The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/240)
  • Patent number: 5300622
    Abstract: Heterocyclic bis(4-hydroxyphenyl)cycloalkanes, as illustrated by 4,4-bis(4-hydroxyphenyl)thiopyran and the corresponding acetylated piperidine, may be prepared by the reaction of bisphenol A or a similar compound with the corresponding thiopyranone or piperidone. The thio compound may be oxidized to the corresponding sulfone. Polycarbonates prepared from said heterocyclic bis(4-hydroxyphenyl)cycloalkanes have high glass transition temperatures and are expected to be ductile.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: April 5, 1994
    Assignee: General Electric Company
    Inventor: John C. Schmidhauser
  • Patent number: 5294619
    Abstract: A series of novel N-alkyl or oxyalkyl arylpiperidine derivatives have been prepared, including their pharmaceutically acceptable acid addition salts, wherein the N-alkyl or oxyalkyl side chain is further substituted by certain aryl or heterocyclic ring groups. These particular compounds are useful in therapy as neuroleptic agents for the control of various psychotic disorders. Typical and preferred member compounds include 4-{{4-{2-[4-(2-methoxyphenyl)-1-piperidinyl]ethyl}phenyl}}thiazole-2-amine , 4-{{4-{4-[4-(2-methoxyphenyl)-1-piperidinyl]-n-butyl}phenyl}}thiazole-2-a mine, 3-{4-[4-(2-methoxyphenyl)-1-piperidinyl]-n-butyl}-1,8,8-trimethyl-3-azabic yclo[3.2.1]octane-2,4-dione, 5-{2-[4-(2-methoxyphenyl)-1-piperidinyl]ethyl}oxindole and 3-{2-[4-(1-naphthyl)-1-piperidinyl]ethyl}-2-methyl-4H-pyrido[1,2-a]pyrimid ine-4-one, respectively. Methods for preparing all these compounds from known starting materials are provided.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: March 15, 1994
    Assignee: Pfizer Inc.
    Inventor: Arthur A. Nagel
  • Patent number: 5272144
    Abstract: Aryloxy- and heteroaryloxy-alkylene derivatives of amines of formula ##STR1## wherein each of A and B is a group of formula (i) to (iii): ##STR2## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is independently:a) hydrogen, halogen, hydroxy, cyano or nitro;b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by halogen,c) C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkylthio;d) C.sub.1 -C.sub.6 alkyl-sulfonyl;e) a substituted amine group --NR.sub.7 R.sub.8 ;f) a --COR.sub.12 group; org) two adjacent groups of R.sub.3, R.sub.4, R.sub.5 and R.sub.6, taken together, form a C.sub.1 -C.sub.4 alkylenedioxy group;each of R.sub.1 and R.sub.2 independently is hydrogen, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: December 21, 1993
    Assignee: Farmitalia Carlo Erba s.r.l.
    Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
  • Patent number: 5258517
    Abstract: A biocatalytic method of preparing optically pure precursors of paroxetine and a method of preparing paroxetine therefrom are disclosed. A racemic trans ester precursor compound of paroxetine is first prepared. The racemic trans ester precursor compound comprises a mixture of (3S,4R) and (3R,4S) enantiomers. The (3R,4S) enantiomer is hydrolyzed biocatalytically to the corresponding (3R,4S)-trans carboxylic acid or alternatively, the (3S,4R) enantiomer is biocatalytically hydrolyzed the to (3S,4R)-trans carboxylic acid in a reaction catalyzed by a isolated enzyme or a microorganism. In the first instance, the unhydrolyzed (3S,4R) enantiomer is separated from the (3R,4S)-trans carboxylic acid, whereas in the second instance the (3S,4R)-trans carboxylic acid is separated from the unhydrolyzed (3R,4S) enantiomer. The (3S,4R) enantiomer obtained following the selective hydrolysis is reduced to form a (-)-trans-(3S,4R) primary alcohol precursor of paroxetine.
    Type: Grant
    Filed: August 6, 1992
    Date of Patent: November 2, 1993
    Assignee: Sepracor, Inc.
    Inventors: Charles M. Zepp, Yun Gao, Donald L. Heefner
  • Patent number: 5231105
    Abstract: An ethylamine derivative of formula (I): ##STR1## wherein A represents a carbon atom or a nitrogen atom;B represents a substituted or unsubstituted aralkyl or aryl group;C represents hydrogen, alkyl, aralkyl, or aryl, each of which may optionally be substituted orC may optionally be bonded to A to form an alkylene bridge which is optionally substituted,Q represents a substituted or unsubstituted aryl group, said group optionally being substituted by hetero atom(s) or substituent(s) optionally containing hetero atom(s); andX represents an alkylene bridge having from 2 to 20 carbon atoms and is optionally substituted with groups which include hetero atoms with the non-hetero atom substituents optionally containing hetero atoms.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: July 27, 1993
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masataka Shoji, Kozo Toyota, Chikahiko Eguchi, Ryota Yoshimoto, Yosikatsu Koyama, Hideki Domoto, Akira Kamimura
  • Patent number: 5210282
    Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: May 11, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard M. Flynn, Patricia M. Savu
  • Patent number: 5202346
    Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is alkylsulfonamido of 1 to 6 carbon atoms, arylsulfonamido of 6 to 10 carbon atoms, --NO.sub.2,--CN, 1-imidazolyl or 1,2,4-triazol-1-yl;Y is ##STR2## --CH.sub.2 --, --O--, --S--, or --SO.sub.2 --; X is --CH.dbd. or --N.dbd.;R.sup.2 is hydrogen when n is 0, otherwise it is hydrogen or --OH;n is one of the integers 0, 1, 2, 3, 4, 5 or 6;A is ##STR3## where R.sup.3 is alkylsulfonamido of 1 to 6 carbons atoms, arylsulfonamido of 6 to 10 carbon atoms, --NO.sub.2, --CN, 1-imidazolyl or 1,2,4-triazol-1-yl; or ##STR4## where R.sup.4 is hydrogen or alkyl of 1 to 6 carbon atoms; with the provisos that;a) X is --CH.dbd. when Y is ##STR5## --O-- or --S-- and when Y is ##STR6## and R.sup.2 is --OH; b) X is --N.dbd. when A is ##STR7## c) A is ##STR8## when Y is --S-- or --SO.sub.2 -- and X is --CH.dbd., and their pharmaceutically acceptable salts are Class III antiarrhythmic agents.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: April 13, 1993
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Jehan F. Bagli, John W. Ellingboe
  • Patent number: 5169855
    Abstract: There are provided piperidine ether derivatives, pharmaceutical and agricultural compositions containing them useful for treating physiological or drug induced psychosis or dyskinesia in a mammal or fungal disease in plants. Also provided are methods for preparing these compounds.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 8, 1992
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
  • Patent number: 5143921
    Abstract: Novel terpene amino alcohols having an antiallergic activity or an activity of improving cerebral function are provided. Also provided are medicinal uses of the alcohols.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: September 1, 1992
    Assignee: Kuraray Co., Ltd.
    Inventors: Koichi Kanehira, Katsushi Eziri, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
  • Patent number: 5112978
    Abstract: A process for preparing alpha-(alkylphenyl)-4-(hydroxy diphenylmethyl)-1-piperidine butanols of formula (I) ##STR1## in which R is a C.sub.1 -C.sub.5 alkyl, by reacting an isonipecotate of formula (II): ##STR2## in which R' is a C.sub.1 -C.sub.5 alkyl or benzyl, with 1-(alkylphenyl)-4-chlorobutanol to obtain the compound (IV) directly ##STR3## and reacting (IV) with phenylmagnesium halide (V) to obtain (I).
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: May 12, 1992
    Assignee: Erregierre Industria Chimica S.p.A.
    Inventor: Egidio Molinari
  • Patent number: 5091393
    Abstract: The invention relates to a group of tertiary 2,5-dialkyl-3-phenylpiperidine derivatives, having opiate-antagonistic activity represented by general formula 4, ##STR1## wherein A.sub.1 is hydrogen, an optionally esterified hydroxyl group or mercapto group, a group NHA.sub.8 or --CONHA.sub.8, wherein A.sub.8 is hydrogen, alkyl having 1-6 C-atoms or alkylcarbonyl having 2-7 C-atoms;A.sub.2 is hydrogen or, when A.sub.1 is hydrogen, one of the other meanings of A.sub.1, orA.sub.1 and A.sub.2 together with the 2 carbon atoms of the benzene ring,constitute a heterocyclic group which consists of five or six ring atoms and which comprises a group --NH-- and optionally as a second hetero atom may comprise an oxygen atom, sulphur atom or nitrogen atom;A.sub.3 and A.sub.4 independently of each other are straight or branched alkyl or alkenyl having 1-6 C-atoms;A.sub.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: February 25, 1992
    Assignee: Duphar International Research B.V.
    Inventors: Jacobus A. Den Hartog, Ineke Van Wijngaarden, Martinus T. Tulp
  • Patent number: 5071851
    Abstract: 4-substituted cyclohexylamines of the formula ##STR1## where R is the group CR.sup.1 R.sup.2 R.sup.3, where R.sup.1, R.sup.2 and R.sup.3 are hydrogen, unsubstituted or substituted alkyl, alkoxy, alkylthio or cycloalkyl, with the proviso that at most one of the substituents R.sup.1, R.sup.2 and R.sup.3 is hydrogen, X is an alkylene group which, together with the N atom, forms a substituted or unsubstituted heterocyclic ring in which up to 2 carbon atoms may be replaced by O, N or S atoms, and salts thereof, and fungicides containing these compounds.
    Type: Grant
    Filed: July 9, 1990
    Date of Patent: December 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Norbert Goetz, Bernhard Zipperer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5068452
    Abstract: Aromatic aldehydes of formula ##STR1## possessing a single or a double bond in the position indicated by the dotted line and wherein symbol X represents a monovalent radical or formula ##STR2## or, when the dotted line represents a single bond, of formula ##STR3## and wherein symbol Z stands for an oxygen atom or for two R.sup.2 O radicals, each of R.sup.1 and R.sup.2 representing an alkyl radical having from 1 to 3 carbon atoms.Aromatic aldehydes (I) posses useful odorous properties and can be used as perfuming ingredients for the preparation of perfume bases and perfumed articles. They can also be used as starting materials for the preparation of useful end-products having herbicide and fungicide properties.Process for the preparation of aromatic aldehydes (I) starting from 8-methoxycuminic aldehyde.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: November 26, 1991
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
  • Patent number: 5036077
    Abstract: The invention relates to compounds of the formula: ##STR1## in which: Ar represents a phenyl group substituted by R.sub.2, R.sub.3 and R.sub.4, or a naphth-1-yl or naphth-2-yl group, unsubstituted or substituted by 1 or 2 halogen atoms;X represents an oxygen atom or a sulfur atom;R.sub.1 represents H or a halogen atom;R.sub.2 represents a halogen atom, a trifluoromethyl group, a phenyl group which is unsubstituted by 1 or 3 halogen atoms, a benzyl group which is unsubstituted or substituted by 1 to 3 halogen atoms, a phenoxy group which is unsubstituted or substituted by 1 to 3 halogen atoms, or a C.sub.1 -C.sub.4 alkyl group;R.sub.3 and R.sub.4 represents H, a halogen atom or a C.sub.1 -C.sub.4 alkyl group; andthe benzyl group substitutes the piperidino radical in the 2-, 3- or 4-position,and their salts with mineral or organic acids.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: July 30, 1991
    Assignee: Sanofi
    Inventors: Didier Van Broeck, Madeleine Mosse
  • Patent number: 5019650
    Abstract: Known and novel 4-aryl-4-piperidinecarbinols and heterocyclic analogs are useful as analgesics. Also provided are novel pyrrolidinecarbinols and hexhydroazepine carbinols which are useful as analgesics, antidepressants and, in some cases, as anorectic agents.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: May 28, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Engelbert Ciganek, Leonard Cook
  • Patent number: 5017572
    Abstract: The present invention relates to compounds of formula: ##STR1## in which: R.sub.1 and R.sub.2 are such that:either R.sub.1 represents a methoxy group in which case R.sub.2 is a group chosen from the following: hydroxyl; C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.5 -C.sub.7 cycloalkyloxy; benzyloxy;or R.sub.2 represents a methoxy group in which case R.sub.1 is a group chosen from the following: hydroxyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.2 -C.sub.8 alkyloxy substituted by a methoxy group; C.sub.1 -C.sub.4 trifluoroalkyloxy; C.sub.3 -C.sub.4 alkenyloxy; C.sub.5 -C.sub.7 cycloalkyloxy; benzyloxy; C.sub.1 -C.sub.4 alkyhlthio;n=2 or 3; andp=4, 5 or 6,as well as their addition salts with mineral or organic acids, said compounds and salts being useful as drugs.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: May 21, 1991
    Assignee: Delalande S.A.
    Inventors: Mona Ward, Pierre-Andre Ph.Settembre, Alain Renaud, Michel Langlois
  • Patent number: 4972009
    Abstract: Compounds possessing both a hindered amine moiety, such as a derivative of 2,2,6,6-tetramethylpiperidine, and a nitrone moiety are valuable stabilizers for protecting polymer compositions against the deleterious effects of actinic light and from the adverse effects of high temperature polymer processing environments. Additionally, the instant compounds present the opportunity for grafting onto preformed polymer backbones.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph Suhadolnik, Ramanathan Ravichandran
  • Patent number: 4971979
    Abstract: Substituted alkadienes of formula: ##STR1## in which R.sub.1 is hydroxy or acetoxy, R.sub.2 is hydrogen, carboxy, alkoxycarbonyl, phenyl or benzoyl, andR.sub.3 is alkylthio or alkoxy and R.sub.4 is naphthoyl or optionally substituted benzoyl,or R.sub.3 is alkoxycarbonyl, cycloalkyloxycarbonyl or cyano and R.sub.4 is alkyl, naphthyl, optionally substituted phenyl, alkylthio, naphthylmethanethio, optionally substituted benzylthio, optionally substituted phenylthio, naphthylthio, phenethylthio or allylthio,or R.sub.3 and R.sub.4 form, with the carbon atom to which they are attached, a ring-system of formula: ##STR2## in which R.sub.5 is hydrogen or alkoxy and X is methylene or S inhibit 5-lipoxygenase and are useful, for example, as anti-inflammatories.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: November 20, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Luc Malleron, Gerard Ponsinet, Gerard Roussel
  • Patent number: 4937346
    Abstract: Compound of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, or benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: June 26, 1990
    Assignee: Per Arvid Emil Carlsson
    Inventors: Folke L. Arvidsson, Per A. E. Carlsson, Uli A. Hacksell, John S. M. Hjorth, Per L. Lindberg, John L. G. Nilsson, Domingo Sanchez, Nils U. E. Svensson, Hakan V. Wikstrom
  • Patent number: 4902801
    Abstract: A process is disclosed for the preparation of a compound of formula (I): ##STR1## wherein Ar is aryl or substituted aryl and R.sup.3 is hydrogen, alkyl or aralkyl, which process comprises reducing a compound of formula (II): ##STR2## wherein Ar and R.sup.3 are as defined with respect to formula (I) and R.sup.4 is alkyl. Compounds of formula (I) are useful as chemical intermediates.
    Type: Grant
    Filed: August 8, 1986
    Date of Patent: February 20, 1990
    Assignee: Beecham Group plc.
    Inventors: Erol A. Faruk, Roger T. Martin
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4871748
    Abstract: Compounds of the formula: ##STR1## wherein R represents hydroxymethyl, alkoxymethyl of 2 to 6 carbon atoms, optionally substituted phenoxymethyl, alkanoyloxymethyl of 3 to 10 carbon atoms, optionally substituted benzoyloxymethyl, alkylsulphonyloxymethyl of 2 to 9 carbon atoms, optionally substituted phenylsulphonyloxymethyl, formyl, aminomethyl optionally substituted by 1 or 2 alkyl groups of 1 to 4 carbon atoms, or hydroxyiminomethyl, and acid addition salts thereof, are useful as rodenticides.
    Type: Grant
    Filed: January 23, 1985
    Date of Patent: October 3, 1989
    Assignee: May & Baker Limited
    Inventor: Leslie R. Hatton
  • Patent number: 4870083
    Abstract: The present invention relates to 1,4-disubstituted-piperidinyl compounds and their use as analgesic agents and as muscle relaxants.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: September 26, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Albert A. Carr, Thaddeus R. Nieduzak, Francis P. Miller, Stephen M. Sorensen
  • Patent number: 4835164
    Abstract: Novel heterocyclicmethanols are disclosed having the formula: ##STR1## wherein Z is pyrrolidinyl, piperidinyl, homopiperidinyl or pyridinyl; R.sup.1 is hydrogen, loweralkyl or carbethoxymethyl;R.sup.2 is hydrogen, loweralkyl, cycloalkyl, phenyl or phenyl-loweralkyl;R.sup.3 is 1 or 2-naphthalenyl, 2,3-dihydroinden-4 or 5-yl, phenyl or phenyl substituted by loweralkyl, loweralkoxy, halogen, trifluoromethyl, phenyl, methylenedioxy, nitro, amino, loweralkylamino, diloweralkylamino, loweracylamino;the 1-position of 2-pyrrolidinyl, 2-piperidinyl or 2-homopiperidinyl may be substituted by an R.sup.4 loweralkyl group, or R.sup.1 may form methylene or --CH.sub.2 -C(O)-bridges with R.sup.4 ;the pharmaceutically acceptable salts and diastereomers thereof, which compounds have antiarrhythmic and/or hypotensive activity in animals.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: May 30, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., Christopher P. Johnson, III
  • Patent number: 4822778
    Abstract: Compounds of the formula (I) ##STR1## optically active isomers thereof, and/or pharmaceutically acceptable acid addition salts thereof are disclosed, wherein R.sup.1 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, 2-hydroxyethyl, 3-hydroxypropyl and 4-hydroxybutyl, and wherein R is selected from the group consisting of ##STR2## in which R.sup.2, R.sup.3 R.sup.4 and R.sup.5 are the same or different and are each independently selected from the group consisting of hydrogen and methyl. Pharmaceutical preparations employing such compounds and method of using such compounds are also disclosed.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: April 18, 1989
    Assignee: Gunnar Aberg
    Inventors: Gunnar A. K. Aberg, Bo T. af Ekenstam
  • Patent number: 4820839
    Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
  • Patent number: 4820717
    Abstract: The present invention relates to new aromatic derivatives of formula: ##STR1## wherein: Alk is an alkylene group with 1 to 10 carbon atoms,R.sub.1 is hydrogen or an alkyl with 1 to 6 carbon atoms,R.sub.2 and R.sub.3 are similar or different and represent a cycloalkyl with 3 to 6 carbon atoms or a striaght or branched alkyl with 1 to 6 carbon atoms, either substituted or non-substituted by a phenyl or methyl phenyl group, or R.sub.2 and R.sub.3 form, together with the atom of nitrogen to which they are bonded, a mono-nitrogenous heterocycle containing no other heteroatom, such as pyrrolidino, piperidino, azepino, hexamethylene-imino, 4-methyl-piperidino, 4-phenyl-piperidino, 1,2,3,4-tetrahydro-2-isoquinolyl, 4-benzyl-piperidino;R.sub.4 is hydrogen, halogen, methyl or phenyl,R.sub.5 is hydrogen, halogen or methyl,or R.sub.4 and R.sub.5 together with the benzene ring to which they are bonded, constitute a 1-naphthyl or 2-naphthyl group,and the pharmaceutically acceptable salts with mineral or organic acids.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: April 11, 1989
    Assignee: Sanofi
    Inventors: Madeleine Mosse, Henri Demarne, Vincenzo Proietto
  • Patent number: 4798894
    Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: January 17, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4757079
    Abstract: Novel compounds of the formula: ##STR1## are described wherein Z is a bicyclic aryl group containing between 9 and 10 ring atoms, up to two of which may be nitrogen and up to one of which may be oxygen or sulfur; A is an ethenyl group which may be lower-alkyl-substituted; and R and R' each represent H or an aliphatic group of 1-4 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: July 12, 1988
    Assignee: Dynamac Corporaton
    Inventor: Allan P. Gray
  • Patent number: 4719219
    Abstract: Compound of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, or benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: January 12, 1988
    Assignee: Per A. E. Carlsson
    Inventors: Folke L. E. Arvidsson, Per A. E. Carlsson, Uli A. Hacksell, John S. M. Hjorth, Per L. Lindberg, John L. G. Nilsson, Domingo Sanchez, Nils U. E. Svensson, Hakan V. Wikstrom
  • Patent number: 4695631
    Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: September 22, 1987
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
  • Patent number: 4690931
    Abstract: Compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, alkyoxy, benzyloxy, alkanoyloxy, or benzoyloxy, or when R.sub.2 is hydroxyl or methoxy in the 4-position and R.sub.3 is hydrogen, R.sub.1 may also represent hydroxymethyl carbamoyl or alkoxycarbonyl,R.sub.2 is hydrogen, halogen, alkyl, hydroxyl, or alkoxy,R.sub.3 is hydrogen or alkyl,R.sub.4 is alkyl (in which case the compounds are (.+-.)-erythro) or when R.sub.3 represents hydrogen, R.sub.4 may also be hydrogen, and R.sub.5 is hydrogen, halogen, alkyl, alkoxy, or three methoxy groups in the 3-, 4- and 5-positions and pharmaceutically acceptable acid addition salts thereof, with the exclusion of compounds wherein:(a) one of R.sub.1 and R.sub.2 is in the 4-position and is hydroxyl, alkoxy or benzyloxy, the other is in the 3-position and is hydrogen, hydroxyl, alkoxy or benzyloxy, and R.sub.3 and R.sub.5 are hydrogen and wherein:(b) R.sub.1 is in the 4-position and is halogen, R.sub.4 is methyl and R.sub.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: September 1, 1987
    Assignee: Synthelabo
    Inventors: Alexander Wick, Jonathan Frost, Bernard Gaudilliere, Jean Bertin, Regis Dupont, Jean Rousseau
  • Patent number: 4686309
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: August 11, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4673683
    Abstract: R.sup.2 and R.sup.3 are hydrogen or alkyl,R.sup.4 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, unsubstituted or substituted aralkyl, COR.sup.5, CO.sub.2 R.sup.6 or CONR.sup.7 R.sup.8,R.sup.5 and R.sup.6 are alkyl, unsubstituted or substituted aryl or unsubstituted or substituted aralkyl,R.sup.7 and R.sup.8 are hydrogen, alkyl, unsubstituted or substituted aryl or unsubstituted or substituted aralkyl andn is 0, 1, 2 or 3,and its plant-tolerated acid addition salts, excluding the compounds where, simultaneously, R.sup.4 is hydrogen, acetyl or propionyl, n is 0 or 1 and R.sup.1, R.sup.2 and R.sup.3 are hydrogen, and fungicides containing the novel piperidines and salts.
    Type: Grant
    Filed: September 5, 1985
    Date of Patent: June 16, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Ludwig Schuster, Norbert Goetz, Ernst-Heinrich Pommer, Eberhard Ammermann
  • Patent number: 4664848
    Abstract: Detergent compositions which comprise from about 0.05 to about 95% by weight of a water-soluble cationic compound having clay soil removal/anti-redeposition properties. These compounds are selected from ethoxylated cationic monoamines, ethoxylated cationic diamines, ethoxylated cationic polyamines, ethoxylated cationic polymers, and mixtures thereof. In addition to the cationic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof. In addition to these detergent surfactants, the detergent composition can optionally comprise from 0 to about 80% by weight of a detergent builder.
    Type: Grant
    Filed: November 22, 1983
    Date of Patent: May 12, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Young S. Oh, Eugene P. Gosselink
  • Patent number: 4661601
    Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: April 28, 1987
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4613597
    Abstract: Compounds are described of the formulae (1a) and 1b) ##STR1## in which: R.sup.1 is -H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl,W is C.sub.1-7 alkyleneX is cis or trans --CH.dbd.CH--,Y is a saturated heterocyclic amino group having 5-8 ring members,R.sup.2 is (i) substituted or unsubstituted phenylalkyl, thienylalkyl or naphthylalkyl or (ii) cinnamyl, and Z is --CH.sub.2 OH, --CHO or --CONHR.sup.4 where R.sup.4 is --H or methyl,and their salts and solvates.These compounds inhibit blood platelet aggregation, bronchoconstriction and vasoconstriction, and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: September 23, 1986
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes
  • Patent number: 4612320
    Abstract: Compounds of the general formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n have the meanings given in the description, are useful for treating cardiac disorders.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: September 16, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Albrecht Franke, Josef Gries, Claus D. Mueller, Dieter Lenke
  • Patent number: 4593037
    Abstract: Certain novel 1-(substituted-alkyl)-3-(3-hydroxyphenyl)piperidine compounds, and the pharmaceutically-acceptable acid-addition salts thereof, possess pharmaceutical activity as neuroleptic agents, and they are useful for treating psychotic disorders, e.g. schizophrenia, in human subjects. In particular, they are useful for alleviating such symptoms as anxiety, agitation, excessive agression, tension and social or emotional withdrawal in psychotic patients.Certain 3-(3-methoxyphenyl)piperidine compounds are useful as chemical intermediates to the aforementioned neuroleptic agents.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: June 3, 1986
    Assignee: Pfizer Inc.
    Inventor: Reinhard Sarges
  • Patent number: 4537963
    Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3,2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.3.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p--MeC.sub.6 H.sub.4 SO.sub.3 -- and MeSO.sub.3 --.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ashokkumar B. Shenvi
  • Patent number: 4536500
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: August 20, 1985
    Assignee: Delalande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4529732
    Abstract: 2-[2-Hydroxy-4-(substituted)phenyl]piperidines and derivatives thereof of the formula ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R.sub.1 is H, benzyl or certain acyl groups, R.sub.2 is H, certain alkyl, alkenyl, alkynyl, hydroxyalkyl, acyl or alkylsulfonyl groups; R.sub.3 is H.sub.2, O, ##STR2## and Z is (C.sub.1 -C.sub.13)alkylene or -(alk.sub.1).sub.m -O-(alk.sub.2).sub.n - where each of (alk.sub.1) and (alk.sub.2) is (C.sub.1 -C.sub.13)alkylene, provided that the number of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl or optionally substituted phenyl; their use as analgesic agents, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: July 16, 1985
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4485109
    Abstract: 4-Aryl-4-piperidinecarbinols, for example, ##STR1## useful as antidepressants and, in some cases, as anorectic agents.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: November 27, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Engelbert Ciganek
  • Patent number: 4482713
    Abstract: Novel quaternary ammonium salts of the general formula[R.sup.1 R.sup.2 R.sup.3 N(A--O).sub.n --R.sup.4 ].sup.+ Z.sup.-where R.sup.1 and R.sup.2 are identical or different and each is alkyl, aryl, aralkyl, alkylaryl, alkoxyalkyl, or a (poly)alkylene glycol radical, or R.sup.1 and R.sup.2, together with the nitrogen atom, are a heterocyclic ring, or one or more substituents R.sup.1 or R.sup.2 are polyfunctional so that the salt contains not less than 2 ammonium groups, R.sup.3 and R.sup.4 are identical or different monovalent radicals of one or more alkylating agents R.sup.3 X or R.sup.4 X, for example an (ar)alk(en)yl halide, sulfate or methosulfate or an (alkyl)aryl-sulfonate or -sulfonic acid ester, A is alkylene of 2 to 10 carbon atoms, n is an integer and Z is either X or another salt-forming anion or a hydroxyl ion, are prepared by N-alkylation and O-alkylation of an alkanolamine with the aid of a phase transfer catalyst and are useful as cationic surfactants, etc.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: November 13, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Rainer Strickler
  • Patent number: 4476311
    Abstract: Analgesic and anti-inflammatory compounds are provided. These compounds possess the following general formula: ##STR1## wherein R=--COOR.sub.5, --CH.sub.2 CO.sub.2 H, ##STR2## wherein A and B=hydrogen, lower alkyl, hydroxy alkyl, lower alkyl amine, substituted lower alkyl amine, aminoalkyl, substituted aminoalkyl;R.sub.5 =lower alkyl;R.sub.1 =aryl, substituted aryl, aralkyl, alkyl, hydrogen, substituted aralkyl and heterocycle;R.sub.2 =aryl, substituted aryl, aralkyl, alkyl, substituted aralkyl, heterocycle, substituted heterocycle, biphenyl, substituted biphenyl, naphthyl, and substituted naphthyl;R.sub.3 =aryl, substituted aryl, hydrogen, aralkyl, substituted aralkyl, alkyl, heterocycle and substituted heterocycle;R.sub.2 and R.sub.3 together form a ring;R.sub.4 =hydrogen, phenyl, substituted phenyl, heterocycle; alkyl, substituted alkyl; or, R.sub.1 and R.sub.4 may form a ring;X=>C.dbd.O, --CH.sub.2 --;Y=--S--CHR.sub.4 --, --O--OHR.sub.4 --, --CHR.sub.4 --, --CR.sub.6 R.sub.7 --CHR.sub.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: October 9, 1984
    Assignee: The Purdue Frederick Company
    Inventors: Bola V. Shetty, Arthur McFadden, Peter Hofer
  • Patent number: 4459410
    Abstract: Diphenylalkanoether and diphenylalkanone oximeether derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each independently an aryl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, di(C.sub.1 -C.sub.4)alkylamino, amino, benzyloxy, hydroxyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkysulfonyl, C.sub.1 -C.sub.4 alkanoylamino, C.sub.1 -C.sub.4 alkylmino and N-(C.sub.1 -C.sub.4)alkyl-N-(C.sub.1 -C.sub.4)alkanoylamino, Z.sup.1 is a group of the formula: ##STR2## (wherein R.sup.3 and R.sup.4 are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or an ar(C.sub.1 -C.sub.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: July 10, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
  • Patent number: 4436909
    Abstract: Cationic surface-active agents which are polyhydroxylated tertiary amines or the quaternary ammonium salts thereof and which are usefully employed in cosmetic compositions, are prepared by condensing on a fatty alcohol, glycerol epihalohydrin alone or together with an epoxide to form polyhalogenated polyethers, which in turn are converted to polyhalogenated glycidyl ethers, the latter being reacted with a secondary amine to form polyhalogenated tertiary amines which are then reacted with sodium or potassium acetate in the presence of a diol to form said polyhydroxylated tertiary amines.
    Type: Grant
    Filed: January 11, 1980
    Date of Patent: March 13, 1984
    Assignee: L'Oreal
    Inventors: Gregoire Kalopissis, Guy Vanlerberghe
  • Patent number: 4430334
    Abstract: Phenethanolamine derivatives in the (+)-erythro form of the formula: ##STR1## wherein X represents a halogen atom, are new compounds useful in therapy.
    Type: Grant
    Filed: April 13, 1982
    Date of Patent: February 7, 1984
    Assignee: Synthelabo
    Inventors: Alexander E. Wick, Jonathan R. Frost
  • Patent number: 4429162
    Abstract: The instant invention relates to compounds of the formula ##STR1## wherein each R.sub.f is independently straight or branched chain perfluoroalkyl of 2 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms;each R.sub.1 is independently straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, or alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substituent, hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, chloro, bromo, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms, and R.sub.2 and R.sub.3 additionally may, together with the carbon atoms to which they are attached, form a fused benzo ring;R.sub.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: January 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Thomas W. Cooke, Robert A. Falk