Oxy Containing Reactant Patents (Class 568/322)
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Patent number: 4474990Abstract: Substantially pure p-phenoxybenzoyl compounds are prepared by reacting diphenyl ether and an appropriate acyl compound in the presence of hydrogen fluoride. The resulting p-phenoxyaryl alkyl ketone can be converted into p-phenoxybenzoic acid or salts thereof, p-phenoxybenzoyl halide or lower alkyl p-phenoxybenzoate for use preparing homo- and copolymers containing a p-phenoxybenzoyl repeating unit.Type: GrantFiled: November 24, 1982Date of Patent: October 2, 1984Assignee: Raychem CorporationInventor: Viktors Jansons
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Patent number: 4460793Abstract: A process for the production of a monochloromethyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkinyl or aryl radical, orR.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted carbocyclic ring,comprising reacting a 1,1-dichloroalkene of the formula ##STR2## with a phenolate of the formula ##STR3## in which R.sup.4 each independently is a halogen atom, a nitro group, or an optionally substituted alkyl, alkoxy or aryl radical,n is 0, 1, 2 or 3, andM is one equivalent of an alkali metal ion or alkaline earth metal ion,thereby to obtain a phenyl ether intermediate, and then subjecting the phenyl ether intermediate to an acid hydrolysis. The products are useful as intermediates in the synthesis of fungicides.Type: GrantFiled: December 11, 1981Date of Patent: July 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4454350Abstract: A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: June 12, 1984Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Michel Desbois
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Patent number: 4453011Abstract: .alpha.,.beta.-and .beta.,.gamma.-unsaturated ketones of formula ##STR1## possessing a double bond in one of the positions indicated by the dashed lines and wherein R and R.sup.1 have the meaning given above and index n stands for integer 1 or 2, are obtained by a process which consists in treating with a strong base in an inert organic solvent a diallyl carbinol of formula ##STR2## wherein symbol R represents a primary, secondary or tertiary alkyl radical, or a substituted or unsubstituted phenyl radical, and symbol R.sup.1 represents a hydrogen atom or an alkyl radical.Type: GrantFiled: August 6, 1982Date of Patent: June 5, 1984Assignee: Firmenich SAInventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
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Patent number: 4453012Abstract: A process for the preparation of phenyl ketones, characterized in that, in a first stage, a halo- or trihalomethylbenzene is reacted with a trihalomethylated aliphatic or aromatic compound in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent, and in that, in a second stage, the resultant product is hydrolyzed. The products are used as intermediates in the synthesis of compounds having a pharmaceutical or phytosanitary (e.g., herbicidal) activity.Type: GrantFiled: June 28, 1982Date of Patent: June 5, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4453010Abstract: Production of a hydroxy arylophenone by reacting an aromatic carboxylic acid Ar(--CO.sub.2 H).sub.p where Ar is an aromatic radical, (--CO.sub.2 H) is an aromatic carboxylic acid group, and p is 1 or 2 with an aromatic compound H--Ar'--OH where Ar' is an aromatic radical and --H and --OH are aromatically bound para to each other in a benzenoid ring, in the presence of an alkyl sulphonic acid, particularly methane sulphonic acid, to produce a hydroxy arylophenone of formula Ar(--CO--Ar'--OH).sub.p where the carbonyl and hydroxyl groups are para to each other in the hydroxyl-containing benzenoid ring of Ar'. The production of the hydroxy arylophenone proceeds through the intermediate ester (H--Ar'--O--CO--).sub.p Ar and the production of the hydroxy arylophenone starting from the ester is also claimed.Type: GrantFiled: January 20, 1982Date of Patent: June 5, 1984Assignee: Imperial Chemical Industries PLCInventor: Philip A. Staniland
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Patent number: 4446078Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl ketones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a carboxylic acid, a precursor or a derivative of this acid in the presence of boron trifluoride in such an amount that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: May 1, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4438043Abstract: A process for the preparation of di- or trifluoromethoxyphenyl ketones or di- or trifluoromethylthiophenyl ketones, characterized in that, in a first stage, a di- or trihalomethoxybenzene or a di- or trihalomethylthiobenzene is reacted with a trihalomethylated aromatic or aliphatic compound in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent and in that, in a second stage, the product of the first stage is hydrolyzed. The resultant products are useful as intermediates in the synthesis of compounds having a pharmaceutical or phytosanitary (e.g., herbicidal) activity.Type: GrantFiled: June 28, 1982Date of Patent: March 20, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4438269Abstract: The novel compound 4-dimethylaminopyridinium chlorochromate has been found to be an effective oxidizing agent for converting alcohols to their respective aldehydes or ketones, especially for the selective conversion of allylic and benzylic alchols to their corresponding aldehydes and ketones.Type: GrantFiled: August 9, 1982Date of Patent: March 20, 1984Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr.
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Patent number: 4399281Abstract: 2,2'-Bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.Type: GrantFiled: September 22, 1981Date of Patent: August 16, 1983Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr.
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Patent number: 4399309Abstract: A process for the preparation of a 1-aryloxy-methyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted alkyl, alkenyl, alkynyl or optionally substituted aryl, orR.sup.1 and R.sup.2 together are an alkylene chain,R.sup.4 each independently is halogen, alkyl, alkoxy, optionally substituted aryl or nitro, andn is 0, 1, 2 or 3,comprising hydrolyzing a 1-halogeno-2-aryloxy-1-alkene of the formula ##STR2## in which Hal is chlorine or bromine, under acidic conditions at a temperature from about 20.degree. to 150.degree. C. until it is about 95 to 100% complete, adding a base, and then bringing the reaction to completion under weakly alkaline conditions at about 20.degree. to 150.degree. C. Advantageously all stages of the reaction are effected in a single vessel at a temperature from about 40.degree. to 100.degree. C.Type: GrantFiled: December 30, 1981Date of Patent: August 16, 1983Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Jorg Stetter, Dieter Arlt
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Patent number: 4398043Abstract: A process for preparing cyclopentenolones of the formula: ##STR1## wherein R.sub.1 is a straight, branched or cyclic alkyl group having not more than 6 carbon atoms, a straight, branched or cyclic alkenyl group having not more than 6 carbon atoms, a straight or branched alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## wherein R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.Type: GrantFiled: November 23, 1981Date of Patent: August 9, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Yukihisa Takisawa, Hiroshi Yamachika
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Patent number: 4393242Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.Type: GrantFiled: July 6, 1981Date of Patent: July 12, 1983Assignee: Merck & Co., Inc.Inventor: Meyer Sletzinger
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Patent number: 4380673Abstract: A secondary alcohol dissolved in a C.sub.12 to C.sub.20 paraffinic hydrocarbon substantially free of aromatics and of sulfur is dehydrogenated to the corresponding ketone at a temperature of 170.degree.-230.degree. C. in the presence of a catalyst of the Raney nickel type containing from 0.1 to 10% by weight of an additional metal consisting of copper, silver, gold, tin, lead, zinc, cadmium, indium or germanium, the ketone being preferably removed, as it is formed, from the reaction medium. A catalyst for use in the present process is provided.Type: GrantFiled: June 26, 1981Date of Patent: April 19, 1983Assignee: Institut Francais Du PetroleInventors: Jean-Paul Bournonville, Roger Snappe, Jean Miquel, Germain Martino
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Patent number: 4358617Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.Type: GrantFiled: September 25, 1981Date of Patent: November 9, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, John B. Hall
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Patent number: 4358409Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.Type: GrantFiled: April 16, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4356326Abstract: A process for producing 3-oxocyclopentenes which comprises treating a furan-carbinol of the formula: ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl group having not more than 6 carbon atoms, an alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom in an aqueous medium in the presence or absence of a catalyst at a pH of 3 to 6.5 to give the corresponding 3-oxocyclopentene of the formula: ##STR3## wherein R.sub.1 is as defined above.Type: GrantFiled: December 5, 1980Date of Patent: October 26, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4337360Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.Type: GrantFiled: September 28, 1979Date of Patent: June 29, 1982Assignee: Merck & Co., Inc.Inventor: Meyer Sletzinger
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Patent number: 4335263Abstract: A process for preparing an aromatic aldehyde represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a lower alkyl group or R.sub.1 and R.sub.2 may jointly form an alkylene group, provided that R.sub.1 and R.sub.2 do not represent a hydrogen atom at the same time.Type: GrantFiled: December 19, 1980Date of Patent: June 15, 1982Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
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Patent number: 4313959Abstract: (Arylmethyl)phenyl-aminocyclohexanols, (arylmethyl)phenyl aminocyclohexenes and (arylmethyl)phenyl-aminocyclohexanes and methods of preparing same are described. These compounds are useful as antidepressants and anticonvulsants.Compounds 8-[2-(phenylmethyl)phenyl]-1,4-dioxaspiro[4,5]-decan-8-ol, 1-[2-(phenylmethyl)phenyl]-4-oxocyclohexanol, and 1-[2-(phenylmethyl)phenyl]-4-oxocyclohexanol oxime, and methods of preparing same are also described. These compounds are useful as intermediates for preparing the antidepressant and anticonvulsant compounds.Type: GrantFiled: April 27, 1981Date of Patent: February 2, 1982Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm
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Patent number: 4304941Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a clay.Type: GrantFiled: August 1, 1980Date of Patent: December 8, 1981Assignee: Hoechst Roussel Pharmaceuticals, Inc.Inventors: Thomas B. K. Lee, Gregory M. Jobin
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Patent number: 4296226Abstract: Vinyl polymers with acetylacetoxy groups form the basis of polymer dispersions which are used as binding agent dispersions in paints, particularly suitable vinyl polymers are obtained by polymerizing an acetylacetoxy compound together with a least one further olefinically unsaturated compound, while using as acetylacetoxy compound an allyl ether derivative of the formula ##STR1## The copolymerization is carried out in particular in emulsion at a temperature in the range of from -30.degree. to 200.degree. C. As comonomers there are used especially vinyl esters and (meth-)acrylic acid esters. The polymerization is commonly effected in the presence of a radical-forming initiator and optionally in the presence of emulsifiers and protective colloids.Type: GrantFiled: July 9, 1980Date of Patent: October 20, 1981Assignee: Hoechst AktiengesellschaftInventors: Helmut Braun, Helmut Rinno, Karl J. Rauterkus
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Patent number: 4289909Abstract: Processes for preparing 1-dichloroacyl-4-(substituted phenoxy)benzenes and intermediates therefor. The processes are characterized by the use of certain catalysts, solvents and reaction conditions which afford improved yields and reaction products which can be purified by simple procedures (e.g. extraction, crystallization, etc.). The processes are especially applicable to manufacturing large quantities of the aforementioned compounds. The products are useful as mite ovacides.Type: GrantFiled: March 3, 1980Date of Patent: September 15, 1981Assignee: Chevron ResearchInventors: Francis J. Freenor, III, Barbara M. Koerber
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Patent number: 4288613Abstract: A method of synthesis of cyclopentanones comprising cyclizing a 4-pentenal, preferably under an ethylene atmosphere, in the presence of a catalytically effective amount of a cyclizing, rhodium(I) para-substituted triarylphosphine catalyst.Type: GrantFiled: December 3, 1979Date of Patent: September 8, 1981Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4282372Abstract: A novel process for producing cyclopentenolones, useful intermediates for producing agricultural chemicals and prostaglandins of the formula (I), ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl group, and R.sub.2 is a hydrogen atom, a lower alkyl, lower alkenyl or lower alkynyl group or a group of the formula, ##STR2## in which R.sub.4 is a hydrogen atom, a methyl group or a halogen atom), --CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.3 --CO.sub.2 R.sub.5, or --(CH.sub.2).sub.5 --CO.sub.2 R.sub.5 (in which R.sub.5 is a hydrogen atom or a lower alkyl group), but R.sub.1 and R.sub.2 are not a hydrogen atom at the same time, characterized in that said cyclopentenolones are derived from a starting material of the formula (III), ##STR3## through intermediates of the formulae (IV), (V) and (II), ##STR4## Many of the intermediates are novel compounds.Type: GrantFiled: October 30, 1979Date of Patent: August 4, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Matsuo, Kazunori Tsushima
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Patent number: 4271319Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.Type: GrantFiled: May 14, 1979Date of Patent: June 2, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4268691Abstract: By condensation of anisoyl chloride with 2,3-dichloroanisole under proper conditions, 2,3-dichloro-4-(hydroxybenzoyl)phenol is obtained directly.Type: GrantFiled: August 9, 1979Date of Patent: May 19, 1981Assignee: Abbott LaboratoriesInventors: Anthony K. L. Fung, Donald E. Morrison, Andre G. Pernet
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Patent number: 4247455Abstract: Novel yellow 2:1 azo-azo or azo-azomethine chrome complexed dye developer particularly useful in diffusion transfer photographic products and processes are presented by this invention. The novel 2:1 chrome complexed dye developers have the following structure: ##STR1## where each A is a phenyl radical; each B is a phenyl or nitrogen containing heterocyclic radical; Y is a silver halide developing substituent; each n is 0 or 1 but at least one n must be 1; R is N or CH; R.sup.1 is ##STR2## if R is N but R.sup.1 is --O-- if R is CH and X is a cation.Type: GrantFiled: August 2, 1978Date of Patent: January 27, 1981Assignee: Polaroid CorporationInventor: Elbert M. Idelson
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Patent number: 4230893Abstract: 4-Hydroxy-3-methoxyphenylacetone, an intermediate for methyldopa, has been prepared from reacting two moles of guaiacol and one mole of a 2-alkoxy propanol followed by basic elimination to form the enol ether of 4-hydroxy-3-methoxy phenyl acetone. The enol ether is subsequently converted to 4-hydroxy-3-methoxy phenyl acetone upon treatment with a strong acid.Type: GrantFiled: September 13, 1979Date of Patent: October 28, 1980Assignee: Merck & Co., Inc.Inventor: George Gal
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Patent number: 4228085Abstract: The present invention relates to a novel organic compound, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone, and(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone.Type: GrantFiled: May 14, 1979Date of Patent: October 14, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4221713Abstract: Cyclisation substrates are disclosed of the formula: ##STR1## wherein: (a) R.sub.1 is H or alkyl of one to four carbon atoms;(b) R.sub.2 is H or alkyl of one to four carbon atoms, with the proviso that R.sub.1 is H when R.sub.2 is alkyl, and with the proviso that R.sub.2 is H when R.sub.1 is alkyl;(c) R.sub.3 is a suitable leaving group selected from the group consisting of hydroxy, alkoxy of one to four carbons, alkoxyalkoxy of two to four carbons, acyloxy of one to about seven carbon atoms, and trialkylsilyloxy of less than fifteen carbons;(d) R.sub.4 is methyl; and(e) R.sub.5(1) and R.sub.Type: GrantFiled: October 23, 1978Date of Patent: September 9, 1980Assignee: Akzona IncorporatedInventors: Filippus J. Zeelen, Marinus B. Groen
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Patent number: 4218472Abstract: New geminally disubstituted indenes are of general formula I ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together form a direct bond or an alkylene group --(CH.sub.2).sub.n --, in which n is an integer from 1 to 4, R.sup.3 is hydrogen, C.sub.1-3 -alkoxy or halogen, and each of R.sup.4 and R.sup.5 is hydrogen or C.sub.1-4 -lower alkyl, or R.sup.4 and R.sup.5 together form an alkylene group --(CH.sub.2).sub.m --, in which m is an integer from 3 to 6; and the corresponding amine oxides, quaternary ammonium compounds and salts with physiologically acceptable acids.The indenes find use in treating incontinence, as a mucous membrane decongestant, as a blood pressure reducing agent, as vasocostrictor or as an anti-reserpine agent.The indenes may be prepared by processes known per se involving(a) synthesing the side chain --CH(OH)CH.sub.2 NR.sup.4 R.sup.Type: GrantFiled: August 1, 1978Date of Patent: August 19, 1980Assignee: AB KabiInventors: Aake N. Joensson, Tomas G. Kempe, Lembit Mikiver, Bengt A. Sparf
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4202840Abstract: Compounds having the following structural formula ##STR1## wherein R is alkyl which are useful as herbicides.Type: GrantFiled: September 29, 1978Date of Patent: May 13, 1980Assignee: Stauffer Chemical CompanyInventors: Reed A. Gray, Chien K. Tseng, Ronald J. Rusay