Process Of Forming A Piperidine Ring From A Pyridine Ring Or From A Partially Hydrogenated Pyridine Ring Patents (Class 546/185)
  • Patent number: 5663350
    Abstract: The present invention relates to a novel process for the preparation of highly potent histamine receptor antagonists, in particular histamine H.sub.3 -receptor antagonists. Also disclosed is a novel process for the preparation of intermediates useful in the preparation of histamine receptor antagonists, in particular H.sub.3 -receptor antagonists.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: September 2, 1997
    Assignee: The University of Toledo
    Inventors: Graham J. Durant, Amin M. Khan
  • Patent number: 5663351
    Abstract: Process for the continuous preparation of 2,2,6,6-tetramethylpiperidine.The reduction of triacetonamine with hydrazine also succeeds continuously by reactive distillation if the hydrazone is first formed and this is continuously transported to the distillation bottoms comprising a high-boiling solvent and an alkali at the base of a distillation column and the resulting 2,2,6,6-tetramethylpiperidine is distilled off as an azeotrope.In this procedure a hydrazine/triacetonamine ratio of 1.5:1 to 2.0:1 is sufficient, in comparison with the conventional synthesis, the product yield being able to be considerably increased (>90%). Moreover, the amounts of alkali and solvent used can be considerably reduced.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: September 2, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Detlef Kampmann, Georg Stuhlmuller
  • Patent number: 5659040
    Abstract: A process for the preparation of the compound of formula (I) ##STR1## or a salt thereof which comprises reducing the compound of formula (II) ##STR2## or a salt thereof. The novel intermediate of formula (II) and processes for preparing it are also described.
    Type: Grant
    Filed: February 29, 1996
    Date of Patent: August 19, 1997
    Assignee: Glaxo Group Limited
    Inventors: Philip Blatcher, Malcolm Carter, Roy Hornby, Martin Richard Owen
  • Patent number: 5606064
    Abstract: The invention relates to a new process for the preparation of benzyl-piperidylmethyl-indanones known as medicaments, which is characterized in that the appropriately substituted pyridinium salts are hydrogenated.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: February 25, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventor: Stephen Lensky
  • Patent number: 5374728
    Abstract: A process for the preparation of 2-aminomethylpiperidine by catalytic hydrogenation of 2-cyanopyridine in the presence of a cobalt-containing catalyst at elevated temperature and under elevated pressure. The reaction can be carried out either in two steps or in a single stage.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: December 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Detlef Kampmann, Gregor Deckers, Claus Kniep
  • Patent number: 5312923
    Abstract: The invention is a highly efficient synthesis for making compounds of the formula: ##STR1## wherein: R.sup.1 is a six membered saturated or unsaturated heterocyclic ring containing one or two heteroatoms wherein the heteroatoms are N; or NR.sup.6, wherein R.sup.6 is H or C.sub.1-10 alkyl;m is an integer from two to six; andR.sup.4 is aryl, C.sub.1-10 alkyl, or C.sub.4-10 aralkyl.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: May 17, 1994
    Assignee: Merck & Co., Inc.
    Inventors: John Y. L. Chung, David L. Hughes, Dalian Zhao
  • Patent number: 5039803
    Abstract: A process for preparing a compound of formula (I): ##STR1## in which Ar represents an aryl or substituted aryl group and R.sup.3 represents an alkyl group, which comprises reducing a compound of formula (II): ##STR2## in which Ar and R.sup.3 are as defined for formula (I), and Hal represents a halogen atom.
    Type: Grant
    Filed: October 19, 1989
    Date of Patent: August 13, 1991
    Assignee: Beecham Pharmaceuticals
    Inventors: Paul Smith, Gillian E. Smith
  • Patent number: 4912220
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: February 3, 1988
    Date of Patent: March 27, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • Patent number: 4861893
    Abstract: A process is disclosed for the preparation of a compound of formula (I): ##STR1## where Ar is aryl or substituted aryl and R.sup.3 and R.sup.4 are the same or different and each is alkyl, which process comprises hydrognating a compound of formula (II): ##STR2## wherein Ar, R.sup.3 and R.sup.4 are as defined with respect to formula (I) and Hal is a halogen atom.Compounds of formula (I) are useful as chemical intermediates.
    Type: Grant
    Filed: August 8, 1986
    Date of Patent: August 29, 1989
    Assignee: Beecham Group PLC.
    Inventor: Gary T. Borrett
  • Patent number: 4743690
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: January 16, 1987
    Date of Patent: May 10, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • Patent number: 4678638
    Abstract: This invention relates to amino hexahydropyridines, and to the preparation and use thereof as corrosion inhibitors.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: July 7, 1987
    Assignee: Petrolite Corporation
    Inventors: Benjamin T. Outlaw, Bernardus A. Oude Alink
  • Patent number: 4675409
    Abstract: A new and novel process for the preparation of encainide (4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]-benzanilide) has been developed. The process utilizes .alpha.-picoline, O-nitrobenzaldehyde, and anisoyl chloride as starting materials.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: June 23, 1987
    Assignee: Bristol-Myers Company
    Inventors: John L. Dillon, Richard H. Spector
  • Patent number: 4659862
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: April 21, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • Patent number: 4581456
    Abstract: The present invention relates to processes for preparing precursors of picenadol, (.+-.)3-(1,3.alpha.-dimethyl-4.alpha.-propyl-4.beta.-piperidinyl)phenol, hydrochloride, a known analgesic. Certain of the compounds prepared by the present process are novel as well.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: April 8, 1986
    Assignee: Eli Lilly and Company
    Inventor: Charles J. Barnett
  • Patent number: 4394507
    Abstract: An improved process for the preparation of 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide has been developed. The process comprises essentially three steps starting with methyl anthranilate and 2-picoline and features a novel low-pressure hydrogenation sequence.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: July 19, 1983
    Assignee: Mead Johnson & Company
    Inventor: Gary D. Madding
  • Patent number: 4377691
    Abstract: A process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol (i.e. ifenprodil) and acid-addition salts thereof, characterized by brominating 4'-hydroxypropiophenone in a single or mixed solvent selected from the group consisting of methanol, ethanol and a saturated aliphatic ether, removing hydrogen bromide formed in the course of the bromination, adding 4-benzylpyridine to the reaction mixture, heating the reaction mixture under reflux in a single or mixed solvent selected from the group consisting of methanol and ethanol, and then subjecting the resultant reaction mixture to catalytic reduction to form 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol hydrobromide in the reaction mixture. The end product (i.e.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: March 22, 1983
    Assignee: Kabushiki Kaisha Cosmos Enterprise
    Inventors: Bompei Yasui, Tomohisa Miyamoto, Katsuyuki Hiraoka, Yoshitaka Sako
  • Patent number: 4276419
    Abstract: An improved process for the preparation of pyridines and/or hydrogenated pyridines that have been substituted with a hydrocarbon group at one or more carbon atoms, .gamma.-cyanoketone, in a gaseous phase and in the presence of hydrogen, is passed in a reaction zone over a first catalyst containing a catalytically active metal or compound of a metal selected from the group copper, silver, gold, iron, nickel, cobalt, ruthenium, rhodium, palladium, osmium, iridium and platinum to form a reaction mixture. A hydrogen-containing gas is separated from the reaction mixture, passed over a second catalyst containing a catalytically active metal or compound of a metal selected from the group iron, nickel and cobalt at a temperature of between 300.degree. and 800.degree. C., and the hydrogen-containing gas so treated is recycled to the reaction zone.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: June 30, 1981
    Assignee: Stamicarbon, B.V.
    Inventors: Egidius J. M. Verheijen, Charles H. Geersheuvels
  • Patent number: 4191828
    Abstract: 2-(2,2-Dicyclohexylethyl)piperidine is prepared via the catalytic hydrogenation of 2-(2,2-diphenylethenyl)pyridine in a single step. High yields are obtained using a rhodium supported catalyst.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: March 4, 1980
    Assignee: Richardson-Merrell Inc.
    Inventors: Stephen W. Horgan, Frank P. Palopoli, David L. Wenstrup