Q Is Hydrogen Or A Lower Saturated Alkyl Substituent Patents (Class 564/215)
- Benzene ring in a substituent E (Class 564/218)
- A ring or polycyclo ring system in a substituent E is attached indirectly to the carboxamide nitrogen or to an amino nitrogen in substituent E by acyclic nonionic bonding (Class 564/219)
- Plural rings in a substituent E (Class 564/221)
- Hydroxy, bonded directly to carbon, or ether 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) (Class 564/223)
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Patent number: 6169200Abstract: The present invention provides a simple and inexpensive method for producing &agr;-hydroxy-&bgr;-aminocarboxylic acids and their esters. An ester of an N-protected &agr;-amino acid ester is converted into a &bgr;-ketosulfoxide, which is then processed with an acid to give an &agr;-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected &agr;-acyloxy-&bgr;-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce &agr;-hydroxy-&bgr;-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.Type: GrantFiled: November 5, 1998Date of Patent: January 2, 2001Assignee: Ajinomoto Co., Inc.Inventors: Takayuki Suzuki, Yutaka Honda, Kunisuke Izawa
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Patent number: 6166253Abstract: 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: September 11, 1998Date of Patent: December 26, 2000Assignee: Showa Denko K.K.Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
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Patent number: 6160020Abstract: Isolated salts of acetaminophen are disclosed. Alkali metal and alkaline-earth metal salts of acetaminophen were formed by reacting the free acid of acetaminophen with the corresponding metal hydroxide and then immediately isolating the resulting salt. These salts have been found to be more water soluble and less bitter in taste than the free acid form of acetaminophen. The isolated salts may also be combined with other active ingredients.Type: GrantFiled: June 19, 1998Date of Patent: December 12, 2000Assignee: McNeill-PPC, Inc.Inventors: Lena A. Ohannesian, David Nadig, John D. Higgins, III, Max Rey, Stephen A. Martellucci
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Patent number: 6072084Abstract: A highly polymerizable N-vinylcarboxylic acid amide having an N-1,3-butadienylcarboxylic acid amide content of 30 ppm or less, a process for producing the same, and a process for producing a homopolymer of N-vinylcarboxylic acid amide or a copolymer thereof with another copolymerizable monomer using the same. Also, a highly polymerizable N-vinylcarboxylic acid amide is produced by thermal cracking or catalytic cracking of N-(1-alkoxyethyl)carboxylic acid amide or ethylidenebiscarboxylic acid amide, wherein the N-vinylcarboxylic acid amide content of the N-(1-alkoxyethyl)carboxylic acid amide or ethylenebiscarboxylic acid amide is 10 wt % or less.Type: GrantFiled: December 2, 1998Date of Patent: June 6, 2000Assignee: Showa Denko K.K.Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
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Patent number: 6057477Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichlorolsocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure. Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: April 16, 1999Date of Patent: May 2, 2000Assignee: Rohm and Haas CompanyInventor: Heather Lynnette Rayle
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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: 6013795Abstract: Briefly, in one aspect, the present invention provides compositions of open-chain, .alpha.-branched fluoroalkylcarbonyl fluorides, and derivatives thereof.Type: GrantFiled: November 4, 1996Date of Patent: January 11, 2000Assignee: 3M Innovative Properties CompanyInventors: Anthony P. Manzara, Wei-Qiang Fan, Richard M. Stern, George G. I. Moore
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Patent number: 5990173Abstract: Novel 2,3,5-trimethyl-4-hydroxyanilide derivatives of general formula I, wherein, e.g., R.sub.1 is phenyl, R.sub.2 is H, R.sub.3 is C.sub.12 H.sub.25, and A is a sulphur atom, are disclosed. A method for preparing said derivatives, pharmaceutical compositions containing at least one of said compounds as active principle, and the use of such derivatives for treating hypercholesterolemia or atherosclerosis.Type: GrantFiled: May 27, 1998Date of Patent: November 23, 1999Assignee: Pierre Fabre MedicamentInventors: Jean-Fran.cedilla.ois Patoiseau, Jean-Marie Autin, Andre Delhon, Philippe Oms, Didier Junquero
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Patent number: 5959147Abstract: This invention concerns a novel organic sulfide compound obtained by the reaction of a mercapto alkanol such as 2-mercapto ethanol with an unsaturated amide such as (meth)acrylamide, maleic acid diamide, or fumaric acid diamide and a method for the production of the organic sulfide compound. The invention enables novel organic sulfide compounds of great commercial utility to be obtained with a high yield on a commercial scale.Type: GrantFiled: August 12, 1997Date of Patent: September 28, 1999Assignee: Nippon Shokubai Co., Ltd.Inventors: Norihiro Wakao, Youichi Hino, Ryuichi Ishikawa
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Patent number: 5919979Abstract: This invention relates to an improvement in a process for the production of an alkyl formamide, wherein a gas-containing carbon monoxide is reacted at elevated temperature and pressure in reaction zone with a nitrogen-containing compound selected from the group consisting of ammonia, a primary or secondary alkylamine, in the presence of a solvent and a catalyst. The improvement comprises utilizing a solvent comprising a polyethylene glycol, polypropylene glycol, polyethylenepropylene glycol, or mixtures, and an alkali metal or alkaline earth metal alkoxide of a polyethylene glycol, polypropylene glycol, polyethylenepropylene glycol or mixtures as the catalyst.Type: GrantFiled: September 28, 1993Date of Patent: July 6, 1999Assignee: Air Products and Chemicals, Inc.Inventors: John William Mitchell, Thomas Albert Johnson
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Patent number: 5892115Abstract: A highly polymerizable N-vinylcarboxylic acid amide having an N-1,3-butadienylcarboxylic acid amide content of 30 ppm or less, a process for producing the same, and a process for producing a homopolymer of N-vinylcarboxylic acid amide or a copolymer thereof with another copolymerizable monomer using the same. Also, a highly polymerizable N-vinylcarboxylic acid amide is produced by thermal cracking or catalytic cracking of N-(1-alkoxyethyl)carboxylic acid amide or ethylidenebiscarboxylic acid amide, wherein the N-vinylcarboxylic acid amide content of the N-(1-alkoxyethyl)carboxylic acid amide or ethylenebiscarboxylic acid amide is 10 wt % or less.Type: GrantFiled: December 23, 1997Date of Patent: April 6, 1999Assignee: Showa Denko Kabushiki KaishaInventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
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Patent number: 5883285Abstract: The present invention provides:a process for producing an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR1## which process comprises reacting a disulfide compound represented by general formula: ##STR2## with a hydroxide of an alkali metal M.sup.1 in the presence of a sulfur compound represented by general formula (2):H.sub.(2-i) S(M.sup.1).sub.i (2)a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR3## which process comprises reacting the above-mentioned alkalimetal salt of an arylmercaptan compound with a halogenofattyacid ester compound represented by general formula (4):X.sup.1 R.sup.2 COOR.sup.3 (4)at pH 7-10; and a process for producing the above-mentioned alkoxycarbonylalkylthioaryl compound, which process comprises reacting the above-mentioned disulfide compound with the above-mentioned hydroxide of an alkali metal M.sup.Type: GrantFiled: November 13, 1997Date of Patent: March 16, 1999Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Tatsuo Sugiyama, Tadashi Nakayama
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Patent number: 5869712Abstract: .alpha.-Amino-substituted acetic acids or acid salts of formula ##STR1## where R represents a hydrogen atom or an alkyl or alkoxy group X represents a hydrogen atom, an alkali metal or alkaline-earth metal or an ammonium residue characterized in that they are totally free of haloacetic acid and alkali metal halide. They are capable of being obtained by reaction, under hot conditions, of glyoxal, or of a precursor of glyoxal, with a secondary amine or one of its salts of formula ##STR2## where R represents a hydrogen atom or an alkyl or alkoxy group, optionally followed by hydrolysis. They may be used as amphoteric surface-active agents for the manufacture of cosmetic compositions.Type: GrantFiled: June 19, 1995Date of Patent: February 9, 1999Assignee: Rhone-Poulenc ChimieInventor: Jean-Marc Ricca
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Patent number: 5852194Abstract: The present invention relates to new N-substituted cis-N-propenyl-acetamides of the general formula (I) ##STR1## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl or hetarylalkyl;a process for their preparation, and their use for the preparation of 2-chloro-5-methyl-pyridine.Type: GrantFiled: June 7, 1996Date of Patent: December 22, 1998Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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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: 5847213Abstract: There is provided a process for producing a tertiary amine compound in one step without using any subsidiary raw material or any solvent, by subjecting a secondary amine compound and an alcohol to an intermolecular dehydration reaction in a gas phase. The process uses, as a catalyst, an oxide containing an alkali metal element and/or an alkaline earth metal element and silicon.Type: GrantFiled: March 3, 1997Date of Patent: December 8, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Akira Kurusu, Yuuji Shimasaki
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Patent number: 5840978Abstract: This invention describes an integrated process for making ethylidene bisformamide in high yield wherein water, which is formed as a reaction by-product, is readily removed from the reaction product mixture without adversely affecting the efficiency of the overall process. The process contemplates isolating the reaction zone from the separation zone and comprises circulating a stream of formamide through a reaction zone containing a solid acidic catalyst and a separation zone; introducing acetaldehyde into the circulating stream of formamide to form a reaction mixture and contacting the reaction mixture with the solid acidic catalyst under reaction conditions sufficient to form a product mixture comprising ethylidene bisformamide and water; and separating water from the product mixture in the separation zone to form a water-depleted product mixture containing ethylidene bisformamide.Type: GrantFiled: March 5, 1993Date of Patent: November 24, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Andrew Francis Nordquist, Francis Peter Petrocelli, Robert Krantz Pinschmidt, Jr., Yin Pang Tsui
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Patent number: 5789619Abstract: A highly polymerizable N-vinylcarboxylic acid amide having an N-1,3-butadienylcarboxylic acid amide content of 30 ppm or less, a process for producing the same, and a process for producing a homopolymer of N-vinylcarboxylic acid amide or a copolymer thereof with another copolymerizable monomer using the same. Also, a highly polymerizable N-vinyl carboxylic acid amide is produced by thermal cracking or catalytic cracking of N-(1-alkoxyethyl)carboxylic acid amide or ethylidenebiscarboxylic acid amide, wherein the N-vinylcarboxylic acid amide content of the N-(1-alkoxyethyl)carboxylic acid amide or ethylenebiscarboxylic acid amide is 10 wt % or less.Type: GrantFiled: January 16, 1996Date of Patent: August 4, 1998Assignee: Showa Denko Kabushiki KaishaInventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
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Patent number: 5763465Abstract: There are disclosed compounds of formula I,Ar--CH.sub.2 CH.sub.2 --NH--CR.sup.1 R.sup.2 --X--Y Iin whichAr represents a group, ##STR1## X represents a C.sub.1-12 alkylene chain optionally interrupted or terminated by one or more groups selected from --S(O).sub.n --, --O--, --C(Z)--, CR.sup.6 R.sup.7, phenylmethyne, --NR.sup.8 --, --CONH--, --NHCO-- and --NHCONH--,Y represents an optionally substituted aryl or cycloalkyl group,Z represents O or S,R.sup.1, R.sup.2, R.sup.5 and R.sup.9 each independently represent hydrogen or alkyl C.sub.1-6,R.sup.3 and R.sup.4 represent hydrogen, or R.sup.3 and R.sup.4 together form a group --S--, --NR.sup.9 -- or --CH.sub.2 --,R.sup.6 and R.sup.7 independently represent hydrogen, alkyl C.sub.1-6, fluoro, cyano, or CF.sub.3, provided that at least one of R.sup.6 and R.sup.7 is other than hydrogen,R.sup.8 represents hydrogen or alkyl C.sub.1-6, or when X is interrupted or terminated by more than one --NR.sup.8 -- group may together with another R.sup.8 group form the chain --CH.Type: GrantFiled: October 31, 1996Date of Patent: June 9, 1998Assignee: Astra Pharmaceuticals LimitedInventors: Roger V. Bonnert, Roger C. Brown, David R. Cheshire, Francis Ince, John Dixon
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Patent number: 5753709Abstract: Certain N-acyl 2-aryl cyclopropylmethylamine derivatives are useful as melatonergic agents.Type: GrantFiled: May 9, 1996Date of Patent: May 19, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Daniel J. Keavy, Michael F. Parker, Ronald J. Mattson, Graham Johnson
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Patent number: 5733935Abstract: A hydroxylamine derivatives of formula (I): ##STR1## wherein R represents ##STR2## in which R.sup.1 and R.sup.2 represents alkyl group, alkenyl group, alkynyl group, cycloalkyl group, haloalkyl group, haloalkynyl group, alkoxy - alkyl group, phenoxy - alkyl group, alkylthio - alkyl group, alkylsulfonyl - alkyl group, alkylamino - alkyl group, phenyl group, benzyl group, phenethyl group, cinnamyl group, pyridyl group, furyl group, thienyl group, X represents CO.sub.2, CO or SO.sub.2, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 represent a hydrogen atom or a lower alkyl group, and n represents 0 or 1, and fungicides contain said compound as an active ingredient.The compounds of the present invention have excellent effects for controlling wood-rot fungi, plant diseases and fungi of humans and animals, and are useful as industrial, agricultural and medical fungicides.Type: GrantFiled: June 17, 1996Date of Patent: March 31, 1998Assignee: Nihon Nohyaku Co., Ltd.Inventors: Nobuharu Andoh, Tsutomu Nishiguchi, Katsutoshi Endo
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Patent number: 5731352Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which A, R.sub.1, R'.sub.1, R.sub.2, R.sub.3 and n are as defined in the description, and medicinal product containing the same useful for treating a mammal afflicted with a disorder of the melatoninergic system.Type: GrantFiled: May 30, 1996Date of Patent: March 24, 1998Assignee: Adir Et CompagnieInventors: Daniel Lesieur, Veronique Leclerc, Patrick Depreux, Philippe Delagrange, Pierre Renard
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Patent number: 5710331Abstract: Preparation of N-alkenyl carboxamides of the general formula I ##STR1## in which the radicals R.sup.1 to R.sup.4 independently stand for hydrogen or for aliphatic, cycloaliphatic, or aromatic radicals, which optionally carry inert substituents, wherein an amide of the general formula II ##STR2## in which the radical R.sup.1 has the above meaning, and a carbonyl compound of the general formula III ##STR3## in which the radicals R.sup.2 to R.sup.4 have the above meanings, are caused to react in the presence of a base, said reaction being eithera) carried out in the presence of a carboxylic acid derivative of the general formula IV ##STR4## in which the radical R.sup.5 stands for hydrogen or an alkyl or aryl group and X is a halogen, alkoxy, or carboxylalkyl radical, orb) continued in the presence of a carboxylic acid derivative of the formula IV, and the amide of the formula I is isolated.Type: GrantFiled: October 26, 1995Date of Patent: January 20, 1998Assignee: BASF AktiengesellschaftInventors: Marc Heider, Thomas Ruhl, Jochem Henkelmann
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Patent number: 5700946Abstract: The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.Type: GrantFiled: April 17, 1996Date of Patent: December 23, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Yuuji Shimasaki, Hideyuki Kanbe, Akira Kurusu
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Patent number: 5686609Abstract: The invention relates to compounds of the formula ##STR1## in which: m is 2 or 3;Ar and Ar' independently are a thienyl group; a substituted or unsubstituted phenyl group; or an imidazolyl group; it also being possible for Ar' to be a benzothienyl group which is unsubstituted or substituted by a halogen; a naphthyl group which is unsubstituted or substituted by a halogen; a biphenyl group; or a substituted or unsubstituted indolyl;X is hydrogen;X' is hydrogen or a hydroxyl group or is joined to X" below to form a carbon-carbon bond, or X and X' together form an oxo group or a dialkylaminoalkoxyimino group of the formula .dbd.N--O--(CH.sub.2).sub.p --Am, in which p is 2 or 3 and Am is a dialkylamino group;Y is a nitrogen atom or a group C(X"), in which X" is hydrogen or forms a carbon-carbon bond with X';Q is hydrogen, a C.sub.1 -C.sub.4 alkyl group or an aminoalkyl group of the formula --(CH.sub.2).sub.Type: GrantFiled: March 11, 1994Date of Patent: November 11, 1997Assignee: SanofiInventors: Xavier Emonds-Alt, Pierre Goulaouic, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5668180Abstract: A compound selected from those of formula (I): ##STR1## in which A, R, Y, R.sup.1, R.sup.2 and R.sup.3 are as defined in the description,and a medicinal product containing the same useful for treating a disorder of the melatoninergic system.Type: GrantFiled: May 30, 1996Date of Patent: September 16, 1997Assignee: Adir Et CompagnieInventors: Daniel Lesieur, Patrick Depreux, Veronique Leclerc, Philippe Delagrange, Pierre Renard
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Patent number: 5654478Abstract: N-Alkenylcarboxamides of the formula I ##STR1## where at least one of the radicals R.sup.1 is hydrogen, the second radical R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by reacting an alkenyl carboxylate of the formula II ##STR2## where R.sup.1 has the abovementioned meanings and R.sup.3 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, and a carboxamide of the general formula III ##STR3## where R.sup.2 has the abovementioned meanings, in the presence of a base.Type: GrantFiled: August 10, 1995Date of Patent: August 5, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Bernd Fiechter
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Patent number: 5641881Abstract: Preparation of N-alkenylcarboxamides of the general formula I ##STR1## where at least one of the radicals R.sup.1 is hydrogen and the second radical R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 -alkyl group, the radical R.sup.2 is an aliphatic, cycloaliphatic, araliphatic or aromatic radical which can be bonded to the radical R.sup.3 to give a 3- to 10-membered bridge member, and the radical R.sup.3 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, from an alkenyl carboxylate of the general formula II ##STR2## where R.sup.1 has the meanings indicated above and R.sup.4 is hydrogen or an aliphatic, cycloaliphatic or aromatic radical, and a carboxamide of the general formula III ##STR3## where the radicals R.sup.2 and R.sup.3 have the meanings indicated above, by reacting the starting compounds in the presence of a base is described.Type: GrantFiled: August 10, 1995Date of Patent: June 24, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider
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Patent number: 5631389Abstract: The present invention relates to a new class of carbohydrate based nonionic surfactant, i.e., alkyl and alkenyl glycasuccinimide, and a process for their manufacture.Type: GrantFiled: April 30, 1996Date of Patent: May 20, 1997Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Van Au, Bijan Harichian
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Patent number: 5625076Abstract: The present invention provides a catalyst which is an oxide comprising silicon and at least one element selected from the group consisting of alkali metals and alkaline earth metals and which is used for gas-phase intramolecular dehydration of a tertiary N-(2-hydroxyalkyl) carboxylic acid amide to synthesize a tertiary N-alkenyl carboxylic acid amide. This catalyst enables continuous and efficient production of a tertiary N-alkenyl carboxylic acid amide from a tertiary N-(2-hydroxyalkyl) carboxylic acid amide without using any auxiliary raw material, and consequently allows for simple and safe production of a tertiary N-alkenyl carboxylic acid amide without generating any by-product (waste product) derived from the auxiliary raw material.Type: GrantFiled: September 18, 1995Date of Patent: April 29, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Yuuji Shimasaki, Hitoshi Yano, Kimio Ariyoshi
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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: 5612368Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which Ar, X, R.sub.1 and R.sub.2 are as defined in the description and a medicinal product containing the same in order to treat a disorder of the melatoninergic system.Type: GrantFiled: October 25, 1995Date of Patent: March 18, 1997Assignee: Adir et CompagnieInventors: Jean Andrieux, Michel Langlois, Pierre Renard, Philippe Delagrange
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Patent number: 5606084Abstract: The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: AlliedSignal Inc.Inventors: Andrew J. Poss, George Shia
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Patent number: 5604261Abstract: A compound which is selected from those of formula (I) : ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base,and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: May 22, 1995Date of Patent: February 18, 1997Assignee: Adir Et CompagnieInventors: Michel Langlois, Pierre Renard, G erard Adam
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Patent number: 5599986Abstract: The present invention relates to a novel process for preparing alkali metal salts of diformylamide and a novel crystalline form of sodium diformylamide.Type: GrantFiled: August 31, 1995Date of Patent: February 4, 1997Assignee: Hoechst Marion Roussel Inc.Inventors: Jonathan C. Evans, Christian T. Goralski, Cynthia L. Rand, Paul C. Vosejpka
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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: 5554792Abstract: Disclosed herein is an N-vinylformamide composition comprising 250 ppm by weight or less of formic acid based on N-vinylformamide.According to the invention, the purity and polymerizing activity of N-vinylformamide are preserved for a long time.Type: GrantFiled: April 13, 1995Date of Patent: September 10, 1996Assignee: Mitsubishi Kasei CorporationInventors: Shigeru Sawayama, Kohichi Satoh
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Patent number: 5538986Abstract: Disclosed are compounds of Formula I: ##STR1## or a pharmaceutically acceptable salt or solvate thereof, wherein: R.sup.3 is alkyl, alkenyl, alkynyl, aryl, alkaryl, aralkyl, cycloalkyl, acyloxymethyl, alkoxy, alkoxymethyl, or alkyl substituted with cycloalkyl;R.sup.4 is H, alkyl, alkenyl, alkoxy, or --OH.Also disclosed are pharmaceutical compositions containing compounds of Formula I, methods for inhibiting tumor necrosis factor-.alpha. and methods for treating septic shock, inflammation, or allergic disease by administering a compound of Formula I.Type: GrantFiled: December 6, 1993Date of Patent: July 23, 1996Assignee: Schering CorporationInventors: Pauline C. Ting, Daniel M. Solomon, Richard J. Friary, Frank J. Villani, John J. Piwinski, Joe F. Lee, Dhiru B. Vashi
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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: 5523485Abstract: A process for preparing high-purity isobutyramide which comprises reacting isobutyryl chloride in toluene or xylene at -15.degree. to 30.degree. C. with ammonia is described.Type: GrantFiled: December 12, 1994Date of Patent: June 4, 1996Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Ernst Buschmann
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Patent number: 5523458Abstract: Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.Type: GrantFiled: April 19, 1994Date of Patent: June 4, 1996Assignee: Takasago International CorporationInventors: Tetsuro Yamasaki, Hidenori Kumobayashi, Noboru Sayo, Toshiyuki Murayama, Noboru Sano, Takero Ishizaki
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Patent number: 5488131Abstract: A method for synthesizing enantiomerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the alpha carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98%, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.Type: GrantFiled: March 23, 1994Date of Patent: January 30, 1996Assignee: California Institute of TechnologyInventor: Andrew G. Myers
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Patent number: 5464872Abstract: A compound which is selected from those of formula (I): ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: January 18, 1995Date of Patent: November 7, 1995Assignee: Adir et CompagnieInventors: Michel Langlois, Pierre Renard, Gerard Adam
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Patent number: 5442116Abstract: The invention provides the substantially geometrically and optically pure trans-stereoisomeric form of a compound of formula (I): ##STR1## wherein R.sup.1 is H or C.sub.1 -C.sub.4 alkyl, together with processes for its preparation. The compounds are intermediates for the preparation of the antidepressant agent known as sertraline.Type: GrantFiled: January 10, 1994Date of Patent: August 15, 1995Assignee: Pfizer Inc.Inventors: Willard M. Welch, Michael T. Williams
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Patent number: 5434190Abstract: N-monosubstituted neoalkanamides of 11 to 14 carbon atoms wherein the substituent on the amide nitrogen is cyclic (aromatic or cycloaliphatic, such as aryl or cycloalkyl) and of at least five carbon atoms, have been discovered to be insect repellent, providing that any aromatic substituent is unsubstituted at the ortho position and that when the neoalkanoyl moiety is pivaloyl the total number of carbon atoms in the N-cyclic neoalkanamide is at least 12. Such neoalkanamides are useful as repellents against cockroaches, including American, German and Oriental cockroaches, and are also effective against mosquitoes (both Anopheles and Aedes), black flies and carpenter ants, and to some extent against deer ticks. They may be applied to areas, locations and items which are desirably to be kept free of such insects, with applications being direct or of solutions or emulsions thereof, preferably by spraying, or in detergent compositions or other products to be applied to such areas, etc.Type: GrantFiled: October 11, 1994Date of Patent: July 18, 1995Assignee: Colgate-Palmolive Co.Inventor: Robert J. Steltenkamp
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Patent number: 5414017Abstract: Compounds of the formula ##STR1## wherein m is zero or 1; n is zero, 1 or 2; p is zero or 1 to 6 provided that m and p are not both zero; R.sub.3 is hydrogen, acyl, or benzyl; and R.sub.1 is hydrogen, alkyl, phenyl, substituted phenyl, phenyl-alkylene, heterocyclic-alkylene, etc. These compounds are useful as cardiovascular agents.Type: GrantFiled: March 26, 1993Date of Patent: May 9, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
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Patent number: 5399743Abstract: A dipeptide derivative having the formula (I):R.sup.1 NH--CH(R.sup.2)--CO--NH--CH(R.sup.3)--COCH.sub.2 F (I)wherein, R.sup.1 is an aliphatic acyl group having 2 to 8 carbon atoms or a benzyloxycarbonyl group; andR.sup.2 and R.sup.3 are independently a hydrogen atom or a straight or branched alkyl group having 1 to 4 carbon atoms and a prophylactic or therapeutic agent containing the same as an active ingredient.Type: GrantFiled: September 16, 1993Date of Patent: March 21, 1995Assignee: Suntory LimitedInventors: Naoki Higuchi, Masayuki Saitoh, Shinjiro Niwata, Yoshinobu Kiso, Yasuhiro Hayashi
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Patent number: 5395971Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).Type: GrantFiled: March 11, 1994Date of Patent: March 7, 1995Assignee: The Board of Regents of The University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5393923Abstract: The present invention is a novel compound which is a 3,5-di-t-butyl-4-hydroxyphenylmethylhydroxylamine or derivative thereof and a pharmaceutically acceptable acid addition or base salt thereof, pharmaceutical composition and methods of use therefor. The invention compounds are now found to have activity as inhibitors of one or both of cyclooxygenase and 5-lipoxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.Type: GrantFiled: October 12, 1993Date of Patent: February 28, 1995Assignee: Warner-Lambert CompanyInventors: Thomas Capiris, David T. Connor, Jagadish C. Sircar