The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/240)
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Patent number: 5300622Abstract: 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: GrantFiled: December 11, 1992Date of Patent: April 5, 1994Assignee: General Electric CompanyInventor: John C. Schmidhauser
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Patent number: 5294619Abstract: 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: GrantFiled: July 29, 1992Date of Patent: March 15, 1994Assignee: Pfizer Inc.Inventor: Arthur A. Nagel
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Patent number: 5272144Abstract: 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: GrantFiled: June 13, 1991Date of Patent: December 21, 1993Assignee: Farmitalia Carlo Erba s.r.l.Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
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Patent number: 5258517Abstract: 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: GrantFiled: August 6, 1992Date of Patent: November 2, 1993Assignee: Sepracor, Inc.Inventors: Charles M. Zepp, Yun Gao, Donald L. Heefner
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Patent number: 5231105Abstract: 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: GrantFiled: May 22, 1989Date of Patent: July 27, 1993Assignee: Ajinomoto Co., Inc.Inventors: Masataka Shoji, Kozo Toyota, Chikahiko Eguchi, Ryota Yoshimoto, Yosikatsu Koyama, Hideki Domoto, Akira Kamimura
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Patent number: 5210282Abstract: 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: GrantFiled: June 30, 1992Date of Patent: May 11, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5202346Abstract: 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: GrantFiled: February 25, 1992Date of Patent: April 13, 1993Assignee: American Home Products CorporationInventors: John A. Butera, Jehan F. Bagli, John W. Ellingboe
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Patent number: 5169855Abstract: 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: GrantFiled: March 28, 1990Date of Patent: December 8, 1992Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
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Patent number: 5143921Abstract: 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: GrantFiled: June 4, 1990Date of Patent: September 1, 1992Assignee: Kuraray Co., Ltd.Inventors: Koichi Kanehira, Katsushi Eziri, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
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Patent number: 5112978Abstract: 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: GrantFiled: September 22, 1989Date of Patent: May 12, 1992Assignee: Erregierre Industria Chimica S.p.A.Inventor: Egidio Molinari
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Patent number: 5091393Abstract: 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: GrantFiled: May 29, 1990Date of Patent: February 25, 1992Assignee: Duphar International Research B.V.Inventors: Jacobus A. Den Hartog, Ineke Van Wijngaarden, Martinus T. Tulp
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Patent number: 5071851Abstract: 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: GrantFiled: July 9, 1990Date of Patent: December 10, 1991Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Norbert Goetz, Bernhard Zipperer, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 5068452Abstract: 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: GrantFiled: April 2, 1990Date of Patent: November 26, 1991Assignee: Firmenich SAInventors: Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
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Patent number: 5036077Abstract: 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: GrantFiled: September 15, 1988Date of Patent: July 30, 1991Assignee: SanofiInventors: Didier Van Broeck, Madeleine Mosse
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Patent number: 5019650Abstract: 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: GrantFiled: August 28, 1989Date of Patent: May 28, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Engelbert Ciganek, Leonard Cook
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Patent number: 5017572Abstract: 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: GrantFiled: April 18, 1989Date of Patent: May 21, 1991Assignee: Delalande S.A.Inventors: Mona Ward, Pierre-Andre Ph.Settembre, Alain Renaud, Michel Langlois
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Patent number: 4972009Abstract: 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: GrantFiled: August 18, 1989Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventors: Joseph Suhadolnik, Ramanathan Ravichandran
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Patent number: 4971979Abstract: 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: GrantFiled: July 19, 1989Date of Patent: November 20, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Luc Malleron, Gerard Ponsinet, Gerard Roussel
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Patent number: 4937346Abstract: 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: GrantFiled: November 30, 1987Date of Patent: June 26, 1990Assignee: Per Arvid Emil CarlssonInventors: 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
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Patent number: 4902801Abstract: 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: GrantFiled: August 8, 1986Date of Patent: February 20, 1990Assignee: Beecham Group plc.Inventors: Erol A. Faruk, Roger T. Martin
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Patent number: 4889953Abstract: 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: GrantFiled: July 22, 1987Date of Patent: December 26, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
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Patent number: 4871748Abstract: 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: GrantFiled: January 23, 1985Date of Patent: October 3, 1989Assignee: May & Baker LimitedInventor: Leslie R. Hatton
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Patent number: 4870083Abstract: The present invention relates to 1,4-disubstituted-piperidinyl compounds and their use as analgesic agents and as muscle relaxants.Type: GrantFiled: October 11, 1988Date of Patent: September 26, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, Thaddeus R. Nieduzak, Francis P. Miller, Stephen M. Sorensen
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Patent number: 4835164Abstract: 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: GrantFiled: February 20, 1987Date of Patent: May 30, 1989Assignee: A. H. Robins Company, IncorporatedInventors: James R. Shanklin, Jr., Christopher P. Johnson, III
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Patent number: 4822778Abstract: 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: GrantFiled: January 19, 1988Date of Patent: April 18, 1989Assignee: Gunnar AbergInventors: Gunnar A. K. Aberg, Bo T. af Ekenstam
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Patent number: 4820839Abstract: 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: GrantFiled: January 23, 1987Date of Patent: April 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
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Patent number: 4820717Abstract: 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: GrantFiled: September 30, 1986Date of Patent: April 11, 1989Assignee: SanofiInventors: Madeleine Mosse, Henri Demarne, Vincenzo Proietto
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Patent number: 4798894Abstract: 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: GrantFiled: May 11, 1987Date of Patent: January 17, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4757079Abstract: 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: GrantFiled: June 24, 1986Date of Patent: July 12, 1988Assignee: Dynamac CorporatonInventor: Allan P. Gray
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Patent number: 4719219Abstract: 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: GrantFiled: October 1, 1984Date of Patent: January 12, 1988Assignee: Per A. E. CarlssonInventors: 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
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Patent number: 4695631Abstract: 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: GrantFiled: June 30, 1982Date of Patent: September 22, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
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Patent number: 4690931Abstract: 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: GrantFiled: September 9, 1985Date of Patent: September 1, 1987Assignee: SynthelaboInventors: Alexander Wick, Jonathan Frost, Bernard Gaudilliere, Jean Bertin, Regis Dupont, Jean Rousseau
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Patent number: 4686309Abstract: 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: GrantFiled: February 15, 1985Date of Patent: August 11, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
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Patent number: 4673683Abstract: 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: GrantFiled: September 5, 1985Date of Patent: June 16, 1987Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Ludwig Schuster, Norbert Goetz, Ernst-Heinrich Pommer, Eberhard Ammermann
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Patent number: 4664848Abstract: 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: GrantFiled: November 22, 1983Date of Patent: May 12, 1987Assignee: The Procter & Gamble CompanyInventors: Young S. Oh, Eugene P. Gosselink
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Patent number: 4661601Abstract: 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: GrantFiled: April 3, 1985Date of Patent: April 28, 1987Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4616082Abstract: 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: GrantFiled: June 7, 1985Date of Patent: October 7, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4613597Abstract: 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: GrantFiled: September 5, 1984Date of Patent: September 23, 1986Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes
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Patent number: 4612320Abstract: 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: GrantFiled: March 12, 1984Date of Patent: September 16, 1986Assignee: BASF AktiengesellschaftInventors: Albrecht Franke, Josef Gries, Claus D. Mueller, Dieter Lenke
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Patent number: 4593037Abstract: 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: GrantFiled: July 26, 1984Date of Patent: June 3, 1986Assignee: Pfizer Inc.Inventor: Reinhard Sarges
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Patent number: 4537963Abstract: 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: GrantFiled: August 11, 1983Date of Patent: August 27, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ashokkumar B. Shenvi
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Patent number: 4536500Abstract: 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: GrantFiled: December 21, 1982Date of Patent: August 20, 1985Assignee: Delalande S.A.Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
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Patent number: 4529732Abstract: 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: GrantFiled: March 14, 1983Date of Patent: July 16, 1985Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4485109Abstract: 4-Aryl-4-piperidinecarbinols, for example, ##STR1## useful as antidepressants and, in some cases, as anorectic agents.Type: GrantFiled: February 25, 1983Date of Patent: November 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Engelbert Ciganek
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Patent number: 4482713Abstract: 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: GrantFiled: July 1, 1982Date of Patent: November 13, 1984Assignee: BASF AktiengesellschaftInventor: Rainer Strickler
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Patent number: 4476311Abstract: 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: GrantFiled: February 19, 1982Date of Patent: October 9, 1984Assignee: The Purdue Frederick CompanyInventors: Bola V. Shetty, Arthur McFadden, Peter Hofer
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Patent number: 4459410Abstract: 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: GrantFiled: October 5, 1981Date of Patent: July 10, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
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Patent number: 4436909Abstract: 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: GrantFiled: January 11, 1980Date of Patent: March 13, 1984Assignee: L'OrealInventors: Gregoire Kalopissis, Guy Vanlerberghe
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Patent number: 4430334Abstract: Phenethanolamine derivatives in the (+)-erythro form of the formula: ##STR1## wherein X represents a halogen atom, are new compounds useful in therapy.Type: GrantFiled: April 13, 1982Date of Patent: February 7, 1984Assignee: SynthelaboInventors: Alexander E. Wick, Jonathan R. Frost
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Patent number: 4429162Abstract: 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: GrantFiled: February 1, 1982Date of Patent: January 31, 1984Assignee: Ciba-Geigy CorporationInventors: Thomas W. Cooke, Robert A. Falk