & Co., Inc.
    Inventors: James W. McManus, John F. Genus
  • Patent number: 4948920
    Abstract: A process for producing phenylpyruvic acid by reacting benzyl chloride with carbon monoxide in the presence of a catalytic amount of a metal carbonyl compound and an inorganic base, in an acetonitrile/water solvent.
    Type: Grant
    Filed: March 24, 1989
    Date of Patent: August 14, 1990
    Assignee: The NutraSweet Company
    Inventors: Clark R. Landis, Hayat Khowaja
  • Patent number: 4946999
    Abstract: The present invention relates to a process for preparing trichostatic acid represented by the following formula [14] ##STR1## by oxidizing (E,E)-7-(4'-dimethylaminophenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoic acid represented by the following formula [13]: ##STR2## and a process for preparing trichostatin A represented by the following formula [15]: ##STR3## by allowing to react trichostatic acid with amine.
    Type: Grant
    Filed: February 22, 1989
    Date of Patent: August 7, 1990
    Assignee: Japan Tobacco Inc.
    Inventors: Koshi Koseki, Kenji Mori
  • Patent number: 4929741
    Abstract: Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula--C(R.sup.14)(R.sup.15)OR.sup.16' (f'):exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
  • Patent number: 4927958
    Abstract: Styryl ketones of the formula ##STR1## wherein R.sup.8 and R.sup.9 are independently hydrogen or lower alkyl or together represent an additional carbon-carbon bond andR.sup.10 is a group of the formula ##STR2## as well as corresponding compounds of the formula ##STR3## wherein R.sup.10' is a group of formula (a), (b), (d) or (e) or a group of the formula--C(R.sup.18)(R.sup.19)OR.sup.20' ; (f')have mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers or duodenal ulcers.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: May 22, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
  • Patent number: 4912255
    Abstract: A process for the production of sodium phenylpyruvate from calcium phenylpyruvate wherein calcium phenylpyruvate is contacted with a sodium carbonate salt in an inert atmosphere.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: March 27, 1990
    Inventor: Albert S. Chan
  • Patent number: 4898952
    Abstract: A highly regioselective synthesis of pyrazoles from a mono-substituted hydrazine and a .beta.-dicarbonyl compound wherein a carboxylic acid moiety is present on the substituent attached to one of the carbonyls.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: February 6, 1990
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: William V. Murray, Michael P. Wachter
  • Patent number: 4888358
    Abstract: Novel 13,14-dihydroprostaglandin derivatives of the formula ##STR1## wherein: m is 1 or 3;R.sub.1 is hydrogen or alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 and R.sub.4 are independently hydrogen or methyl;R.sub.5 is alkyl, CF.sub.3 (CH.sub.2).sub.n -- in which n is an integer of 3-5, cycloalkyl, or optionally substituted phenyl, benzyl or phenoxy; orR.sub.4 and R.sub.5 taken together with the carbon to which they are attached is cycloalkyl of 4-8 carbon atoms;X is cis --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -- when m is 3, orX is --CH.sub.2 CH.dbd.C.dbd.CH-- when m is 1;and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.;or a pharmaceutically acceptable salt thereof,have been prepared. They are useful in particular for their antihypertensive and anti-ulcerogenic properties.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: December 19, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joan Huguet, Joseph M. Muchowski, Maria T. Lara
  • Patent number: 4853481
    Abstract: Alkyl-substituted aromatic ketones are prepared by reacting alkylbenzenes with carboxylic anhydrides in the presence of a Friedel-Crafts catalyst by performing the reaction in the presence of a tertiary amine or diamine.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: August 1, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochem Henkelmann, Manfred Eggersdorfer, Walter Grosch, Alfred Schuhmacher, Hardo Siegel
  • Patent number: 4803294
    Abstract: This invention relates to novel intermediate compounds which are useful for producing the halogenated protease inhibitors that are the subject matter of U.S. Pat. No. 4,469,885. In particular, the invention relates to novel methods and intermediates for making said protease inhibitors, the intermediate compounds being of the formula: ##STR1## wherein R.sub.1 is: (a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.6 is:(a) straight or branched chain higher alkyl having 13-25 carbon atoms; or(b) straight or branched chain higher alkenyl having 13-25 carbon atoms;wherein R.sub.5 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) benzyl;wherein R.sub.7 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.2 is:(a) --Cl, --Br, or --I; or(b) --CF.sub.3.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: February 7, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 4801616
    Abstract: This invention provides certain diphenylmethane derivatives, their pharmaceutical formulations, and their use in treating inflammation and arthritis in mammals.
    Type: Grant
    Filed: March 25, 1986
    Date of Patent: January 31, 1989
    Assignee: Eli Lilly and Company
    Inventor: D. Mark Gapinski
  • Patent number: 4800231
    Abstract: Novel keto-diesters are produced by a 2:1 condensation of lower alkyl esters of .alpha.,.beta.-ethylenically unsaturated carboxylic acids and aldehydes having two hydrogen atoms as portions of a formyl group, in the presence of a thiazolium salt as catalyst and a tertiary amine.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: January 24, 1989
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4778925
    Abstract: Para substituted benzoic acid derivatives of general formula (1) ##STR1## and their physiologically compatible salts, where R.sup.1 may be H, isopropyl, t-butyl p0 X may be ##STR2## and R.sup.2 may be --OH, --OR', where R' is a linear or branched, saturated or unsaturated C.sub.1 to C.sub.3 alkylmoiety, or a --NHCH.sub.2 COOH-- group, have hypolipedemic activity. They may be obtained by known methods either from the corresponding unsaturated ketones or from saturated hydroxycompounds, where the esterified benzoic acid moiety may be saponified or converted to a carboxymethylamide.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: October 18, 1988
    Assignee: Klinge Pharma GmbH
    Inventors: Helmut Grill, Friedemann Reiter, Michael Schliack, Roland Loser, Klaus Seibel
  • Patent number: 4766235
    Abstract: Unsaturated camphor derivatives have an activity in the topical and systemic treatment of acne, psoriasis and other dermatological disorders.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: August 23, 1988
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Gerard Lang, Braham Shroot, Serge Forestier, Alain Lagrange
  • Patent number: 4761496
    Abstract: An alkylene or dialkyl ketal of the formula ##STR1## wherein R.sup.3 is halo, carboxy or (C.sub.1 -C.sub.12)alkyl, alkoxy, acyl, acyloxy, carbalkoxy or alkylthio.R.sup.1 is (C.sub.1 -C.sub.12)alkyl, (C.sub.6 -C.sub.20)aryl or (C.sub.7 -C.sub.21)alkylaryl or aralkyl; andR.sup.2 is (C.sub.1 -C.sub.12)alkyl or the two R.sup.2 taken together are (C.sub.2 -C.sub.12)alkylene.An alpha-enol ether of the formula ##STR2## wherein R.sup.1 and R.sup.3 are as defined above and R.sup.2 is (C.sub.1 -C.sub.12)alkyl.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: August 2, 1988
    Assignee: Eastman Kodak Company
    Inventors: Joseph R. Zoeller, Charles E. Sumner, Jr.
  • Patent number: 4736057
    Abstract: This invention concerns novel (4-substituted-2-phenylcyclohexyl)alkenoic and alkanoic acid derivatives of the formula I wherein one of Ra and Rb is hydrogen, hydroxy, (1-6C)alkyl, (1-6C)alkoxy, (3-6C)alkenyloxy or phenyl(1-4C)alkoxy and the other of Ra and Rb is hydrogen, (1-6C)alkyl, (1-6C)alkoxy or (3-6C)alkenyloxy; or Ra and Rb together form a (2-4C)alkylenedioxy or oxo group; benzene ring X optionally bears a substituent selected from halogeno, (1-6C)alkyl, (1-6C)alkoxy, hydroxy, (2-6C)alkanoyloxy, (1-6C)alkanoylamino, trifluoromethyl and nitro; n is 3-5; Y is ethylene or vinylene; and in the cyclohexane ring, the substituents at positions 1 and 2 have cis- or trans-relative stereochemistry; and the pharmaceutically acceptable salts, (1-6C)alkyl esters and (1-6C)alkanesulphonamides thereof. The compounds of formula I possess valuable pharmacological properties of use in medicines.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: April 5, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Allen J. Guildford, Ralph W. Turner
  • Patent number: 4703110
    Abstract: The application discloses certain benzoic acid compounds, the same being more adequately described as benzoic acid derivatives having a para substituent which is a substituted phenyl radical attached to the benzoic acid in the para position by any one of a variety of linking groups, representative compounds being p-(3,4-diisopropylphenylcarbamoyl) benzoic acid and p-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarbamoyl)benzoic acid, pharmaceutical compositions thereof, method of treating therewith, method of diagnosis therewith, and method for the preparation thereof. The compounds and compositions are useful for diagnosis of leukemia types, the treatment of dermatological disorders, and as differentiation-inducing agents for neoplastic cells.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: October 27, 1987
    Assignee: Koichi Shudo
    Inventor: Koichi Shudo
  • Patent number: 4689344
    Abstract: A novel class of compounds has been found to be effective in blocking cholesterol and neutral lipid synthesis in-vivo without adversely affecting energy metabolism, useful for the treatment of obesity, hyperlipidemia and maturity-onset diabetes. The active compounds have the general formula ##STR1## or in-vivo hydrolyzable functional derivatives of the carboxylic groups thereof,whereinR.sub.1 and R.sub.2 each independently represents an unsubstituted or substituted hydrocarbyl or hetercyclyl radical;X and Y each independently represents hydrogen, optionally substituted lower alkyl, halogen, cyano, carboxy, lower alkoxycarbonyl or carbamoyl; andQ represents a diradical consisting of a linear chain of 8 to 14 carbon atoms, one or more of which may be replaced by heteroatoms, said chain being optionally substituted by inert substituents and one or more of said carbon or heteratom chain members optionally forming part of a ring structure.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: August 25, 1987
    Assignee: Epis S.A.
    Inventor: Jacob Bar-Tana
  • Patent number: 4689426
    Abstract: Novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenone and process for production thereof. The novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenones are represented by the following formula (I): ##STR1## wherein R.sub.a represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a substituted or unsubstituted phenyl group, R.sub.b represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms, and X represents a halogen atom. The novel cyclopentenones possess excellent pharmaceutical activities including anti-tumor activity, antiviral activity and antimicrobial activity.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: August 25, 1987
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Toshio Tanaka, Seizi Kurozumi