Hydroxy, Bonded Directly To Carbon, Ether Or Nitrogen In A Substituent E (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/224)
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Patent number: 6017426Abstract: A process for the preparation of ceramide-type compounds by reacting, an amino alcohol with a carboxylic acid of defined structures, where the reaction is conducted with irradiation with microwaves and at a temperature of less than or equal to 180.degree. C.Type: GrantFiled: June 11, 1998Date of Patent: January 25, 2000Assignee: L'OrealInventors: Didier Semeria, Michel Philippe
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Patent number: 5932595Abstract: The present invention relates to compounds of Formula I: ##STR1## that are matrix metalloprotease inhibitors, pharmaceutical compositions containing them, methods for their use and methods of preparing these compounds.Type: GrantFiled: December 18, 1996Date of Patent: August 3, 1999Assignees: Syntex (U.S.A.) Inc., Agouron Pharmaceuticals, Inc.Inventors: Steven Lee Bender, Chris Allen Broka, Jeffrey Allen Campbell, Arlindo Lucas Castelhano, Lawrence Emerson Fisher, Robert Than Hendricks, Keshab Sarma
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Patent number: 5869653Abstract: An improved process for the catalytic hydrogenation of nitriles. The basic process comprises contacting the nitrile with hydrogen in the presence of a sponge or Raney cobalt catalyst under conditions for effecting conversion of the nitrile group to the primary amine. The improvement in the hydrogenation process resides in effecting the hydrogenation in the presence of a catalytic amount of lithium hydroxide and water. To achieve a catalytic amount of lithium hydroxide, the catalyst may be pretreated with the lithium hydroxide and/or the reaction may be carried out with the lithium hydroxide present in the reaction medium.Type: GrantFiled: October 30, 1997Date of Patent: February 9, 1999Assignee: Air Products and Chemicals, Inc.Inventor: Thomas Albert Johnson
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Patent number: 5863945Abstract: This invention relates to amide derivatives represented by the following formula (1), amide derivative synthesis intermediates represented by the following formula (2), (3) or (4), and external skin care preparations, cosmetic hair care formulations and bath medicines containing the amide derivatives (1): ##STR1## wherein R.sup.1 and R.sup.1a are, for example, tetradecyl or hexadecyl, R.sup.2 is, for example, tridecyl or pentadecyl, R.sup.3 is, for example, ethylene or trimethylene, R.sup.3a is, for example, trimethylene, and R.sup.4, R.sup.4a and R.sup.4b are, for example, methoxy or ethoxy. When added to external skin care preparations, bath medicines and cosmetic hair care formulations, the amide derivatives (1) exhibit advantageous effects such as skin-roughness preventing/curing effects and hair touch-feeling improving effects.Type: GrantFiled: November 24, 1997Date of Patent: January 26, 1999Assignee: Kao CorporationInventors: Koichi Murayama, Masahide Hoshino, Hiroshi Kusuoku, Minoru Nagai, Kiyoko Sugino
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Patent number: 5852214Abstract: A process for producing N-(1-alkoxyethyl)carboxylic amides by reacting alcohols of 1-5 carbon atoms with N-vinylcarboxylic amides in the presence of an acidic catalyst, or by utilizing unreacted starting material, unreacted intermediate or unrecovered product for synthesis of N-(1-alkoxyethyl)carboxylic amides. A process for producing N-(1-alkoxyethyl)carboxylic amides by adding a water-soluble strong acid during reaction between a carboxylic amide and a starting material containing acetaldehyde and alcohol and/or a starting material containing an acetal, in an amount of 2.times.10.sup.-3 to 3.times.10.sup.-1 equivalents to 1 mole of the carboxylic amide in the starting material, and using a strongly acidic ion-exchange resin as the catalyst.Type: GrantFiled: April 4, 1997Date of Patent: December 22, 1998Assignee: Showa Denko K.K.Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
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Patent number: 5708167Abstract: Proposed is a novel and very efficient method for the preparation of an N-vinyl compound such as N-vinyl-2-pyrrolidone and N-vinyl-N-ethyl acetamide by the thermal decomposition of an N-(.alpha.-acyloxyethyl) compound which is a novel compound obtained by the addition reaction between an NH group-containing compound such as 2-pyrrolidone and N-ethyl acetamide and a vinyl carboxylate, e.g., vinyl acetate, in the presence of an alkali, e.g. alkali metal hydroxide. The reaction mixture after completion of this addition reaction as such, i.e. without isolating the N-(.alpha.-acyloxyethyl) compound, such as N-(.alpha.-acetoxyethyl)-2-pyrrolidone and N-(.alpha.-acetoxyethyl)-N-ethyl acetamide, is heated to effect in situ formation of the desired N-vinyl compound which can then be isolated by distillation under reduced pressure in a very high overall yield.Type: GrantFiled: August 23, 1995Date of Patent: January 13, 1998Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
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Patent number: 5665877Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: May 17, 1996Date of Patent: September 9, 1997Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
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Patent number: 5648544Abstract: A process for the preparation of 2-aminoalkane-1,3-diols by a single step reduction of alkyl 2-oximino-3-oxoalkanoates. The reduction is carried out in the presence of at least one hydride, in a solvent, under inert atmosphere and at a controlled initial temperature.Synthetic yields are markedly improved.Type: GrantFiled: November 29, 1995Date of Patent: July 15, 1997Assignee: L'OrealInventors: Didier Semeria, Michel Philippe
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Patent number: 5616711Abstract: A method of producing an aminobutene derivative of formula (I) by allowing a butenol derivative of formula (II) to react with an amide derivative of formula (III) is disclosed. The aminobutene derivative of formula (I) can be deprotected to produce an aminobutene derivative of formula (I-1) or an aminobutene derivative of formula (I-2): ##STR1## The aminobutene derivative of formula (I-A) can also be deprotected to produce the aminobutene derivative of formula (I-B). Any or all of the above aminobutene derivatives are useful as intermediates for producing anti-ulcer drugs, and anti-ulcer drugs having an inhibitory effect on gastric acid secretion based on the antagonism against histamine H.sub.2 receptor.Type: GrantFiled: August 6, 1993Date of Patent: April 1, 1997Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Hajime Matsumoto, Masakatsu Matsumoto, Yasuo Sekine, Masato Nishimura, Akihiko Hosoda
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Patent number: 5614647Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: May 25, 1995Date of Patent: March 25, 1997Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
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Patent number: 5580904Abstract: According to the present invention, a novel compound group which can pass through blood-brain barrier (BBB) with carrying a drug thereon and stay within brain to release the drug and a well-known compound group having the properties described above are provided.The compound represented by the general formula ##STR1## wherein, R.sup.1 represents C.sub.1-6 alkyl which may be substituted by a group selected from hydroxyl, carboxyl, amino group which may be substituted by C.sub.1-6 alkyl, and a five- to seven-membered saturated heterocyclic ring,R.sup.2 represents hydrogen or C.sub.1-6 alkyl,R.sup.3 represents hydrogen or C.sub.1-6 alkyl which may be substituted by hydroxyl,R.sup.4 represents hydrogen or C.sub.1-6 alkyl,R.sup.5 represents an amino acid residue, or --S--R.sup.6 or --CO--R.sup.6 wherein R.sup.6 represents C.sub.1-14 alkyl which may be substituted by a five- to seven-membered saturated ring; C.sub.Type: GrantFiled: June 24, 1994Date of Patent: December 3, 1996Assignee: Drug Delivery System Institute, Ltd.Inventors: Toyoaki Ishikura, Teruomi Ito, Takashi Kato, Kazutoshi Horie, Hiroshi Ishihara, Takashi Senou
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Patent number: 5574185Abstract: An improved process for producing N-(.alpha.-alkoxyethyl)formamide by reacting formamide with acetaldehyde in the presence of a basic catalyst, thereby giving N-(.alpha.-hydroxyethyl)formamide, and reacting it with a primary or secondary alcohol in the presence of an acid catalyst, thereby giving N-(.alpha.-alkoxyethyl)formamide, characterized in that the basic catalyst is alkali metal bicarbonate or alkali metal hydrogenphosphate.Type: GrantFiled: November 16, 1994Date of Patent: November 12, 1996Assignee: Mitsubishi Chemical CorporationInventors: Shin-ichi Sato, Kiyoji Kuma
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Patent number: 5541347Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.Type: GrantFiled: October 3, 1994Date of Patent: July 30, 1996Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
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Patent number: 5527963Abstract: An improved process for producing N-vinylformamide including the steps of evaporating N-(.alpha.-substituted-ethyl)formamide or ethylidenebisformamide under reduced pressure and thermally decomposing the vapor at 150.degree.-600.degree. C., wherein the improvement comprises performing thermal decomposition by means of a pyrolysis reactor which is made up of two stages, the first being an unpacked tubular reactor constructed such that liquid flows down and the second being a packed tubular reactor, while keeping the vapor temperature at 200.degree.-400.degree. C. at the outlet of the unpacked tubular reactor and the inside temperature of the packed tubular reactor at 200.degree.-600.degree. C.Type: GrantFiled: October 16, 1994Date of Patent: June 18, 1996Assignee: Mitsubishi Chemical CorporationInventors: Shin-ichi Sato, Yasuharu Mori, Toshimitsu Inoue
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Patent number: 5523463Abstract: A process for the manufacture of N-protected .alpha.-aminoketones and N-protected .alpha.-aminoalcohols of the formula ##STR1## wherein X is halogen, one of Q.sup.1 and Q.sup.2 is hydrogen and the other is hydroxy or Q.sup.1 and Q.sup.2 together are oxo, R.sup.1 is an amino protecting group and R.sup.2 is hydrogen or the characterizing group of an .alpha.-aminocarboxylic acid,starting from the corresponding lower alkyl N-protected .alpha.-aminocarboxylates via corresponding lower alkyl N-silyl protected .alpha.-aminocarboxylates.Type: GrantFiled: August 21, 1995Date of Patent: June 4, 1996Assignee: Hoffmann-La Roche Inc.Inventor: Hans Hilpert
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Patent number: 5446201Abstract: Process for preparing di(3-(2-chloroethylsulfonyl)-1-propyl)amine hydrochloride, byreacting 1 mol of an N,N-diallylcarboxamide of the formula (1)R-CON(CH.sub.2 --CH.dbd.CH.sub.2).sub.2 (1)in which R is hydrogen, alkyl(C.sub.1 -C.sub.6) or cycloalkyl(C.sub.4 -C.sub.8) with about 4 to about 8 mol of mercaptoethanol at temperatures of about 0.degree. to about -70.degree. C. in the presence of pure oxygen or a mixture of oxygen with an inert gas or an inert gas mixture, if appropriate in an inert organic solvent, to give the carboxamide of the formula (2)R--CON(CH.sub.2 --CH.sub.2 --CH.sub.2 --S--CH.sub.2 --CH.sub.2 --OH).sub.2(2)in which R has the abovementioned meaning,hydrolyzing this compound with the aqueous solution of an alkaline agent at temperatures of about 40.degree. to about 120.degree. C.Type: GrantFiled: November 30, 1993Date of Patent: August 29, 1995Assignee: Hoechst AGInventors: Heinrich Angenendt, Michael Meier, Wolfram Schams
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Patent number: 5444154Abstract: The present invention relates to a series of novel crosslinked polymers. The compounds of the present invention are prepared by the reaction of chloracetic acid with a pendant hydroxyl group which is present on a polyoxyalkylene polymer, followed by the reaction of the halo-ester with a protein or amino acid to give a crosslinked protein compound. In a preferred embodiment the polyoxyalkylene glycol has been prepared by the reaction of both ethylene oxide and propylene oxide. In a more preferred embodiment, the ethylene oxide is at the terminal portion of the molecule and the propylene oxide is in the center. The proteins of the present invention plate out on the surface of hair skin and once dry act as humectants, trapping moisture to the hair. This results in hair which is fuller, has less static and is cosmetically more appealing. This combination of properties makes these polymers ideally suited for use in personal care applications.Type: GrantFiled: June 15, 1994Date of Patent: August 22, 1995Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5278341Abstract: The invention relates to N-acyl-aminoalkyl-2-hydroxyethylsulfides of formula R--CONH--(CH.sub.2).sub.n --S--CH.sub.2 --CH.sub.2 --OH, where R is a hydrogen atom or a (C.sub.1 -C.sub.4) alkyl group and n is an integer between 3 and 6, and to a method for preparing them. The method consists in reacting compounds of formula R--CONH--(CH.sub.2).sub.m --CH.dbd.CH.sub.2, where R has the above-mentioned meaning and m is an integer between 1 and 4, with the equivalent quantity of mercaptoethanol at approximately 15.degree. to approximately 150.degree. C. in the presence of a radical starter and in the presence or in the absence of a solvent which is inert to the reactants and to radical reactions.Type: GrantFiled: September 4, 1992Date of Patent: January 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Michael Meier, Heinrich Angenendt, Peter Mischke
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Patent number: 5177263Abstract: A formaldehyde-free latent crosslinking monomer represented by the formula ##STR1## in which R.sup.1 and R.sup.2 are C.sub.1 -C.sub.3 alkyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, or R.sup.4 --C(O)--; and R.sup.4 is C.sub.1 -C.sub.3 alkyl or C.sub.6 -C.sub.8 aryl, contains an allyl group capable of undergoing addition copolymerization and a dialkoxy ethyl group capable of crosslinking under acidic conditions. The monomer can be copolymerized with comonomers to form emulsion polymers for use as formaldehyde-free binders in nonwoven textiles. Methods for the preparation of the monomer, the polymers, and the nonwoven fabrics are described.Type: GrantFiled: September 24, 1991Date of Patent: January 5, 1993Assignee: National Starch and Chemical Investment Holding CorporationInventors: John C. Leighton, Dennis Neigel, Carmine P. Iovine
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Patent number: 5155228Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.Type: GrantFiled: May 16, 1991Date of Patent: October 13, 1992Assignee: Merck & Co., Inc.Inventors: Todd K. Jones, Sander G. Mills, Richard Desmond
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Patent number: 5144074Abstract: Carboxamides having the structural formula:R.sup.1 CHR.sup.2 CH(OR.sup.3)NHCR.sup.4 Owherein:R.sup.1 is H, C.sub.1 -C.sub.6 alkyl or aryl;R.sup.2 is H, C.sub.1 -C.sub.6 alkyl;R.sup.3 is benzyl, C.sub.1 -C.sub.8 alkyl or hydroxyalkyl; andR.sup.4 is H, C.sub.1 -C.sub.6 alkyl or aryl;are synthesized by reacting an aldehyde having the structural formula: R.sup.1 CHR.sup.2 CHO wherein R.sup.1 and R.sup.2 are as defined above, with an alcohol having the structural formula: R.sup.3 OH, wherein R.sup.3 is as defined above, and an amide having the structural formula: R.sup.4 CONH.sub.2 wherein R.sup.4 is as defined above, in the presence of a strong acid catalyst at a temperature in the range of 0.degree.-200.degree. C.Type: GrantFiled: February 24, 1988Date of Patent: September 1, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Mark L. Listemann, Ronald Pierantozzi, John N. Armor
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Patent number: 5103002Abstract: Ceramide derivatives of the following general formula ##STR1## are described, wherein the individual radicals have the following meanings:X=--NH or --CH.sub.2,R.sub.1 =H or C.sub.1-11 -alkyl,R.sub.2 =C.sub.2-9 -alkenyl, wherein the double bond is in .alpha. position to the OR.sub.3 groupR.sub.3 =H, C.sub.1-6 -alkyl or C.sub.1-6 -acyl andR.sub.4 =OH, C.sub.1-6 -alkoxy or morpholino.These ceramide derivatives represent inhibitors of the biosynthesis of sphingolipids.Type: GrantFiled: May 17, 1990Date of Patent: April 7, 1992Inventor: Felix Wieland
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Patent number: 5068397Abstract: Tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R.sub.f --E.sub.n --X--CH.sub.2).sub.3 CCH.sub.2 OH prepared from halogenated neopentyl alcohols and thiols of the formula R.sub.f --E.sub.n --SH, amines of the formula R.sub.f --E.sub.n --NH--R, alcohols of the formula R.sub.f --E.sub.n --OH, perfluoro-acids or amides, are described. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives, to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R.sub.f -neopentyl alcohol containing three perfluoroalkyl hetero groups.Type: GrantFiled: August 15, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
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Patent number: 5041659Abstract: Disclosed is a method which comprises introducing into a reaction zone a feed which comprises a hydroxyl compound reactant, R"OH, at least one amide reactant selected from R-CONH.sub.2 and R-CONHR', and an inorganic catalyst, thereby reacting R"OH with said amide reactant to produce a rection mixture containing at least one disubstituted amide selected from R-CONHR".sub.2 and R-CONHR'R", whereineach of R, R' and R" contains no acetylenic unsaturation and 1 to 30 carbon atoms,each of R, R' and R" is selected from a hydrocarbyl group and a hydrocarbyl group that is substituted with a group selected from carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, and hydroxyl,wherein said inorganic catalyst is selected from phosphates and sulfates of a Group 13 element and of a Group 2 metal having an atomic weight less than 145, and mixtures thereof.Type: GrantFiled: April 26, 1990Date of Patent: August 20, 1991Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Sandra L. Denman
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Patent number: 5015773Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.Type: GrantFiled: August 4, 1989Date of Patent: May 14, 1991Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 5011854Abstract: A hydroxamic acid compound represented by the general formula (I) or a salt thereof; ##STR1## wherein R.sup.1 represents a hydrogen atom, or a substituted or unsubstituted alkanoyl group, R.sup.2 represents an unsubstituted alkanoyl, substituted lower alkanoyl or substituted lower alkyl group, and m represents an integer of 3 to 7, which are useful for the prevention and/or treatment of diseases caused by lipoxygenase-mediated metablites.Type: GrantFiled: December 7, 1989Date of Patent: April 30, 1991Assignee: Kyowa Hakko Kogyo Co. Ltd.Inventors: Mitsuru Takahashi, Shigeto Kitamura, Hiroshi Kase, Masaji Kasai, Isao Kawamoto, Takao Iida, Hiroshi Sano, Hiromitsu Saito, Koji Yamada, Chikara Murakata
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Patent number: 4997984Abstract: A process for the preparation of an N-(.alpha.-alkoxyethyl)carboxylic acid amide represented by the following formula [I]: ##STR1## wherein R stands for a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group or an aryl group, and R.sup.1 stands for an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group,which comprises reacting an ethylidene-bisamide represented by the following formula [II]:CH.sub.3 CH(NHCOR).sub.2 [II]wherein R stands for a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group or an aryl group,with an alkanol in the presence of an acid catalyst. According to this process, a high-purity N-(.alpha.-alkoxyethyl)carboxylic acid amide, which is valuable as an intermediate for the production of an N-vinylcarboxylic acid amide and the like, can be easily prepared from cheap and easily available starting materials.Type: GrantFiled: December 19, 1989Date of Patent: March 5, 1991Assignee: Shawa Denko K.K.Inventors: Shuichi Sugita, Tetsuo Kudo, Kuniomi Marumo
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Patent number: 4958005Abstract: A fluorine-containing composition represented by formula (I) ##STR1## wherein X represents a group containing a polyfluoroaliphatic group having from 3 to 26 carbon atoms; R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; p represents an integer of from 1 to 100; and Y represents a group represented by formula (II) or formula (III) ##STR2## wherein R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; and Z represents an iodine atom, a sulfonate group, or a sulfate group, ##STR3## wherein R represents a hydrogen atom or an aliphatic group having from 1 to 3 carbon atoms; n represents an integer of from 2 to 3; and Z.sup.1 represents an iodine atom, a bromine atom, a chlorine atom, or a hydroxyl group; and a process for preparing the same.Type: GrantFiled: September 20, 1988Date of Patent: September 18, 1990Assignee: Daikin Industries, Ltd.Inventors: Takeo Saegusa, Masatoshi Miyamoto, Yoshiyuki Sano
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Patent number: 4876299Abstract: A compound of formula I ##STR1## in which R, R.sub.1, R.sub.10 and R.sub.11 are organic radicals. These compounds are suitable as U.V. absorbers.Type: GrantFiled: April 1, 1987Date of Patent: October 24, 1989Assignee: Sandoz Ltd.Inventor: Lajos Avar
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Patent number: 4826960Abstract: The process for the reaction of bicyclic amide acetals with reactive protic compounds of the general Formula ##STR1## wherein Y represents a member selected from the group consisting of ##STR2## R.sup.1 represents a member selected from the group consisting of hydrogen, an alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and R.sup.2 represents a member selected from the group consisting of an alkyl group having from 1 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, an alkylene ether group having from 1 to 50 carbon atoms, an arylene ether group having from 6 to 50 carbon atoms such as ethyl carbamate to form novel products which are useful as curing agents, blowing agents and monomers is disclosed.Type: GrantFiled: April 11, 1986Date of Patent: May 2, 1989Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4822483Abstract: A collector composition for use in froth flotation processes comprises two collectors. One of the collectors is preferably an N-(hydrocarbyl)-alpha, omega-alkanediamine, an (omega-aminoalkyl) hydrocarbon amide or mixture thereof. The second collector is a thiocarbonate, a thionocarbamate, a thiophosphate, thiocarbinilide, thiophosphinate, mercaptan, xanthogen formate, xanthic ester or mixture thereof. The collector composition floats a broad range of metal-containing minerals.Type: GrantFiled: March 23, 1987Date of Patent: April 18, 1989Assignee: The Dow Chemical CompanyInventors: Richard R. Klimpel, Robert D. Hansen
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Patent number: 4762829Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.Type: GrantFiled: October 23, 1986Date of Patent: August 9, 1988Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
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Patent number: 4762548Abstract: Herbicidally active thiolcarbamates are employed in combination with a certain amide extender compound, the latter in sufficient quantity to minimize soil degradation and to prolong the soil life of the former. As a result, the herbicidal effectiveness of the thiolcarbamate herbicide is significantly enhanced and prolonged, rendering a single application or multiple applications of the herbicide effective over a longer period of time. Such herbicidal compositions can optionally contain a non-phytotoxic antidotally effective amount of thiolcarbamate herbicide antidote.Type: GrantFiled: August 12, 1985Date of Patent: August 9, 1988Assignee: Stauffer Chemical Co.Inventors: Reed A. Gray, Ferenc M. Pallos
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Patent number: 4742058Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.Type: GrantFiled: July 14, 1986Date of Patent: May 3, 1988Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
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Patent number: 4692538Abstract: New and more efficient chemical processes are provided for preparing (.alpha.S, 5S)-.alpha.-amino-3-chloro-2-isoxazoline-5-acetic acid (AT-125), (.alpha.S, 5S)-.alpha.-amino-3-bromo-2-isoxazoline-5-acetic acid (bromo AT-125) and the C-5 epimers thereof. The disclosed processes allow the above-mentioned antitumor agents to be produced in high yield and purity with substantially fewer steps than prior art chemical procedures.Type: GrantFiled: May 28, 1985Date of Patent: September 8, 1987Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Terrence W. Doyle, Yulin Chiang
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Patent number: 4670591Abstract: N-.alpha.-alkoxyethylformamides of the formula ##STR1## where R is C.sub.1 -C.sub.18 -alkyl, are prepared by reacting a vinyl ether of the formulaCH.sub.2 .dbd.CH--OR (II),where R has the meaning stated in the formula I, with formamide in the presence of an acidic or basic catalyst at from -10.degree. to 150.degree. C.Type: GrantFiled: May 14, 1986Date of Patent: June 2, 1987Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Erwin Hahn, Rolf Fikentscher
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Patent number: 4665230Abstract: A process for preparing a poly(alkylene amido-ether) polyols by reaction of a bicyclic amide acetal with a polyol at a temperature in the range of from 140.degree.-240.degree. C. and the use of these poly(alkylene amido-ether) polyols in the formation of polyurethanes are described.Type: GrantFiled: June 6, 1985Date of Patent: May 12, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4661288Abstract: Water-soluble zwitterionic compounds having clay soil removal/anti-redeposition properties. The zwitterionic compounds are selected from monozwitterionic compounds, dizwitterionic compounds, polyzwitterionic compounds, and zwitterionic polymers. These zwitterionic compounds are useful in detergent compositions at from about 0.05 to about 95% by weight. In addition to the zwitterionic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof.Type: GrantFiled: March 8, 1985Date of Patent: April 28, 1987Assignee: The Procter & Gamble CompanyInventors: Donn N. Rubingh, Eugene P. Gosselink
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Patent number: 4626582Abstract: Acryloxymethyl fatty compounds are provided which are useful as monomers in the preparation of radiation curable coatings. The preferred compounds are acrylate or methacrylate esters of 9(10)-(hydroxymethyl)stearonitrile, 9(10)-(hydroxymethyl)-N,N-dimethylstearamide, methyl 9(10)-(hydroxymethyl)-stearate, N-acetyl-N-methyl 9(10)-(hydroxymethyl)-nonadecanamine, 9(10)-cyano-octadecanol, 9(10)-(carboxydimethylamino)octadecanol, 9(10)-(carboxymethyoxy)octadecanol and 9(10)-(N-acetyl-N-methyl-aminomethyl)octadecanol.Type: GrantFiled: February 28, 1985Date of Patent: December 2, 1986Assignee: Henkel CorporationInventors: Michael J. Virnig, James P. Clark, Edward D. DiDomenico
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Patent number: 4600520Abstract: Borated adducts of alkyl diamines and alkoxides impart effective multifunctional friction reducing and high temperature stabilizing characteristics to compositions comprising hydrocarbyl lubricants and fuels.Type: GrantFiled: December 27, 1983Date of Patent: July 15, 1986Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4600796Abstract: A process for preparing a class of polyols resulting from the reaction of a bicyclic amide acetal with an alkanolamine is described.Type: GrantFiled: June 3, 1985Date of Patent: July 15, 1986Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4568774Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.Type: GrantFiled: October 1, 1984Date of Patent: February 4, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4549975Abstract: Borated adducts of alkyl diamines, alkoxides and lower carboxylic acids impart effective multifunctional friction reducing and high temperature stabilizing characteristics to compositions comprising hydrocarbyl lubricants and fuels.Type: GrantFiled: December 27, 1983Date of Patent: October 29, 1985Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4529822Abstract: This invention relates to preparing formamide compounds in a process which comprises reacting an amine with a formylalkanolamine in the presence of carbon monoxide in which the mole ratio of amine to formylalkanolamine ranges from 0.2:1 to 5:1. The reaction is conducted at a temperature ranging from about 50.degree. to 300.degree. C. and a pressure ranging from about 100 to 10,000 psig. The amine employed in the reaction has the formula: ##STR1## wherein R' is hydrogen, an alkyl group of 1 to 10 carbon atoms, cyclohexyl, or --R"--O--R'", wherein R" is a divalent alkylene group of 2 to 4 carbon atoms and R'" is an alkyl group of 1 to 3 carbon atoms; and R is hydrogen or an alkyl group of 1 to 10 carbon atoms. The formylalkanolamine employed in the reaction has the formula: ##STR2## wherein R is an alkylene group of 1 to 3 carbon atoms, z is 0 or 1 and y is 1 or 2 and the sum of y and z is 2.Type: GrantFiled: October 19, 1983Date of Patent: July 16, 1985Assignee: Texaco, Inc.Inventors: Roger G. Duranleau, Clifford L. Lambert, Jr.
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Patent number: 4425360Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.Type: GrantFiled: September 8, 1981Date of Patent: January 10, 1984Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
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Patent number: 4418077Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.Type: GrantFiled: August 21, 1981Date of Patent: November 29, 1983Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
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Patent number: 4390466Abstract: Novel aqueous liquid detergents having superior soil penetration, dissolving and suspending properties comprising a lower alkanolacetamide and/or a liquid hydrocarbon such as an isoparaffinic hydrocarbon. The detergents may be used in laundering natural or synthetic fabrics or general purpose cleaning.Type: GrantFiled: April 30, 1981Date of Patent: June 28, 1983Inventor: Harold Weinberger
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4326067Abstract: The process of the invention for preparing a N-(2-substituted aminoethyl)amide of the formula: ##STR1## comprises contacting one or more compounds of the formula: ##STR2## with an amine of the formula: ##STR3## wherein A is nitrogen or a quaternary nitrogen of the formula: ##STR4## wherein B is ##STR5## when A is nitrogen and B is ##STR6## when A is IV; whereinX.sup..crclbar. is a counterion;b is zero or one; andR.sub.1 -R.sub.9 are as defined in the specification.In a preferred embodiment, the process is catalyzed by a Lewis acid or a protonic acid with a non-nucleophilic counterion.Type: GrantFiled: December 3, 1980Date of Patent: April 20, 1982Assignee: The Dow Chemical CompanyInventor: Michael J. Fazio
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Patent number: 4322553Abstract: The disclosure herein relates to a new process for the preparation of N-(halomethyl)acylamides by reacting the corresponding N-(alkoxymethyl)acylamide with thionyl chloride or thionyl bromide in the presence of a Lewis Acid catalyst.Type: GrantFiled: February 2, 1981Date of Patent: March 30, 1982Assignee: Monsanto CompanyInventor: John P. Chupp