Q Is Hydrogen Or A Lower Saturated Alkyl Substituent Patents (Class 564/215)
  • Patent number: 6169200
    Abstract: 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: Grant
    Filed: November 5, 1998
    Date of Patent: January 2, 2001
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takayuki Suzuki, Yutaka Honda, Kunisuke Izawa
  • Patent number: 6166253
    Abstract: 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: Grant
    Filed: September 11, 1998
    Date of Patent: December 26, 2000
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
  • Patent number: 6160020
    Abstract: 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: Grant
    Filed: June 19, 1998
    Date of Patent: December 12, 2000
    Assignee: McNeill-PPC, Inc.
    Inventors: Lena A. Ohannesian, David Nadig, John D. Higgins, III, Max Rey, Stephen A. Martellucci
  • Patent number: 6072084
    Abstract: 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: Grant
    Filed: December 2, 1998
    Date of Patent: June 6, 2000
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
  • Patent number: 6057477
    Abstract: 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: Grant
    Filed: April 16, 1999
    Date of Patent: May 2, 2000
    Assignee: Rohm and Haas Company
    Inventor: Heather Lynnette Rayle
  • Patent number: 6017426
    Abstract: 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: Grant
    Filed: June 11, 1998
    Date of Patent: January 25, 2000
    Assignee: L'Oreal
    Inventors: Didier Semeria, Michel Philippe
  • Patent number: 6013795
    Abstract: Briefly, in one aspect, the present invention provides compositions of open-chain, .alpha.-branched fluoroalkylcarbonyl fluorides, and derivatives thereof.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: January 11, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Anthony P. Manzara, Wei-Qiang Fan, Richard M. Stern, George G. I. Moore
  • Patent number: 5990173
    Abstract: 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: Grant
    Filed: May 27, 1998
    Date of Patent: November 23, 1999
    Assignee: Pierre Fabre Medicament
    Inventors: Jean-Fran.cedilla.ois Patoiseau, Jean-Marie Autin, Andre Delhon, Philippe Oms, Didier Junquero
  • Patent number: 5959147
    Abstract: 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: Grant
    Filed: August 12, 1997
    Date of Patent: September 28, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Norihiro Wakao, Youichi Hino, Ryuichi Ishikawa
  • Patent number: 5919979
    Abstract: 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: Grant
    Filed: September 28, 1993
    Date of Patent: July 6, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John William Mitchell, Thomas Albert Johnson
  • Patent number: 5892115
    Abstract: 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: Grant
    Filed: December 23, 1997
    Date of Patent: April 6, 1999
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
  • Patent number: 5883285
    Abstract: 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: Grant
    Filed: November 13, 1997
    Date of Patent: March 16, 1999
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Tatsuo Sugiyama, Tadashi Nakayama
  • Patent number: 5869712
    Abstract: .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: Grant
    Filed: June 19, 1995
    Date of Patent: February 9, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventor: Jean-Marc Ricca
  • Patent number: 5852194
    Abstract: 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: Grant
    Filed: June 7, 1996
    Date of Patent: December 22, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 5852214
    Abstract: 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: Grant
    Filed: April 4, 1997
    Date of Patent: December 22, 1998
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
  • Patent number: 5847213
    Abstract: 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: Grant
    Filed: March 3, 1997
    Date of Patent: December 8, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Akira Kurusu, Yuuji Shimasaki
  • Patent number: 5840978
    Abstract: 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: Grant
    Filed: March 5, 1993
    Date of Patent: November 24, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrew Francis Nordquist, Francis Peter Petrocelli, Robert Krantz Pinschmidt, Jr., Yin Pang Tsui
  • Patent number: 5789619
    Abstract: 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: Grant
    Filed: January 16, 1996
    Date of Patent: August 4, 1998
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Kunitoshi Wakabayashi, Kenji Shimamura, Shun-ichi Nagamatsu
  • Patent number: 5763465
    Abstract: 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: Grant
    Filed: October 31, 1996
    Date of Patent: June 9, 1998
    Assignee: Astra Pharmaceuticals Limited
    Inventors: Roger V. Bonnert, Roger C. Brown, David R. Cheshire, Francis Ince, John Dixon
  • Patent number: 5753709
    Abstract: Certain N-acyl 2-aryl cyclopropylmethylamine derivatives are useful as melatonergic agents.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: May 19, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Daniel J. Keavy, Michael F. Parker, Ronald J. Mattson, Graham Johnson
  • Patent number: 5733935
    Abstract: 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: Grant
    Filed: June 17, 1996
    Date of Patent: March 31, 1998
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Nobuharu Andoh, Tsutomu Nishiguchi, Katsutoshi Endo
  • Patent number: 5731352
    Abstract: 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: Grant
    Filed: May 30, 1996
    Date of Patent: March 24, 1998
    Assignee: Adir Et Compagnie
    Inventors: Daniel Lesieur, Veronique Leclerc, Patrick Depreux, Philippe Delagrange, Pierre Renard
  • Patent number: 5710331
    Abstract: 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: Grant
    Filed: October 26, 1995
    Date of Patent: January 20, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Marc Heider, Thomas Ruhl, Jochem Henkelmann
  • Patent number: 5700946
    Abstract: 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: Grant
    Filed: April 17, 1996
    Date of Patent: December 23, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideyuki Kanbe, Akira Kurusu
  • Patent number: 5686609
    Abstract: 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: Grant
    Filed: March 11, 1994
    Date of Patent: November 11, 1997
    Assignee: Sanofi
    Inventors: Xavier Emonds-Alt, Pierre Goulaouic, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5668180
    Abstract: 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: Grant
    Filed: May 30, 1996
    Date of Patent: September 16, 1997
    Assignee: Adir Et Compagnie
    Inventors: Daniel Lesieur, Patrick Depreux, Veronique Leclerc, Philippe Delagrange, Pierre Renard
  • Patent number: 5654478
    Abstract: 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: Grant
    Filed: August 10, 1995
    Date of Patent: August 5, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Bernd Fiechter
  • Patent number: 5641881
    Abstract: 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: Grant
    Filed: August 10, 1995
    Date of Patent: June 24, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider
  • Patent number: 5631389
    Abstract: 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: Grant
    Filed: April 30, 1996
    Date of Patent: May 20, 1997
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Robert Vermeer, Van Au, Bijan Harichian
  • Patent number: 5625076
    Abstract: 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: Grant
    Filed: September 18, 1995
    Date of Patent: April 29, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yuuji Shimasaki, Hitoshi Yano, Kimio Ariyoshi
  • Patent number: 5616711
    Abstract: 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: Grant
    Filed: August 6, 1993
    Date of Patent: April 1, 1997
    Assignee: Fujirebio Inc.
    Inventors: Hiroshi Ikawa, Hajime Matsumoto, Masakatsu Matsumoto, Yasuo Sekine, Masato Nishimura, Akihiko Hosoda
  • Patent number: 5612368
    Abstract: 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: Grant
    Filed: October 25, 1995
    Date of Patent: March 18, 1997
    Assignee: Adir et Compagnie
    Inventors: Jean Andrieux, Michel Langlois, Pierre Renard, Philippe Delagrange
  • Patent number: 5606084
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Andrew J. Poss, George Shia
  • Patent number: 5604261
    Abstract: 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: Grant
    Filed: May 22, 1995
    Date of Patent: February 18, 1997
    Assignee: Adir Et Compagnie
    Inventors: Michel Langlois, Pierre Renard, G erard Adam
  • Patent number: 5599986
    Abstract: The present invention relates to a novel process for preparing alkali metal salts of diformylamide and a novel crystalline form of sodium diformylamide.
    Type: Grant
    Filed: August 31, 1995
    Date of Patent: February 4, 1997
    Assignee: Hoechst Marion Roussel Inc.
    Inventors: Jonathan C. Evans, Christian T. Goralski, Cynthia L. Rand, Paul C. Vosejpka
  • Patent number: 5580904
    Abstract: 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: Grant
    Filed: June 24, 1994
    Date of Patent: December 3, 1996
    Assignee: Drug Delivery System Institute, Ltd.
    Inventors: Toyoaki Ishikura, Teruomi Ito, Takashi Kato, Kazutoshi Horie, Hiroshi Ishihara, Takashi Senou
  • Patent number: 5574185
    Abstract: 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: Grant
    Filed: November 16, 1994
    Date of Patent: November 12, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shin-ichi Sato, Kiyoji Kuma
  • Patent number: 5554792
    Abstract: 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: Grant
    Filed: April 13, 1995
    Date of Patent: September 10, 1996
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Shigeru Sawayama, Kohichi Satoh
  • Patent number: 5538986
    Abstract: 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: Grant
    Filed: December 6, 1993
    Date of Patent: July 23, 1996
    Assignee: Schering Corporation
    Inventors: Pauline C. Ting, Daniel M. Solomon, Richard J. Friary, Frank J. Villani, John J. Piwinski, Joe F. Lee, Dhiru B. Vashi
  • Patent number: 5527963
    Abstract: 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: Grant
    Filed: October 16, 1994
    Date of Patent: June 18, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shin-ichi Sato, Yasuharu Mori, Toshimitsu Inoue
  • Patent number: 5523485
    Abstract: 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: Grant
    Filed: December 12, 1994
    Date of Patent: June 4, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Ernst Buschmann
  • Patent number: 5523458
    Abstract: 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: Grant
    Filed: April 19, 1994
    Date of Patent: June 4, 1996
    Assignee: Takasago International Corporation
    Inventors: Tetsuro Yamasaki, Hidenori Kumobayashi, Noboru Sayo, Toshiyuki Murayama, Noboru Sano, Takero Ishizaki
  • Patent number: 5488131
    Abstract: 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: Grant
    Filed: March 23, 1994
    Date of Patent: January 30, 1996
    Assignee: California Institute of Technology
    Inventor: Andrew G. Myers
  • Patent number: 5464872
    Abstract: 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: Grant
    Filed: January 18, 1995
    Date of Patent: November 7, 1995
    Assignee: Adir et Compagnie
    Inventors: Michel Langlois, Pierre Renard, Gerard Adam
  • Patent number: 5442116
    Abstract: 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: Grant
    Filed: January 10, 1994
    Date of Patent: August 15, 1995
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Michael T. Williams
  • Patent number: 5434190
    Abstract: 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: Grant
    Filed: October 11, 1994
    Date of Patent: July 18, 1995
    Assignee: Colgate-Palmolive Co.
    Inventor: Robert J. Steltenkamp
  • Patent number: 5414017
    Abstract: 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: Grant
    Filed: March 26, 1993
    Date of Patent: May 9, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
  • Patent number: 5399743
    Abstract: 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: Grant
    Filed: September 16, 1993
    Date of Patent: March 21, 1995
    Assignee: Suntory Limited
    Inventors: Naoki Higuchi, Masayuki Saitoh, Shinjiro Niwata, Yoshinobu Kiso, Yasuhiro Hayashi
  • Patent number: 5395971
    Abstract: 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: Grant
    Filed: March 11, 1994
    Date of Patent: March 7, 1995
    Assignee: The Board of Regents of The University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5393923
    Abstract: 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: Grant
    Filed: October 12, 1993
    Date of Patent: February 28, 1995
    Assignee: Warner-Lambert Company
    Inventors: Thomas Capiris, David T. Connor, Jagadish C. Sircar