Processes Patents (Class 564/343)
  • Patent number: 5349090
    Abstract: Arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and a liquid carboxylic acid at a temperature of less than about 60.degree. C.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: September 20, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, George Kvakovszky, Charlet R. Lindley
  • Patent number: 5349109
    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: August 26, 1993
    Date of Patent: September 20, 1994
    Assignee: The Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5322963
    Abstract: Intermediate compounds (formula [III]and [IV]) useful as starting materials for the synthesis of amino acid derivatives which have renin inhibitory activity and which are useful as remedies for hypertension are prepared stereoselectively in high yield, without requiring complicated process steps. In this method, by reaction of .alpha.-amino aldehyde derivative [I] and compound [II] in the presence of BF.sub.3.OEt.sub.2, as shown in the following reaction formula, .alpha.-amino-.beta.-hydroxy-.delta.-ketone derivative [III] is prepared, and furthermore, by reducing it as required, compound [IV] is obtained: ##STR1## (where R.sup.1 is a protective group on the amino group, R.sup.2 is a lower alkyl group which may be branched, and R.sup.4 is a cyclohexyl group or phenyl group).
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: June 21, 1994
    Assignee: Japan Tobacco, Inc.
    Inventors: Saizo Shibata, Eiji Shirakawa, Yasuki Yamada, Koji Ando, Itsuo Uchida
  • Patent number: 5322964
    Abstract: There is disclosed a process for the preparation of an alpha-aminoketone salt of formula I ##STR1## which comprises reacting a nitrosated keto ester of formula II ##STR2## with a carboxylic anhydride of formula IV ##STR3## under the conditions of catalytic hydrogenation, to a compound of formula III ##STR4## which compound of formula III is then hydrolysed with an acid H.sub.n A to the salt I, in which formulae above R.sub.1 is C.sub.1 -C.sub.6 alkyl, phenoxy-C.sub.1 -C.sub.4 alkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl, or phenyl or C.sub.7 -C.sub.9 phenylalkyl which are substituted by halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, hydroxy or cyano, R.sub.2 is C.sub.1 -C.sub.4 alkyl or cyclohexyl, n is 1 to 3, R.sub.3 is C.sub.1 -C.sub.4 alkyl and A is the radical of an organic or mineral protic acid.Pyrroles suitable as co-stabilisers for PVC can be prepared from alpha-aminoketone salts of formula I.
    Type: Grant
    Filed: September 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Drewes, Hans-Helmut Friedrich
  • Patent number: 5284962
    Abstract: A continuous process employing at least two reaction stages for manufacturing pesticides from methyl isocyanate and oxime or phenol reactants in water.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: February 8, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Terence A. Rensi
  • Patent number: 5276191
    Abstract: According to the invention, there is provided a process for the preparation of an aminoalkyl p-hydroxyphenyl ketone comprising reacting phenol with a nitrile, in the presence of a Lewis acid catalyst, to cause condensation thereof, the process being characterised in that the reaction is carried out in a medium comprising a nitroalkane solvent for the reactants.
    Type: Grant
    Filed: October 29, 1991
    Date of Patent: January 4, 1994
    Assignee: Fine Organics Limited
    Inventors: James I. Grayson, Graham Heyes
  • Patent number: 5198585
    Abstract: Acid addition salts of arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and strong acid in a dipolar aprotic solvent.
    Type: Grant
    Filed: July 5, 1991
    Date of Patent: March 30, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • Patent number: 5182401
    Abstract: A process for the preparation of a 3-amino-2-(het)aroyl-acrylic acid derivative fo the formula ##STR1## in which Y represents a nitrile, or an ester group, --COOR.sub.1, or an acetyl group, whereR.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, andR denotes optionally substituted alkyl, cyclopropyl, alkoxy, phenyl or amino,A represents nitrogen or C--R.sub.2, whereR.sub.2 denotes hydrogen, methyl, halogen, nitro, methoxy or cyano,X.sub.1 and X.sub.2 are identical or different and denote halogen, andX.sub.3 denotes hydrogen, halogen or nitro andX.sub.4 denotes halogen, nitro, methoxy or methylthio, which comprises reacting a 3-dialkylamino-2-(het)aroyl-acrylic acid derivative of the formula ##STR2## in which R.sub.3 and R.sub.4 are the same or different and represent an alkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which they are bonded, form a ring,with a primary amine of the formula R--NH.sub.2 in the presence of at least one equivalent of an acid HX in a solvent or in excess acid.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: January 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 5132457
    Abstract: In a method for producing 2(R)-2-methyl-3-dimethylamino-propiophenone (d-DAMP), a chiral ester of the formula ##STR1## wherein R is an alkyl of from 1 to about 5 carbon atoms, is provided. The chiral easter of formula (I) is converted into a chiral amino-alcohol of the formula ##STR2## and the chiral amino-alcohol is oxidized so as to form d-DAMP.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: July 21, 1992
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventor: Jacob Mathew
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • Patent number: 4980377
    Abstract: The present invention relates to the preparation of new 1-(aminophenyl)-2-aminopropanone derivatives of the general formula: ##STR1## in which X is NH.sub.2, Y is H or a halogen atom, Z is H or a halogen atom, R.sub.1 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl and R.sub.2 is H or C.sub.1 -C.sub.4 alkyl, or R.sub.1 and R.sub.2, taken together, can form, with the nitrogen atom to which they are bonded, a heterocyclic group selected from the group consisting of the pyrrolidino, morpholino, thiomorpholino, piperidino, hexamethyleneimino, piperazino, 4-methyl-piperazino, 4-(.beta.-hydroxyethyl)piperzaino, 4-phenylpiperazino and 4-(p-chlorophenyl)piperazino groups, and addition salts thereof.These new derivatives are useful as pharmaceuticals. They are obtained by deacetylation of the corresponding acetylated products.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: December 25, 1990
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4978773
    Abstract: A new process for the preparation of 2,6-dichlorodiphenylamine derivatives is described, which process provides the desired active compound in a high yield and with a very high degree of purity by a technically simple and realizable procedure.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: December 18, 1990
    Assignee: Heumann Pharma GmbH & Co.
    Inventors: Ingomar Grafe, Helmut Schickaneder, Kurt H. Ahrens
  • Patent number: 4973756
    Abstract: An alpha-hydroxyl-alpha,alpha-di(inert-substituted)-gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)-alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha-di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Marion Laboratories, Inc.
    Inventors: Hans Wynberg, Wolter T. Hoeve, Gerrit A. Barf, Johannes N. Koek, David R. Borcherding
  • Patent number: 4906781
    Abstract: A method for the preparation of 4'-(substituted)-amino-2-(substituted)amino-3',5'-dichloroacetophenone and salts thereof. The method involves the chlorination of the corresponding 4'-(substituted)amino-2-(substituted) aminoacetophenone and acid addition salts thereof in the presence of an anhydrous or aqueous solvent selected from ethyl alcohol, t-butyl alcohol and acetic acid. The invention describes the preparation of 4'-amino-2-(t-butylamino)-3',5'-dichloroacetophenone and the hydrochloride thereof.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: March 6, 1990
    Assignee: American Cyanamid Company
    Inventor: Thomas W. Drabb, Jr.
  • Patent number: 4886914
    Abstract: The present invention relates to a process for the preparation of alpha alkyl amino aldehydes of formula ##STR1## in which R is alkyl or aralkyl possibly substituted, characterized in that N,O-dimethylhydroxylamine is reacted, in a basic medium, on a blocked amine ester of an amino acid of formula ##STR2## and in that the product obtained is reduced with the aid of a hydride such as the double hydride of lithium-aluminum.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: December 12, 1989
    Assignee: Sanofi
    Inventors: Bertrand Castro, Jean Fehrentz
  • Patent number: 4861854
    Abstract: A photosensitive polyimide precursor composed of the structural units (A) represented by the following general formula (I) and the structural units (B) represented by the following general formula (II), in which the ratio of the molar quantity of the structural units (A) to the sum of the molar quantity of the structural units (A) and that of the structural units (B) is 0.01 or greater, and having a viscosity of 100 cP or above as measured at 25.degree. C. in the state of a 10% by weight solution in N-methylpyrrolidone: ##STR1## wherein R.sub.1 represents a tetravalent aromatic hydrocarbon residue; R.sub.2 represents a divalent aromatic hydrocarbon residue; X, identical or different represents a halogen or an alkyl group; and m represents 0 or an integer from 1 to 4. The photosensitivity of the present photosensitive polyimide precursor is about 20 to 100 times that of conventional products. After heat dehydration cyclization, it shows a heat resistance of 400.degree. C. or above.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 29, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akitoshi Sugio, Takao Kawaki, Makoto Kobayashi, Katsushige Hayashi, Masahito Watanabe
  • Patent number: 4816489
    Abstract: The present invention relates to the preparation of new derivatives selected from the group consisting of:(i) 1-(aminophenyl)-2-(alkylamino)ethanones of the formula: ##STR1## in which R is CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3 ; and (ii) addition salts thereof.These new derivatives are useful in therapy, in particular as antidepressants or stimulants for the CNS. They are prepared from 1-(acetylaminophenyl)-2-(alkylamino)ethanone derivatives by deacetylation.
    Type: Grant
    Filed: September 10, 1987
    Date of Patent: March 28, 1989
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4730075
    Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: March 8, 1988
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4695652
    Abstract: .beta.-Aminoethyl ketones are obtained in a low-polluting manner by Mannich condensation of an aryl ketone having an acidic H with an aldehyde and ammonia or an amine by carrying out the reaction in organic nitriles in the presence of a sulphonic acid or in gycol either in the presence of a sulphonic acid or sulphuric acid.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: September 22, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Florin Seng, Josef Bremen
  • Patent number: 4670535
    Abstract: The photosensitive polyimide precursor of the invention has a recurring unit represented by the following general formula [I]: ##STR1## (R.sub.1 represents a tetravalent aromatic hydrocarbon residue; R.sub.2 and R.sub.3 each represent a divalent aromatic or aliphatic hydrocarbon residue; and R.sub.4 represents a divalent aromatic hydrocarbon residue represented by ##STR2## wherein R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12, identical or different, each represent hydrogen atom, a halogen group or an alkyl group). The photosensitive polyimide precursor of the invention has a viscosity of 50 centipoises or above as measured at 23.degree. C. in the state of a 10% (by weight) solution in N,N-dimethylacetamide. Its photosensitivity is as high as about 20-100 times that of prior products. After heat cyclization, it exhibits a heat resistance of 400.degree. C. or above.
    Type: Grant
    Filed: June 17, 1986
    Date of Patent: June 2, 1987
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akitoshi Sugio, Takao Kawaki, Katsushige Hayashi
  • Patent number: 4603019
    Abstract: This invention relates to new N-(methoxyphenacyl)-amine derivatives selected from the group consisting of(i) the N-(methoxyphenacyl)-alkylamines of the general formula ##STR1## wherein A is OCH.sub.3, and R is C.sub.3 -C.sub.8 -alkyl or C.sub.3 -C.sub.8 -hydroxyalkyl; and,(ii) addition salts thereof.These new derivatives are useful as pharmaceuticals, in particular as peripheral vasodilating agents.
    Type: Grant
    Filed: November 23, 1984
    Date of Patent: July 29, 1986
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4587248
    Abstract: 4-alkyl-thiophenyl-ethanolamines are disclosed, which are compounds having a therapeutical activity against blood-platelet aggregation, and against lipemia and improving the cerebral circulation, said ethanolamines having the general formula: ##STR1## wherein R and R.sub.1 are alkyl substituents and R.sub.2 is a substituent having an amine character. Due to the presence of two asymmetry centers in their molecule, the compounds concerned can be prepared in the "threo" and the "erythro" configuration: mixtures of the "threo" and the "erythro" forms have also proven effective.
    Type: Grant
    Filed: May 27, 1982
    Date of Patent: May 6, 1986
    Inventors: Giorgio Cantarelli, Giampaolo Picciola, Franco Ravenna, Mario Riva
  • Patent number: 4408074
    Abstract: A process for preparing 1-(3,5-dimethoxy-4-hydroxy phenyl)-2-(N-methylamino) ethanol hydrochloride is described by reacting 2,6-dimethoxyphenol with anhydrous chloral in the presence of a catalyst, hydrolyzing 1-(3,5-dimethoxy-4-hydroxyphenyl)2,2,2-trichloro ethanol and subsequently isolating the 3,5-dimethoxy-4-hydroxyphenyl glyoxal thus obtained; finally, this compound, in the form of the bisulfite, is directly converted to the desired product by amination with methylamine in the presence of hydrogen with a hydrogenation catalyst and the final product is converted into the hydrochloride.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: October 4, 1983
    Assignee: Dr. Lo. Zambeletti S.p.A.
    Inventors: Massimo Signorini, Attilio Trebbi, Luigi Molteni
  • Patent number: 4326077
    Abstract: Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group --NR'R" wherein R' and R" are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.
    Type: Grant
    Filed: September 22, 1980
    Date of Patent: April 20, 1982
    Assignee: Chevron Research Company
    Inventors: William L. Schinski, David C. K. Chan, Irene C. Huang
  • Patent number: 4322530
    Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4317932
    Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4317930
    Abstract: Novel phenethylamine derivatives represented by the general formula: ##STR1## wherein R is a lower alkyl group, C.sub.n H.sub.2n is a branched or straight alkylene group, A is a phenyl group unsubstituted or substituted with hydroxy, a lower alkoxy or a lower alkylene dioxy group, and n is an integer from 1 to 4, and pharmacologically acceptable acid addition salts thereof, and bronchdilator containing the same. These bronchdilator has an intense and durable bronchdilating effect and a weak heart stimulating action.
    Type: Grant
    Filed: March 16, 1977
    Date of Patent: March 2, 1982
    Assignee: Eisai Co., Ltd.
    Inventors: Noriyasu Hirose, Shigeru Souda
  • Patent number: 4314081
    Abstract: 3-Aryloxy-3-phenylpropylamines and acid additions salts thereof, useful as psychotropic agents, particularly as anti-depressants.
    Type: Grant
    Filed: January 10, 1974
    Date of Patent: February 2, 1982
    Assignee: Eli Lilly and Company
    Inventors: Bryan B. Molloy, Klaus K. Schmiegel
  • Patent number: 4313005
    Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: January 26, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Randall J. Daughenbaugh
  • Patent number: 4288624
    Abstract: A process or acylating or sulfenylating 1-amino-2-phenyl-1-butene-3-ones to prepare the corresponding 4-acyl or 4-substituted-thio compounds provides intermediates useful for preparing herbicides.
    Type: Grant
    Filed: August 21, 1980
    Date of Patent: September 8, 1981
    Assignee: Eli Lilly and Company
    Inventors: Riaz F. Abdulla, Lawrence A. Morgan
  • Patent number: 4282251
    Abstract: Cinnamylalkyl-1-naphthylmethylamines, useful as antimycotic agents, and processes for their production.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: August 4, 1981
    Assignee: Sandoz Ltd.
    Inventor: Daniel Berney