Nitrogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/329)
  • Patent number: 4725602
    Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: February 16, 1988
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Patent number: 4711855
    Abstract: A derivative of 3,5,3'-triiodothyronine having the following general formula: ##STR1## in which m is an integer from 2 to 4, n is an integer from 1 to 4, and R is a monovalent, unsubstituted, fully unsaturated five- or six-membered monocyclic heterocyclic group containing either one or two nitrogen atoms as the only hetero atoms.
    Type: Grant
    Filed: February 5, 1985
    Date of Patent: December 8, 1987
    Assignee: Ciba Corning Diagnostics Corp.
    Inventor: Richard R. Feinberg
  • Patent number: 4699984
    Abstract: Shown is the process which comprises heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-dimethylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Also shown are the 3-step synthesis of 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid from 2-fluorobenzaldehyde and the five step synthesis of 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolin ecarboxylic acid, a highly potent antibacterial agent, starting with 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Other intermediates shown in said five step synthesis include 3-(2,6-dimethyl-4-pyridinyl)-4-fluorobenzeneamine and diethyl 4-fluoro-3-(2,6-dimethyl-4-pyridinyl)anilinomethylenemalonate.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: October 13, 1987
    Assignee: Sterling Drug Inc.
    Inventor: Baldev Singh
  • Patent number: 4692513
    Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: September 8, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
  • Patent number: 4686309
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: August 11, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4681971
    Abstract: The invention relates to pyrrolinones of formula (1) ##STR1## wherein R.sub.1 is an alkyl group containing at least 2 carbon atoms, an aralkyl group, an isocyclic or heterocyclic aromatic radical and R is an alkyl or aryl group.The invention also relates to aminodicarboxylates of formula (2) ##STR2## wherein R.sub.1 is as defined in claim 1 and R and R' are the same or different and are alkyl or aryl.The aminodicarboxylates of formula (2) are prepared by condensing a disuccinate of the formulaR'OOCCH.sub.2 CH.sub.2 COORwith a nitrile of the formula R.sub.1 CN, in the presence of a strong base and zinc chloride.The pyrrolinones of formula (1) are obtained by reacting the aminodicarboxylates of formula (2) in the presence of a strong base in an organic solvent.The compounds of formulae (1) and (2) are valuable intermediates for pigments.
    Type: Grant
    Filed: November 1, 1985
    Date of Patent: July 21, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Johannes Pfenninger, Abul Iqbal, Alain C. Rochat
  • Patent number: 4677206
    Abstract: There is described a photographic system wherein development of an exposed photosensitive element with an aqueous alkaline photographic developing composition is effected in the presence of a compound which releases a quaternary in alkaline environment. Photographic products and processes utilizing such compounds are also disclosed.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: June 30, 1987
    Assignee: Polaroid Corporation, Patent Dept.
    Inventor: John M. Dolphin
  • Patent number: 4677128
    Abstract: (Arylthio)pyridylalkanol derivatives of the formula: ##STR1## in which: Ar denotes an optionally substituted aryl radical,R denotes a hydrogen atom or an optionally substituted alkyl radical, an optionally substituted aryl radical or an optionally substituted aralkyl radical,R.sub.1 denotes an alkyl radical, and n equals 0, 1, 2, 3 or 4.
    Type: Grant
    Filed: February 26, 1985
    Date of Patent: June 30, 1987
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Pierre Place, Claude Anding, Jean-Claude Debourge
  • Patent number: 4675328
    Abstract: Polycyclic salts of the formulaA-XN+CH.sub.2 --(Y).sub.n --(CH.sub.2).sub.p --(Z).sub.q --L--(T).sub.r --M IwhereinA.sup.- is the anion of a strong organic or inorganic acid;XN.sup.+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R.sup.1, R.sup.2 and R.sup.3 ;n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15;Y is CH.sub.2, C(H,OH) or C(O):Z is O, S, CH.sub.2, C(O), NQ.sup.1, SO.sub.2, C(O)O, OC(O), C(O)N(Q.sup.1) or N(Q.sup.1)C(O);L is p-phenylene substituted by R.sup.4 ; andM is phenyl substituted by R.sup.5 and R.sup.6,T has one of the meanings given above, for Z or is C(CH.sub.3).sub.2, C.sub.2 H.sub.4, C(Q.sup.2).dbd.C(Q.sup.3), C.tbd.C, CH.sub.2 C(O), C(O)CH.sub.2, CH.sub.2 O or OCH.sub.2,R.sup.1 is a group Ar, Ar-C.sub.1-4 -alkyl, ArO or ArC(O),Ar is phenyl substituted by R.sup.7, R.sup.8 and R.sup.9 ;R.sup.2 and R.sup.3 individually are H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.6 H.sub.
    Type: Grant
    Filed: January 15, 1986
    Date of Patent: June 23, 1987
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Jean-Marie Cassal, Albrecht Edenhofer, Henri Ramuz
  • Patent number: 4649202
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrochloride, and heating the brominated product in the presence or absence of any added base or hydrogen acceptor to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: March 10, 1987
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Venkataraman Ramachandran
  • Patent number: 4645771
    Abstract: The disclosure concerns novel 1-benzyl-1,2,3,6-tetrahydropyridine derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or a (1-4C)-alkyl radical, and benzene ring A bears one or two substituents selected from combinations of halogeno, (1-4C)-alkyl, (1-4C)-alkoxy, hydroxy, nitro, cyano, carboxamido, carboxyl, [(1-4C)-alkoxy]carbonyl, hydroxymethylene, amino, (1-4C)-alkanoylamino, (1-4C)-alkylsulphonamido, [(1-4C)-alkoxy]carbonyloxy, (1-4C)-alkanoyloxy and optionally substituted benzoyloxy radicals, and their pharmaceutically acceptable salts; pharmaceutical compositions thereof; analogy processes for their manufacture; and methods of medical treatment employing such derivatives.The compounds of formula I are inhibitors of the aggregation of blood platelets and are of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 24, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Stuart D. Mills
  • Patent number: 4640926
    Abstract: 3,5-Substituted-2-pyridylalkylaminothiadiazole compounds are disclosed which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: February 3, 1987
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George S. Sach
  • Patent number: 4637902
    Abstract: A base precursor represented by the following general formula (A) or (B): ##STR1## wherein A.sub.1, A.sub.2, A.sub.5, A.sub.6, A.sub.7, and A.sub.8 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a substituted aryl group, an acyl group, or a heterocyclic group, and A.sub.1 and A.sub.2 can combine to form a ring and two of A.sub.5, A.sub.6, A.sub.7, and A.sub.8 can combine to form a ring, A.sub.3 and A.sub.4 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, or an aralkyl group, and A.sub.3 and A.sub.4 can combine to form a ring or A.sub.3 and A.sub.4 can be a double bond forming an imino group from ##STR2## and X represents a nucleophilic group.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: January 20, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroyuki Hirai, Ken Kawata
  • Patent number: 4634783
    Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: January 6, 1987
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama
  • Patent number: 4629727
    Abstract: Compounds of formula I ##STR1## in which n=0 or 1; in which, when n=0, R.sub.1 is H, an alkyl, a cycloalkyl, a cycloalkylmethyl, an alkenyl or, an alkynyl group a heterocyclic ring or an optionally substituted phenyl ring or when n=1, R.sub.1 is H or an alkyl group;in which R.sub.2 and R.sub.3 are H or an alkyl group;in which A is a group of formula III--(CH.sub.2).sub.x --W--(CH.sub.2).sub.y -- IIIin which W is an oxygen atom or a group of formula --S(O).sub.m --, a group of formula --CR.sub.12 R.sub.13 --, a cycloalkylidene group or a cycloalkylene group; x is 0 or an integer from 1 to 5; y is 0 or an integer from 1 to 5.in which R.sub.4 is a carbocyclic ring, a heterocyclic ring, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an amido group, an acyloxy group, a hydroxy group, a thiol group, or a group of formula --OR.sub.20, --SR.sub.20, --SOR.sub.20 or SO.sub.2 R.sub.20.in which R.sub.5, R.sub.6 and R.sub.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: December 16, 1986
    Assignee: The Boots Company PLC
    Inventors: Antonin Kozlik, Wilfred H. Wells
  • Patent number: 4625033
    Abstract: A process for preparing 1H-pyrrolo-[3,2-c]-pyridine or 5-aza-indole in high yield, comprising condensing 3-methyl-4-nitropyridine-1-oxide with a compound having a formula ##STR1## wherein R represents a di-loweralkylamino, morpholino, piperidino or pyrrolidino group and R.sub.1 and R.sub.2, which are the same or different, each represent a loweralkoxy group or a group R as defined; to form an enamine having a formula: ##STR2## wherein R is as define and subjecting the enamine IV to reduction cyclization; the enamines IV are new compounds.
    Type: Grant
    Filed: May 28, 1985
    Date of Patent: November 25, 1986
    Assignee: Sanofi
    Inventors: Jean-Robert Dormoy, Alain Heymes
  • Patent number: 4610819
    Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 9, 1986
    Assignee: A. H. Robins Company, Inc.
    Inventors: Young S. Lo, Albert D. Cale, Jr.
  • Patent number: 4608379
    Abstract: Compounds containing a cation of formula Ia ##STR1## and a pharmaceutically acceptable anion are anti-fungal agents. In formula Ia and Ib R.sub.1 is alkyl of at least 3 carbon atoms or aralkyl; R.sub.2 and R.sub.5 are hydrogen, lower alkyl, lower alkoxy, halogen or nitro; R.sub.6 and R.sub.7, when separate, are lower alkyl or aryl(lower)alkyl or, when joined together, are --(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 -- (where A is --(CH.sub.2).sub.n --, O, S or NR.sub.8 where n is O, 1 or 2 and R.sub.8 is lower alkyl) or a mono- or di-(lower alkyl) substitution product thereof.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: August 26, 1986
    Assignee: John Wyeth & Brother Limited
    Inventor: John T. A. Boyle
  • Patent number: 4604467
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrohalide, and heating the brominated product in an inert solvent and in the presence of a base to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl- 1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Paul F. Ranken
  • Patent number: 4602087
    Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)--CON(R.sub.4)--, --O--C.sub.1-3 alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkyene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.
    Type: Grant
    Filed: May 18, 1984
    Date of Patent: July 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian Luthi, Hans R. Meyer, Kurt Weber
  • Patent number: 4584381
    Abstract: Compounds of the formula: ##STR1## where R.sup.1 is halogen or nitro; R.sup.2 is C.sub.1-4 alkyl; and R.sup.3 is a C.sub.1-3 alkylene group are intermediates to 2-(3,5-disubstituted pyridyl-alkyl amino)-5-pyridylmethyl-4-pyrimidone derivatives which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: April 22, 1986
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George S. Sach
  • Patent number: 4565820
    Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]-furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: January 21, 1986
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4564628
    Abstract: Novel compounds useful as dopamine receptor agonists for the treatment of various diseases of the central nervous system such as Parkinson's disease and related disorders having the structural formula ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are each selected from the group consisting of H, and OA; A is H or ##STR2## R.sub.5 is selected from the group consisting of alkyl and aromatic residues; n is 2 or 3; and R.sub.1 is selected from the group consisting of 3-hydroxyphenyl, 4-hydroxyphenyl, 3-pyridyl, 4-pyridyl, ##STR3## where X is S, O or NH; and pharmaceutically acceptable salts thereof. Also disclosed is a method for inducing a dopaminergic response in a patient by adminstering a pharmacologically-effective amount of one of the foregoing compounds.
    Type: Grant
    Filed: August 13, 1984
    Date of Patent: January 14, 1986
    Assignee: Nelson Research & Development Co.
    Inventor: Alan S. Horn
  • Patent number: 4558133
    Abstract: Novel dyestuffs of the general formula ##STR1## wherein R designates a lower alkyl or alkenyl radical andR.sup.1 and R.sup.2 designate lower alkyl or alkenyl radicals which, together with the nitrogen atom to which they are bonded, can form a 5-membered or 6-membered heterocyclic ring,and whereinR, R.sup.1 and R.sup.2 can be substituted by non-ionic radicals, and at least one of the radicals R, R.sup.1 and R.sup.2 is substituted by an aryl radical, directly or via a bridge, orone of the radicals R.sup.1 or R.sup.2 represents an aryl radical, the ring a can be substituted by 1 or 2 methyl or ethyl radicals,the ring b can be substituted by 1 or 2 methyl, ethyl, methoxy or ethoxy radicals or by 1 halogen atom andAn.sup.- represents an anion,are particularly suitable for dyeing paper.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Beecken
  • Patent number: 4554282
    Abstract: New substituted 2,2-dimethyl-5-phenoxypentanoic acid benzamides which are useful as anti-arteriosclerotic agents are disclosed. These compounds elevate the high density lipoprotein fraction of cholesterol, and also lower the low density lipoprotein fraction of cholesterol.
    Type: Grant
    Filed: August 5, 1983
    Date of Patent: November 19, 1985
    Assignee: Warner-Lambert Company
    Inventors: Ila Sircar, Ann Holmes
  • Patent number: 4554352
    Abstract: 4-(Bromophenyl)pyridines, useful in preparing bactericides, are prepared by reacting a 4-phenylpyridine with bromine in the presence of an excess of a Lewis acid catalyst, preferably aluminum chloride.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: November 19, 1985
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Patent number: 4552964
    Abstract: A 4-(1-chlorovinyl)pyridine, preferably 4-(1-chlorovinyl)pyridine itself, is reacted with a butadiene, preferably chloroprene, to prepare a 4-(1-chlorocyclohex-3-enyl)pyridine. The preferred products are useful as intermediates in the preparation of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4552963
    Abstract: The yield of Diels-Alder product obtained by reacting a haloprene with a 4-vinylpyridine is increased by conducting the reaction in the presence of a boron trifluoride catalyst, preferably a boron trifluoride etherate. The product obtained by the reaction, a mixture of 4-(chlorocyclohex-3-enyl)pyridines, is useful in the production of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4551460
    Abstract: Pyrido[2,1-b]quinazoline derivatives of the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as hereinafter set forth, are described. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions as well as for the treatment of vascular disorders involving thrombosis.
    Type: Grant
    Filed: March 2, 1983
    Date of Patent: November 5, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Jefferson W. Tilley
  • Patent number: 4550167
    Abstract: Diels-Alder products obtained by reacting a haloprene with a 4-vinylpyridine, i.e., mixtures of 4-(halocyclohex-3-enyl)pyridine isomers, are reacted with a relatively strong acid, i.e., an acid having a dissociation constant of at least 1.7.times.10.sup.-5 at 25.degree. C., to form salts which are readily separated and/or reduced.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: October 29, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4550107
    Abstract: Disclosed are novel condensed diazepinones of formula I ##STR1## wherein B is a fused ring selected from ##STR2## X is --CH-- or, when B is ortho-phenylene, X can also be nitrogen; A.sub.1 is C.sub.1 -C.sub.2 alkylene; A.sub.2 is C.sub.1 -C.sub.2 when it is in the 2-position relative to the saturated heterocyclic ring nitrogen or a single bond or methylene when it is in the 3- or 4-position; R.sub.1 is C.sub.1 -C.sub.3 alkyl; R.sub.2 is C.sub.1 -C.sub.7 alkyl, optionally hydroxy-substituted on at least one of its second to seventh carbon, or C.sub.3 -C.sub.7 cycloalkyl, optionally hydroxy substituted, or C.sub.3 -C.sub.7 cycloalkylmethyl; or R.sub.1 and R.sub.2 can, together with the nitrogen therebetween, be a 4- to 7-membered saturated monocyclic, heterocyclic ring which can optionally include an oxygen or N--CH.sub.3 ; R.sub.3 is hydrogen, chlorine, or methyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.5 is hydrogen, chlorine or C.sub.1 -C.sub.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: October 29, 1985
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Wolfhard Engel, Gunter Trummlitz, Wolfgang Eberlein, Gerhard Mihm, Gunther Schmidt, Rudolf Hammer, Antonio Giachetti
  • Patent number: 4532252
    Abstract: 3,5-Substituted-2-pyridylalkylamino derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: December 9, 1983
    Date of Patent: July 30, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George S. Sach
  • Patent number: 4532326
    Abstract: 4-(3-Aminophenyl)pyridines, useful in the preparation of 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids, are prepared by heating a 2-amino-4-(4-pyridinyl)benzoic acid at decarboxylation temperatures.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: July 30, 1985
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Patent number: 4526974
    Abstract: The invention provides a process for preparing 2-pyridylalkylamines by reacting an alkali metal derivative of a 2-methylpyridine with a haloalkylamine. The compounds are useful as intermediates in the preparation of compounds having histamine H.sub.1 - and H.sub.2 -antagonist activity.
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: July 2, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Brian M. Adger, Antonietta R. Mastrocola
  • Patent number: 4515952
    Abstract: The invention provides a process for preparing 2-pyridylalkylamines, substituted in one of the 3- or 5-positions by bromo and in the other by C.sub.1-4 alkyl, by reacting an appropriate C.sub.1-4 alkyl substituted 2-pyridylalkylamine with an electrophilic brominating agent. Said 2-pyridylalkylamines are useful as intermediates in the synthesis of compounds useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: May 7, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Brian M. Adger, David J. O'Rourke
  • Patent number: 4509970
    Abstract: Novel substituted phenylphosphinyloxy- and phenylphosphinylthio-iminocarboxylates, synthesis thereof, intermediates therefor, and the use of said novel compounds for the control of weeds.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: April 9, 1985
    Assignee: Zoecon Corporation
    Inventor: Shy-Fuh Lee
  • Patent number: 4506075
    Abstract: 3-Methyl-4-(4-pyridinyl)benzeneamines, useful as cardiotonic agents, are prepared by reaction of pyridine, benzoyl chloride and an appropriate 3-methyl-N,N-di-lower-alkylbenzeneamine in the presence of copper powder and decomposing the reaction mixture with alkali and, if desired, reacting a resulting 3-methyl-4-(4-pyridinyl)N,N-di-lower-alkylbenzeneamine with hydrogen bromide and pyridine to obtain 3-methyl-4-(4-pyridinyl)benzeneamine.
    Type: Grant
    Filed: April 14, 1983
    Date of Patent: March 19, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4493931
    Abstract: The present invention provides a multistep process for the preparation of .beta.-cyclo-substituted ethylamines of the general formula:-Ar--CH.sub.2 --CH.sub.2 --NH.sub.2 (I)in which AR is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly- substituted, wherein said compounds represent a class of intermediates which can be converted to 4,5,6,7-tetrahydro[3,2-C] or [2,3-C]pyridines wherein the latter are useful for anti-inflammatory, vasodilator or blood platelet aggregation inhibition activities.
    Type: Grant
    Filed: June 29, 1982
    Date of Patent: January 15, 1985
    Assignee: Sanofi
    Inventors: Isaac Chekroun, Alain Heymes
  • Patent number: 4486593
    Abstract: The present invention provides novel 2-, 3-, or 4-pyridinylmethylamino arylic acids which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and 5-lipoxygenase inhibitors and as such represent useful pharmacological agents.
    Type: Grant
    Filed: January 19, 1983
    Date of Patent: December 4, 1984
    Assignee: The Upjohn Company
    Inventor: Chiu-Hong Lin
  • Patent number: 4447616
    Abstract: 2-And/or 6-pyridylethylamino-substituted fluorans useful as color formers, particularly in pressure-sensitive carbonless duplicating systems and thermal-responsive marking systems are prepared by the interaction of (pyridylethylaminophenyl)carbonylbenzoic acids with 4-hydroxy- or alkoxyanilines or by the interaction of (disubstituted aminophenyl)carbonylbenzoic acids with N-pyridylethyl-4-hydroxy- or alkoxy acetanilides. The (pyridylethylaminophenyl)carbonylbenzoic acid intermediates required for the fluorans are prepared by interacting a N-pyridylethyl-3-hydroxyaniline with a substituted or unsubstituted phthalic anhydride. The N-pyridylethyl-4-hydroxy- or alkoxyanilines and the N-pyridylethyl-3-hydroxyanilines are prepared by interacting the respective aniline with a vinylpyridine.
    Type: Grant
    Filed: November 30, 1982
    Date of Patent: May 8, 1984
    Assignee: Sterling Drug Inc.
    Inventors: William M. Hung, Edward E. Ehlinger
  • Patent number: 4446321
    Abstract: Novel 4-aryl-or heteroaryl-2,6-bis[(substituted-amino)phenyl]pyridines which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting a 2-, 3- or 4-R.sub.1 R.sub.2 N-acetophenone with an aryl or heteroaryl aldehyde in the present of ammonia or an ammonia-releasing agent.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: May 1, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4439609
    Abstract: This invention relates to 4-substituted aminomethyl pyridines with a butanamine, oxypropioamine or thiomethylamine substituent at the 2 position. The compounds are reacted with pyridones to form compounds which have histamine H.sub.2 -antagonist activity.
    Type: Grant
    Filed: February 16, 1983
    Date of Patent: March 27, 1984
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: David G. Cooper, George S. Sach
  • Patent number: 4431811
    Abstract: New decaprenylamines and the acid addition salts thereof, useful for controlling virus infections in animals, are described.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: February 14, 1984
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Hiroyasu Koyama, Yasuhiro Komatsu, Reiko Kubota, Toshihiro Takahashi
  • Patent number: 4415578
    Abstract: 3-Methyl-4-(4-pyridinyl)benzeneamines, useful as cardiotonic agents, are prepared by reaction of pyridine, benzoyl chloride and an appropriate 3-methyl-N,N-di-lower-alkylbenzeneamine in the presence of copper powder and decomposing the reaction mixture with alkali and, if desired, reacting a resulting 3-methyl-4-(4-pyridinyl)-N,N-di-lower-alkylbenzeneamine with hydrogen bromide and pyridine to obtain 3-methyl-4-(4-pyridinyl)benzeneamine.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: November 15, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4385058
    Abstract: This invention relates to 2-amino-4-pyrimidone derivatives, in which the amino group is substituted by a methylthioethyl, butyl or oxypropyl group bearing a terminal 4-dialkylaminomethyl-2-pyridyl group. The compounds have histamine H.sub.2 -antagonist activity. A specific compound of this invention is 2-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-5-(6-methyl-3- pyridylmethyl)-4-pyrimidone.
    Type: Grant
    Filed: September 16, 1981
    Date of Patent: May 24, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: David G. Cooper, George S. Sach
  • Patent number: 4383112
    Abstract: Chiral Schiff bases according to the general formula: ##STR1## and transition metal complexes thereof, wherein C.sup.* is an asymmetric carbon atom, R.sup.1 and R.sup.2, which may be the same or different are alkyl, aralkyl, aryl or alkaryl, R.sup.3 is hydrogen, alkyl, aralkyl, aryl or alkaryl, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen or lower alkyl or, where n is 1, may with the cyclic ring to which CR.sup.4 R.sup.
    Type: Grant
    Filed: July 8, 1980
    Date of Patent: May 10, 1983
    Assignee: Imperial Chemical Industries Limited
    Inventors: Dale A. Laidler, David J. Milner
  • Patent number: 4381305
    Abstract: New derivatives of 1,2-ethylenediamine and salts thereof endowed with vascular antispasmodic and antiallergic activity; processes for preparing them, some new intermediates useful in their preparation and pharmaceutical compositions containing them.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: April 26, 1983
    Assignee: Simes S.p.A.
    Inventors: Cesare Casagrande, Giorgio Ferrari
  • Patent number: 4380668
    Abstract: This invention relates to new decaprenylamines and the acid addition salts thereof, which are useful for controlling virus infection of vertebrate animals.
    Type: Grant
    Filed: November 19, 1980
    Date of Patent: April 19, 1983
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Hiroyasu Koyama, Yasuhiro Komatsu, Reiko Kubota, Toshihiro Takahashi
  • Patent number: 4377585
    Abstract: Disclosed and claimed are a cardiac composition and a method for increasing cardiac contractility using an effective amount of a cardiotonic 4-[4-(or 3)-AcNH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridine (I) or pharmaceutically-acceptable salt thereof, where R.sub.2 is hydrogen, methyl, ethyl or hydroxyl, R.sub.6 is hydrogen, methyl or ethyl, R.sub.3 and R.sub.5 are each hydrogen or methyl, and Ac is hydrogen, hydroxyacetyl, acetoxyacetyl, .alpha.-hydroxypropionyl, .alpha.-acetoxypropionyl, methyoxyacetyl, 2-butenoyl or carbamyl or when NHAc is attached to the 4-position of the phenyl ring Ac also is formyl, n-propanoyl, 2,2-dimethyl-n-propanoyl or 3-carboxypropanoyl or when NHAc is attached to the 3-position of the phenyl ring Ac also is acetyl. Novel compounds shown and claimed are 4-[4-(or 3)-Ac'NH-phenyl]-2-R.sub.2 -3-R.sub.3 -5-R.sub.5 -6-R.sub.6 -pyridines (II) or pharmaceutically-acceptable acid-addition salts thereof, where R.sub.2, R.sub.3, R.sub.5 and R.sub.
    Type: Grant
    Filed: July 20, 1981
    Date of Patent: March 22, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Donald F. Page
  • Patent number: 4363503
    Abstract: Novel 4-aryl-or heteroaryl-2,6-bis[(substituted-amino)phenyl]pyridines which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting a 2-, 3- or 4-R.sub.1 R.sub.2 N-acetophenone with an aryl or heteroaryl aldehyde in the present of ammonia or an ammonia-releasing agent.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: December 14, 1982
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung