Abstract: Isomerization of an unsymmetrical ketoxime ether is effected using at least one Lewis acid selected from titanium chloride, titanium bromide, aluminum chloride, aluminum bromide, boron chloride, and boron bromide as isomerizing agents. Examples of the Lewis acid are titanium tetrachloride, titanium trichloride, aluminum trichloride, aluminum tribromide, boron trichloride, and boron tribromide. The ketoxime ether is preferably an anti-isomer or a syn-isomer of a compound represented by the formula (I) or a mixture of the anti-isomer and the syn-isomer: ##STR1## wherein R.sub.1 represents an aryl group, an aralkyl group or an alkyl group and R.sub.2 and R.sub.3 each represents an aralkyl group or an alkyl group, with a proviso that R.sub.1 and R.sub.2 are not identical.
Abstract: A group of functionalized triamine chelants and their derivatives that form complexes with radioactive metal ions are disclosed. The complexes can be covalently attached to a protein or an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes.
Type:
Grant
Filed:
April 26, 1989
Date of Patent:
March 31, 1992
Assignee:
The Curators of the University of Missouri
Inventors:
David E. Troutner, Christy S. John, Maroor R. A. Pillai
Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
Type:
Grant
Filed:
August 21, 1989
Date of Patent:
September 10, 1991
Assignee:
Merck & Co., Inc.
Inventors:
Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
Abstract: Disclosed are a process for producing a substituted phenoxyacetaldehyde oxime of the formula: ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises allowing a substituted phenoxyacetaldehyde dialkylacetal of the formula: ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification) to react with hydroxylamine; a process for producing a substituted phenoxyethylamine of the formula: ##STR3## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises reducing a substituted phenoxyacetaldehyde oxime of the formula (II) with hydrogen in the presence of a Raney-nickel catalyst; and a substituted phenoxyacetaldehyde oxime of the formula: ##STR4## (wherein R.sup.1, R.sup.2 and R.sup.6 are as defned in the specification).
Type:
Grant
Filed:
October 26, 1990
Date of Patent:
July 9, 1991
Assignees:
Ube Industries Ltd., Sankyo Co., Ltd.
Inventors:
Kikuo Ataka, Koji Imaoka, Kiyotaka Yoshii, Kenji Hirotsu
Abstract: The invention relates to a process for preparing oximes starting from saturated primary (cyclo)aliphatic amines optionally substituted by groups which are inert under the reaction conditions, by reacting the saturated primary amine with oxygen, the reaction being conducted in the liquid phase in the presence of at least a catalyst based on compounds belonging to Group IV B of the Periodic System, thereby obtaining the corresponding aliphatic and cycloaliphatic oximes.
Abstract: 2-Cyclohexylpropanal derivatives are disclosed. The derivatives are represented by the following formula (I): ##STR1## wherein P is a hydrogen atom and Q represents a group --CH.dbd.N--OH or a group --CH(OR).sub.2, wherein each R represents a lower alkyl group or two R's together form a lower alkylene group which may have a lower alkyl substituent, or P and Q together form a group ##STR2## wherein R' is a lower alkyl group. The compounds possess floral, fruity, or green odors and are useful for preparing perfume compositions.
Type:
Grant
Filed:
August 29, 1989
Date of Patent:
December 18, 1990
Assignee:
Kao Corporation
Inventors:
Junji Koshino, Yoshiaki Fujikura, Manabu Fujita, Nao Toi
Abstract: The invention concerns a catalytic process for the manufacture of oximes by ammoximation of the corresponding carbonyl compounds, characterized in that the catalyst is a solid composition consisting of silicon, titanium and oxygen, chemically combined with each other, and in that the titanium amount, expressed as TiO.sub.2, ranges from 1 to 95% by weight, the XR diffractogam of said composition being a smooth-trend line (halo), typical of the amorphous solids.
Type:
Grant
Filed:
September 15, 1989
Date of Patent:
November 6, 1990
Assignee:
Montedipe, S.p.A.
Inventors:
Mario Padovan, Fausto Genoni, Giuseppe Leofanti, Guido Petrini, Paolo Roffia, Alberto Cesana
Abstract: A process for preparing an oxime, which comprises reacting a ketone or an aldehyde with nitrogen monoxide and hydrogen in the presence of a platinum group metal catalyst to form the corresponding oxime.
Abstract: A process for producing an oxime derivative, which comprises protecting the hydroxyimino group of an oxime compound with a protecting agent, subjecting the protected oxime compound to a given reaction, and thereafter deprotecting the reaction product, wherein a 2-alkenylating agent is used as the protecting agent.
Abstract: A useful brain perfusion imaging agent comprises ##STR1## wherein R completes a four or five member ring. The agent is stable in vitro permitting its use up to six to eight hours after preparation.
Abstract: The invention relates to a process of producing ketoximes, characterized in that a secondary alcohol, corresponding to the desired ketoxime, is partially oxidated in the liquid phase with O.sub.2, an oxidated mixture being thereby formed, which contains an excess of unreacted alcohol, the ketone corresponding to said alcohol, and H.sub.2 O.sub.2, and that said oxidated mixture is directly reacted with NH.sub.3 in the liquid phase (without isolating the alcohol, the ketone and H.sub.2 O.sub.2) in the presence of an ammoximation catalyst.
Type:
Grant
Filed:
July 25, 1988
Date of Patent:
January 16, 1990
Assignee:
Montedipe S.p.A.
Inventors:
Paolo Roffia, Giuseppe Paparatto, Alberto Cesana, Giorgio Tauszik
Abstract: Dihaloformaldoximes of the formula: ##STR1## wherein R, X, X.sup.1 and Y are as defined herein having biocidal, fungicidal and pesticidal activity are disclosed.
Abstract: Pesticidally active novel .alpha.-methylsulphonylbenzaldoxime and their carbamates of the formula ##STR1## in which Y represents H or --CO--NH--R,R represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 5 halogen atoms, cyanoalkyl having 1 to 6 carbon atoms in the alkyl part, tosyl, benzyl, cycloalkyl having 5 to 7 carbon atoms which is optionally monosubstituted to pentasubstituted by alkyl having 1 to 4 carbon atoms, or phenyl which is optionally monosubstituted to pentasubstituted by alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl or halogenoalkoxy in each case having 1 to 4 carbon atoms and 1 to 5 halogen atoms, and halogen, these substituents being identical or different,Hal represents halogen, andx represents hydrogen or halogen.
Type:
Grant
Filed:
April 8, 1988
Date of Patent:
August 22, 1989
Assignee:
Bayer Aktiengesellschaft
Inventors:
Christa Fest, Gerd Hanssler, Wilhelm Brandes
Abstract: Novel propylene amine oxime ligands have the formula ##STR1## where each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 or R.sub.8 may be hydrogen, hydrocarbon, carboxyl, amine, amide or nitrile, provided that, if R.sub.1 is the same as R.sub.9 and R.sub.2 is the same as R.sub.7, then R.sub.8 is not H. These unsymmetrical ligands form complexes with Technetium-99m which are capable, on injection into mammals, of crossing the blood-brain barrier and of being retained in the brain for a time to permit diagnosis.
Abstract: The invention concerns a catalytic process for the manufacture of oximes by reaction, in the liquid phase, of the corresponding carbonylic compounds with NH.sub.3 and H.sub.2 O.sub.2, in which process the catalyst is substantially consisting of a crystalline material with a zeolitic structure containing silicon and titanium, subjected, before use, to an activating treatment with H.sub.2 O.sub.2.
Type:
Grant
Filed:
June 8, 1987
Date of Patent:
December 27, 1988
Assignee:
Montedipe S.p.A.
Inventors:
Paolo Roffia, Mario Padovan, Giuseppe Leofanti, Maria A. Mantegazza, Giordano De Alberti, Giorgio R. Tauszik
Abstract: A family of propylene amine oxime ligands has the formula 2 ##STR1## wherein preferably R.sup.1 is Cl-C4 alkyl or phenyl and each of R, R.sup.2, R.sup.3 and R.sup.4 is H or Cl-C4 alkyl. The technetium-99m complexes of these ligands are lipophilic neutral complexes useful as diagnostic radiopharmaceuticals and particularly for brain scanning. The ligands show stereoisomerism. The preparation and properties of the dl- and meso-stereoisomers, and of the d- and l-enantiomers, are described. The l-enantiomer and the dl-stereoisomer of the preferred compound (2, R=R.sup.1 =R.sup.2 =CH.sub.3, R.sup.3 =R.sup.4 =H) show good retention in the brain.
Type:
Grant
Filed:
March 11, 1986
Date of Patent:
December 6, 1988
Assignee:
Amersham International plc
Inventors:
Lewis R. Canning, David P. Nowotnik, Rudi D. Neirinckx, Ian M. Piper
Abstract: Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group].
Abstract: The invention relates to compounds of antihypertensive and antithrombotic activity of the formula or its pharmaceutically acceptable salt: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, or lower alkoxyphenyl,R.sup.2 is hydrogen or lower alkyl,R.sup.4 is lower alkyl,R.sup.6 is hydrogen or lower alkyl,R.sup.7 is lower alkyl which is optionally substituted by hydroxy or lower alkanoyloxy, andR.sup.10 is hydrogen or lower alkyl which is optionally substituted by carboxy or esterified carboxy.
Abstract: A compound of the formula: ##STR1## wherein R is a hydrogen atom, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkenyloxy group, a C.sub.3 -C.sub.4 alkynyloxy group, a C.sub.1 -C.sub.4 alkylthio group, a dichlorocyclopropylmethoxy group or a methyldichlorocyclopropylmethoxy group, X is a chlorine atom or a bromine atom and Y is a hydrogen atom, a fluorine atom or a chlorine atom, which is useful as a herbicide.
Type:
Grant
Filed:
February 3, 1987
Date of Patent:
April 26, 1988
Assignee:
Sumitomo Chemical Company, Limited
Inventors:
Toru Haga, Eiki Nagano, Masayuki Takase, Ryo Sato
Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.
Abstract: Ortho-aminomethylphenol compounds of the formula: ##STR1## wherein X is hydrogen or halogen, R is hydrogen or alkyl having 1 to 4 carbon atoms and A is alkyl having 1 to 4 carbon atoms, phenyl, benzyl or a bivalent radical selected from --(CH.sub.2).sub.3 -- and --O(CH.sub.2).sub.2 -- and joined together with the 3 or 5 position of the benzene nucleus to form a bicycle, or pharmaceutically acceptable salts thereof, a method of preparing said compounds and a pharmaceutical composition containing said compounds, are disclosed.Such compounds exhibit antiinflammatory, analgesic, diuretic and antihypertensive activities, so they are useful in the treatment for diseases caused by inflammation, edema or hypertension.
Abstract: 2-(1'-Hydroxyimino-ethyl)-1,3,3,4,4-pentamethylcyclopentene is a novel odorant. A process for its manufacture, fragrance compositions containing same and methods for improving fragrance compositions by adding same thereto are disclosed.
Abstract: Carbon-carbon double bonds are hydrogenated selectively in a compound containing a reducible, nitrogen-containing group if the hydrogenation is carried out in the presence of a ruthenium complex catalyst. Also disclosed are new ruthenium complexes for use in such selective hydrogenation.
Type:
Grant
Filed:
October 11, 1984
Date of Patent:
June 16, 1987
Assignee:
Bayer Aktiengesellschaft
Inventors:
Paul Fiedler, Rudolf Braden, Hartmuth Buding
Abstract: The invention concerns the novel odorants 2,2,4-trimethyl-1-phenyl-3-pentanone oxime, 2,4,4-trimethyl-5-phenyl-3-hexanone oxime and 2,4,4-trimethyl-5-phenyl-3-heptanone oxime, a process for making same, odorant compositions containing same and methods for preparing improved odorant compositions using same.
Abstract: Improved processes for the conversion to oximes by selective oxidation, in the vapor phase, of saturated primary aliphatic or alicyclic amines having 2 to 12 carbon atoms especially cyclohexylamine to cyclohexanone oxime with elemental oxygen, in a reaction zone, in the presence of an effective amount of a catalyst comprising an oxygen-containing tungsten compound and alumina by (1) periodically regenerating the oxygen-containing tungsten catalyst by heating same at about 250.degree. C.-300.degree. C. in the presence of elemental oxygen, or (2) maintaining the temperature of the oxygen-containing tungsten catalyst in a range of about 100.degree. C.-145.degree. C. or (3) employing higher mol fractions of oxygen and of amine in a range of about 0.2-0.4 in the vapor phase are disclosed. An improved method of preparing an oxygen-containing tungsten on an alumina catalyst is also disclosed.
Type:
Grant
Filed:
December 20, 1982
Date of Patent:
December 24, 1985
Assignee:
Allied Corporation
Inventors:
Jean Yamanis, Emery J. Carlson, John N. Armor
Abstract: A process for the production of oximes which comprises contacting, in the vapor phase, a primary saturated aliphatic or alicyclic amine of 2 to 12 carbon atoms with an elemental oxygen gas in the presence of an effective amount of a catalyst comprising an alumina or oxygen-containing tungsten substance on a metal oxide support using temperatures between about 130.degree. and 230.degree. C. at atmospheric pressure is disclosed. Preferred alumina catalysts are alumina xerogels, .gamma.-alumina and acidic, fluorinated alumina. Preferred oxygen-containing tungsten catalysts are WO.sub.3 on .gamma.-alumina or WO.sub.3 on alumina xerogels.
Abstract: Cyclobutanone oxime carbamates of the formula ##STR1## wherein n is 1 to 5 and X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio. A process for obtaining the compounds of the formula I and their use in pest control as well as the cyclobutanone oximes used as intermediates are described.
Abstract: 1,2-Dihydropyrido[3,4-b]pyrazines are provided which possess antifungal and anticancer activity. The compounds have the structure: ##STR1## wherein x has a value of 1, 2 or 3; R.sub.1 is a lower alkyl group, R.sub.2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, alkenyl radicals having from about two to about 15 carbon atoms, cycloalkyl radicals having from about three to about 20 carbon atoms, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, a halogen radical, provided that when x has a value of 1 and R.sub.2 is in the para position and R.sub.3 and R.sub.4 are both hydrogen, R.sub.
Type:
Grant
Filed:
March 3, 1982
Date of Patent:
May 22, 1984
Assignee:
Southern Research Institute
Inventors:
Carroll G. Temple, Jr., John A. Montgomery, Robert D. Elliott, Glynn P. Wheeler
Abstract: The invention is preemergence herbicidal methods employing novel dinitroanilines for control of certain grasses and broadleaf weeds in the presence of graminaceous crops, especially rice.
Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.
Abstract: Acetaldehyde oxime, a commercially useful intermediate in the production of pesticides, is prepared by oximating acetaldehyde with an aqueous hydroxylamine-containing solution to form an aqueous oximation reaction mixture and recovering acetaldehyde oxime from the aqueous oximation reaction mixture by distilling a mixture of acetaldehyde oxime and water directly from the aqueous oximation reaction mixture.
Type:
Grant
Filed:
December 18, 1980
Date of Patent:
April 6, 1982
Assignee:
Allied Corporation
Inventors:
John H. Bonfield, Stephen E. Belsky, Donald Pickens
Abstract: Processes for the treatment of toxic and malodorous wastestreams produced in the manufacture of methomyl and related compounds are provided. In these processes, methomyl and related compounds are oxidized with chlorine at a temperature of at least about 70.degree. C., preferably in the range of about 70.degree.-95.degree. C., preferably under acidic conditions, and then the resulting intermediate compounds are hydrolyzed with NaOH, KOH or Ca(OH).sub.2 at a temperature of at least about 70.degree. C., preferably in the range of about 70.degree.-100.degree. C., and at a reaction medium pH of at least about 9.5. The process is preferably carried out continuously.
Abstract: This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.
Type:
Grant
Filed:
December 30, 1980
Date of Patent:
December 8, 1981
Assignee:
Polaroid Corporation
Inventors:
James R. Bartels-Keith, Eva R. Karger, Jean B. Rogers
Abstract: A method for the preparation of 3,3,7-trimethyl-2,9-dioxatricyclo[3.3.1.0.sup.4,7 ]nonane (lineatin, a general name), an aggregation pheromone of an ambrosia beetle, represented by the formula (I), ##STR1## which comprises reacting a keto lactone represented by the formula (II), ##STR2## with diisobutylaluminum hydride and subsequently, treating with an acid; and a method for the preparation of said keto lactone represented by the above formula (II), which comprises oxidizing a hydroxy lactone represented by the formula (III), ##STR3## with chromic acid.
Abstract: The present invention relates to certain novel substituted 2,6-dinitroaniline compounds. It further relates to certain preemergence herbicidal methods employing said novel dinitroanilines for the selective control of certain grasses and broadleaved weeds in the presence of graminaceous crops, especially rice. This invention also relates to the postemergence control of crabgrass and certain broadleaved weeds in the presence of established turf grasses.
Abstract: Oximes of propene trimers and propene tetramers are disclosed which are new compositions of matter. These oximes are useful as perfume components in, e.g., colognes and perfumes and as fragrances in detergents and cosmetics.
Abstract: Novel substituted 11-amino-undeca-4,8-dienal and 11-amino-undecanal aldehyde-derivatives of the formulae Ia ##STR1## in which R.sub.1 to R.sub.6, Y and m are as defined in patent claim 1, and processes for their preparation are described. The compounds of the formulae Ia and Ib can be catalytically hydrogenated to novel 1,11-diaminoundecanes, which, in turn, can be used, for example, for the preparation of polycondensation products, in particular transparent polyamides, or as curing agents for epoxide resins.
Abstract: Novel 4-monoalkylamino-benzaldehydes, 4-mono-alkylamino-alkanophenones, and 4-monoalkylamino-benzophenones, and derivatives and salts thereof, are disclosed which are useful as anti-atherosclerotic agents.
Abstract: A novel process of preparing ketoxime carbamate by forming a halogenated intermediate which is reacted with an alkali metal compound and an isocyanate.
Abstract: Polycyclic aziridines, such as 0-[2-(dimethylamino)ethyl]oxime of 1a,10b-dihydrodibenzo-[3,4,6,7]cyclohept[1,2-b]-N-methylazirin-6(1H)-one, useful for alleviating depression in mammals.