Three-membered Alicyclic Ring Containing Patents (Class 558/434)
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Patent number: 5380911Abstract: An improved manufacturing procedure for the preparation and isolation of cyclopropylnitrile is provided. 4-Halobutyronitrile is reacted with an alkali metal base in the presence of an aprotic polar solvent, an inorganic salt and a catalytic amount of water at an elevated temperature. The reaction product cyclopropylnitrile is isolated by azeotropic distillation.Type: GrantFiled: December 2, 1993Date of Patent: January 10, 1995Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5336670Abstract: Compounds of the formula ##STR1## wherein X is hydrogen, halogen or an optionally substituted alkyl, Y is selected from the group consisting of hydrogen, halogen optionally substituted alkyl, an optionally substituted aryl or arylalkyl, --(CH.sub.2).sub.m Si (Alk.sub.1).sub.3, --(CH.sub.2).sub.n OAlk.sub.2 or --(CH.sub.2).sub.p SAlk.sub.3, m, n and p are an integer from 0 to 6, Alk.sub.1, Alk.sub.2 and Alk.sub.3 are alkyl and R is alkyl of 1 to 18 carbon atoms or the remainder of an alcohol used in the pyrethrinoid series having pesticide properties.Type: GrantFiled: December 17, 1992Date of Patent: August 9, 1994Assignee: Roussel-UclafInventors: Marc Benoit, Jean-Pierre Demoute, Jean-Marc Girodeau
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Patent number: 5334745Abstract: 3-Aminopropionitriles of the general formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 independently of one another are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.8 -aminoalkyl, C.sub.1 -C.sub.8 -cyanoalkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.7 -C.sub.20 -aralkyl or aryl,are prepared by a process in which an amine of the general formula II ##STR2## is reacted with an acrylonitrile of the general formula III ##STR3## where the substituents have the abovementioned meanings, in a molar ratio of from 0.9:1 to 100:1 over a heterogeneous catalyst at from 40.degree. to 200.degree. C. and from 1 to 350 bar.Type: GrantFiled: May 28, 1993Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Martin Brudermueller, Tom Witzel, Franz Merger
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Patent number: 5332825Abstract: This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5332826Abstract: This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5260285Abstract: Novel substituted imidazopyridazines of formula (I) which are useful as angiotensin II antagonists, are disclosed.Type: GrantFiled: November 25, 1991Date of Patent: November 9, 1993Assignee: Merck & Co., Inc.Inventors: Eric E. Allen, William J. Greenlee, Prasun K. Chakravarty, Malcolm MacCoss, Arthur A. Patchett, Thomas F. Walsh
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Patent number: 5241087Abstract: A method of enantiomerically enriching chiral cyanohydrins is disclosed that involves selective cleavage of the unwanted enantiomer into its cleavage products HCN and the corresponding aldehyde or ketone by use of an enantioselective dehydrocyanation catalyst, coupled with simultaneous removal of at least one of the dehydrocyanation products.Type: GrantFiled: March 9, 1992Date of Patent: August 31, 1993Assignee: Bend Research, Inc.Inventor: Paul van Eikeren
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Patent number: 5175170Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloakylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloakylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 29, 1991Date of Patent: December 29, 1992Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5169973Abstract: Alpha-aminonitriles can be synthesized by the reaction, at ambient temperature without use of catalyst, of essentially stoichiometric amounts of amine, aldehyde (either monoaldehyde or dialdehyde) and trimethylsilyl cyanide.Type: GrantFiled: April 15, 1991Date of Patent: December 8, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Jean-Pierre LeBlanc
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Patent number: 5126349Abstract: Substituted 3-thio-2-propynenitriles are prepared which correspond to the formula:R--S--C.tbd.C--C.tbd.Nwherein R is an alkyl, cyclic alkyl, aryl, or heterocyclo group.These compounds have been found to exhibit a high degree of antimicrobial activity in industrial and commercial applications and compositions containing these compounds are so employed.Type: GrantFiled: December 26, 1990Date of Patent: June 30, 1992Assignee: The Dow Chemical CompanyInventors: Connie I. Deford, Charles D. Gartner, Kalakota S. Reddy, John K. Swayze, David E. Wallick, Warren L. Treptow, George A. Paul, Billy R. Hardas
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Patent number: 5106984Abstract: 2-Hydrocarbyl-3,6-dichloropyridines are prepared from dichloromethyl hydrocarbyl ketones and acrylonitrile in a two-step process involving an addition reaction under basic conditions to form intermediate 1,1-dichloro-3-cyanopropyl hydrocarbyl ketones and a subsequent cyclization reaction in the presence of hydrogen chloride. Thus, 3,6-dichloro-2-methylpyridine is prepared from 1,1-dichloro-2-propanone and acrylonitrile by the formation and further reaction of 4,4-dichloro-5-oxo-hexanenitrile. The intermediates and products are novel compounds useful in the preparation of herbicides and nitrification inhibitors.Type: GrantFiled: February 24, 1987Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Marc E. Halpern, Jon A. Orvik, Thomas J. Dietsche
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Patent number: 5077427Abstract: A process for preparing .alpha.-formylamino nitriles of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroaromatic radicals with 3 to 10 carbon atoms, by reacting cyanohydrins of the formula II ##STR2## with the formamide III ##STR3## in the presence of acids, entails adding at least one ammonium salt to the reaction mixture.Type: GrantFiled: December 13, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fikentscher, Michael Kroener
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Patent number: 5077426Abstract: A process for preparing .alpha.-formylamino nitriles of the formula Ia ##STR1## and Ib ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each is hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroarometic radicals with 3 to 10 carbon atoms, with the priviso that at least one of R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 is hydrogen, comprises reacting an iminodiacetonitrile of the formula II ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, with formamide of the formula III ##STR4## in the presence of formic acid or with a compound which provides formic acid, in the presence of acids.Type: GrantFiled: December 13, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fikentscher, Michael Kroener
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Patent number: 5030655Abstract: A compound selected from the group consisting of all possible isomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and cycloalkyl and cycloalkylalkyl of 3 to 8 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and acyl of 1 to 9 carbon atoms, X.sub.1 and X.sub.2 are individually selected from the group consisting of fluorine, chlorine, bromine, iodine, --CF.sub.3, --CN, --COOR and ##STR2## R is alkyl of 1 to 8 carbon atoms, Hal is chlorine, bromine or fluorine and R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and residue of an alcohol used in pyrethrinoid synthesis having excellent pesticidal properties.Type: GrantFiled: September 25, 1989Date of Patent: July 9, 1991Assignee: Roussel UclafInventors: Jean Tessier, Jacques Demassey, Jean-Pierre Demoute
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Patent number: 4985582Abstract: Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo-[2,2,3]-nonanes, having 2 or 3 ring hetero atoms selected from O, S and N substituted at the 1-position by a carbocyclic group other than an alkynylphenyl group, and substituted at the 4-position and optionally substituted at the 3 and/or 5 position, are valuable pesticides, particularly insecticides and acaricides. Various cyclization processes are disclosed to form the various bicyclo ring systems.Type: GrantFiled: September 1, 1989Date of Patent: January 15, 1991Assignee: The Wellcome Foundation Ltd.Inventor: John P. Larkin
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Patent number: 4945177Abstract: Novel 2,2-dibromo-3-oxonitriles of Formula I,R--CO--CBr.sub.2 --CN (I)in which R represents in each case a possibly substituted or unsubstituted aliphatic, cycloaliphatic, aromatic or heterocyclic group, with the exception of a phenyl group substituted with 1 to 3 chlorine atoms, can be obtained in that a carboxylic acid ester of Formula IIR--CO--OR' (II)in which R has the significance indicated for Formula I, and in which R' represents a straight chain or branched alkyl group with 1 to 4 carbon atoms, is reacted with acetonitrile in the presence of a strong base, the 3-oxonitrile produced is isolated from the reaction mixture and reacted in a solvent inert with respect to bromine and in the presence of a hydrogen bromide acceptor, possibly under cooling, and the 2,2-dibromo-3-oxonitrile of Formula I obtained is isolated from the reaction mixture.Type: GrantFiled: December 23, 1986Date of Patent: July 31, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Horst-Juergen Krause, Hans-Theo Leinen, Rudolf Lehmann
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Patent number: 4920231Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.Type: GrantFiled: March 30, 1989Date of Patent: April 24, 1990Assignee: Roussel UclafInventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4888357Abstract: Disclosed herein are novel .beta.-cycloalkyl-.beta.-oxopropionitriles which exhibit anti-inflammatory/antiarthritic activities.Type: GrantFiled: January 26, 1988Date of Patent: December 19, 1989Assignee: Bristol-Myers CompanyInventor: William T. Han
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Patent number: 4886891Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.Type: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4808749Abstract: Novel esters in all possible isomeric forms of the formula ##STR1## wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkyl-alkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --OH, --SH, --OR', --SR', --NO.sub.2, ##STR2## --CN, --SO.sub.3 H, --PO.sub.4 H.sub.2, ##STR3## --SO.sub.2 AlK.sub.2, --SO.sub.3 AlK.sub.3, aryl optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF.sub.3, --OCF.sub.3, --SCF.sub.3 and ##STR4## R' is alkyl of 1 to 8 carbon atoms, R" and R"' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.sub.Type: GrantFiled: November 18, 1986Date of Patent: February 28, 1989Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4785019Abstract: N-cyanoalkyl-N-haloalkylthio alkyl-, aryl- and aralkyl-carboxamides of the general formula: ##STR1## wherein R is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 4 halogen atoms; lower alkoxyalkylene; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 16 carbon atoms; or substituted aryl or substituted aralkyl both substituted with 1 to 3 substituents independently selected from phenyl, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, halogen, nitro, cyano, ##STR2## wherein R.sup.4 is hydrogen or lower alkyl of 1 to 6 carbon atoms, ##STR3## wherein R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms; R.sup.1 and R.sup.2 are independently hydrogen, or lower alkyl of 1 to 6 carbon atoms; and R.sup.Type: GrantFiled: February 27, 1986Date of Patent: November 15, 1988Assignee: Chevron Research CompanyInventor: Joseph E. Moore
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Patent number: 4780129Abstract: Cyclohexenone derivatves of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or substituted alkenyl or alkynyl, A is alkoxycarbonyl, carboxyl, cyano or trifluoromethyl, B is hydrogen or methyl, X is straight-chain, branched or cyclic alkylene, Z is hydrogen or alkoxycarbonyl and n is 0 or 1, and salts thereof, and their use for combatting unwanted plant growth.Type: GrantFiled: February 13, 1987Date of Patent: October 25, 1988Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Ulrich Schirmer, Michael Keil, Bruno Wuerzer, Norbert Meyer
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Patent number: 4728743Abstract: 3-oxonitriles are produced by reaction of carboxylic acid esters with carboxylic acid nitriles in the presence of 70 to 80% suspension of sodium hydride in white oil. The oxonitrile are intermediate products for the production of 3-oxocarboxylic acid amides or esters and pesticides.Type: GrantFiled: July 13, 1987Date of Patent: March 1, 1988Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann, Elizabeth Wolf-Heuss
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Patent number: 4714777Abstract: The subject invention relates to novel cyclopropanone hydrate derivatives of the structural formula ##STR1## whereinR.sub.1 and R.sub.2 are selected from the group consisting of --H, --(CH.sub.2).sub.n -- where n is an integer between 1 and 20, preferably 2 and 10, --COCH.sub.2 NH.sub.2, and ##STR2## and R.sub.3 and R.sub.4 selected from the group consisting of --H, --OH, 13 NH.sub.2, --CN, --COOR.sub.5, --COOH, --SH, --(CH.sub.2).sub.n OH, --(CH.sub.2).sub.n NH.sub.2, --(CH.sub.2).sub.n COOH, --(CH.sub.2).sub.n COOR.sub.5, --CCH.sub.3 OH (CH.sub.2).sub.n COOH, halogen and C.sub.7 -C.sub.10 arakyls, where n is an integer between 1 and 20, preferably 1 and 10, and R.sub.5 is an alkyl radical having between 1 and 20, preferably 1 and 10, carbon atoms;and to a process for the synthesis thereof.Type: GrantFiled: January 6, 1986Date of Patent: December 22, 1987Assignee: University of PittsburghInventors: Paul Dowd, Christopher Kaufman, Robert H. Abeles
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Patent number: 4652556Abstract: Compounds of the formula: ##STR1## wherein R is aryl of 6 to 12 carbon atoms or aralkyl of 7 to 14 carbon atoms either optionally substituted with 1 to 3 substituents independently selected from lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, lower alkylsulfinyl of 1 to 6 carbon atoms, lower alkylsulfonyl of 1 to 6 carbon atoms, halogen, trihalomethyl, nitro, cyano or carboxyl; alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms, or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 3 halogen atoms; lower alkoxyalkylene; lower alkylene carbalkoxy; lower alkylthioalkylene; lower alkylsulfinylalkylene; or lower alkylsulfonylalkylene; R.sup.1 and R.sup.2 are independently hydrogen, lower alkyl of 1 to 6 carbon atoms, aryl of 6 to 12 carbon atoms, or thienyl, or taken together form an alkylene bridge to give a cycloalkyl group of 3 to 10 carbon atoms; and R.sup.Type: GrantFiled: August 19, 1985Date of Patent: March 24, 1987Assignee: Chevron Research CompanyInventors: Joseph E. Moore, Yuh-Lin Yang, Robert K. Griffith, David C. K. Chan
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Patent number: 4642372Abstract: A process for the preparation of cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein Z is selected from the group consisting of --CN, --COOH and --COOR.sub.1, R.sub.1 is alkyl of 1 to 6 carbon atoms and R.sub.2 and R.sub.3 are alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms comprising reacting at low temperatures in a solvent in the presence of a strong base a compound of the formula ##STR2## wherein Z has the above definitions and R is alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms with a sulfone of the formula ##STR3## wherein R.sub.2 and R.sub.3 have the above definitions and Y is an aromatic group followed by aqueous treatment to obtain a compound of the formula ##STR4## wherein Y, R, R.sub.2, R.sub.Type: GrantFiled: July 29, 1985Date of Patent: February 10, 1987Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4605749Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.Type: GrantFiled: June 20, 1985Date of Patent: August 12, 1986Assignee: State of Israel, Prime Minister's Office, Atomic Energy CommissionInventors: Ouri Buchman, Ilan Pri-Bar
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Patent number: 4602038Abstract: Novel cyclopropane carboxylates in all isomeric forms of the formula ##STR1## wherein A is selected from the group consisting of --O--, --S--, ##STR2## and --SO.sub.2 --, R.sub.1 is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms optionally containing at least one heteroatom in the carbon chain and optionally substituted with at least one halogen, aryl of 6 to 18 carbon atoms and aralkyl of 7 to 18 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen, optionally unsaturated alkyl of 1 to 12 carbon atoms, optionally unsaturated cycloalkyl of 3 to 12 carbon atoms and residue of other alcohols used in pyrethrinoids having pesticidal activity for combatting insects, acariens of vegetables and warm-blooded animals and nematodes and novel intermediates.Type: GrantFiled: June 8, 1984Date of Patent: July 22, 1986Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Joseph Cadiergue