Chalcogen Attached Directly To The Carbocyclic Ring Of The Quinoline Ring System By Nonionic Bonding Patents (Class 546/177)
  • Patent number: 4613607
    Abstract: Antiarhythmic medicaments containing, as active substance, a compound of the formula: ##STR1## in which n is 1 or 2, X and Y are fixed in positions 5, 6, 7 or 8 on the quinoline cycle and each represents a hydrogen atom or an alkoxy group having 1 to 3 carbons, R is a hydrogen atom or an alkyl group having 1 to 4 carbons, cycloalkyl having 3 to 8 carbons, phenyl or phenyl substituted by alkoxy having 1 to 4 carbons, R.sub.1 is a hydrogen atom or an alkyl group having 1 to 4 carbons or a phenylalkyl group of which the alkyl part has 1 to 3 carbons, R.sub.2 is a hydrogen atom, an alkyl group having 1 to 2 carbons or an alkenyl group having 2 to 4 carbons.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: September 23, 1986
    Assignee: Pharmuka Laboratoires
    Inventors: Claude G. A. Gueremy, Michel A. P. Mestre, Christian L. A. Renault
  • Patent number: 4600776
    Abstract: Cationic enamine dyestuffs of the general formula ##STR1## in which the symbols have the meaning given in the description, are used for dyeing natural and synthetic substrates and compositions which can be dyed with cationic dyestuffs, in particular paper.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlheinrich Meisel, Roderich Raue
  • Patent number: 4548935
    Abstract: Dihydropyridine anti-ischaemic and anti-hypertensive agents of the formula: ##STR1## and their pharmaceutically acceptable salts; wherein R is aryl or heteroaryl; R.sup.1 and R.sup.2 are each independently C.sub.1 -C.sub.4 or 2-methoxyethyl; n is 1 or 2; m is 1, 2 or 3; X is a 5 or 6 membered aromatic heterocyclic group which is linked to the adjacent alkoxymethyl group by a ring carbon atoms thereof; and Z is a group--NR.sup.3 R.sup.4 or a 5 to 6 membered nitrogen containing heterocyclic group; where R.sup.3 is H or C.sub.1 -C.sub.4 alkyl; R.sup.4 is H, C.sub.1 -C.sub.4 alkyl, CO(C.sub.1 -C.sub.4 alkyl), COCF.sub.3, CONR.sup.5 R.sup.6, SO.sub.2 (C.sub.1 -C.sub.4 alkyl) or a heterocyclic or SO.sub.2 -heterocyclic group, wherein the heterocyclic group is optionally substituted; R.sup.5 and R.sup.6 and each independently H or C.sub.1 -C.sub.4 alkyl or taken together with the nitrogen atom to which they are attached, they form a pyrrolidinyl, piperidyl, morpholino, piperazinyl or N-(C.sub.1 -C.sub.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: October 22, 1985
    Assignee: Pfizer Inc.
    Inventors: David Alker, Peter E. Cross, Simon F. Campbell
  • Patent number: 4547509
    Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, acylamino, dialkyl amino, trihalomethyl, halogen, nitro, hydroxy or cyano;X is in the 5, 6 or 7 position and is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3, S(CH.sub.2).sub.n or (CH.sub.2).sub.n ;Y is O(CH.sub.2).sub.n, S(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3 where R.sub.3 is H, alkyl or (CH.sub.2).sub.n ;R.sub.2 is monosubstituted or independently disubstituted H, hydroxy, alkyl, halogen, nitro, alkoxy, carboxyl, alkylcarboxy, trihalomethyl, cyano, trifluoromethyl, dialkylamino or acylamino;Z is O, S or (NR.sub.3).sub.2 where R.sub.3 is H, alkyl or aryl; andn is 0 to 10 inclusiveuseful in the treatment of ischemic heart disease and hypertriglyceridemia.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: October 15, 1985
    Assignee: USV Pharmaceutical Corp.
    Inventors: John H. Musser, Charles A. Sutherland
  • Patent number: 4529798
    Abstract: Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: July 16, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shephard
  • Patent number: 4472403
    Abstract: The invention is concerned with novel quinicine and cinchonicine derivatives having cardiovascular activities of the formula or a salt thereof, ##STR1## in which A--B is --CH.sub.2 --CH.sub.2, --CHOH--CH.sub.2 --, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4)--; R.sup.1 is hydrogen, hydroxy or lower alkoxy; R.sup.2 is ethyl or vinyl; R.sup.3 is C.sub.2-8 alkyl, C.sub.1-8 hydroxyalkyl, lower alkoxy-alkyl or lower alkanoyloxyalkyl, C.sub.
    Type: Grant
    Filed: October 28, 1980
    Date of Patent: September 18, 1984
    Assignee: A.C.F. Chemiefarma N.V.
    Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
  • Patent number: 4460594
    Abstract: Compounds of the formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is hydroxy, C.sub.1-4 alkoxy or an in-vivo hydrolysable acyloxy group:R.sub.2 is hydrogen, C.sub.1-4 alkyl, hydroxy, C.sub.1-4 alkoxy or an in-vivo hydrolysable acyloxy group;R.sub.4 is benzofuryl, benzothienyl, indolyl, quinolyl, isoquinolyl,2,3-dihydrobenzofuryl, 2,3-dihydrobenzylthienyl or 2,3-dihydroindolyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, hydroxy or acyloxy, trifluoromethyl, halogen or nitro; andA is a bond or C.sub.1-6 alkylene,a process for their preparation, and pharmaceutical compositions containing them.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: July 17, 1984
    Assignee: Beecham Group p.l.c.
    Inventor: Roger E. Markwell
  • Patent number: 4443453
    Abstract: The invention is concerned with novel quinoline derivatives of the formula ##STR1## or a salt thereof, in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2 --, --CH.sub.2 --CHOH--, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4)--, R.sup.1 is hydrogen, hydroxy or lower alkoxy, R.sup.2 is lower alkyl, R.sup.3 is ethyl or vinyl, R.sup.4 is lower alkyl, whereby the substituents at the 3- and 4-position of the piperidine ring are in the cis-position. The compounds of the formula may be in the form of the optically active enantiomers and/or their therapeutically acceptable salts. Furthermore the invention provides pharmaceutical compositions possessing cardiovascular activities in which as active compound at least a compound of the above formula is used. Methods for the preparation of the pharmaceutical compositions and of the active compounds are also included by the invention.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: April 17, 1984
    Assignee: ACF Chemiefarma N.V.
    Inventors: Hans B. Trijzelaar, Ronus de Bode, Handricus B. A. Welle
  • Patent number: 4442106
    Abstract: The invention is concerned with novel quinoline derivatives having cardiovascular activities of formula 1 ##STR1## in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.5)--CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.5)--; R.sup.1 is hydrogen, hydroxy or lower alkoxy; R.sup.2 is lower alkyl, hydroxy, lower alkoxy or CF.sub.3 ; R.sup.3 is ethyl or vinyl; R.sup.4 is C.sub.1-9 alkyl, C.sub.2-9 hydroxyalkyl or lower alkoxyalkyl, C.sub.5-6 cycloalkyl, C.sub.3-6 cycloalkyl lower alkyl, cyano lower alkyl, lower alkenyl, lower alkynyl, tetrahydrofurfuryl, mono- or di-lower alkylamino lower alkyl; mono- or di-lower alkylamino lower hydroxyalkyl; phenyl C.sub.1-4 alkyl, phenyl C.sub.1-4 hydroxy-alkyl, diphenyl C.sub.1-4 alkyl, benzoyl C.sub.1-4 alkyl, furyl C.sub.1-4 alkyl, thienyl C.sub.1-4 alkyl, furoyl C.sub.1-4 alkyl or thienoyl C.sub.1-4 alkyl, which groups may be optionally substituted in the aromatic nucleus, and R.sup.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: April 10, 1984
    Assignee: ACF Chemiefarma N.V.
    Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
  • Patent number: 4442107
    Abstract: The invention is concerned with quinoline derivatives having cardiovascular activities of the formula ##STR1## or a salt thereof, in which A--B is --CH.sub.2 --CH.sub.2 --, --CHOH--CH.sub.2, --CH.sub.2 --CHOH--, --C(O)--CH.sub.2 --, --CH.sub.2 --C(O)--, --C(NOR.sup.4)--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --C(NOR.sup.4), R.sup.1 is hydrogen, hydroxy or lower alkoxy, R.sup.2 is hydroxy, lower alkoxy, trifluoromethyl, R.sup.3 is ethyl or vinyl and R.sup.4 is lower alkyl. The compounds of the formula may be in the form of their optically active enantiomers and/or their therapeutically acceptable salts. Furthermore the invention provides pharmaceutical compositions possessing cardiovascular activities, in which as active compound at least a compound of the above formula is used. Methods for the preparation of the pharmaceutical compositions and of the active compounds are also disclosed and covered by the invention.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: April 10, 1984
    Assignee: ACF Chemiefarma N.V.
    Inventors: Hans B. Trijzelaar, Ronus de Bode, Hendricus B. A. Welle
  • Patent number: 4380633
    Abstract: Methine dyes from tetrahydroquinoline compounds containing N-thioether substituents, in general produce bright yellow shades when applied to polyester fabrics by conventional dyeing procedures, have improved properties such as dyeability, fastness to light, resistance to sublimation, insensitivity to pH changes, and dye at the boil and under pressure to the same depth of shade. These compounds are particularly useful in the thermal fixation technique for dyeing polyester materials.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: April 19, 1983
    Assignee: Eastman Kodak Company
    Inventors: Clarence A. Coates, Jr., Max A. Weaver
  • Patent number: 4369322
    Abstract: The known synthesis for the production of aromatic substituted acetonitriles by reaction of aromatic substances with cyanogen chloride in the gas phase is improved by feeding the starting materials in gaseous form and separated from each other into the reactor. The process can be used to synthesize in general aromatic and especially hetero-aromatic substituted acetonitrile.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: January 18, 1983
    Assignee: Degussa AG
    Inventors: Peter Schalke, Axel Kleemann
  • Patent number: 4305932
    Abstract: The present invention deals with derivatives of 6-ethoxy-1,2,-dihydro-2,2,4-trimethylquinoline (called "Ethoxyquin"), processes for their preparation and their utility inter alia, as active ingredient of a pharmaceutical composition. Said compounds have, inter alia, under biological conditions anti-oxidant properties, may be used to protect Vitamin-E-deficient animals, and act as growth promoting agents.
    Type: Grant
    Filed: January 23, 1978
    Date of Patent: December 15, 1981
    Assignee: Abic Ltd.
    Inventors: Emil Menachemoff, Oded Awerbuch, Raphael R. G. Haber
  • Patent number: 4282230
    Abstract: Imidazolylethoxy derivatives of quinoline-2- or 4-methanols having the general formula ##STR1## and their acid addition salts are useful as antifungal and antibacterial agents.
    Type: Grant
    Filed: November 15, 1979
    Date of Patent: August 4, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Hans Hoehn
  • Patent number: 4260742
    Abstract: Methine dyes from tetrahydroquinoline compounds containing N-thioether substituents, in general produce bright yellow shades when applied to polyester fabrics by conventional dyeing procedures, have improved properties such as dyeability, fastness to light, resistance to sublimation, insensitivity to pH changes, and dye at the boil and under pressure to the same depth of shade. These compounds are particularly useful in the thermal fixation technique for dyeing polyester materials.
    Type: Grant
    Filed: April 4, 1979
    Date of Patent: April 7, 1981
    Assignee: Eastman Kodak Company
    Inventors: Clarence A. Coates, Jr., Max A. Weaver
  • Patent number: 4238612
    Abstract: A process for the conversion of compounds of the formula: ##STR1## in which R is a hydrogen atom or a substituent and for which the carbon carrying the vinyl group has the rectus configuration, into the corresponding compounds of formula (I) for which the carbon carrying the vinyl group has the sinister configuration, and vice versa, which comprises subjecting a compound of formula (I) for which the carbon carrying the vinyl group has the rectus or sinister configuration, partially or entirely salified, to a heating at a temperature above 50.degree. C. in a protic solvent or a mixture of protic solvents in the presence or absence of formaldehyde, and isolating the compound of formula (I) for which the carbon carrying the vinyl group has the sinister or rectus configuration thus formed.
    Type: Grant
    Filed: March 21, 1979
    Date of Patent: December 9, 1980
    Assignee: Pharmindustrie
    Inventors: Jean-Jacques Barieux, Marie-Christine Dubroeucq, Francois Rocquet
  • Patent number: 4202985
    Abstract: Imidazolylethoxy derivatives of quinoline-3-methanols having the general formula ##STR1## and their acid addition salts are useful as antifungal and antibacterial agents.
    Type: Grant
    Filed: October 25, 1978
    Date of Patent: May 13, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Hans Hoehn
  • Patent number: 4161601
    Abstract: Methine dyes from tetrahydroquinoline compounds containing N-thioether substituents, in general produce bright yellow shades when applied to polyester fabrics by conventional dyeing procedures, have improved properties such as dyeability, fastness to light, resistance to sublimation, insensitivity to pH changes, and dye at the boil and under pressure to the same depth of shade. These compounds are particularly useful in the thermal fixation technique for dyeing polyester materials.
    Type: Grant
    Filed: May 31, 1977
    Date of Patent: July 17, 1979
    Assignee: Eastman Kodak Company
    Inventors: Clarence A. Coates, Jr., Max A. Weaver
  • Patent number: 4139537
    Abstract: Cardiac arrhythmias can be treated by administering an effective amount of 3-aryloxy-1-(2-or 4-iminodihydro-1-pyridyl)-2-propanol or phamaceutically acceptable acid addition compound. Many new effective compounds of this type are disclosed.
    Type: Grant
    Filed: June 29, 1976
    Date of Patent: February 13, 1979
    Assignee: Cooper Laboratories, Inc.
    Inventors: Julius Diamond, Ronald A. Wohl