Carboxyl Bonded Directly To Naphthylene Ring System Patents (Class 562/467)
  • Patent number: 6403827
    Abstract: The present invention provides crystalline 2-hydroxynaphthalene-3-carboxylic acid (BON) characterized in that the average particle size is equal to or more than 157 &mgr;m and the proportion of the particles of which particle size is less than 74 &mgr;m is equal to or less than 14%. The crystalline composition of the present invention can be prepared by a process comprising the step of recrystallizing BON, especially at a high temperature, or by carrying out the acid precipitation step in the method for preparing BON at a high temperature.
    Type: Grant
    Filed: January 3, 2001
    Date of Patent: June 11, 2002
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo K.
    Inventors: Ryuzo Ueno, Masaya Kitayama, Nobutaka Izumichi, Hiroyuki Kato
  • Patent number: 6316396
    Abstract: The invention relates to amphiphilic compounds of the general formula (I) with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyolethers. The amphiphilic compounds of this invention are highly surface active and are suitable as emulsifiers, demulsifiers, detergents, dispersants and hydrotropes for industrial and domestic purposes, e.g. in the fields of metalworking, ore separation, surface treatment, washing and cleaning, cosmetics, medicine and food processing and preparation.
    Type: Grant
    Filed: April 9, 1999
    Date of Patent: November 13, 2001
    Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und Chemie
    Inventors: Klaus Kwetkat, Wolfgang Schröder
  • Patent number: 6316665
    Abstract: An oxidation free process for converting a hydroxy substituted aromatic to an aromatic diacid which comprises reacting a hydroxy substituted aromatic with excess basic salt in the presence of carbon dioxide at disproportionation/isomerization reaction conditions.
    Type: Grant
    Filed: August 22, 2000
    Date of Patent: November 13, 2001
    Assignee: Shell Oil Company
    Inventors: Thomas Fairchild Brownscombe, Garo Vaporciyan, Narayana Mysore, Susan Secor Pfrehm
  • Patent number: 6284924
    Abstract: A novel compound represented by the general formula (1) or salts thereof. The compound is useful as a structural component of polymers such as polyesters and polyamides. The compound wherein Y1, Y2, Y3, and/or Y4 are carboxy groups is especially useful as a structural component of a liquid crystal polymer with improved weld strength and anisotropy.
    Type: Grant
    Filed: January 4, 2001
    Date of Patent: September 4, 2001
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Naoko Mori
  • Patent number: 6242609
    Abstract: 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: Grant
    Filed: April 7, 1999
    Date of Patent: June 5, 2001
    Assignee: Konica Corporation
    Inventor: Fumio Ishii
  • Patent number: 6194608
    Abstract: The present invention provides a process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids, in which alkali metal salt(s) of hydroxynaphthalenecarboxylic acid(s) are separated and purified from a mixture of alkali metal salts of hydroxynaphthalenecarboxylic acids by treating it with a nonionic porous synthetic adsorbent using water or water and water-soluble organic solvent(s).
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: February 27, 2001
    Assignee: Kabushiki Kaisha Veno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kuniyo Yanagawase, Yoshiro Uchiyama, Shigeji Mori
  • Patent number: 6156750
    Abstract: Novel pharmaceutically/cosmetically-active bicyclic aromatic compounds have the structural formula (I): ##STR1## 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: January 13, 1999
    Date of Patent: December 5, 2000
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 6143905
    Abstract: 1,7-Disubstituted perylene-3,4,9,10-tetracarboxylic dianhydrides I and perylene-3,4,9,10-tetracarboxylic acids Ia ##STR1## where R is substituted or unsubstituted aryloxy, arylthio, hetaryloxy or hetarylthio,their preparation and use as pigments, laser dyes and precursors for preparing fluorescent dyes, polymeric colorants, pigments and pigment additives, and 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic diimides (VI) as intermediates thereof.
    Type: Grant
    Filed: June 18, 1998
    Date of Patent: November 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Arno Bohm, Harald Arms, Georg Henning, Peter Blaschka
  • Patent number: 6124498
    Abstract: In one embodiment, the present invention provides a compound comprising: ##STR1## wherein A=H or OHX=OH, a halogen, OR, NHR, NR'R" where R, R', and R"=H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or heterocyclic, substituted or unsubstituted; andR.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 =H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cyloalkenyl, aryl or heterocyclic, substituted or unsubstituted, wherein R.sub.1 includes at least one methylene spacer through which R.sub.1 is attached to said compound. The present invention also provides methods for making hydroxynaphthoic acids.
    Type: Grant
    Filed: April 28, 1998
    Date of Patent: September 26, 2000
    Assignee: University Of New Mexico
    Inventors: David L. Vander Jagt, Lorraine M. Deck, Robert E. Royer
  • Patent number: 6080888
    Abstract: Arylolefinic compounds are prepared by reacting aryl halide with an olefinic compound in the presence of a polar liquid reaction medium containing (a) secondary or tertiary amine as a hydrogen halide acceptor (b) a catalyst system formed from (i) Pd or Pd(0) compound, and/or Pd(I) salt or Pd(II) salt, and (ii) a tertiary phosphine ligand, and (c) a reaction accelerating amount of water in the range of about 0.5 to about 5 weight percent of the total weight of the reaction mixture. The arylolefinic compounds can be converted to an arylcarboxylic acid by hydrocarboxylation with CO in a reaction medium freed of amine and containing water and a Pd catalyst system as above in which a copper component may be included, and which preferably includes an ether such as THF.
    Type: Grant
    Filed: January 8, 1997
    Date of Patent: June 27, 2000
    Assignee: Albemarle Corporation
    Inventors: Tse-Chong Wu, Kannappan C. Chockalingham, W. Dirk Klobucar, Gary D. Focht
  • Patent number: 5936120
    Abstract: The invention provides deoxygossylic compounds having useful biological activities, and methods for the synthesis of these and related compounds. The invention further provides valuable intermediates for the synthesis of the compounds, and pharmaceutical compositions containing biologically active compounds according to the invention.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: August 10, 1999
    Assignee: University of New Mexico
    Inventors: Robert D. Royer, Lorraine M. Deck, David L. VanderJagt
  • Patent number: 5925487
    Abstract: A toner resin composition comprising a toner resin and the metal salt or complex of a carbocyclic hydroxy caboxylic acid containing at least one methylene group optionally substituted by hydroxy or amino such as 4-(N-methyl-N-2-hydroxyethyl)aminomethyl-3-hydroxy-2-naphthoic acid. Iron and zinc salts are preferred.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: July 20, 1999
    Assignee: Zeneca Limited
    Inventors: David Melville Fawkes, Peter Gregory, James Stanley Campbell
  • Patent number: 5919970
    Abstract: Compounds of the formulaY.sub.3 (R.sub.4)--X--Y.sub.1 (R.sub.1 R.sub.2)--Z--Y.sub.2 (R.sub.2)--A--Bwhere the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist or retinoid inverse agonist type biological activity.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: July 6, 1999
    Assignee: Allergan Sales, Inc.
    Inventors: Tae K. Song, Min Teng, Roshantha A. Chandraratna
  • Patent number: 5874614
    Abstract: Novel and very useful forms of sodium (S)-2-(6-methoxy-2-naphthyl)propionate are provided. These forms are sodium (S)-2-(6-methoxy-2-naphthyl)propionate monohydrate having an average particle size significantly larger than about 70 microns--the size of conventional sodium (S)-2-(6-methoxy-2-naphthyl)propionate--and a chiral purity of at least 98% (S)-enantiomer. Process technology enabling the production of such novel products is also described. The provision of such novel products makes possible significant improvements in processing time, plant capacity and product handling operations.
    Type: Grant
    Filed: December 11, 1997
    Date of Patent: February 23, 1999
    Assignee: Albemarle Corporation
    Inventors: Hao V. Phan, Robert H. Allen, Richard A. Coats
  • Patent number: 5859293
    Abstract: A process for the extraction and isolation of concentrated carnosic acid from plant matter of the Labiatae family including contacting the plant matter with a water-miscible solvent to form a plant extract and adjusting the pH of the plant extract to a level between 7 and 10 while adding water in an amount sufficient to cause precipitation of impurities while retaining the carnosic acid salt in solution. The impurities are separated and the remaining aqueous solution is acidified to precipitate a highly purified carnosic acid product which is essentially odorless, flavorless and colorless.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: January 12, 1999
    Assignee: Hauser, Inc.
    Inventors: David T. Bailey, Steven L. Richheimer, Virginia R. Bank, Benjamin T. King
  • Patent number: 5859292
    Abstract: Sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed from (S)-2-(6-methoxy-2-naphthyl)propionic acid having a chiral purity of at least about 82%, but below 99%. This is done by distilling a two-phase mixture formed from (i) the (S)-2-(6-methoxy-2-naphthyl)propionic acid, (ii) water, (iii) sodium hydroxide, sodium oxide and/or at least one basic inorganic sodium salt in an amount proportioned to neutralize from about 50 to about 99% of said acid, and optionally but preferably, (iv) an inert organic solvent that has a boiling point of at least 95.degree. C. at 760 mm Hg such that water is removed from said mixture, and a pot residue containing sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed.
    Type: Grant
    Filed: December 11, 1997
    Date of Patent: January 12, 1999
    Assignee: Albemarle Corporation
    Inventors: Hao V. Phan, Robert E. Young
  • Patent number: 5827855
    Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1 represents a group of formula (II) or (III): ##STR2## R.sup.2 is alkyl, alkenyl or alkynyl; R.sup.3 and R.sup.4 are each hydrogen, alkyl, alkenyl or alkynyl; R.sup.5 is hydrogen or a carboxy-protecting group; R.sup.a is a group of formula --OR.sup.6 ; R.sup.6 is hydrogen; R.sup.6a and R.sup.6b are each hydrogen, a hydroxy-protecting group, alkyl, alkanesulfonyl, halogenated alkanesulfonyl or arysulfonyl, and their salts and esters. Such compounds inhibit the synthesis of cholesterol, and can be used for the treatment and prophylaxis of hypercholesterolemia and of various cardiac disorders.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: October 27, 1998
    Assignee: Sankyo Company, Limited
    Inventors: Hiroshi Kogen, Sadao Ishihara, Teiichiro Koga, Eiichi Kitazawa, Nobufusa Serizawa, Kiyoshi Hamano
  • Patent number: 5808142
    Abstract: A process for the preparation of 2-hydroxynaphthalene-6-carboxylic acid using potassium carbonate and CO at temperatures above 260.degree. C. and at a pressure of at least 10 bar comprises using 2-hydroxynaphthalene-3-carboxylic acid and/or 2-hydroxynaphthalene-3,6-dicarboxylic acid and/or their potassium salts and, if desired, potassium .beta.-naphtholate as starting materials.The process according to the invention enables a considerable increase, by reusing the secondary products, in the product selectivity with regard to 2-hydroxy-naphthalene-6-carboxylic acid.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: September 15, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegbert Rittner, Hans-Martin Ruffer, Jorg Schmid, Thomas Wisser
  • Patent number: 5792876
    Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: August 11, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5780675
    Abstract: The invention provides deoxygossylic compounds having useful biological activities, and methods for the synthesis of these and related compounds. The invention further provides valuable intermediates for the synthesis of the compounds, and pharmaceutical compositions containing biologically active compounds according to the invention.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: July 14, 1998
    Assignee: The University of New Mexico
    Inventors: Robert D. Royer, Lorraine M. Deck, David L. VanderJagt
  • Patent number: 5770766
    Abstract: The present invention provides a method for effectively separating independent hydroxynaphthalene-carboxylic acids by treating a mixture containing various kinds of hydroxynaphthalene-carboxylic acids with nonionic porous synthetic adsorbents having as a basic structure aromatic copolymers mainly composed of styrene and divinyl benzene or methacryl copolymers mainly composed of monomethacrylates and dimethacrylates.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: June 23, 1998
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kuniyo Yanagawase, Yoshiro Uchiyama, Shigeji Mori
  • Patent number: 5763487
    Abstract: Novel pharmaceutically/cosmetically-active bicyclic aromatic compounds have the structural formula (I): ##STR1## 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: January 22, 1996
    Date of Patent: June 9, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • 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: 5686586
    Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.In the formula, X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: November 11, 1997
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5668176
    Abstract: Phenoxyphenylacetic acids and derivatives of the general structural formula I ##STR1## have endothelin antagonist activity and are useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, benign prostatic hyperplasia, inflammatory diseases including Raynaud's disease and asthma.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: September 16, 1997
    Assignee: Merck & Co. Inc.
    Inventors: Scott W. Bagley, Theodore P. Broten, Prasun K. Chakravarty, Daljit S. Dhanoa, Kenneth J. Fitch, William J. Greenlee, Nancy Jo Kevin, Gerard R. Kieczykowski, Douglas J. Pettibone, James R. Tata, Ralph A. Rivero, Thomas F. Walsh, David L. Williams, Jr., Jay M. Matthews, Richard B. Toupence
  • Patent number: 5574036
    Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted polycyclic acetylene compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(f): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: November 12, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Bruno Charpenter
  • Patent number: 5550284
    Abstract: Alkoxynaphthalenecarboxylic acid is produced by a process comprising the addition of 1,3-butadiene to alkoxyalkylbenzene to yield an adduct. The adduct is cyclized in the presence of an acid catalyst to alkoxyalkyltetralin. The tetralin derivative is then dehydrogenated to produce aloxyalkylnaphthalene, which is oxidized to alkoxynaphthalenecarboxylic acid.
    Type: Grant
    Filed: August 16, 1994
    Date of Patent: August 27, 1996
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Toshio Sato, Ikuo Ito, Kazuhiko Maeda, Keiichi Yokota, Takeshi Namekata, Akihiko Nemoto
  • Patent number: 5547983
    Abstract: Aromatic bicyclic compounds of formula (I) ##STR1## where R.sub.1 is specifically --H, CH.sub.3, --CH.sub.2 OH, --OH, --CHO, --CONH.sub.2, --COOH, --COOalkyl, --SH, S-alkyl, etc. . . . ; R.sub.2 is H; R.sub.3 is H, aryl, aralkyl or lower alkyl optionally substituted by a hydroxyl, a lower alkoxy or a --CO--R.sub.12, R.sub.12 being specifically H, lower alkyl, hydroxyl, lower alkoxy, or R.sub.2 and R.sub.3 together form a naphthalene ring with the benzene ring; R.sub.4 is a linear branched or unbranched alkyl having 1 to 15 carbon atoms or a cycloaliphatic radical; R.sub.5 represents specifically --(CH.sub.2).sub.n --R.sub.13, --CH.dbd.CH--(CH.sub.2).sub.n --R.sub.13, n being 0 or 1 to 6, R.sub.13 representing --COR.sub.15, monohydroxyalkyl, polyhydroxyalkyl, epoxy lower alkyl or --O--CO--R.sub.16, R.sub.15 representing specifically --OH, --Oalkyl, --Oaryl, R.sub.16 being specifically H, lower alkyl, aryl, or aralkyl; R.sub.6 and R.sub.7 are H, a halogen, lower alkyl or --OR.sub.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: August 20, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventor: Bruno Charpentier
  • Patent number: 5543564
    Abstract: This invention embodies a process for releasing acidic organic compounds in high yield and good purity from aqueous solutions of their salts which comprises converting the salts by carbon dioxide to their corresponding free acidic organic compounds and metal hydrogen carbonates, removing the acidic organic compounds from the mixture by extraction with an essentially water-insoluble organic solvent, and re-extracting the organic phase with carbon dioxide containing water. Using this process, the acidic organic compounds are completely released from their corresponding salts, i.e., the organic solution is free of salt. The acidic organic compounds released by the claimed process are organic compounds which contain acidic protons which can be replaced by metals. Some examples are carboxylic acids, sulfonic acids, phosphonic acids, phenols, naphthols, and aliphatic alcohols.
    Type: Grant
    Filed: January 11, 1995
    Date of Patent: August 6, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: J urgen Kulpe, Heinz Strutz, Hans-Martin R uffer, Siegbert Rittner
  • Patent number: 5525728
    Abstract: A process for the production of sclareolide comprising the steps of: (1) providing an aqueous composition comprised of: (a) water; (b) sclareol, abienol, or a mixture of sclareol and abienol, (c) an effective amount of a ruthenium catalyst; and, (d) an emulsifying agent; (2) forming an aqueous alkaline composition by adding an alkali metal hydroxide to said aqueous composition; (3) reacting said aqueous alkaline composition with an oxidizing agent to form a crude product; andeither: (4) further reacting said crude product with base to form the salt of 8.alpha.-hydroxy-11-carboxyl-12, 13, 14, 15, 16-pentanorlabdane and; (5) reacting said salt with acid to form sclareolide;or: (4) heating said crude product to form sclareolide.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: June 11, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Markus Schneider, Theo Stalberg, Thomas Gerke
  • Patent number: 5523457
    Abstract: This invention relates to a retinoid mpound of formula I ##STR1## in which Y is --CO--NH--, --CR.sup.2 .dbd.CR.sup.3 --, --CO--O--, --O--CO--, --C(.dbd.S)--NH--, --C.tbd.C--, --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --CH.sub.2 --;A is --(CH.sub.2).sub.t -- or a bond;Q is phenyl optionally substituted with one to three same or different C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halogen, or --CO.sub.2 R.sup.4 ;R.sup.1 is --CO.sub.2 Z, --CONHR.sup.5, C.sub.1-6 alkyl, --CH.sub.2 OH, or --CHO;R.sup.2, R.sup.3, R.sup.4, R.sup.5, and Z are independently hydrogen or C.sub.1-6 alkyl;t is one to six.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 4, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: John E. Starrett, Jr., Muzammil M. Mansuri, David R. Tortolani
  • Patent number: 5426111
    Abstract: Compounds of formula ##STR1## Ar is selected from (a) phenyl, (b) phenyl substituted with one or more groups selected from halogen, cyano, alkyl, haloalkyl, alkoxy, and alkoxycarbonyl, (c) furyl, (d) furyl substituted with one or more groups selected from halogen, alkyl, and alkoxy, (e) pyridyl, (f) pyridyl substituted with one or more groups selected from halogen, alkyl, and alkoxy, (g) thienyl, and (h) thienyl substituted with one or more groups selected from halogen, alkyl, and alkoxy; L is selected from alkylene of one to three carbon atoms, alkenylene of two to three carbon atoms, and alkynylene of two to three carbon atoms, and ##STR2## wherein p is an integer of 1 to 4, inclusive, and R.sup.4 is selected from the group consisting of hydrogen, alkyl of one to four carbon atoms, halogen, haloalkyl of one to four carbon atoms, and alkoxy of one to six carbon atoms;R.sup.1 is alkyl; R.sup.2 is hydrogen or alkyl; m is 1 or 2; Z is oxygen or CHOR.sup.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: June 20, 1995
    Assignee: Abbott Laboratories
    Inventors: Joseph F. Dellaria, James D. Ratajczyk, Clint D. W. Brooks, Anwer Basha
  • Patent number: 5403953
    Abstract: Compound of formula (I): ##STR1## in which: R.sub.1 represents halogen, or hydroxy, alkyl, alkoxy, cyano, amino, mercapto, alkylthio or phenoxy,R.sub.2 and R'.sub.2 represent two hydrogen when the ring is unsaturated, or alternatively identical or different, represent hydrogen or halogen, or hydroxy, alkyl, alkoxy, cyano, amino or oxo when the ring is saturated,R.sub.3 represents any one of the following groups: ##STR2## in which: m represents 1, 2 or 3,X represents oxygen or sulfur or N-R, R.sub.5 or R.sub.6, which are identical or different, represent hydrogen or alkyl or trifluoromethyl or form (C.sub.3 -C.sub.6) cycloalkyl,n represents 0, 1 or 2,R.sub.7 represents hydroxy, alkoxy, amino, or --O--CH.sub.2 --CO--NRR',R.sub.4 represents hydrogen or halogen or alkyl, alkoxy or trihaloalkyl.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: April 4, 1995
    Assignee: Adir et Compagnie
    Inventors: Guillaume de Nanteuil, Michel Vincent, Christine Lila, Jacqueline Bonnet, Armel Fradin
  • Patent number: 5380922
    Abstract: 1-Hydroxy-2-naphthalene carboxylate (hydroxynaphthoate) salt of 4-hydroxy-a.sup.1 -[[[6-(4-phenylbutoxy)hexyl]-amino]methyl]-1,3-benzendimethanol in the form of spherical accretions of microcrystals, the spherical accretions being free-flowing, friable and micronisable and preferably having a mean particle size of from 70 to 300 mm and a mean surface area from 4 to 12 m.sup.2 g.sup.-1. The hydroxynaphthoate salt in the claimed form may be prepared by quenching a hot organic/aqueous organic solution containing the salt with a cold organic/aqueous organic solvent.
    Type: Grant
    Filed: May 14, 1993
    Date of Patent: January 10, 1995
    Assignee: Glaxo Group Limited
    Inventors: Steven F. Beach, David W. S. Latham, Tony G. Roberts, Colin B. Sidgwick
  • Patent number: 5344970
    Abstract: A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl.This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Albemarle Corporation
    Inventor: Charles H. Kolich
  • Patent number: 5340931
    Abstract: Allene compounds have the formula:(CH.sub.2 .dbd.C.dbd.CH--O).sub.n --R--(A).sub.m (I)in which R is a substituted or unsubstituted mono- or polyvalent benzene, naphthalene, anthracene, azobenzene, bisphenol or polyphenyl (containing 2 to 10 benzene rings connected in line) nucleus, or a group--Ph--R.sup.1 --Ph-- (II)(in which each group Ph is a phenylene, halophenylene, alkylphenylene, cyanophenylene or alkoxyphenylene group, and the chain R.sup.1 linking the two group Ph is a C.sub.1 -C.sub.6 aliphatic hydrocarbon or an alicyclic hydrocarbon group, the chain optionally being interrupted by one or more oxygen atoms); A is a carboxyl or sulphonyl group or a group --CH.dbd.C.dbd.CH.sub.2 ; n is an integer of from 1 to 10; m is 0, 1, 2 or 3; and the sum of m and n is equal to the valence of the group R.They may be prepared by isomerization of corresponding propargyloxy compounds.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: August 23, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Hiromichi Kayano, Kei Aoki, Keizou Ishii
  • Patent number: 5338773
    Abstract: The invention provides dental cement compositions and methods of using them for binding hard tooth material, metal and ceramic. The cement compositions include polymerizable acid reactive ethylenically unsaturated monomers, and a source of cations reactive therewith, to further crosslink the resulting polymer. The cements have superior adhesion to tooth without separately acid etching dentin or enamel. Compositions of are useful as dental luting cements, liners, bases and restoratives.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: August 16, 1994
    Assignee: Dentsply Research & Development Corp.
    Inventors: Kewang Lu, Chin-Teh Huang, Paul Hammesfahr
  • 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: 5332857
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 26, 1994
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5258532
    Abstract: A fused ring compound having hydroxy, carboxylic acid and hydroxyalkyl substituent groups and the metal salts or complexes thereof. The hydroxyalkyl group is especially a hydroxymethyl group. The compound is prepared by reaction of the hydroxy carboxylic acid derivative with formaldehyde in an alkaline medium at a temperature of not more than 50.degree. C. The compounds, especially the metal salts or complexes thereof, can be used to provide corrosion inhibition of metals, for example iron.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries PlC
    Inventor: John R. Lawson
  • Patent number: 5212303
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents (i) ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --0--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: May 18, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5210276
    Abstract: Phenylethanolamino- and phenylethanolaminomethyltetralines of formula (I) ##STR1## wherein X represents a hydrogen atom, a halogen atom, a (C.sub.1 -C.sub.4)alkyl group or a trifluoromethyl group,A represents a bond between the --COOR group and the tetraline ring, a (C.sub.1 -C.sub.4)alkylene or a (C.sub.2 -C.sub.4)alkenylene group,R is hydrogen or a (C.sub.1 -C.sub.4)alkyl group, andn is 0 or 1and their salts, are typically prepared by reaction of an epoxide of formula (IIa) ##STR2## with a tetraline derivative of formula (III) ##STR3## wherein A and n are as defined above and R' is a (C.sub.1 -C.sub.4)alkyl group, optionally followed by basic hydrolysis to obtain the compounds (I) wherein R is hydrogen.The new compounds show very interesting properties as antidepressant and intestinal spasmolytic agents.The new intermediates of formula (III) are also claimed.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 11, 1993
    Assignee: Elf Sanofi
    Inventors: Domenico Badone, Umberto Guzzi, Roberto Cecchi
  • Patent number: 5196575
    Abstract: A method of separating isomers of functionalized aromatic compounds using solvent-modified supercritical carbon dioxide is disclosed and claimed. In one embodiment, isomers of hydroxynaphthoic acid are separated by selective extraction of the more soluble species.
    Type: Grant
    Filed: February 19, 1992
    Date of Patent: March 23, 1993
    Assignee: Hoechst Celanese Corp.
    Inventor: Mark J. Sebastian
  • Patent number: 5169978
    Abstract: Novel (naphthyloxy)benzoic/naphthoic acid compounds, polymerizable into thermotropic polymers have the formulae: ##STR1## in which R is hydrogen, a straight or branched chain aliphatic or cycloaliphatic hydrocarbon radical having from 1 to 4 carbon atoms or a radical ##STR2## wherein R' is a methyl or ethyl radical, or salt thereof.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: December 8, 1992
    Assignee: Societe ATOCHEM
    Inventor: Jean-Philippe Gillet
  • Patent number: 5155229
    Abstract: Derivatives of pravastatin are provided which are useful in inhibiting cholesterol biosynthesis and in preparing radiolabeled compounds useful in the radioimmunoassay (RIA) of pravastatin and derivatives thereof. The pravastatin derivatives have the structure ##STR1## wherein R is hydroxy, lower alkylamine, arylamine, arylalkylamine or heterocyclic alkylamine such as histamine, tyramine, O-benzyltyramine, methyl tyrosinate as well as iodinated derivatives thereof.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: October 13, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi
  • Patent number: 5151545
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: September 29, 1992
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5151549
    Abstract: A compound represented by the formula: ##STR1## and a compound represented by the formula: ##STR2## wherein R is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, which is an intermediate for producing the above compound (1) are disclosed.
    Type: Grant
    Filed: March 5, 1992
    Date of Patent: September 29, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Koyama, Takefumi Abe
  • Patent number: 5146025
    Abstract: A compound represented by the formula: ##STR1## and a compound represented by the formula: ##STR2## wherein R is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, which is an intermediate for producing the above compound (1) are disclosed.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: September 8, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Koyama, Takefumi Abe
  • Patent number: 5126371
    Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: June 30, 1992
    Assignee: BASF Akteingesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: RE34805
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: December 6, 1994
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon