Phenanthridines (including Hydrogenated) Patents (Class 546/108)
  • Patent number: 5541195
    Abstract: 1-Acylpiperidine compound of the formula I ##STR1## in which R.sub.1 is an optionally substituted aralkyl, aryloxyalkyl, heteroaralkyl, aroyl, heteroaroyl, cycloalkylcarbonyl, aralkanoyl, heteroarylalkanoyl, aralkoxycarbonyl or arylcarbamoyl radical or the acyl radical of an .alpha.-amino acid which is optionally N-substituted by lower alkanoyl or carbamoyl-lower-alkanoyl, R.sub.2 is cycloalkyl or an optionally substituted aryl or heteroaryl radical, R.sub.3 is hydrogen, alkyl, carbamoyl or an alkanoyl or alkenoyl radical which is optionally substituted by carboxyl or esterified or amidated carboxyl, R.sub.4 is an optionally substituted aryl or optionally partially hydrogenated heteroaryl radical, X.sub.1 is methylene, ethylene, a direct linkage, an optionally ketalised carbonyl group or an optionally etherified hydroxymethylene group, X.sub.2 is alkylene, carbonyl or a direct linkage, and X.sub.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: July 30, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Schilling, Silvio Ofner, Siem J. Veenstra
  • Patent number: 5523212
    Abstract: Aryl N-alkylacridanthiocarboxylate compounds which produce chemiluminescence. The compounds produce light with peroxide and peroxidase. The compounds are used as a substrate in assays for various analytes.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: June 4, 1996
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka DeSilva, Zahra Arghavani
  • Patent number: 5491072
    Abstract: N-alkylacridan carboxylic acid derivative compounds (I) are used to generate chemiluminescence by the action of a peroxidase enzyme and an oxidant. The compounds I are useful in assays of all types.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: February 13, 1996
    Assignee: Lumigen, Inc.
    Inventors: Hashem Akhavan-Tafti, Renuka Desilva, Katsuaki Sugioka
  • Patent number: 5489603
    Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5434165
    Abstract: An aromatic amino-substituted compound represented by formula: ##STR1## wherein A represents CH, N, or N.fwdarw.O; R.sub.1 represents a nitro group or an amino group; R.sub.2 represents a hydrogen atom, a lower alkyl group, or an acyl group; and R.sub.3 represents a group: ##STR2## wherein m represents 0 or 1; n represents an integer of from 0 to 3; R.sub.4 and R.sub.5 each represents a hydrogen atom or a lower alkyl group; R.sub.6 and R.sub.7 each represents a hydrogen atom or a straight chain or branched lower alkyl group; R.sub.4 and R.sub.6 may be joined together to form an alkylene chain forming a heterocyclic ring; R.sub.5 and R.sub.7 may be joined together to form an alkylene chain forming a heterocyclic ring and R.sub.6 and R.sub.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: July 18, 1995
    Assignee: Sanawa Kagaku Kenkyusho Company, Ltd.
    Inventors: Masayasu Kurono, Yutaka Baba, Tomoo Suzuki, Tsunemasa Suzuki, Kiyotaka Hirooka, Kiichi Sawai
  • Patent number: 5401847
    Abstract: Heteromultimeric fluorophores are provided for binding to DNA, which allow for the detection of DNA in electrical separations and preparation of probes having high-fluorescent efficiencies and large Stokes shifts. In addition, by appropriate choice of fluorescent molecules, one can use a single narrow wavelength band excitation light source, while obtaining fluorescent emissions having sufficient separation to be readily discriminated.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: March 28, 1995
    Assignee: Regents of the University of California
    Inventors: Alexander N. Glazer, Scott C. Benson
  • Patent number: 5338847
    Abstract: Described are a class of chemiluminescent compound characterized by the presence an aryl ester, thioester or amide of a carboxylic acid substituted heterocyclic ring that is susceptible to chemical attack (such as by oxidic attack) to dissociate the heterocyclic ring to a transient compound. The heterocyclic ring is ring carbon-bonded to the carbonyl of the ester, thioester and amide moiety and possesses a heteroatom in an oxidation state that allows chemiluminescence by dissociating a compound ("intermediate") that decays to produce chemiluminescence, at the carbon bonded to the carbonyl. The aryl ring or ring system is ring carbon-bonded to the oxygen, sulfur or nitrogen of the ester, thioester or amide, as the case may be, and contains at least three substituents on a six-member ring. The substitution on the six-member ring comprises three or more groups acting in concert to sterically and electronically hinder hydrolysis of the ester, thioester or amide linkage.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: August 16, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5321136
    Abstract: A chemiluminescent label compound and conjugate containing the same, in which the compound involves a fused ring system comprising a(i) hetercyclic ring as a fused member thereof in which the heterocyclic ring contains(a) one or more nitrogen heteroatoms in the ring;(b) at least one saturated or unsaturated ring in fused state with the heterocyclic ring;(c) an available carbon atom in the heterocyclic ring that is adjacent to a carbon forming a fused ring with the heterocyclic ring; and(d) at least one substituent that is peri relative said available carbon of the heterocyclic ring, which substituent serves to enhance the hydrolytic stability of the chemiluminescent label compound; and(ii) a leaving group coupled to the heterocyclic ring through a carbon adjacent to a fused ring carbon such that the leaving group and heterocyclic ring join to form a difunctional carboxy-containing linkage in which the carboxy carbon is directly bonded to the carbon of the heterocyclic ring adjacent to a fused ring carbon,(a)
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 14, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5312921
    Abstract: Novel fluorescent dyes are provided, characterized by having a fluorophore joined to a polycationic chain of at least two positive charges. The dyes are found to provide for high enhancement upon binding to nucleic acid and have strong binding affinities to the nucleic acid, as compared to the fluorophore without the polycationic chain. The dyes find use in detection of dsDNA in gel electrophoresis and solution at substantially higher sensitivities using substantially less dye.
    Type: Grant
    Filed: May 14, 1993
    Date of Patent: May 17, 1994
    Assignee: Regents of the University of California
    Inventors: Alexander N. Glazer, Scott C. Benson
  • Patent number: 5290936
    Abstract: A novel chemiluminescent labeling compositions comprising an ester, thiolester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinguished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with --NO.sub.2 meta or para substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: March 1, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Iraj Beheshti, Harlen Koelling
  • Patent number: 5284951
    Abstract: A novel chemiluminescent labeling compositions comprising an ester, thioester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinguished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with meta and/or para substituents thereon that possess an electron withdrawing capacity characterized as a .sigma..sub.p value greater than 0 and less than 1.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 8, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Frank McCapra, Iraj Beheshti
  • Patent number: 5284952
    Abstract: A chemiluminescent labeling composition comprising an ester, thioester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinquished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with meta and/or para --SO.sub.2 -- substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 8, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Kastooriranganathan Ramakrishnan
  • Patent number: 5283334
    Abstract: A chemiluminescent compound possessing an aryl ester, thioester or amide of a carboxylic acid substituted heterocyclic ring or ring system that is susceptible to chemical attack to dissociate the heterocyclic ring to a transient compound. The heterocyclic ring is ring carbon-bonded to the carbonyl of the ester, thioester or amide moiety and possesses a heteroatom in an oxidation state that allows chemiluminescence by dissociating a compound at the carbon bonded to the carbonyl that decays to produce chemiluminescence. The heterocyclic ring or ring sustem contains bonded to it through an organic moiety, a functional group that is functionally reactive with an active hydrogen containing compound. The aryl ring is a ring or ring system that is ring carbon-bonded to the oxygen, sulfur or nitrogen of the ester, thioester or amide, as the case may be, and contains substituents on a six-member ring that act to sterically and electronically hinder hydrolysis of the ester, thioester or amide linkage.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 1, 1994
    Assignee: London Diagnostics, Inc.
    Inventor: Frank McCapra
  • Patent number: 5281712
    Abstract: A novel chemiluminescent labeling compositions comprising an ester or thiolester covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinquished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with quaternary ammonium meta or para substituents thereon.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: January 25, 1994
    Assignee: London Diagnostics, Inc.
    Inventors: Frank McCapra, Beheshti Iraj, Kastooriranganathan Ramakrishnan
  • Patent number: 5274097
    Abstract: Novel 1,3-disubstituted pyrrolidines active on the central nervous system of the formula ##STR1## wherein A--denotes phenyl or hetaryl, which is optionally fused with aromatic, saturated or unsaturated cyclic or heterocyclic hydrocarbons, where this radical can optionally be substituted,X--denotes --O--CH.sub.2 --, --CH.sub.2 --O-- or --O--,n--denotes a number from 1 to 19, andB--denotes cyano or a group of the formula --COOR.sup.1, --CONR.sup.2 R.sup.3, --SO.sub.2 NR.sup.2 R.sup.3, --SO.sub.m R.sup.4, --NR.sup.5 R.sup.6, or --C.tbd.C--CH.sub.2 --NR.sup.5 R.sup.6,and salts thereof.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: December 28, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Schohe, Peter-Rudolf Seidel, Jorg Traber, Thomas Glaser
  • Patent number: 5254478
    Abstract: Use in magnetometry by electronic paramagnetic resonance (EPR) of tetracyanoquinodimethane derivatives in accordance with the formula: ##STR1## in which AH.sup.+ is a cation derived from a heterocyclic aromatic base having at least three aromatic rings and a single NH.sup.+ group included in at least one of the rings, AH.sup.+ being e.g. acridinium or benzoquinolinium.
    Type: Grant
    Filed: March 19, 1991
    Date of Patent: October 19, 1993
    Assignee: Commissariat a l'Energie Atomique
    Inventor: Mehdi Moussavi
  • Patent number: 5246709
    Abstract: A dosage form is disclosed comprising an antiemetic and antinausea drug for treating vomiting and nausea.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: September 21, 1993
    Assignee: Alza Corporation
    Inventors: Francisco Jao, Hoa T. Huynh, Patrick S. L. Wong
  • Patent number: 5204470
    Abstract: Azabicyclic compounds of formula ##STR1## and their pharmaceutically acceptable acid addition salts are disclosed. In the formula, ##STR2## is an optionally substituted heteroaryl group containing at least one hetero atom X; n is 2, 3 or 4; m is 1 or 2; R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.3-5 -alkenyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-C.sub.1-2 alkyl or aryl- or heteroaryl-C.sub.1-2 -alkyl; and the --(CH.sub.2).sub.m ##STR3## moiety is ortho to the hetero atom X. The compounds exhibit activity as 5-HT.sub.3 -antagonists and can be used, inter alia, for the treatment of neuropsychiatric disorders.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: April 20, 1993
    Assignee: John Wyeth & Brother, Limited
    Inventor: Ian A. Cliffe
  • Patent number: 5100904
    Abstract: A novel prolinal derivatives of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms,R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]possess inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent as a amnesia.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: March 31, 1992
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
  • Patent number: 5068334
    Abstract: This invention relates to pharmaceutical compositions containing quinolin-2,5-diones of formula ##STR1## wherein A, B, R.sup.1 to R.sup.3 and X are defined hereinbelow, some of which are novel, which compounds have valuable pharmacological properties, particularly analgesic antipyretic and/or antiphlogistic effects, to new intermediates and processes for preparing them.
    Type: Grant
    Filed: September 27, 1989
    Date of Patent: November 26, 1991
    Assignee: Karl Thomae GmbH
    Inventors: Erich Muller, Josef Nickl, deceased, Armin Heckel, Gunther Engelhardt
  • Patent number: 5041452
    Abstract: Novel diamides having a nitrogen-containing heterocyclic moiety such as pyridyl are disclosed that are useful for improving feed utilization efficiency of ruminants and for improving lactation of lactating ruminants.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Alan W. White
  • Patent number: 5030631
    Abstract: Novel tricyclic arylsulfonamides useful for treating hypertension and bronchoconstiction, as well as to their pharmaceutical compositions and methods for using the same.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 9, 1991
    Assignee: Schering Corporation
    Inventor: Barr E. Bauer
  • Patent number: 4960890
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4954509
    Abstract: A compound, or a solvate or salt thereof, of formula (I): ##STR1## in which: RCO is an acyl group in which the group R contains a substituted or unsubstituted carbocyclic aromatic or heterocyclic aromatic ring and R.sub.1 R.sub.2 are independently hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.4 -12 cycloalkylalkyl groups or together form a C.sub.2-8 branched or linear polymethylene or C.sub.2-6 alkenylene group optionally substituted with a hetero-atom;R.sub.3 is hydrogen, C.sub.1-6 alkyl, or phenyl, or R.sub.3 together with R.sub.1 forms a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --, group; R.sub.4 and R.sub.5, which may be the same or different and may be attached to the same or different carbon atoms of the isoquinoline nucleus, are each hydrogen, halogen, hydroxy, C.sub.1-6 alkyl, aryl, or R.sub.4 together with R.sub.5 form a --(CH.sub.2).sub.p -- group, where p is an integer of from 1 to 5 and one or more of the --(CH.sub.2)-- moieties is optionally substituted by a C.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: September 4, 1990
    Assignee: Dr. Lo. Zambeletti S.p.A.
    Inventors: Vittorio Vecchietti, Giuseppe Giardina
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4952589
    Abstract: This invention relates to aminoalkylphenoxyalkyl substituted heterocycles. These compounds antagonize the action of histamine on histamine H.sub.2 -receptors in the brain. A compound of the invention is 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]benzthiazole.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: August 28, 1990
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Thomas H. Brown, Robert C. Mitchell, Ian R. Smith, Rodney C. Young
  • Patent number: 4929625
    Abstract: Novel ethers of formula ##STR1## their heteroaromatic N-oxides, and the pharmaceutically acceptable acid additions of the compounds of formula (I) and their N-oxides possess 5-HT.sub.3 -antagonistic activity. In the formula ##STR2## represents an optionally substituted heteroaryl group containing a hetero atom X and --B represents a saturated azabicyclic ring such as quinuclidyl or tropanyl.
    Type: Grant
    Filed: August 1, 1988
    Date of Patent: May 29, 1990
    Assignee: John Wyeth and Brothers Limited
    Inventor: Ian A. Cliffe
  • Patent number: 4895951
    Abstract: Novel diamides having a nitrogen-containing heterocyclic moiety such as pyridyl are disclosed that are useful for improving feed utilization efficiency of ruminants and for improving lactation of lactating ruminants.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: January 23, 1990
    Assignee: Eastman Kodak Company
    Inventor: Alan W. White
  • Patent number: 4761403
    Abstract: Hydroxy quinol-1-one and quinol-2-one based compounds found to be potent inhibitors of 5-, 12-, and 15-lipoxygenase enzymes.
    Type: Grant
    Filed: April 9, 1986
    Date of Patent: August 2, 1988
    Assignee: Abbott Laboratories
    Inventors: Bruce P. Gunn, James B. Summers, Jr.
  • Patent number: 4751309
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: June 14, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4739062
    Abstract: A new widely-applicable method has been found for synthesis of 9,10-anthraquinones and similar chemical compounds of wide use in industry and pharmacology, by reacting suitable aromatic substrates with activated dicarboxylic acids (more particularly dichlorides) in the presence of metal halides. The special characteristics of the reaction are the good yields, high selectivity, the possibility of operating in a single reactor and the use of starting compounds which are cheap and easily available on the market.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: April 19, 1988
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Franca Bigi, Giovanni Casiraghi, Giuseppe Casnati, Giovanni Sartori
  • Patent number: 4739063
    Abstract: Selective hydrogenation of the unsaturated nitrogen-containing ring in heterocyclic aromatic compounds is promoted by the use of hydrogenation catalysts selected from the group consisting of iridium, iridium dioxide, rhenium, molybdenum oxide, tungsten oxide, chromium trioxide, ferric oxide, iron pentacarbonyl, cobalt oxide-molybdenum oxide and copper chromite.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: April 19, 1988
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 4739064
    Abstract: Selective hydrogenation of the unsaturated nitrogen-containing ring in heterocyclic aromatic compounds is promoted by the use of at least one hydrogenation catalyst selected from the group consisting of nickel, cobalt, palladium, platinum, ruthenium and rhodium in the presence of reaction modifiers exemplified by carbon monoxide, carbon disulfide and hydrogen sulfide.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: April 19, 1988
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 4736058
    Abstract: A novel prostacyclins expressed by the following formula (1) ##STR1## wherein a symbol between the 2-position and 3-position indicates single bond or double bond; G indicates --CO.sub.2 R.sup.5 or --CONR.sup.6 R.sup.7 in which R.sup.5 is a hydrogen atom, C.sub.1 -C.sub.10 alkyl group, substituted or unsubstituted alicyclic group, substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, tri (C.sub.1 -C.sub.7) hydrocarbon-silyl group, or one equivalent cation, R.sup.6 and R.sup.7 are identical or different and each representing a hydrogen atom, or C.sub.1 -C.sub.10 alkyl group, or R.sup.6 and R.sup.7 are substituted or unsubstituted five to six-membered ring which may join together with a nitrogen atom to which they are linked and further contain a hetero atom; R.sup.1 indicates a hydrogen atom, or methyl group; R.sup.2 indicates an unsubstituted C.sub.3 -C.sub.8 alkyl group substituted or unsubstituted alicyclic group, or substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: April 5, 1988
    Assignee: Teijin Limited
    Inventors: Shiro Ikegami, Seizi Kurozumi
  • Patent number: 4687747
    Abstract: Disclosed are novel chemiluminescent compounds and their method of use in luminometric immunoassays. The compounds, comprising salts of phenanthridinium esters, are particularly useful in sandwich immunoassays.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: August 18, 1987
    Assignee: Mallinckrodt, Inc.
    Inventor: Wayne H. T. Lin
  • Patent number: 4665180
    Abstract: This invention relates to certain substituted tetrahydropyrimidines and derivatives thereof, including the preparation and uses thereof.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: May 12, 1987
    Assignee: Petrolite Corporation
    Inventor: Bernardus A. Oude Alink
  • Patent number: 4560761
    Abstract: Quaternary ammonium compounds containing an anhydride groups are prepared by halogenating dimethylmaleic anhydride and reacting the halogenated product with a tertiary amine. The products are useful as surfactants, biocides and as cosurfactants in enhanced oil recovery.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: December 24, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventors: Ellis K. Fields, Mark L. Winzenburg
  • Patent number: 4539406
    Abstract: An improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## wherein M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x III, wherein R.sup.a is selected from electron donating substituents, e.g. alkoxy or dialkylamino, and hydrocarbon substituents e.g. alkyl, at least one R.sup.a being an electron donating substituent, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be isolated as acid addition salts.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: September 3, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • 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: 4506093
    Abstract: 3-Sulfoxy-1,2-propylene glycols-1-esters of tricyclo 4.2.2.0.sup.2,5) dec-9-ene-3,4,7,8-tetracarboxylic acid are prepared. These compounds are useful as surfactants, biocides and as cosurfactants in enhanced oil recovery.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: March 19, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4405626
    Abstract: 1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl;R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R.sub.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: September 20, 1983
    Assignee: Pfizer Inc.
    Inventor: Michael R. Johnson
  • Patent number: 4400385
    Abstract: 1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9 (8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl;R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R.sub.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: August 23, 1983
    Assignee: Pfizer Inc.
    Inventor: Michael R. Johnson
  • Patent number: 4382943
    Abstract: An aryl ether derivative of the formula ##STR1## in which A is an oxygen atom or an >N--R.sub.1 grouping,R.sub.1 is a hydrogen atom or a lower alkyl radical,B is an alkylene radical containing 2 to 4 carbon atoms,R.sub.2 and R.sub.3 each independently is a hydrogen or halogen atom, hydroxyl group or lower alkyl, lower alkoxy or lower alkanoyl radical,R.sub.4 is a hydrogen atom or an acyl radical, andn is an integer from 1 to 5,or a pharmacologically acceptable salt thereof, which possesses anti-allergic activity.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: May 10, 1983
    Assignee: Boehringer Mannheim GmbH
    Inventors: Werner Winter, Walter-Gunar Friebe, Androniki Roesch, Otto-Henning Wilhelms
  • Patent number: 4380542
    Abstract: 1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: April 19, 1983
    Assignee: Pfizer
    Inventor: Michael R. Johnson
  • Patent number: 4358597
    Abstract: A thiocarbamate compound selected from the group of thiocarbamate compounds consisting of 1,3,4-thiadiazole-2-thiol-5- monothiocarbamate; 1,3,4-thiadiazole-2,5-dithiocarbamate; 1,3,4-thiadiazole-2-thiol-5-mono(dithiocarbamate) and 1,3,4-thiadiazole-2,5-di(dithiocarbamate). These thiocarbamate compounds can be represented by the general formula ##STR1## where R' is a monovalent radical individually selected from the group consisting of a hydrogen radical and the radical ##STR2## wherein X is selected from the group consisting of .dbd.O and .dbd.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4351833
    Abstract: 9-Amino-1-hydroxyoctahydrobenzo[c]quinoline derivatives of formula ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein R is hydrogen, COR.sub.7 or SO.sub.2 R.sub.8 where R.sub.7 is hydrogen, alkyl, having from one to five carbon atoms; alkenyl and alkynyl each having from two to six carbon atoms; trifluoromethyl, benzyl, furyl, thienyl, pyridyl or R.sub.9 C.sub.6 H.sub.4 where R.sub.9 is H, NH.sub.2, F, Cl, Br, Ch.sub.3 or OCH.sub.3 ; R.sub.8 is alkyl having from one to five carbon atoms or R.sub.9 C.sub.6 H.sub.4 ; R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.
    Type: Grant
    Filed: August 27, 1981
    Date of Patent: September 28, 1982
    Assignee: Pfizer Inc.
    Inventor: Michael R. Johnson
  • Patent number: 4340737
    Abstract: 1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo-[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl;R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- to 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholine and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R.sub.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: July 20, 1982
    Assignee: Pfizer Inc.
    Inventor: Michael R. Johnson
  • Patent number: 4328230
    Abstract: There are described compounds of formula I, ##STR1## in which R.sub.5 to R.sub.8 may be a variety of substituents, or an adjacent pair of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a chain--COCH.dbd.C(COOH)NRh--,or one of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a group of formula II, ##STR2## in which Ra, Rb and Rc have the same significances as R.sub.5, R.sub.6, R.sub.7 and R.sub.8,X is an optionally interrupted or substituted hydrocarbon chain,Rg and Rh, which may be the same or different are each alkyl, alkenyl, phenyl-alkyl, alkanoyl, benzoyl or phenylalkanoyl,or Rg and R.sub.8 and/or Rh and Rc in formula II, together form a chain --(CH.sub.2).sub.n --, and n is 2, 3 or 4.There are also described processes for making the compounds and pharmaceutical, e.g. anti-allergic, compositions containing the compounds.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: May 4, 1982
    Assignee: Fisons Limited
    Inventors: Roger C. Brown, Hugh Cairns, Anthony R. Payne
  • Patent number: 4309545
    Abstract: 9-Amino-1-hydroxyoctahydrobenzo[c]quinoline derivatives of formula ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein R is hydrogen, COR.sub.7 or SO.sub.2 R.sub.8 where R.sub.7 is hydrogen, alkyl, having from one to five carbon atoms; alkenyl and alkynyl each having from two to six carbon atoms; trifluoromethyl, benzyl, furyl, thienyl, pyridyl or R.sub.9 C.sub.6 H.sub.4 where R.sub.9 is H, NH.sub.2, F, Cl, Br, CH.sub.3 or OCH.sub.3 ; R.sub.8 is alkyl having from one to five carbon atoms or R.sub.9 C.sub.6 H.sub.4 ; R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: January 5, 1982
    Assignee: Pfizer Inc.
    Inventor: Michael R. Johnson
  • Patent number: 4251659
    Abstract: Polyfluorohydroxyisopropyl: -indolines, -tetrahydroquinolines, and -benzazepines, such a .alpha.,.alpha.-bis(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-6-methano l, useful as intermediates for antihypertensives.
    Type: Grant
    Filed: December 22, 1977
    Date of Patent: February 17, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul E. Aldrich, Gilbert H. Berezin