Carboxyl Bonded Directly To Naphthylene Ring System Patents (Class 562/467)
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Patent number: 6403827Abstract: 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: GrantFiled: January 3, 2001Date of Patent: June 11, 2002Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo K.Inventors: Ryuzo Ueno, Masaya Kitayama, Nobutaka Izumichi, Hiroyuki Kato
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Patent number: 6316396Abstract: 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: GrantFiled: April 9, 1999Date of Patent: November 13, 2001Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und ChemieInventors: Klaus Kwetkat, Wolfgang Schröder
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Patent number: 6316665Abstract: 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: GrantFiled: August 22, 2000Date of Patent: November 13, 2001Assignee: Shell Oil CompanyInventors: Thomas Fairchild Brownscombe, Garo Vaporciyan, Narayana Mysore, Susan Secor Pfrehm
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Patent number: 6284924Abstract: 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: GrantFiled: January 4, 2001Date of Patent: September 4, 2001Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Naoko Mori
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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: 6194608Abstract: 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: GrantFiled: November 19, 1998Date of Patent: February 27, 2001Assignee: Kabushiki Kaisha Veno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kuniyo Yanagawase, Yoshiro Uchiyama, Shigeji Mori
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Patent number: 6156750Abstract: 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: GrantFiled: January 13, 1999Date of Patent: December 5, 2000Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 6143905Abstract: 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: GrantFiled: June 18, 1998Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Arno Bohm, Harald Arms, Georg Henning, Peter Blaschka
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Patent number: 6124498Abstract: 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: GrantFiled: April 28, 1998Date of Patent: September 26, 2000Assignee: University Of New MexicoInventors: David L. Vander Jagt, Lorraine M. Deck, Robert E. Royer
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Patent number: 6080888Abstract: 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: GrantFiled: January 8, 1997Date of Patent: June 27, 2000Assignee: Albemarle CorporationInventors: Tse-Chong Wu, Kannappan C. Chockalingham, W. Dirk Klobucar, Gary D. Focht
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Patent number: 5936120Abstract: 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: GrantFiled: December 10, 1997Date of Patent: August 10, 1999Assignee: University of New MexicoInventors: Robert D. Royer, Lorraine M. Deck, David L. VanderJagt
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Patent number: 5925487Abstract: 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: GrantFiled: June 27, 1997Date of Patent: July 20, 1999Assignee: Zeneca LimitedInventors: David Melville Fawkes, Peter Gregory, James Stanley Campbell
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Patent number: 5919970Abstract: 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: GrantFiled: April 24, 1997Date of Patent: July 6, 1999Assignee: Allergan Sales, Inc.Inventors: Tae K. Song, Min Teng, Roshantha A. Chandraratna
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Patent number: 5874614Abstract: 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: GrantFiled: December 11, 1997Date of Patent: February 23, 1999Assignee: Albemarle CorporationInventors: Hao V. Phan, Robert H. Allen, Richard A. Coats
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Patent number: 5859293Abstract: 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: GrantFiled: July 14, 1997Date of Patent: January 12, 1999Assignee: Hauser, Inc.Inventors: David T. Bailey, Steven L. Richheimer, Virginia R. Bank, Benjamin T. King
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Patent number: 5859292Abstract: 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: GrantFiled: December 11, 1997Date of Patent: January 12, 1999Assignee: Albemarle CorporationInventors: Hao V. Phan, Robert E. Young
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Patent number: 5827855Abstract: 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: GrantFiled: December 28, 1995Date of Patent: October 27, 1998Assignee: Sankyo Company, LimitedInventors: Hiroshi Kogen, Sadao Ishihara, Teiichiro Koga, Eiichi Kitazawa, Nobufusa Serizawa, Kiyoshi Hamano
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Patent number: 5808142Abstract: 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: GrantFiled: September 13, 1994Date of Patent: September 15, 1998Assignee: Hoechst AktiengesellschaftInventors: Siegbert Rittner, Hans-Martin Ruffer, Jorg Schmid, Thomas Wisser
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Patent number: 5792876Abstract: 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: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5780675Abstract: 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: GrantFiled: April 28, 1995Date of Patent: July 14, 1998Assignee: The University of New MexicoInventors: Robert D. Royer, Lorraine M. Deck, David L. VanderJagt
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Patent number: 5770766Abstract: 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: GrantFiled: July 10, 1997Date of Patent: June 23, 1998Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kuniyo Yanagawase, Yoshiro Uchiyama, Shigeji Mori
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Patent number: 5763487Abstract: 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: GrantFiled: January 22, 1996Date of Patent: June 9, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5716624Abstract: 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: GrantFiled: December 15, 1994Date of Patent: February 10, 1998Assignee: C.I.R.D. GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5686586Abstract: 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: GrantFiled: October 4, 1996Date of Patent: November 11, 1997Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5668176Abstract: 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: GrantFiled: October 18, 1996Date of Patent: September 16, 1997Assignee: 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
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Patent number: 5574036Abstract: 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: GrantFiled: April 26, 1995Date of Patent: November 12, 1996Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Bruno Charpenter
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Patent number: 5550284Abstract: 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: GrantFiled: August 16, 1994Date of Patent: August 27, 1996Assignee: Sumikin Chemical Co., Ltd.Inventors: Toshio Sato, Ikuo Ito, Kazuhiko Maeda, Keiichi Yokota, Takeshi Namekata, Akihiko Nemoto
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Patent number: 5547983Abstract: 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: GrantFiled: August 22, 1994Date of Patent: August 20, 1996Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)Inventor: Bruno Charpentier
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Patent number: 5543564Abstract: 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: GrantFiled: January 11, 1995Date of Patent: August 6, 1996Assignee: Hoechst AktiengesellschaftInventors: J urgen Kulpe, Heinz Strutz, Hans-Martin R uffer, Siegbert Rittner
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Patent number: 5525728Abstract: 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: GrantFiled: October 17, 1994Date of Patent: June 11, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Markus Schneider, Theo Stalberg, Thomas Gerke
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Patent number: 5523457Abstract: 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: GrantFiled: June 2, 1995Date of Patent: June 4, 1996Assignee: Bristol-Myers Squibb CompanyInventors: John E. Starrett, Jr., Muzammil M. Mansuri, David R. Tortolani
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Patent number: 5426111Abstract: 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: GrantFiled: November 23, 1994Date of Patent: June 20, 1995Assignee: Abbott LaboratoriesInventors: Joseph F. Dellaria, James D. Ratajczyk, Clint D. W. Brooks, Anwer Basha
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Patent number: 5403953Abstract: 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: GrantFiled: November 23, 1993Date of Patent: April 4, 1995Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Michel Vincent, Christine Lila, Jacqueline Bonnet, Armel Fradin
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Patent number: 5380922Abstract: 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: GrantFiled: May 14, 1993Date of Patent: January 10, 1995Assignee: Glaxo Group LimitedInventors: Steven F. Beach, David W. S. Latham, Tony G. Roberts, Colin B. Sidgwick
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Patent number: 5344970Abstract: 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: GrantFiled: December 22, 1993Date of Patent: September 6, 1994Assignee: Albemarle CorporationInventor: Charles H. Kolich
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Patent number: 5340931Abstract: 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: GrantFiled: March 15, 1989Date of Patent: August 23, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Hiromichi Kayano, Kei Aoki, Keizou Ishii
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Patent number: 5338773Abstract: 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: GrantFiled: April 19, 1993Date of Patent: August 16, 1994Assignee: Dentsply Research & Development Corp.Inventors: Kewang Lu, Chin-Teh Huang, Paul Hammesfahr
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Patent number: 5338881Abstract: 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: GrantFiled: July 23, 1990Date of Patent: August 16, 1994Assignee: Eastman Chemical CompanyInventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
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Patent number: 5332857Abstract: 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: GrantFiled: July 6, 1992Date of Patent: July 26, 1994Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5258532Abstract: 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: GrantFiled: December 10, 1991Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries PlCInventor: John R. Lawson
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Patent number: 5212303Abstract: 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: GrantFiled: September 28, 1992Date of Patent: May 18, 1993Assignee: Centre International de Recherches Dermatologiques (CIRD)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5210276Abstract: 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: GrantFiled: February 18, 1992Date of Patent: May 11, 1993Assignee: Elf SanofiInventors: Domenico Badone, Umberto Guzzi, Roberto Cecchi
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Patent number: 5196575Abstract: 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: GrantFiled: February 19, 1992Date of Patent: March 23, 1993Assignee: Hoechst Celanese Corp.Inventor: Mark J. Sebastian
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Patent number: 5169978Abstract: 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: GrantFiled: December 16, 1991Date of Patent: December 8, 1992Assignee: Societe ATOCHEMInventor: Jean-Philippe Gillet
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Patent number: 5155229Abstract: 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: GrantFiled: July 1, 1991Date of Patent: October 13, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi
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Patent number: 5151545Abstract: 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: GrantFiled: March 27, 1990Date of Patent: September 29, 1992Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5151549Abstract: 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: GrantFiled: March 5, 1992Date of Patent: September 29, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takeshi Koyama, Takefumi Abe
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Patent number: 5146025Abstract: 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: GrantFiled: February 12, 1990Date of Patent: September 8, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takeshi Koyama, Takefumi Abe
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Patent number: 5126371Abstract: 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: GrantFiled: August 20, 1990Date of Patent: June 30, 1992Assignee: BASF AkteingesellschaftInventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
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Patent number: RE34805Abstract: 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: GrantFiled: July 10, 1992Date of Patent: December 6, 1994Assignee: Centre International de Recherches Dermatologiques (CIRD)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon