Esterified Phenolic Hydroxy Patents (Class 560/109)
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Patent number: 4406814Abstract: Disclosed is a new family of Liquid Crystalline Materials for use in optical display devices having the general formula: ##STR1## The members of the family of materials are characterized by having a broad nematic operating range in conjunction with low viscosity and exhibit fast response times to a controlled electrical field in the lower temperature regions of their nematic operating range and may be mixed with other members of the family or with other liquid crystalline materials and/or homologous non-liquid crystalline materials.Type: GrantFiled: April 10, 1981Date of Patent: September 27, 1983Assignee: Eaton CorporationInventor: Joseph P. Ferrato
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Patent number: 4405523Abstract: Process for the concurrent synthesis of benzophenone, anthraquinone, and o-dibenzoylbenzene by pyrolysis of benzoic acid salts of yttrium, erbium, and dysprosium and mixtures thereof at temperatures of from about 200.degree. C. to 500.degree. C. and a pressure of about 0.1 to about 100 atmospheres. In an alternative method, a benzoic acid compound is passed through an oxide of yttrium, erbium, dysprosium and mixtures thereof in the presence of steam.Type: GrantFiled: March 24, 1982Date of Patent: September 20, 1983Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4393231Abstract: Fluorine-containing phenyl benzoate compounds which have the general formula: ##STR1## wherein R is a C.sub.1 -C.sub.12 perfluoroalkyl group, a C.sub.1 -C.sub.12 alkyl group, a C.sub.1 -C.sub.12 alkoxy group, a C.sub.2 -C.sub.13 alkanoyloxy group, a C.sub.2 -C.sub.13 alkoxycarbonyl group, a C.sub.2 -C.sub.13 alkoxycarbonyloxy group or a C.sub.2 -C.sub.13 alkyldioxycarbonyl group and X is a C.sub.1 -C.sub.12 alkyl group, a C.sub.1 -C.sub.12 alkoxy group, a cyano group, a trifluoromethyl group or a nitro group with the proviso that X is trifluoromethyl when R is other than perfluoroalkyl are useful as components of liquid crystals.Type: GrantFiled: September 11, 1981Date of Patent: July 12, 1983Assignee: Daikin Kogyo Co., Ltd.Inventors: Susumu Misaki, Masahiro Suefuji, Tamio Mitote, Naotake Matsumura
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Patent number: 4387058Abstract: Novel phenyl and naphthyl esters of 2-(1-oxo-alkoxy)ethyl carbamic acids are prepared. The compounds are useful as pharmacological and agricultural agents.Type: GrantFiled: October 2, 1981Date of Patent: June 7, 1983Assignee: The Dow Chemical CompanyInventor: Chester E. Pawloski
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Patent number: 4340603Abstract: Novel, transient inotropic prodrug forms of the N-(2-phenylethyl)-.omega.-phenylalkylamines, notably of dobutamine, have (i) the structural formula (I): ##STR1## with the proviso that at least one R.sup.1, R.sup.2 or OR.sup.1, when R.sup.7 and/or R.sup.10 is OR.sup.1, must be R.sup.3 COXCH(R.sup.4)-- or R.sup.3 COXCH(R.sup.4)O--, respectively.Type: GrantFiled: August 13, 1980Date of Patent: July 20, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4336396Abstract: This invention relates to a process for the preparation of 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-phenol esters (I) and their salts with organic and inorganic acids comprising the reaction of thymol with a salt of an 1-halo-dimethylaminoethane to obtain ethylamine-N,N-dimethyl-2-(thymyloxy) (II), the subsequent reaction of (II) with an acylating agent according to the Friedel and Kraft reaction to obtain 4-[2-(dimethylamino)-ethoxy]-2-methyl-5-(1-methylethyl)-1-acyl-benzene (III) and the oxidation of (III) to obtain the products (I) which, if desired, may be transformed in their salts with organic or inorganic acids.This process allows to obtain the products (I) in high quality and quantity without isolating any intermediate product.Type: GrantFiled: December 4, 1980Date of Patent: June 22, 1982Assignee: Blasinachim S.p.A.Inventors: Claudio Giordano, Aldo Belli
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Patent number: 4335052Abstract: A process for the preparation of Benzaldehydes substituted in the nucleus is disclosed by oxidation of the corresponding benzyl halides. The process is performed in the presence of water using aminoxides of tertiary amines.Type: GrantFiled: November 24, 1980Date of Patent: June 15, 1982Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunther Bernhardt, Egon-Norbert Petersen, Gerhard Daum
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Patent number: 4327224Abstract: Alpha-[(lower alkylamino)alkyl]-4-hydroxy-3-(alkylthio, akylsulfinyl or alkylsulfonyl)benzenemethanols which have .beta.-adrenergic blocking activity and which are therefore useful in controlling tachycardia are prepared by reduction of the corresponding (lower alkylamino)alkyl 4-hydroxy-3-(akylthio, akylsulfinyl or alkylsulfonyl)phenyl ketones.Type: GrantFiled: June 25, 1976Date of Patent: April 27, 1982Assignee: Sterling Drug Inc.Inventor: Sydney Archer
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Patent number: 4314070Abstract: An improved process for producing meta-phenoxy benzoic acids and their lower alkyl esters in improved yields and with higher selectivity by reacting an alkali metal phenate with a lower alkyl ester of meta-halobenzoic acid in the presence of a copper sulfate catalyst.Type: GrantFiled: May 14, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc Inc.Inventors: Fred G. Schreiber, Peter S. Gradeff
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Patent number: 4285971Abstract: Halogenated phenol esters of the formula ##STR1## wherein X represents chlorine or fluorine and R represents hydrogen, alkyl of 1 to 22 carbon atoms, alkenyl of 2 to 22 carbon atoms, benzyl which is unsubstituted or substituted by chlorine or bromine atoms, or phenyl which is unsubstituted or substituted by alkyl or alkoxy, each of 1 to 4 carbon atoms, carboxyl, chlorine and/or bromine. The invention also relates to a method of protecting organic and inorganic material from attack by microorganisms, in particular of providing textiles with an antimicrobial and rotproof finish, of protecting wood from rot, and of preventing the formation of slime in the manufacture of paper.Type: GrantFiled: July 30, 1979Date of Patent: August 25, 1981Assignee: Ciba-Geigy CorporationInventor: Rene Muntwyler
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Patent number: 4275219Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: INTERx Research CorporationInventor: Jacob A. Zupan
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Patent number: 4271311Abstract: Esterification of phenolic compounds which comprises reacting a phenolic compound and a carboxylic acid using a catalyst consisting essentially of an alkali metal compound and a boron compound wherein said alkali metal compound is at least one member selected from the group consisting of alkali metal salts of boric acid, alkali metal polyborates, alkali metal hydroxides, and alkali metal borohydrides and said boron compound is at least one member selected from the group consisting of boric acid, boric anhydride, alkali metal polyborates, alkali metal salts of boric acid and alkali metal borohydrides.Type: GrantFiled: July 13, 1979Date of Patent: June 2, 1981Assignee: Standard Oil Company (Indiana)Inventors: William W. Knickmeyer, James Spanswick, James R. Stephens
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Patent number: 4266080Abstract: Perfluoroalkyl compounds containing ether groups have the formulaR.sub.f R.sub.1 SCH.sub.2 CH.sub.2 O T Zwherein R.sub.f is a perfluoroalkyl, R.sub.1 is alkylene or alkyleneoxy or aminoalkylene, T is alkylene, and Z is hydrogen; hydroxy; NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 each is alkyl or together with nitrogen form a heterocyclic ring; N.sup.+ R.sub.3 R.sub.4 (R.sub.5)X.sub.z.sup.-y, where R.sub.5 is hydrogen, oxide, alkyl, or substituted alkyl, X is an anion, and y is 1 or 2; z is 0 or 1 or is --OCH.sub.2 CH.sub.2 SR.sub.1 R.sub.f ; can be prepared directly by free-radical catalyzed addition of a perfluoroalkylthiol to a vinyl ether or subsequent reaction. These compounds are useful as surfactants and oil spill collecting agents.Type: GrantFiled: February 2, 1978Date of Patent: May 5, 1981Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Karl F. Mueller
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Patent number: 4260803Abstract: p- and o-chloromethylbenzoic acid phenyl esters and thiophenyl esters of the formula ##STR1## wherein X represents oxygen or sulfur and R the radical of a mononuclear or polynuclear phenol or thiophenol which is unsubstituted or which bears additional substituents which may include the substituent ##STR2## wherein X is as above. The components can be produced by reacting p- or o-chloromethylbenzoyl chloride with univalent or polyvalent, mononuclear or polynuclear phenols or the thiophenols in the presence of inert solvents and tertiary amines in a catalytic or stoichiometric amount, amides in a catalytic amount, or in an aqueous alkaline medium.Type: GrantFiled: July 2, 1979Date of Patent: April 7, 1981Assignee: Dynamit Nobel AktiengesellschaftInventor: Egon N. Petersen
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Patent number: 4249019Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.Type: GrantFiled: November 13, 1978Date of Patent: February 3, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
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Patent number: 4244969Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.Type: GrantFiled: February 13, 1975Date of Patent: January 13, 1981Assignee: Aktiebolaget HassleInventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
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Patent number: 4230849Abstract: A process for the activation of carboxylic acids which is useful for the subsequent conversion of said carboxylic acids into their corresponding amides or esters, based on reacting a 2-oxazolidinone with phosphorus pentachloride and subsequent addition of a salt of the carboxylic acid to be activated.Type: GrantFiled: July 2, 1979Date of Patent: October 28, 1980Assignee: Antibioticos, S.A.Inventors: Antonio L. Palomo Coll, Jose Diago Meseguer
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4226783Abstract: A process for .alpha.-chlorination of side chains of electronegatively substituted aromatic compounds with dichlorine monoxide.Type: GrantFiled: July 3, 1978Date of Patent: October 7, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh
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Patent number: 4227015Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.Type: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: 4225619Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is perfluoroalkyl of 1 to 8 carbon atoms or 2,2,3,3-tetrafluoro-cyclobutyl,R.sub.2 and R.sub.4, which may be identical to or different from each other, are each hydrogen, alkyl of 1 to 10 carbon atoms, aliphatic acyl of 2 to 18 carbon atoms, benzoyl, salicyloyl or phenylacetyl, andR.sub.3 and R.sub.5, which may be identical to or different from each other, are each alkyl of 3 to 18 carbon atoms, halogen, nitro, p-toluenesulfonyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclododecyl, methylcyclohexyl, dimethylcyclohexyl, benzyl, methylthio or ##STR2## where R.sub.1, R.sub.2 and R.sub.4 have the meanings previously defined,Q is --CH.sub.2 -- or --S--, andG is R.sub.5, as above defined, orQ is R.sub.3, as above defined, andG is --CH.sub.2 -- or --S--,R.sub.3 may, in addition, also be hydroxyl, methoxy, methyl or cyano, andR.sub.5 may also be methyl, orone of substituents R.sub.3 and R.sub.Type: GrantFiled: March 19, 1979Date of Patent: September 30, 1980Assignee: Boehringer Ingelheim GmBHInventors: Rolf Brickl, Hans Eberhardt, Karl-Richard Appel, Uwe Lechner, Walter Merk
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Patent number: 4200763Abstract: Isopropylphenyl esters are converted to di- or tri-hydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.Type: GrantFiled: May 11, 1979Date of Patent: April 29, 1980Assignee: The Upjohn CompanyInventor: Sheng-Hong A. Dai
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Patent number: 4182761Abstract: Acyloxy-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared either by esterification of the corresponding hydroxy-substituted compounds or by reacting a haloalkyl diketone with an alkali metal salt of an acyloxy-substituted phenol.Type: GrantFiled: June 7, 1978Date of Patent: January 8, 1980Assignee: Sterling Drug Inc.Inventors: Joseph C. Collins, Guy D. Diana
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Patent number: 4173706Abstract: A novel process for producing fluorinated organic compounds containing a difluoromethylene group, essentially characterized by reacting organic compounds containing a carbonyl function with molybdenum hexafluoride at room temperature and under atmospheric pressure.Type: GrantFiled: April 6, 1978Date of Patent: November 6, 1979Assignee: Institute National de Recherche Chimique AppliqueeInventors: Francois Mathey, Jean Bensoam
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Patent number: 4164510Abstract: Isopropylphenyl esters are converted to di- or trihydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.Type: GrantFiled: February 21, 1978Date of Patent: August 14, 1979Assignee: The Upjohn CompanyInventor: Sheng-Hong A. Dai
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Patent number: 4139545Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: April 30, 1975Date of Patent: February 13, 1979Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
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Patent number: 4138581Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-.alpha.-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.Type: GrantFiled: February 2, 1976Date of Patent: February 6, 1979Assignee: Sterling Drugs Inc.Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway
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Patent number: 4129586Abstract: Compounds which contain azo or peroxide linkages as well as the radical of an ultraviolet light stabilizing group are described. These compounds function as polymerization initiators which cause an ultraviolet light stabilization group to be chemically bound to the polymer.Type: GrantFiled: June 6, 1977Date of Patent: December 12, 1978Assignee: Pennwalt CorporationInventors: Chester S. Sheppard, Ronald E. MacLeay
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Patent number: 4105787Abstract: This invention covers diacylated derivatives of .gamma.-glutamyl dopamine selected from the group consisting of ##STR1## where R is a C.sub.1 -C.sub.12 straight or branched chain alkyl radical, a phenyl ring or a substituted phenyl ring and R' is H or a C.sub.1 -C.sub.7 alkyl, and a pharmaceutically acceptable acid addition salt thereof.The compounds of this invention are useful to increase the renal blood flow by being administered to warm-blooded animals by clinically accepted routes of administration such as oral, parenteral, rectal and the like.Type: GrantFiled: May 3, 1977Date of Patent: August 8, 1978Assignee: Abbott LaboratoriesInventors: Peter H. Jones, Carroll W. Curs, Jaroslav Kyncl
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Patent number: 4102922Abstract: A method is provided for the removal of contaminating alkanes from the vaporized carbonylation products of a process wherein carboxylic acids are produced by the reaction in the liquid phase of an alcohol or an ester, halide or ether derivative of said alcohol with carbon monoxide in the presence of a catalyst system containing a rhodium or iridium component and an iodine or bromine component. The method involves distillation of the alkane-containing vaporized carbonylation products, phase separation of the overhead from said distillation, further distillation of a slipstream of the resulting heavy phase using carbon monoxide as stripping gas and removal of the alkanes as the bottoms stream from the latter distillation.Type: GrantFiled: October 12, 1976Date of Patent: July 25, 1978Assignee: Monsanto CompanyInventor: Jerry L. Price
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Patent number: 4088783Abstract: Compounds of the formula: ##STR1## wherein R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C.sub.1 -C.sub.5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an ##STR2## WHEREIN R is as defined above and R.sub.3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion, are extremely valuable in the treatment of conditions responsive to sympathomimetic agents.The compounds of this invention find therapeutic application to warm-blooded animals (e.g., humans) in the management of asthma, nasal congestion and as decongestants, vasoconstrictors, mydriatic agents, and anti-glaucomatous agents in the practice of opthalmology.Type: GrantFiled: October 18, 1976Date of Patent: May 9, 1978Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Sun-Shine Yuan