Naphthyl In Acid Moiety Patents (Class 560/100)
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Patent number: 4957648Abstract: A spin fiber lubricant composition is disclosed. The composition is essentially comprised of a liquid carrier having therein an ester of the general structural formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrocarbyl groups preferably in the form of alkyl groups containing 1-6 carbon atoms. The composition has been found to be useful in connection with providing materials with lubricating properties which are desirable for the spinning of fibers.Type: GrantFiled: February 7, 1990Date of Patent: September 18, 1990Assignee: The Lubrizol CorporationInventors: Richard Yodice, Gregory A. Lentz
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Patent number: 4940696Abstract: 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: November 16, 1987Date of Patent: July 10, 1990Assignee: Centre International de Recherches Dermatologioues (CIRD)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 4931589Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 acyloxy or hydroxyl;R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.Type: GrantFiled: July 13, 1988Date of Patent: June 5, 1990Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
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Patent number: 4921632Abstract: Liquid Crystal compounds represented by the following formula are disclosed. ##STR1## wherein R and R' are independently selected from alkyl groups containing 1.about.20 carbon atoms; X is --O--, --O--CO--O-- or direct bond; A.sub.1 and A.sub.2 are independently cyclic groups (such as phenylene and biphenylene), said cyclic groups may be substituted with 1.about.4 fluorine, chlorine or bromine atoms, or 1 or 2 substituent groups selected from the group consisting of cyano, nitro and trifluoromethyl groups; Y is --CO--O--, --O--CO--, --C.tbd.C--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --CH.sub.2 S--, --SCH.sub.2 -- or direct bond; and * represents asymmetric atom providing optical activity.Type: GrantFiled: August 19, 1988Date of Patent: May 1, 1990Assignees: NEC Corporation, Sanyo Chemical Industries, Ltd.Inventors: Toyokazu Nakamura, Yuzi Kato, Shohei Naemura, Chizuka Tani, Masahiro Satoh, Kunikiyo Yoshio, Hiroshi Kishiki, Hiroshi Hoshino
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Patent number: 4916156Abstract: The present invention relates to aromatic derivatives of the formula: ##STR1## in which: n represents an integer between 2 and 10;R.sub.1 and R.sub.2 are identical or different and represent a cycloalkyl containing 3 to 6 carbon atoms or an alkyl containing from 1 to 6 carbon atoms which is unsubstituted or substituted by a phenyl or benzyl group; orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, form a heterocycle selected from pyrrolidin-1-yl, piperidino, azepin-1-yl, hexamethyleneimino, 4-methylpiperidino, 4-benzylpiperidino, 4-phenylpiperidino, 1,2,3,4-tetrahydroisoquinol-2-yl, morpholino and imidazol-1-yl groups;R.sub.3 represents a hydrogen, a halogen, a methyl or a phenyl;R.sub.4 represents a hydrogen, a halogen or a methyl; or R.sub.3 and R.sub.4, taken together with the benzene ring to which they are bonded, form a naphth-1-yl or naphth-2-yl group;Y represents a direct bond, a methyleneoxy group, a methylenethio group or a vinylene group; andR.sub.Type: GrantFiled: April 6, 1988Date of Patent: April 10, 1990Assignee: SanofiInventors: Madeleine Mosse, Vincenzo Proietto
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Patent number: 4912250Abstract: Disclosed is a process for the co-production of an aromatic carboxylic esters and alkyl iodide by the carbonylation of an aromatic iodide in the absence of a Bronsted base and in the presence of an ether and a nickel catalyst.Type: GrantFiled: February 6, 1989Date of Patent: March 27, 1990Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanny C. Treece
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Patent number: 4904817Abstract: Disclosed is an improved process for the manufacture of aromatic carboxylic acid esters by the carbonylation of aromatic iodides wherein the amount of the corresponding unesterified carboxylic acid in the product obtained from the process is minimized. The process comprises carbonylating an aromatic iodide in the presence of carbon monoxide, a Group VIII metal catalyst, an inorganic adsorbent and an alkanol to co-produce an aromatic carboxylic acid ester and an alkyl iodide.Type: GrantFiled: February 21, 1989Date of Patent: February 27, 1990Assignee: Eastman Kodak CompanyInventor: Guy R. Steinmetz
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Patent number: 4904661Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 16, 1987Date of Patent: February 27, 1990Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 4898944Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g.Type: GrantFiled: October 27, 1988Date of Patent: February 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4897397Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.Type: GrantFiled: December 16, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Neng Y. Shih, David J. Blythin
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Patent number: 4892940Abstract: An aromatic naphthyl compound of the formula ##STR1## wherein n is 0 or 1,R' is hydrogen, OH, acyloxy, alkoxy or NH.sub.2,R" is hydrogen or lower alkoxy, or R' and R" taken together form an oxo, methano or hydroxy-imino radical,R is --CH.sub.2 OH or --COR.sub.8,R.sub.8 is hydrogen, --OR.sub.9 or ##STR2## R.sub.9 is hydrogen, alkyl having 1-20 carbon atoms, mono or polyhydroxyalkyl, aryl, aralkyl, the residue of a sugar or ##STR3##is 1, 2 or 3,r' and r" each independently represent hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, benzyl, the residue of amino acid or the residue of aminated sugar, or r' and r" together form a heterocycle,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen, lower alkyl, alkoxy having 1-4 carbon atoms, fluoroalkoxy, CF.sub.3, cycloalkyl, lower acyl, halogen, OH, amino, acylamino or alkoxy carbonyl,R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl or when n=1, R.sub.5 and R.sub.Type: GrantFiled: May 22, 1987Date of Patent: January 9, 1990Assignee: L'OrealInventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
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Patent number: 4886907Abstract: New polysubstituted derivatives of naphtalene.These derivatives correspond to the following formula: ##STR1## in which: R.sub.1 to R.sub.4 is H or CH.sub.3R.sub.5 is(i) ##STR2## (ii) --C.tbd.N (iii) ##STR3## or (iv) the radical: 2-oxazolinylm is 0 or 1R.sub.8 is H, alkyl, OR.sub.11, R.sub.11 being H, alkyl or ##STR4## R.sub.13 being alkyl or aryl or R.sub.8 is ##STR5## when m=1, r' and r" representing H, alkyl mono or polyhydroxyalkyl, aryl or a heterocycle when they are taken together, R.sub.9 is H or alkyl, R.sub.10 is H, alkyl and the acetals of the said compounds, ##STR6## --OR.sub.14, R.sub.14 being H, alkyl, mono or polyhydroxyalkyl, aryl or aralkyl a rest of a sugar or represents ##STR7## being 0, 1, 2, or 3 R.sub.6 represents a hydrogen atom or a lower alkyl radical,R.sub.7 represents H, alkyl, halogen, hydroxyl, sulfydryl, alkoxy, alkylthio, acyloxy, acylthio, acylamino or primary, secondary or tertiary amino and the salts of the said compounds.Type: GrantFiled: April 17, 1987Date of Patent: December 12, 1989Assignee: Centre International De Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4886619Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.Type: GrantFiled: May 29, 1987Date of Patent: December 12, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Eugene P. Janulis
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Patent number: 4885383Abstract: A process for the preparation of methyl carboxylates by the reaction of mono or dicarboxylic acids having more than 5 carbon atoms and methanol in the presence of acidic catalysts at temperatures from 100.degree. to 150.degree. C. and below the boiling point of the carboxylates being produced.Type: GrantFiled: September 23, 1988Date of Patent: December 5, 1989Assignee: Hoeschst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer, Peter Lappe
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Patent number: 4877898Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.Type: GrantFiled: June 12, 1986Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
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Patent number: 4876381Abstract: The invention relates to a compound of the formula (II) ##STR1## and the corresponding isomers and salts, in which formula: a and b are integers which independently of one another can assume the values 0 or 1,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 -alkyl radical or a C.sub.1 -C.sub.4 -alkoxy radical,R.sub.6 represents a C.sub.1 -C.sub.6 -alkyl radical,R.sub.5 and R.sub.12 represent a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, with the proviso that R.sub.5 cannot represent hydrogen if a=b=0 andR.sub.11 has various meanings.These compounds have useful dermatological properties.Type: GrantFiled: August 18, 1987Date of Patent: October 24, 1989Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
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Patent number: 4868329Abstract: The instant invention involves a process for preparing carboxylic acid esters which comprises coreacting a carboxylic acid and an aliphatic mono or polyol by maintaining one of the reactants in a reactor at elevated temperatures and adding the other reactant to the reactor over a period of time. By employing this process esterification times are significantly reduced.Type: GrantFiled: March 7, 1988Date of Patent: September 19, 1989Assignee: Hoechst Celanese Corp.Inventors: Thomas M. Powanda, Robert H. Imes, George L. Collins
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Patent number: 4866200Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a palladium catalyst.Type: GrantFiled: August 4, 1988Date of Patent: September 12, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4851564Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a rhodium catalyst.Type: GrantFiled: February 22, 1988Date of Patent: July 25, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4849454Abstract: Novel antiandrogenic compositions comprising an anti-androgenically effective amount of at least one compound of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is alkyl of 1 to 2 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 8 carbon atoms optionally interrupted with a heteroatom, formyl and acyl of an organic carboxylic acid of 2 to 18 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, the dotted lines indicate optional presence of a double bond between the 4(5) and 5a(6) carbons and the wavy line indicates that R.sub.4 may be in the .alpha.- or .beta.Type: GrantFiled: April 24, 1986Date of Patent: July 18, 1989Assignee: Roussel UclafInventors: Marie-Madeleine Bouton, Jean Jacques, Andre Pierdet
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Patent number: 4847406Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a ruthenium catalyst.Type: GrantFiled: January 12, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4845119Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent of each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: February 18, 1986Date of Patent: July 4, 1989Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 4833240Abstract: Bicyclic aromatic compounds, having the following formula: ##STR1## in which: n=0 or 1;R' represents H, OH, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 acyloxy;R" represents H or C.sub.1 -C.sub.4 alkoxy;or R' and R" taken together form an oxo (.dbd.O), methano (.dbd.CH.sub.2) or hydroximino (.dbd.N--OH) radical;R represents --CH.sub.2 OH or --COR.sub.7 ;R.sub.7 represents H, OR.sub.8, or ##STR2## R.sub.8 represents H, C.sub.1 -C.sub.4 alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl, optionally substituted, a sugar residue or ##STR3## where p is 1, 2 or 3 and r' and r" represent H, lower alkyl, monohydroxyalkyl, optionally interrupted by a heteroatom, polyhydroxyalkyl, optionally substituted aryl or benzyl, an amino acid residue or an aminated sugar residue or taken together with the nitrogen atom to which they are attached form a heterocycle;A represents methylene or dimethylene, substituted or not with lower alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent H or lower alkyl,R.sub.1 and R.sub.Type: GrantFiled: July 17, 1987Date of Patent: May 23, 1989Assignee: Centre International de Recherches Dermatologiques (CIRD)Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
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Patent number: 4833164Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).Type: GrantFiled: March 19, 1986Date of Patent: May 23, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Douglas G. Batt
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Patent number: 4831184Abstract: This invention relates to new chemical compounds having valuable pharmaceutical activity. It particularly relates to stereoisomeric compounds possessing hypotensive activity, i.e., angiotensin converting enzyme inhibitory (ACEI) activity and having the structure ##STR1## wherein R and R.sub.9 are independently hydroxy, lower alkoxy, lower alkenoxy, di(lower alkyl)amino-lower alkoxy, hydroxy-lower alkoxy, acylamino-lower alkoxy, acryloxy-lower alkoxy, aryloxy, aryloxyl-lower alkoxy, amino, lower alkylamino, di-lower alkylamino, hydroxyamino, or aryl-lower alkylamino;R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are independently hydrogen, alkyl, alkenyl or alkynyl containing up to 20 carbon atoms, aryl or aryl-lower alkyl having from 7 to 12 carbon atoms, heterocyclic or heterocyclic-lower alkyl having from 6 to 12 carbon atoms, cycloalkyl or cycloalkyl-alkyl containing up to 20 carbon atoms in the cycloalkyl group, provided that each of R.sub.1 and R.sub.2 and R.sub.4 and R.sub.Type: GrantFiled: February 14, 1983Date of Patent: May 16, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Raymond D. Youssefyeh, Jerry W. Skiles, John T. Suh, Howard Jones
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Patent number: 4827018Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a nickel catalyst.Type: GrantFiled: October 22, 1987Date of Patent: May 2, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4826969Abstract: A bicyclic naphthalenic compound has the formula ##STR1## wherein A represents methylene or dimethylene, substituted or not by lower alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or lower alkyl, orR.sub.1 and R.sub.3 taken together form a methylene or dimethylene bridge when A represents dimethylene,R' represents hydrogen, OH, alkoxy having 1-4 carbon atoms, acyloxy having 1-4 carbon atoms or amino,R" represents hydrogen or alkoxy having 1-4 carbon atoms, orr' and R" taken together form an oxo, methano or hydroxyimino group,R represents --CH.sub.2 OH or --COR.sub.5,R.sub.5 represents hydrogen, --OR.sub.6 or ##STR2## R.sub.Type: GrantFiled: October 14, 1986Date of Patent: May 2, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
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Patent number: 4824988Abstract: In a process for preparing a (trifluoromethyl)napthalene by reacting a halonapthalene with a trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent and separating out the inorganic ingredients of the final reaction mixture in the recovery of the product, the cuprous iodide is recovered by washing the separated inorganic ingredients with an alcohol and a carboxylic acid and then with water to purify the cuprous iodide.Type: GrantFiled: October 26, 1987Date of Patent: April 25, 1989Assignee: Ethyl CorporationInventors: Ronny W. Lin, Venkataraman Ramachandran
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Patent number: 4824989Abstract: A (trifluoromethyl)naphthalene which has been prepared by reacting a halonaphthalene with a trifluoroacetate salt in the presence of cuprous iodide and a dipolar aprotic solvent is recovered by (1) replacing the dipolar aprotic solvent in the final reaction mixture with an alkane containing 6-12 carbons, (2) heating the resultant slurry to a temperature sufficient to dissolve the organic ingredients, (3) allowing the inorganic ingredients of the slurry to settle, (4) decanting the organic layer, and (5) cooling to precipitate the (trifluoromethyl)naphthalene.Type: GrantFiled: March 3, 1987Date of Patent: April 25, 1989Assignee: Ethyl CorporationInventor: Gary D. Heidebrecht
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Patent number: 4822904Abstract: Perfluoroalkylaromatic compounds containing at least two carbons in the perfluoroalkyl group are prepared by reacting an aromatic bromide or iodide with a potassium perfluoroalkanoate corresponding to the formula KOOC(CF.sub.2).sub.n CF.sub.3 wherein n is an integer of at least one in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: December 12, 1985Date of Patent: April 18, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814480Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with a tetraalkylammonium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814482Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide, a phase transfer agent, and a dipolar aprotic solvent.Type: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4808748Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: December 12, 1985Date of Patent: February 28, 1989Assignee: Ethyl CorporationInventors: Ronny W. Lin, Robert I. Davidson
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Patent number: 4806676Abstract: A process for preparing an aromatic carboxylic ester and an alkyl iodide by carbonylating an aromatic iodide in the presence of an ether, a catalytic amount of a transition metal and a strong acid promoter.Type: GrantFiled: June 20, 1988Date of Patent: February 21, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4803296Abstract: A process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and an iridium catalyst.Type: GrantFiled: May 11, 1988Date of Patent: February 7, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4790963Abstract: A process for producing an ester is disclosed comprising contacting a gaseous reactant containing at least one organic hydroxy compound and a mixture of carbon monoxide and hydrogen with an ester synthesis catalyst of the formulaM.sub.a A.sub.b RuCu.sub.c N.sub.z O.sub.xwhereinM is selected from the group consisting of Ce, Cr, Fe, Mn and mixtures thereof,A is an alkali metal, alkaline earth metal or mixture thereof,a is from 0 to about 1,b is from 0.002 to about 10,c is from 0.2 to about 20,z is from 0 to about 196 by weight,x is the number of oxygens needed to fulfill the valence requirements of the other elements.The organic hydroxy compound can be provided separately or formed by contacting a mixture of carbon monoxide and hydrogen with an alcohol synthesis catalyst at an elevated temperature and pressure. The alcohol synthesis catalyst and ester synthesis catalyst can be in tandem or mixed.Type: GrantFiled: August 20, 1984Date of Patent: December 13, 1988Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
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Patent number: 4788218Abstract: Novel compounds having the general formula: ##STR1## wherein: R.sup.1 is hydrogen or an acyl substituent of the formula:--(C.dbd.O)--R.sup.2wherein:R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkylene, haloalkyl, aryl, haloaryl or arylalkylene are described. These compounds have both gonadotropic and antigonadotropic properties depending upon the dosage level, and are therefore useful in therapy in the control of male fertility in mammals, particularly in human beings. These compounds combine gonadotropic, antigonadotropic and androgenic properties in the same compound. Their use with LHRH antagonists on male fertility control is also disclosed.Type: GrantFiled: April 28, 1986Date of Patent: November 29, 1988Assignee: SRI InternationalInventors: Masato Tanabe, David F. Crowe, George Detre, Peters, Richard H., Mitchell A.g34 Avery
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Patent number: 4786731Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.Type: GrantFiled: August 5, 1987Date of Patent: November 22, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell
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Patent number: 4783548Abstract: A process for preparing a 3,4-dihydro 2-naphthanoic acid or an ester thereof comprises heating an alpha-vinyl cinnamic acid or a (C.sub.1 -C.sub.12)alkyl, (C.sub.6 -C.sub.12)aryl, (C.sub.6 -C.sub.12)aralkyl or (C.sub.6 -C.sub.12)alkylaryl ester thereof at a temperature effective to cyclize said acid or ester thereof and obtain the corresponding 3,4-dihydro 2-naphthanoic acid or ester thereof. The alpha-vinyl cinnamic acid or ester thereof may be obtained by contacting crotonic anhydride and a benzaldehyde substituted with halo or (C.sub.1 -C.sub.12)alkyl, acyl, acyloxy, carboxy, carbalkoxy, alkylthiol or alkoxy.A process for preparing 2-naphthanoic acid or an ester thereof comprises the above steps to prepare a 3,4-dihydro-2-naphthanoic acid, and dehydrogenating said 3,4-dihydro 2-naphthanoic acid or ester thereof to obtain the 2-naphthanoic acid.Type: GrantFiled: September 16, 1987Date of Patent: November 8, 1988Assignee: Eastman Kodak CompanyInventor: Joseph R. Zoeller
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Patent number: 4783549Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which --R.sub.1, R.sub.3 and R.sub.4 are each indepenently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 -acyloxy or hydroxyl;--R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;--R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.Type: GrantFiled: September 4, 1985Date of Patent: November 8, 1988Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
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Patent number: 4780563Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a palladium catalyst.Type: GrantFiled: October 19, 1987Date of Patent: October 25, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4778918Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a rhodium catalyst.Type: GrantFiled: November 2, 1987Date of Patent: October 18, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4778917Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and a ruthunium catalyst.Type: GrantFiled: November 2, 1987Date of Patent: October 18, 1988Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4767882Abstract: Tetrahydronaphthalene derivatives of the formula: ##STR1## wherein either one of R.sup.1 and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and the other is acetyl and R.sup.3 is hydrogen or methyl in a racemic or optically active form, which are useful as perfumes or intermediates for production of perfumes, are prepared from an R.sup.4 -benzene and pyrocine through the intermediary compounds of the formula: ##STR2## wherein R.sup.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy present at either one of 6- and 7-positions and A is hydrogen, carboxyl, C.sub.2 -C.sub.5 alkoxycarbonyl, halogen, methyl, hydroxymethyl or halomethyl.Type: GrantFiled: August 26, 1986Date of Patent: August 30, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Gohfu Suzukamo, Yoji Sakito
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Patent number: 4761497Abstract: 2-Naphtanoic acid or ester thereof is prepared by heating a compound selected from the group consisting of ketals and enol ethers or esters of an alpha-acetyl cinnamic acid or ester thereof at a temperature effective to cyclize the compound and form said 2-naphthanoic acid or ester thereof.Type: GrantFiled: October 13, 1987Date of Patent: August 2, 1988Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Charles E. Sumner, Jr.
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Patent number: 4748253Abstract: Process for preparing esters of alkanoic acids via rearrangement of alpha-haloketals in the presence of a Lewis acid.The rection is preferably carried out in the presence of catalytic amounts of a Lewis acid and of a diluent at a temperature in the range from about 0.degree. to the reflux temperature of diluent.The esters thus obtained are useful as intermediate products for preparing drugs.The process involves the preparation of new alpha-haloketals.Type: GrantFiled: December 10, 1981Date of Patent: May 31, 1988Assignee: Blasinachim S.p.A.Inventors: Claudio Giordano, Aldo Belli, Fulvio Uggeri, Giovanni Villa
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Patent number: 4740331Abstract: Salts having the formula:Y--NH.sub.3.sup..sym..RCO.sub.2.sup..crclbar. Iin which Y is a group of formula R.sup.1 XCH.sub.2 CH(OH)CH.sub.2 --, R and R.sup.1 are the same or different and each is a straight- or branched chain alkyl group having from 1 to 18 carbon atoms, a straight- or branched chain alkenyl group having from 2 to 18 atoms, a cycloalkyl group having from 4 to 12 ring atoms, an aryl group having 6-10 ring atoms, or an aralkyl group having from 7 to 10 carbon atoms; and X is O,CO.sub.2, NR.sup.2 or S and R.sup.2 is hydrogen, a straight- or branched chain alkyl group having from 1 to 18 carbon atoms or an alkenyl group having from 2 to 18 C atoms. These salts are useful as corrosion inhibitors.Type: GrantFiled: February 7, 1986Date of Patent: April 26, 1988Assignee: Ciba-Geigy CorporationInventors: Emyr Phillips, David Wilson
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Patent number: 4736065Abstract: A compound of Formula I: ##STR1## wherein: Ar represents a polynuclear carboxyclic or heterocyclic fused ring system having at least one carbocylic or heterocyclic ring of aromatic character, the polynuclear ring system optionally carrying one or more of the substituents halogen, C.sub.1 -C.sub.6 alkyl --CF.sub.3, or --OCF.sub.y H.sub.3-y, wherein y is 0-3;n is 0 or 1 and m is 1-11Z represents a group of Formula: ##STR2## wherein: R.sub.A and R.sub.B which may be identical or different each represent hydrogen or methyl;R.sub.C represents methyl;R.sub.D represents methyl, ethyl, n-propyl, isopropyl, t-butyl, or vinyl; andR.sub.E represents hydrogen or methyl or wherein:R.sub.C and R.sub.D together with C.sub..beta. form a cyclopropane or a cyclobutane ring or goether form a methylene group (.dbd.CH.sub.2) or wherein:R.sub.A and R.sub.B together with C.sub..alpha. and C.sub..beta. form a cyclobutane ring.Type: GrantFiled: September 17, 1986Date of Patent: April 5, 1988Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, David A. Pulman, Diana M. Johnson
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Patent number: 4732912Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --,wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: April 27, 1984Date of Patent: March 22, 1988Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill