Tetracyclo Ring System Having The Diazine Ring As One Of The Cyclos Patents (Class 544/246)
  • Patent number: 5077403
    Abstract: A process for the production of a compound of the formula ##STR1## where R.sub.1 and R.sub.2 each are alkyl C.sub.1 -C.sub.16, aryl, aralkyl, alkenyl, alkynyl, cyano, carboxy and esters, carboximido, N-monosubstituted and N,N-disubstituted carboximido with alkyl, aralkyl, and aryl groups; R.sub.3 is tertiary butyldimethyl silyl, R.sub.4 is tertiarybutyldimethylsilyl, trimethylsilyl, X=O or NH comprising condensing a compound of the formula ##STR2## wherein R.sub.3 and R.sub.4 are as defined above with a compound of either the formula: ##STR3## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.5 is C.sub.1 -C.sub.4 ; in the presence of a reaction-inert solvent at a temperature of from 50.degree.to about 150.degree. C. forming an intermediate and oxidizing the intermediate product, to form the desired compound of formula I. The products are antiviral.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: December 31, 1991
    Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence Plantations
    Inventors: Elie Abushanab, Chandra Vargeese
  • Patent number: 5047554
    Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: September 10, 1991
    Assignee: Pfizer Inc.
    Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
  • Patent number: 4980343
    Abstract: Therapeutic compositions comprising the new derivatives of aminooxodihydroisoindolo-quinazoline of the formula ##STR1## are useful in inhibiting the growth of colon and rectal tumors.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: December 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Valentino Stella, Laman A. Al-Razzak, Hans-Joachim Kabbe
  • Patent number: 4925943
    Abstract: Derivatives of 2-(2-aminobenzyl or 2-nitrobenzyl)-1,2,3,4-tetrahydroisoquinoline of the formula ##STR1## in which each of substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 or R.sub.8 may represent either a hydrogen atom, a straight or branched chain alkyl group, a straight or branched chain alkoxy group, a hydroxy group or corresponding esters, a phenoxy group, a benzyloxy group, a methylenedioxy bridge (--O--CH.sub.2 --O--) when this substituent is connected with an adjacent carbon, a halogen, a nitro group, an amine function corresponding to primary or secondary or tertiary amine, or quarternary ammonium;each of substituents R.sub.9 or R.sub.10 may represent either a hydrogen atom, a straight or branched chain alkyl group, an arylalkyl group, an amine function corresponding to primary or secondary or tertiary amine or quarternary ammonium, or may each be oxygen atoms;each of substituents R.sub.11 or R.sub.
    Type: Grant
    Filed: January 5, 1988
    Date of Patent: May 15, 1990
    Inventors: Isabelle Kanmacher, Jean-Francois Stambach, Louis Jung, Christa Schott, Jean-Claude Stoclet, Christiane Heitz
  • Patent number: 4847378
    Abstract: Chromogenic polycyclic azamethines of formula ##STR1## wherein T.sub.1 and T.sub.2 are each independently of the other lower alkyl, cycloalkyl, benzyl, or, when taken together, are alkylene,Q is --CH or, preferably, N,W is alkylene, alkenylene, 1,2-cycloalkylene or 1,2-arylene,R is hydrogen, lower alkyl, aryl or aralkyl, andY is alkyl or alkenyl, each unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or is aralkyl, and the ring A is unsubstituted or substituted by halogen, cyano, hydroxy, lower alkyl, lower alkoxy, lower alkylcarbonyl, lower alkylcarbonyloxy, lower alkylamino, di-lower alkylamino or lower alkylcarbonylamino, and the ring B is unsubstituted or substituted by halogen, cyano, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxyalkoxy or aralkoxy or a glycol ether group.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: July 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 4845220
    Abstract: The invention relates to vattable 2-aryl-4,6-diaminopyrimidines of formula ##STR1## wherein A.sub.1 and A.sub.2 are identical or different vattable radicals, andAr is an aryl radical.These pyrimidines are particularly suitable vat dyes for dyeing or printing textile fibres made from natural or regenerated cellulose. They give light- and wetfast orange, red or violet dyeings.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 4, 1989
    Inventor: Hans Altermatt
  • Patent number: 4666526
    Abstract: Azine pigments having the probable structure ##STR1## wherein the rings designated by T, R', X and X' can be substituted or expanded to naphthalene systems. The pigments can be prepared by reacting compounds having the probable structures ##STR2## in the presence of hydrazine. The compounds having the probable structures (IV) and (IVa) are formed by reacting isatoic anhydrides or anthranilic acid esters or anthranilic acid amides with at least one mol of an aminoiminoisoindolenine.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: May 19, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Meinhard Rolf, Rutger Neeff
  • Patent number: 4667035
    Abstract: The novel compounds of the general formula I ##STR1## where R and R.sup.1 are substituents and the rings A can be substituted and/or can carry fused rings, are useful intermediates for the preparation of, for example, dyes and active ingredients.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: May 19, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Rolf-Dieter Kohler
  • Patent number: 4582902
    Abstract: Pigments that can be used to color plastics, paints, and printing inks have the structural formula ##STR1## wherein each R.sup.1, each R.sup.3, and R.sup.7 represent hydrogen, halogen, nitro, or lower alkyl and each R.sup.2, each R.sup.4, each R.sup.5, and R.sup.6 represent hydrogen or halogen.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: April 15, 1986
    Assignee: Sun Chemical Corporation
    Inventor: Terence R. Chamberlain
  • Patent number: 4581172
    Abstract: Pyrimidone derivatives of the formula ##STR1## wherein n is the integer 1 or 0; A.sup.1 and A.sup.2 are independently methylene or mono-lower alkyl or di-lower alkyl methylene; X is methylene, mono-lower alkyl or di-lower alkyl methylene, nitrogen or lower alkyl nitrogen; R is hydrogen or lower alkyl; and Y and Z taken together are the group .dbd.NR.sup.5, or R and Z taken together form a N--C--bond and Y is a group --N(H)R.sup.5 ; R.sup.1, R.sup.2 and R.sup.3 are hydrogen, lower alkyl or lower alkoxy, or R.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 taken together are methylenedioxy or ethylenedioxy; R.sup.4 is hydrogen or lower-alkyl; R.sup.5 is phenyl or phenyl substituted by one or more of R.sup.6, R.sup.7 and R.sup.8 which, independently, are chlorine, fluorine, bromine, lower-alkyl or lower-alkoxy; and provided that at least one of the methylene groups A.sup.1 and A.sup.2 is mono-lower alkyl or di-lower alkyl methylene, when R.sup.
    Type: Grant
    Filed: April 25, 1984
    Date of Patent: April 8, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ado Kaiser, Frank Kienzle
  • Patent number: 4581450
    Abstract: Pigments that can be used to color plastics, paints, and printing inks have the structural formula ##STR1## wherein each R.sup.1, each R.sup.3, and R.sup.7 represent hydrogen, halogen, nitro, or lower alkyl and each R.sup.2, each R.sup.4, each R.sup.5, and R.sup.6 represent hydrogen or halogen.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: April 8, 1986
    Assignee: Sun Chemical Corporation
    Inventor: Terence R. Chamberlain
  • Patent number: 4503227
    Abstract: The invention relates to chromogenic dihydroquinazolines of the general formula ##STR1## wherein the ring A is a monocyclic or polycyclic, unsubstituted or substituted heterocyclic radical which may contain further heteroatoms as ring members,each of X.sub.1, X.sub.2 and Y independently of one another is hydrogen, halogen, lower alkyl, lower alkanoylamino, or a group of the formula ##STR2## X.sub.3 is hydrogen, halogen, lower alkyl or lower alkoxy; each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, Z.sub.1 and Z.sub.2 independently of one another is C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or is cycloalkyl, phenyl, or phenyl or benzyl each substituted by halogen, nitro, lower alkyl or lower alkoxy, and the radicals R may also be hydrogen; oreach pair of substituents (R.sub.1 and R.sub.2), (R.sub.3 and R.sub.4) and (Z.sub.1 and Z.sub.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: March 5, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Balli, Sigmund Gunzenhauser, Ian J. Fletcher, Davor Bedekovic
  • Patent number: 4465833
    Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: August 14, 1984
    Assignees: Hughes Aircraft Company, Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Robert H. Boschan
  • Patent number: 4447607
    Abstract: The present invention provides novel dibenzo diazocines which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.
    Type: Grant
    Filed: November 5, 1982
    Date of Patent: May 8, 1984
    Assignee: The Upjohn Company
    Inventor: Roy A. Johnson
  • Patent number: 4409224
    Abstract: Pyrimido[1,6-a]indole derivatives characterized by having a substituted ethyl group at position 5 and optionally being further substituted at various positions on the pyrimido[1,6-a]indole nucleus are disclosed. The foregoing compounds are useful as antihypertensive agents in a mammal. Methods for their preparation also are disclosed.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: October 11, 1983
    Assignee: American Home Products Corp.
    Inventor: Ivo L. Jirkovsky
  • Patent number: 4400506
    Abstract: What are disclosed are compounds of the formula ##STR1## wherein, X is oxygen, sulfur, or halogen, useful as intermediates in the preparation of certain pyrimido(6,1-a)isoquinolin-4-ones having pharmaceutical utilities, and methods for making said intermediates.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: August 23, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bansi Lal, Adolf D'Sa, Horst Dornauer, Noel J. de Souza
  • Patent number: 4273773
    Abstract: Tricyclic isoindole derivatives characterized by having a 1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole or 1,3,4,10b-tetrahydropyrimido[6,1-a]isoindol-6(2H)-one nucleus are disclosed. The foregoing compounds are useful antihypertensive agents.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: June 16, 1981
    Assignee: American Home Products Corporation
    Inventors: Christopher A. Demerson, Leslie G. Humber, Jean-Marie Ferland
  • Patent number: 4247699
    Abstract: The reaction of isatoic anhydrides with malononitrile in a reaction-inert solvent in the presence of a base to produce 2-amino-3-cyano-4-hydroxy-quinolines and 2-amino-.alpha.,.alpha.-dicyanoacetophenones which are then hydrolyzed and decarboxylated under acid or base conditions to produce 2-amino-4-hydroxy-quinolines, useful as intermediates for preparation of 1-oxo-1H-6-alkoxy-pyrimido[1,2-a]quinoline-2-carboxylic acids and esters of value as antiallergy agents.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: January 27, 1981
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4217452
    Abstract: The invention relates to a new synthesis for the preparation of tetracyclic compounds of the general formula: ##STR1## as well as the pharmaceutically acceptable salts thereof, in which: n is the number 1 or 2,m is the number 1, if n=2 and the number 2, if n=1,R.sub.1 and R.sub.2 stand for hydrogen, hydroxy, halogen, lower alkyl (1-4 C), lower alkoxy (1-4 C) or trifluoromethyl andR.sub.3 represents hydrogen, alkyl (1-6 C), aralkyl (7-10 C) or an amino alkyl group (1-6 C), in which the nitrogen atom has been substituted by two alkyl groups (1-4 C), or the nitrogen atom forms part of a heterocyclic 5- or 6-membered ring,having valuable biological properties.
    Type: Grant
    Filed: December 27, 1976
    Date of Patent: August 12, 1980
    Assignee: Akzona Incorporated
    Inventor: Jacques Olivie
  • Patent number: 4216326
    Abstract: N-{3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
    Type: Grant
    Filed: May 3, 1978
    Date of Patent: August 5, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4142049
    Abstract: Disclosed are novel benzo[g]Pyrido[2,1-b]-quinazolinones which are active as anti-allergy agents and thus have utility in the treatment of allergic reactions such as bronchial asthma.
    Type: Grant
    Filed: December 5, 1977
    Date of Patent: February 27, 1979
    Assignee: Warner-Lambert Company
    Inventors: Charles F. Schwender, Brooks R. Sunday