Utilizing A Formamide, Heavy Metal Salt, Aluminum Halide, Organosilicon Compound, Organophosphorus Compound, Or A Compound Containing Nitrogen And Sulfur Patents (Class 558/312)
  • Patent number: 11517554
    Abstract: The present invention is directed to a method for preventing and/or treating Alzheimer's disease. The method comprises administering to a subject in need thereof an effective amount of dapansutrile. The method reduces neuroinflammation and improves the cognitive functions such as learning and memory processes of the subject. Dapansutrile can be administered to the subject orally at a dose of 100-2000 mg/day for 3 months to 5 years or longer.
    Type: Grant
    Filed: July 29, 2020
    Date of Patent: December 6, 2022
    Assignee: OLATEC THERAPEUTICS LLC
    Inventor: Charles A. Dinarello
  • Publication number: 20120157524
    Abstract: The present invention relates to purified 3-methanesulfonylpropionitrile or a pharmaceutically acceptable salt thereof, and a method for preparing such compound. The compound has at least 90% (w/w) purity. The present invention is also directed to a pharmaceutical composition comprises the purified compound and a pharmaceutically acceptable carrier. The present invention is further directed to a method for treating inflammation, inflammatory-related disorders, or pain, by administering 3-methanesulfonylpropionitrile or a pharmaceutically acceptable salt or solvate thereof to a subject in need thereof.
    Type: Application
    Filed: December 13, 2011
    Publication date: June 21, 2012
    Inventor: Joseph St. Laurent
  • Patent number: 7939688
    Abstract: Process for preparing nitriles by reacting N-alkylcarboxamides (RCO—NHR1) or ammonium salts of carboxylic acids (RCOO—NH3R1+) or carboxylic acids in the presence of alkylamines or ammonium salts (RCOOH+NH2R1, RCOOH+NH3R1+), respectively, R being an arbitrarily substituted linear or branched C1-C12-alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl, alkynyl or aryl or heteroaryl radical and R1 being an arbitrary substituted, linear or branched C2-C1 alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl or alkynyl radical, with phosphonic anhydrides in the presence of an optional base in an organic solvent at a temperature in the range from ?30 to 180° C.
    Type: Grant
    Filed: July 5, 2006
    Date of Patent: May 10, 2011
    Assignee: Archimica GmbH
    Inventors: Andreas Meudt, Sven Nerdinger, Claudius Boehm
  • Publication number: 20080242884
    Abstract: Process for preparing nitriles by reacting N-alkylcarboxamides (RCO—NHR1) or ammonium salts of carboxylic acids (RCOO—NH3R1+) or carboxylic acids in the presence of alkylamines or ammonium salts (RCOOH+NH2R1, RCOOH+NH13R1+) respectively, R being an arbitrarily substituted linear or branched C1-C12-alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl, alkynyl or aryl or heteroaryl radical and R1 being an arbitrary substituted, linear or branched C2-C1 alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl or alkynyl radical, with phosphonic anhydrides in the presence of an optional base in an organic solvent at a temperature in the range from ?30 to 180° C.
    Type: Application
    Filed: July 5, 2006
    Publication date: October 2, 2008
    Inventors: Andreas Meudt, Sven Nerdinger, Claudius Boehm
  • Patent number: 7394091
    Abstract: There is provided composite nano-particles comprising nano-crystal particles dispersed stably and individually in suspension in high concentration without mutual aggregation of the nano-particles. A determined amount of pure water or deionized water is poured into a reactor, into which is introduced nitrogen gas at rate of 300 cm3/min for a given time while agitating with a stirrer to remove dissolved oxygen in the pure water, allowing to stand in an atmosphere of nitrogen. Next, the inside of the reactor is maintained in an atmosphere of nitrogen and sodium citrate as a dispersion-stabilizing agent, an aqueous solution of MPS as a surface-modifying agent, an anion aqueous solution for co-precipitation as a nano-crystal and a cation aqueous solution are added, in that order. Then, an aqueous solution of sodium silicate is added to the reactor, which is then allowed to stand in the dark place in an atmosphere of nitrogen after agitation.
    Type: Grant
    Filed: July 16, 2003
    Date of Patent: July 1, 2008
    Assignee: Keio University Faculty of Science and Technology
    Inventors: Tetsuhiko Isobe, Yasushi Hattori, Shigeo Itoh, Hisamitsu Takahashi
  • Patent number: 6353126
    Abstract: An improved process for the commercial production of malononitrile by the dehydration of cyanoacetamide employs cyanuric chloride in the presence of a catalytic amount of N,N-dimethylformamide and in a polar solvent that is removed by vacuum distillation at a temperature below 100° C. The N,N-dimethylformamide is added in a molar ratio of 0.16 moles for each mole of cyanoacetamide present in the starting solution.
    Type: Grant
    Filed: June 30, 1999
    Date of Patent: March 5, 2002
    Assignee: Creanova Inc.
    Inventors: Chitoor S. Subramaniam, Zheng Wang
  • Patent number: 6248917
    Abstract: 2-Hydroxybenzonitrile is prepared by passing 2-hydroxybenzamide in the gas phase over a heterogeneous catalyst thereby effecting dehydration of the 2-hydroxybenzamide to produce 2-hydroxybenzonitrile.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: June 19, 2001
    Assignee: Huels Aktiengesellschaft
    Inventor: Wolfgang Kleemiss
  • Patent number: 5972833
    Abstract: A method of preparing a catalyst having the elements and the proportions indicated by the following empirical formula:VSb.sub.m A.sub.a D.sub.d O.sub.xwhereA is one or more Ti, Sn, where Sn is always presentD is one or more Li, Mg, Ca, Sr, Ba, Co, Fe, Cr, Ga, Ni, Zn, Ge, Nb, Zr, Mo, W, Cu, Te, Ta, Se, Bi, Ce, In, As, B, Al and Mn whereinm is 0.5 to 10a is greater than zero to 10d is zero to 10x is determined by the oxidation state of the cations present,comprising making an aqueous slurry of a mixture of source batch materials comprising compounds of said elements to be included in the final catalyst, followed by drying and heat calcining the mixture to an active catalyst, wherein the source batch material for the tin is a solution which comprises SnO.sub.2.xH.sub.2 O wherein x.gtoreq.0 dispersed in tetraalkyl ammonium hydroxide wherein the tetraalkyl ammonium hydroxide is defined by the following formula:C.sub.n H.sub.2n+1 NOHwherein 5.gtoreq.n.gtoreq.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: October 26, 1999
    Assignee: The Standard Oil Company
    Inventors: James Frank Brazdil, Jr., Joseph Peter Bartek
  • Patent number: 5965764
    Abstract: Process for producing a nitrile by dehydration reaction of an amide in the presence of a carboxylic acid having the same radical as the amide, or by adding urea to a carboxylic acid with the carboxylic acid either molten or dissolved in a solvent, where the amount of urea used is less than about 0.8 in molar ratio to the carboxylic acid, or when an exhaust gas distillate line connected to the reactor is kept at about 60.degree. C. or higher, or while a gas that is inert to the reaction is fed into the reaction and the produced nitrile and water are concurrently distilled out.
    Type: Grant
    Filed: August 5, 1998
    Date of Patent: October 12, 1999
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Mamoru Ishikawa
  • Patent number: 5891916
    Abstract: A compound represented by the formula: ##STR1## wherein Ar.sup.1 and Ar.sup.2 independently represent an optionally substituted aromatic group; Q represents an optionally substituted divalent aliphatic hydrocarbon group optionally containing O or S; R.sup.1 represents H, acyl group, etc.; and X represents an electron-withdrawing group, an optionally substituted aromatic group, a group of the formula: ##STR2## wherein R.sup.2 and R.sup.3 independently represent H, acyl group or an optionally substituted hydrocarbon group, etc., etc.; or salts thereof are useful as an excellent anti-neurodegenerative agent.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: April 6, 1999
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Yoshihiro Sugiura, Ken-ichi Naruo, Hideki Takahashi
  • Patent number: 5854172
    Abstract: A method of preparing a catalyst having the elements and the proportions indicated by the following empirical formula:VSb.sub.m A.sub.a D.sub.d O.sub.xwhereA is one or more Ti, Sn, where Sn is always presentD is one or more Li, Mg, Ca, Sr, Ba, Co, Fe, Cr, Ga, Ni, Zn, Ge, Nb, Zr, Mo, W, Cu, Te, Ta, Se, Bi, Ce, In, As, B, Al and Mn whereinm is 0.5 to 10a is greater than zero to 10d is zero to 10x is determined by the oxidation state of the cations present,comprising making an aqueous slurry of a mixture of source batch materials comprising compounds of said elements to be included in the final catalyst, followed by drying and heat calcining the mixture to an active catalyst, wherein the source batch material for the tin is a solution which comprises SnO.sub.2.xH.sub.2 O wherein x.gtoreq.0 dispersed in tetraalkyl ammonium hydroxide wherein the tetraalkyl ammonium hydroxide is defined by the following formula:C.sub.n H.sub.2n+1 NOHwherein5.gtoreq.n.gtoreq.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: December 29, 1998
    Assignee: The Standard Oil Company
    Inventors: James Frank Brazdil, Jr., Joseph Peter Bartek
  • Patent number: 5817827
    Abstract: The present invention relates to a process for the dehydration of amides to nitrites which comprises carrying out the dehydration in the presence of an adduct of sulphur trioxide and an amine as the dehydrating reagent in a basic reaction mixture. Thereby, for example, aliphatic, aromatic and heteroaromatic amides are dehydrated to the corresponding nitrites, such as 5-carbamoyl-4-methyl-oxazole to 5-cyano-4-methyl-oxazole, a valuable intermediate in the synthesis of pyridoxine.
    Type: Grant
    Filed: October 22, 1996
    Date of Patent: October 6, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bonrath, Horst Pauling
  • Patent number: 5747535
    Abstract: The present invention relates to a novel selective thrombin inhibitor having the following formula (I), which is also effective by oral administration: ##STR1## in which R.sup.1 represents acetyl substituted with aryl or aryloxy, or represents sulfonyl substituted with substituted or unsubstituted aryl or N-containing heterocyclic group,X represents a group of formula ##STR2## R.sup.2 and R.sup.3 independently of one another represent hydrogen; cycloalkyl substituted or unsubstituted with carboxyl or alkoxycarbonyl; arylalkyloxy; hydroxy; or lower alkyl substituted or unsubstituted with carboxyl, alkoxycarbonyl or hydroxy, orR.sup.2 and R.sup.3 together with nitrogen atom to which they are attached can form a piperidine group substituted with carboxyl or alkoxycarbonyl,R.sup.4 represents hydrogen, lower alkyl or lower alkoxy,R.sup.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: May 5, 1998
    Assignee: LG Chemical Ltd.
    Inventors: Yeong Soo Oh, Sang Soo Kim, Sang Yeul Hwang, Mi Kyung Yun, Seong Ryul Hwang, Seong Won Hong, Yong Hee Lee, Yi Na Jeong, Koo Lee, You Seung Shin
  • Patent number: 5659051
    Abstract: There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro or a group of the RCONH wherein R is C.sub.1 -C.sub.20 alkyl, phenyl, phenyl-substituted (C.sub.1 -C.sub.20) alkyl, phenyl (C.sub.1 -C.sub.20)alkoxyphenyl or (C.sub.1 -C.sub.20) alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): ##STR3## wherein A.sup.1 and A.sup.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Hideki Ushio, Yukari Fujimoto, Tsutomu Matsumoto, Masayoshi Minai, Katsuichi Yasunaga, Hiroshi Sogabe, Takahiro Kotera
  • Patent number: 5637748
    Abstract: Syntheses of fluorinated amide and fluorinated nitrile compounds are improved by use of particular media for the reactions. Fluorinated amide can also be synthesized in high yield in a neat reaction.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: June 10, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Vinayakam Subramanyam
  • Patent number: 5497237
    Abstract: A method of converting a field of a regenerative signal in a VTR is provided wherein when image is reproduced at a nonstandard play speed, field data of a predetermined field number is formed using an inter-field signal with respect to a still part, and field data of a predetermined number is formed using only an inter-line signal with respect to a moving part; with respect to a carrier chrominance signal of a different field which will be interlaced, a signal processing is performed in such a way that when composite video signals are inputted in a normal direction, a phase is inverted, while when the composite video signals are inputted in a reverse direction, the phase is not inverted; and when abnormality occurs in an input state of the composite video signals, field data of a predetermined field number is formed using only the inter-line signal.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: March 5, 1996
    Assignee: Hitachi, Ltd.
    Inventors: Kyoichi Hosokawa, Hitoaki Owashi, Kazuhiko Yoshizawa, Miyoko Yoshikoshi, Toshiaki Takahashi, Yasuo Inagaki, Koutaro Okiguchi
  • Patent number: 5138086
    Abstract: A method for preparing an .alpha.,.beta.-unsaturated nitrile comprises bringing an .alpha.-oxycarboxylic acid amide represented by the following general formula: ##STR1## wherein R' and R" each represents a hydrogen atom or an alkyl group, with the proviso that at least one of R' and R" represents an alkyl group, into contact with a solid acid catalyst with heating in the presence of water in a molar ratio of not more than 15 with respect to the .alpha.-oxycarboxylic acid amide. The method makes it possible to directly produce an .alpha.,.beta.-unsaturated nitrile at high yield and high selectivity utilizing an .alpha.-oxycarboxylic acid amide as a starting material, which can easily be obtained from an .alpha.-oxynitrile.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: August 11, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tadatoshi Honda, Sinji Tokunoh
  • Patent number: 5075486
    Abstract: The invention relates to the preparation of di-n-propylacetonitrile, according to a process consisting in heating N-(1-propyl-n-butyl)formamide to a temperature of between 350.degree. C. and 550.degree. C. and in the absence of oxygen, in the presence of a catalyst consisting of a silica impregnated with 0.1 to 10% by weight of alkali metal cations.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: December 24, 1991
    Assignee: Sanofi
    Inventors: Michel Bouisset, Christian Forqlly, Andre Bousquet, Alain Heymes
  • Patent number: 5059709
    Abstract: A novel process for producing .alpha.-[(dialkylamino) substituted-methylene].beta.-oxo-(substituted) propanenitriles of the formula: ##STR1## where R, R.sub.1 and R .sub.2 are defined in the specification by reacting a substituted isoxazole with a diaklylamide dimethylacetal is provided.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: October 22, 1991
    Assignee: American Cyanamid Company
    Inventors: John P. Dusza, Robert F. Church
  • Patent number: 4922016
    Abstract: N-(sulfonylmethyl)formamides are obtained by reacting a sulfinic acid, formaldehyde and formamide in the presence of a second acid and a controlled amount of water. The formamides can be converted to the corresponding sulfonylmethylisocyanides.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: May 1, 1990
    Assignee: Gist-Brocades N.V.
    Inventor: Nicolaas C. M. E. Barendse
  • Patent number: 4908452
    Abstract: A facile and mild process for the preparation of nitriles from reagent sensitive primary carboxamides is described. The process utilizes a (carboxysulfamoyl)ammonium hydroxide compound as the dehydrating agent. It is useful for preparing nitriles which have present other groups which are sensitive to the more conventional methods of dehydration or to other methods of nitrile synthesis. Some novel nitriles prepared by the new method are also described.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 13, 1990
    Assignee: Merck & Co., Inc.
    Inventor: David A. Claremon
  • Patent number: 4908138
    Abstract: Hydroxyacetonitrile diphosphonic acid corresponding to the following general formula ##STR1## in which M represents H or a cation of a base, and salts thereof; to a process for their preparation comprising reacting 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl or heteroaryl radical, with nitrous acid, the secondary product R.sup.1 -COOH and unreacted starting material are separated off from the reaction mixture and the hydroxyacetonitrile diphosphonic acid is obtained in the form of a salt by addition of a base; and to the use of the above compounds as complexing agents and as thresholders.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: March 13, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Helmut Blum, Siglinde Hemmann
  • Patent number: 4883894
    Abstract: The present invention relates to a process for the production in continuous of isophthalodinitrile or terephthalodinitrile by simultaneous amidation and dehydration of the respective acid chlorides in steam phase on a fixed bed of a dehydration catalyst.
    Type: Grant
    Filed: March 24, 1987
    Date of Patent: November 28, 1989
    Assignee: Caffaro s.p.a. Societa per l'Industria Chimica ed Elettrochimica
    Inventors: Enrico Pontoglio, Sandro Parodi, Giancarlo Caretti
  • Patent number: 4822903
    Abstract: An improved fluorinated siliceous catalyst, well adapted for the catalytic synthesis of aromatic/aliphatic nitriles from their corresponding formamides, formanilides or amides, is comprised of a plurality of silica particulates, the specific surface of which ranging from about 200 to about 300 m.sup.2 /g, having a total pore volume ranging from about 1 to about 1.5 cm.sup.3 /g, with an average pore diameter ranging from about 100 to about 200 .ANG., having an exchange pH of less than about 3, and with the fluorine content thereof bonded to the silica, expressed in F.sup.31 , ranging from about 0.05 to about 2% by weight based upon the silica, and the sodium content thereof, expressed as Na.sub.2 O, being less than about 1% by weight, also based upon the silica.
    Type: Grant
    Filed: May 27, 1986
    Date of Patent: April 18, 1989
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Roland Jacques, Michel Reppelin, Laurent Seigneurin
  • Patent number: 4801730
    Abstract: Glycerides are reacted with ammonia in an amount of at least 200 liters per kilogram of glyceride per hour, at a temperature of 220.degree. to 300.degree. C., and in the presence of special catalysts. Of the product mixture which is formed and removed from the reaction with the excess ammonia, and which is composed essentially of the components water, the desired glycerol and fatty acid nitrile containing fatty acid and fatty acid amide, the latter component is returned to the reaction during the glyceride reaction. After completion of the glyceride reaction, which is indicated when the product mixture contains virtually no more glycerol, all the fatty acid nitrile containing fatty acid and fatty acid amide is further treated, in an after-reaction with a reduced amount of ammonia and at higher temperature, in order to convert the fatty acid and fatty acid amide impurities into fatty acid nitrile.
    Type: Grant
    Filed: November 19, 1987
    Date of Patent: January 31, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Stuhler, Kurt Fischer
  • Patent number: 4743702
    Abstract: Aliphatic dinitriles are prepared by reacting aliphatic dicarboxylic acids with ammonia in excess at from 200.degree. to 500.degree. C. in the presence of zeolites as catalysts.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: May 10, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Hubert Lendle, Peter Magnussen, Hans Leitner, Jost H. Manegold, Wolfgang Leitenberger