Tricyclo Ring System Having The Five-membered Hetero Ring As One Of The Cyclos Patents (Class 548/427)
  • Patent number: 5652369
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and --N(R.sup.7)--CH(R.sup.8)(R.sup.9) are as claimed herein or their pharmaceutically acceptable acid addition salts inhibit proteases of viral origin and can be used as medicaments for the treatment of viral infections. They can be manufactured according to generally known procedures.
    Type: Grant
    Filed: April 6, 1995
    Date of Patent: July 29, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Balraj Krishan Handa, Peter James Machin, Joseph Armstrong Martin, Sally Redshaw, Gareth John Thomas
  • Patent number: 5650427
    Abstract: A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl;R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or combined with R.sup.1 to form a C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 akynyl, (CH.sub.2).sub.n --X--Ar where X is O, S, or NH, 3,3,3-trifluoropropyl, --(CH.sub.2).sub.m --R.sup.9 where m is 2 or 3 and R.sup.9 is phenyl, 2-thiophenyl or 3-thiophenyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH.sub.2 OR.sup.2, C(O)C(O)OR.sup.1, C(O)CO NR.sup.1 R.sup.2, --(CH.sub.2).sub.q --NR.sup.1 R.sup.2 where q is 0 to 5, C.dbd.NOR.sup.2, 2(4,5-dihydro)oxazolyl, or COR.sup.10 where R.sup.10 is H, R.sup.1, NR.sup.1 R.sup.2 or CF.sub.3 ; R.sup.4 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 22, 1997
    Assignee: The Upjohn Company
    Inventors: Hakan Vilhelm Wikstrom, Per Arvid Emil Carlsson, Bengt Ronny Andersson, Kjell Anders Ivan Svensson, Stig Thomas Elebring, Nils Peter Stjernlof, Arthur Glenn Romero, Susanne R. Haadsma-Svensson, Chiu-Hong Lin, Michael Dalton Ennis
  • Patent number: 5646298
    Abstract: The present invention describes cyclopropylindole cytotoxic prodrugs of formulas (I), (II) and (III) as shown in the specification. The present invention is also directed to a method for the site-specific treatment of neoplastic diseases in a mammal which method includes the following steps: (i) administering to an afflicted mammal an effective amount of a targeting agent- enzyme donor peptide conjugate wherein the targeting agent is selected from the group of antibodies, monoclonal antibodies, adhesion molecules and tumor cell surface binding ligands; (ii) administering to the afflicted mammal an effective amount of an enzyme acceptor dimer thereby forming active enzymatic sites at a tumor cell surface; and (iii) administering to the afflicted mammal a therapeutically effective amount of an enzyme-activateable, cytotoxic pro-drug thereby releasing the cytotoxic drug at the tumor site.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: ProCoron, Inc.
    Inventor: Michael J. Powell
  • Patent number: 5646173
    Abstract: The invention relates to tricyclic pyrrole derivatives useful as 5-HT selective agents of the formula ##STR1## wherein R.sup.1 to R.sup.4 are, independently, hydrogen, halogen, lower alkyl, phenyl, cycloalkyl or lower alkoxy and R.sup.2 additionally is lower alkoxycarbonyl, acyloxy or mesyloxy;R.sup.5 to R.sup.7 are, independently, hydrogen or lower alkyl;X is --CH.sub.2 CH(C.sub.6 H.sub.5)--, --CH.dbd.C(C.sub.6 H.sub.5)--, --YCH.sub.2 --, --CH.dbd.CH-- or --(CR.sup.11 R.sup.12).sub.n ;R.sup.11 and R.sup.12 are, independently, hydrogen, phenyl, lower alkyl or halogen;n is 1 to 3 andy is O or S,as well as pharmaceutically acceptable salts of basic compounds of formula I with pharmaceutically acceptable acids.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: July 8, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Bos, Jurgen Wichmann, Ulrich Widmer
  • Patent number: 5639778
    Abstract: A compound of formula (I) and pharmaceutically acceptable salts thereof, where Z is R.sub.3 and X and Y form (a), or X is R.sub.3 and Y and Z form (a) or (b); R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, --CH.sub.2 --C.sub.3-7 cycloalkyl, phenyl (optionally substituted with halogen or C.sub.1-6 alkyl), -thiophenyl (optionally substituted with halogen or C.sub.1-6 alkyl), or C.sub.1-6 alkyl phenyl; R.sub.3 are independently hydrogen, halogen, --O--C.sub.1-6 alkyl or C.sub.1-6 alkyl; R.sub.4 is a valence bond, CH.sub.2 or oxygen; R.sub.5 and R.sub.6 are independently hydrogen, sulfur, --S--C.sub.1-6 alkyl, halogen, CON(R.sub.3).sub.2, --COCF.sub.3, --CO--C.sub.1-6 alkyl, --CO phenyl, oxygen, --CHO, CN except that when Y and Z form (b), R.sub.1 and R.sub.2 are hydrogen or a C.sub.1-6 alkyl and R.sub.3 is hydrogen, then at least one of R.sub.5 and R.sub.6 must be other than hydrogen.
    Type: Grant
    Filed: September 7, 1995
    Date of Patent: June 17, 1997
    Assignee: Pharmacia & Upjohn Company
    Inventors: Bengt R. Andersson, Per A. E. Carlsson, Lars O. Hansson, Clas A. Sonesson, N. Peter Stjernlof, Kjell A. I. Svensson, R. Nicholas Waters, Susanne R. Haadsma-Svensson
  • Patent number: 5639874
    Abstract: To sequence DNA automatically, DNA marked with near infrared fluorescent dyes are electrophoresed in a plurality of channels through a gel electrophoresis slab wherein the DNA samples are resolved in accordance with the size of DNA fragments in the gel electrophoresis slab into fluorescently marked DNA bands. The separated samples are scanned photoelectrically with a laser diode and a sensor, wherein the laser scans with scanning light at a scanning light frequency within the absorbance spectrum of said fluorescently marked DNA samples and light is sensed at the emission frequency of the marked DNA. The light is modulated from said laser at a predetermined modulation frequency and fluorescent light emitted by said DNA bands at said modulation frequency is detected, whereby background noise from the medium through which the light is transmitted is discriminated against.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: June 17, 1997
    Assignee: Li-Cor, Inc.
    Inventors: Lyle Richard Middendorf, Gabor Patonay
  • Patent number: 5622983
    Abstract: Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, colorectal tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: April 22, 1997
    Assignee: Warner-Lambert Company
    Inventors: David C. Horwell, Martyn C. Pritchard, Edward Roberts, Reginald S. Richardson, Julian Aranda
  • Patent number: 5597823
    Abstract: The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a tricyclic heterocyclic ring system; which is an .alpha.-1 adrenergic antagonist and is useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: January 28, 1997
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, Robert J. Altenbach, Fatima Z. Basha, William A. Carroll, Irene Drizin, Steven W. Elmore, James F. Kerwin, Jr., Suzanne A. Lebold, Edmund L. Lee, Kevin B. Sippy, Karin R. Tietje, Michael D. Wendt
  • Patent number: 5585499
    Abstract: Novel cytotoxic agents comprising a cell binding agent chemically linked to one or more analogue or derivative of CC-1065 are described. The therapeutic use of the cytotoxic agents is also described. These cytotoxic agents have therapeutic use because they deliver the cytotoxic drugs to a specific cell population in a targeted fashion.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Immunogen Inc.
    Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
  • Patent number: 5574060
    Abstract: The present invention provides a compound having the structure: ##STR1## wherein X, Y, and Z are independently H, Cl, Br, F, OCH.sub.3, I, or an alkyl group having 1 to 6 carbon atoms; and R is ##STR2## wherein n is 0 to 6, X' and Y' are independently H, Cl, F, CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, OCH.sub.3, OH, CF.sub.3, OCF.sub.3, NO.sub.2, NH.sub.2, N(CH.sub.3).sub.2, NHCOCH.sub.3, NCS, NHCOCH.sub.2 Br, or N.sub.3, and (CH.sub.2).sub.n, if present, may be substituted with OH, OCH.sub.3, or an alkyl or alkenyl group having 1 to 3 carbon atoms. The present invention also provides a pharmaceutical composition comprising the compound above and a pharmaceutically acceptable carrier. The present invention further provides a method for treating a disease characterized by a dopamine deficiency which comprises administering to a subject in need of such treatment an amount of the pharmaceutical composition above effective to treat the disease.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: November 12, 1996
    Assignees: The United States of America as represented by the Department of Health and Human Services, Office of Technology Transfer, Research Triangle Institue
    Inventors: Richard Rothman, Frank J. Carroll, Bruce Blough, Samuel W. Mascarella
  • Patent number: 5574039
    Abstract: The invention relates to TS-inhibiting compounds of the formula ##STR1## where W is an alkylene group; D is a structure having two rings that are unsubstituted or substituted, where (i) one ring is a phenyl ring and (ii) the other ring is a phenyl ring or a 6-membered heterocyclic ring; R is a hydrogen atom or an alkyl group; and X and Y together form ##STR2## and to salts of these compounds. The moiety W can be CH.sub.2, and D can be a phenyl ring bridged through a sulfonyl group to another ring.
    Type: Grant
    Filed: September 22, 1994
    Date of Patent: November 12, 1996
    Assignee: Agouron Pharmaceuticals, Inc.
    Inventors: Michael D. Varney, Gifford P. Marzoni, Cynthia L. Palmer, Judith P. Deal, Terence R. Jones
  • Patent number: 5521181
    Abstract: The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are .alpha.-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: May 28, 1996
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, Robert J. Altenbach, William A. Carroll, Irene Drizin, Suzanne A. Lebold, Edmund L. Lee, Kevin B. Sippy, Karin R. Tietje, Diane M. Yamamoto, James F. Kerwin, Jr.
  • Patent number: 5491236
    Abstract: This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein R, R.sub.1 and A are as defined in claim 1. These compounds are useful to treat central nervous system disorders.
    Type: Grant
    Filed: December 4, 1991
    Date of Patent: February 13, 1996
    Assignee: The Upjohn Company
    Inventor: Chiu-Hong Lin
  • Patent number: 5486611
    Abstract: This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula I: ##STR1## wherein X is --(CH.sub.2).sub.n -- or --C(R.sub.1)(H)--; R is C.sub.1 -C.sub.8 alkyl; and R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8) alkynyl, aryl and benzyl.These compounds are useful to treat central nervous system disorders and are unexpectedly resistant to metabolism by the liver and have superior oral plasma bioavailability.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: January 23, 1996
    Assignee: The Upjohn Company
    Inventors: Chiu-Hong Lin, Susanne R. Haadsma-Svensson, Robert B. McCall, Arthur G. Romero, William H. Darlington, Michael D. Ennis
  • Patent number: 5475092
    Abstract: Novel cytotoxic agents comprising a cell binding agent chemically linked to one or more analogue or derivative of CC-1065 are described. The therapeutic use of the cytotoxic agents is also described. These cytotoxic agents have therapeutic use because they deliver the cytotoxic drugs to a specific cell population in a targeted fashion.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: December 12, 1995
    Assignee: Immunogen Inc.
    Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
  • Patent number: 5453505
    Abstract: The present invention relates to iminium ion substituted cyanine dyes having a fluoresence absorbance of between about 500 and 900 nm, a reduced tendency to aggregate and enhanced photostability. The cyanine dyes of the present invention are represented by the formula ##STR1## wherein n is 0, 1, 2 or 3;m is 0, 1, 2 or 3;R.sub.1 and R.sub.2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;R.sub.3 and R.sub.4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;R.sub.5 and R.sub.6 are independently selected from the group consisting of (CH.sub.2).sub.p X where p is 1-18 and X is a functional group that reacts with amino, hydroxyl and sulfhydryl nucleophiles;R.sub.7 and R.sub.8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl groups and where R.sub.7 and R.sub.8 are taken together to form a five- or six- membered heterocyclic ring;R.sub.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: September 26, 1995
    Assignee: Biometric Imaging, Inc.
    Inventors: Linda G. Lee, Sam L. Woo
  • Patent number: 5440042
    Abstract: Disclosed is a novel near-infrared absorbing dye of formula: ##STR1## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;n is an integer of 2 or 3;R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;R.sup.3 represents a ring chosen from the set consisting of aryl, substituted aryl, and heterocyclic containing 5 or 6 carbons in the ring;R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together may represent the atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;R.sup.8, R.sup.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: August 8, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Dietrich M. Fabricius, Gregory C. Weed
  • Patent number: 5338861
    Abstract: Substituted lactams of the formula ##STR1## can be prepared from lactam N-carboxylates or lactim O-carboxylates of the formulae ##STR2## by thermal or mixed thermal and catalysed CO.sub.2 elimination at 80.degree.-450.degree. C. Lactams substituted on the N atom by aliphatic groups such as those produced herein are useful as industrial aprotic solvents.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: August 16, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Hans-Josef Buysch, Otto Immel, Lothar Puppe
  • Patent number: 5330981
    Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: July 19, 1994
    Assignee: Istituto Gentili S.p.A.
    Inventors: Sergio Rosini, Maurizio Mian
  • Patent number: 5326876
    Abstract: A process for preparing an alkyl sulfonate derivative comprises causing a nitrogen-containing heterocyclic compound represented by the following formula (1): ##STR1## wherein X represents --O--, --S--, --NR.sup.1 --, --Se--, --Te-- or --CR.sup.2 R.sup.3 --, in which each of R.sup.1, R.sup.2 and R.sup.3 independently represents a hydrogen atom or a lower alkyl group, Y represents a hydrogen atom, a mercapto group, an arylthio group, an aralkyl group, a sulfo group, a halogen atom, an alkyl group, an alkylthio group, an alkylsulfonyloxy group or an arylsulfonyloxy group and each of R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group which may be substituted with a sulfo group, an aryloxy group, an alkylthio group, a haloalkyl group, a halogen atom, a cyano group, a carboxy group or a sulfo group, otherwise R.sup.4 and R.sup.5, R.sup.6 and R.sup.6, R.sup.6 and R.sup.7 and R.sup.7 and R.sup.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: July 5, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Ken Kawata
  • Patent number: 5294522
    Abstract: A novel photochromic compound as a photoreactive material making use of photochromism is provided, which compound is expressed by the following formula (1) or (2)): ##STR1## wherein R is alkyl, alkoxy, perfluoroalkyl or cyano; X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are each H, halogen, alkyl, alkoxy, cyano, alkanoyloxy or alkyloxycarbonyl, or a substituted or unsubstituted benzene ring is formed by condensation between at adjacent groups among X.sub.1 to X.sub.6 ; Y is Y.sub.1 C=CY.sub.2, O, S, SO, SO.sub.2 or NY.sub.3 wherein Y.sub.1 and Y.sub.2 are each as defined in the case of the above X.sub.1 to X.sub.6 and Y.sub.3 is H, alkyl, alkanoyl, alkyloxycarbonyl or aryl; and the symbol refers to occurrence of E- or Z-isomer, and which compound is useful as rewritable optical memory element or photo-display element and also as solar energy-storage material, duplicating material, masking material, optical filter, toys, etc.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: March 15, 1994
    Assignee: Chisso Corporation
    Inventors: Manabu Uchida, Masahiro Irie
  • Patent number: 5288748
    Abstract: A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl;R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or combined with R.sup.1 to form a C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 akynyl, (CH.sub.2).sub.n --R"--Ar where R" is O, S, or NH, 3,3,3-trifluoropropyl, --(CH.sub.2).sub.m --R.sup.9 where m is 2 or 3 and R.sup.9 is phenyl, 2-thienyl or 3-thienyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH.sub.2 OR.sup.2, C(O)C(O)OR.sup.1, C(O)CO NR.sup.1 R.sup.2, --(CH.sub.2).sub.q --NR.sup.1 R.sup.2 where q is 0 to 5, C.dbd.NOR.sup.2, 2(4,5-dihydro)oxazolyl, or COR.sup.10 where R.sup.10 is H, R.sup.1, NR.sup.1 R.sup.2 or CF.sub.3 ; R.sup.4 is hydrogen, C.sub.1 -C.sub.3 alkyl, cyclopropylmethyl, CF.
    Type: Grant
    Filed: July 1, 1992
    Date of Patent: February 22, 1994
    Assignee: The Upjohn Company
    Inventors: Hakan V. Wikstrom, Per A. E. Carlsson, Bengt R. Andersson, Kjell A. I. Svensson, Stig T. Elebring, Nils P. Stjernlof, Arthur G. Romero, Susanne R. Haadsma-Svensson, Chiu-Hong Lin, Michael D. Ennis
  • Patent number: 5278316
    Abstract: Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: January 11, 1994
    Assignee: Warner-Lambert Company
    Inventors: David C. Horwell, Martyn C. Pritchard, Reginald S. Richardson, Edward Roberts, Julian Aranda
  • Patent number: 5276053
    Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: January 4, 1994
    Assignee: Warner-Lambert Company
    Inventor: Graham Johnson
  • Patent number: 5268486
    Abstract: A luminescent cyanine dye having generally the following structure ##STR1## wherein the dotted lines represent one to three rings having 5 to 6 atoms in each ring. R.sub.3, R.sub.4, R.sub.8 and R.sub.9 groups are attached to the rings. At least one of the R.sub.8 and R.sub.9 groups is a sulfonic acid or sulfonate group and at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.7 groups is a reactive moiety that reacts with amino, hydroxy or sulfhydryl nucleophiles.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: December 7, 1993
    Assignee: Carnegie-Mellon Unversity
    Inventors: Alan S. Waggoner, Lauren A. Ernst, Ratnakar B. Mujumdar
  • Patent number: 5268485
    Abstract: A naphthalocyanine derivative having at least one substituent of the formula: SO.sub.2 R.sup.1, wherein R.sup.1 is an alkyl group, a substituted alkyl group or an aryl group is excellent in ability to absorb diode laser beams and suitable for use in an optical recording medium.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: December 7, 1993
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Mitsuo Katayose, Nobuyuki Hayashi, Seiji Tai, Takayuki Akimoto, Koichi Kamajima, Hideo Hagiwara
  • Patent number: 5244888
    Abstract: Substituted 8-alkoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroles; 5-alkoxy-2,3,4,4a,9,9a-hexahydro-1-H-indeno[2,1-c]pyridines; and 9-alkoxy-2,3,3a,4,5,9a-hexahydro-1H-benz[e]isoindoles are selective 5-HT receptor agents and are thus useful in the treatment of anxiety, depression, and hypertension.
    Type: Grant
    Filed: July 9, 1991
    Date of Patent: September 14, 1993
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Michael D. Meyer, Kevin B. Sippy
  • Patent number: 5238950
    Abstract: A method of inhibiting the binding of PDGF using compounds of the formula I ##STR1## useful in the treatment of atherosclerosis, cancer, retinal detachment, pulmonary fibrosis, arthritis, psoriasis and glomerulonephritis, and restenosis following angioplasty or vascular surgery is disclosed.Also disclosed are pharmaceutical compositions and novel PDGF inhibitory compounds of the formula ##STR2## or a pharmaceutically acceptable addition salt thereof, useful in the treatment of atherosclerosis, cancer, retinal detachment, pulmonary fibrosis, arthritis, psoriasis and glomerulonephritis, and restenosis following angioplasty or vascular surgery.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: August 24, 1993
    Assignee: Schering Corporation
    Inventors: John W. Clader, Harry R. Davis, Deborra Mullins, Stuart Rosenblum, Jay Weinstein
  • Patent number: 5229522
    Abstract: Novel bis-(indolyl)ethylenes, process for their production and record systems utilizing such bis-(indolyl)ethylene chromogens are described.Bis-(indolyl)ethylenes of the following general formula are prepared: ##STR1## wherein each L.sup.1 and L.sup.2 is the same or different and is each independently selected from indole moieties (J1) through (J4) (L.sup.1 need not be the same as L.sup.2), ##STR2## wherein Z is hydrogen, alkyl (C.sub.1 -C.sub.8), substituted or unsubstituted aryl, aralkyl, aroxyalkyl, alkoxyalkyl or halogen.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: July 20, 1993
    Assignee: Appleton Papers Inc.
    Inventor: Ponnampalam Mathiaparanam
  • Patent number: 5204467
    Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 20, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5200519
    Abstract: Preparation of novel mono(indolylethylenyl) phthalides is disclosed. Specifically, these compounds are chromogenic mono(indolylethylenyl)phthalides of the formula ##STR1## wherein A is as hereinafter defined and selected from moieties of the type ##STR2## wherein L is an indole moiety as hereinafter defined; wherein B is a moiety of the type ##STR3## as hereinafter defined. The process disclosed comprises condensing indolylethylene with a keto acid or its derivative and an electron acceptor in an organic solvent.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: April 6, 1993
    Assignee: Appleton Papers Inc.
    Inventor: Ponnampalam Mathiaparanam
  • Patent number: 5180736
    Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: January 19, 1993
    Assignee: Warner-Lambert Company
    Inventor: Graham Johnson
  • Patent number: 5180733
    Abstract: Compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein M is 0, 1 or 2 and n is 0 or 1;R.sup.1 is hydrogen or lower alkyl;R.sup.2 is C.sub.1 -C.sub.6 -alkyl substituted with a heterocyclic group or C.sub.7 -C.sub.16 -arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxy, amino and C.sub.1 -C.sub.6 -alkylamino;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, halogen, and halo-C.sub.1 -C.sub.6 -alkyl, or any two of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 taken together form a methylenedioxy group; andR.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: January 19, 1993
    Assignee: Abbott Laboratories
    Inventors: Fatima Z. Basha, John F. DeBernardis, Robert J. Altenbach
  • Patent number: 5162544
    Abstract: Pyrroline- or indoline-containing phthalides of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other lower alkyl, C.sub.5 -C.sub.7 cycloalkyl or benzyl or, when taken together, are C.sub.4 -C.sub.6 alkylene,Y is alkyl or not more than 12 carbon atoms, unsubstituted or substituted by halogen, cyano, hydroxy or lower alkoxy, or is benzyl,X is hydrogen, alkyl of 1 to 12 carbon atoms or an aryl radical, and the ring A is a benzene or naphthalene ring which is unsubstituted or substituted by one or more members selected from the group consisting of halogen, cyano, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which contains 6 ring atoms and which may contain an aromatic fused ring, which ring B as well as the fused ring may be substituted.These phthalides are particularly suitable for use as color formers in pressure- or heat-sensitive recording materials and give lightfast yellow, orange or red images.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: November 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rox Phaff
  • Patent number: 5137909
    Abstract: An indole derivative represented by the general formula (I) ##STR1## wherein R is hydrogen, lower alkyl having 1 to 6 carbons, carboxymethyl, or substituted or unsubstituted aralkyl; R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may be the same with or different from each other and are hydrogen, halogen, lower alkyl having 1 to 6 carbons, lower alkoxy having 1 to 6 carbons, acyl, substituted or unsubstituted amino, nitro, hydroxy, acyloxy, substituted or unsubstituted aralkyl, substituted or unsubstituted aryloxy, or substituted or unsubstituted aralkyloxy, or a combination of R.sup.2 and R.sup.3 may be methylenedioxy;R.sup.5 is hydrogen, lower alkyl having 1 to 6 carbons, or substituted or unsubstituted aralkyl; R and R.sup.4, or R.sup.1 and R.sup.5 may form together a six-membered ring constituted of methylene chains which may contain a heteroatom;R.sup.6 and R.sup.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: August 11, 1992
    Assignee: Kyorin Seiyaku Kabushiki Kaisha
    Inventors: Hidehiko Miura, Naoki Harano, Yasuo Takano, Toshiro Mochizuki, Yoshinori Takahashi, deceased, Takashi Nagayama
  • Patent number: 5106990
    Abstract: The present invention relates to a dye represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, each represents a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkyl group having a substituent selected from the group consisting of a sulfonic group, carboxyl group and hydroxyl group, and Z.sup.1 and Z.sup.2 each represents a group of non-metallic atoms necessary for the formation of a benzo-condensed of naphtho-condensed ring, or a benzo-condensed or naphtho-condensed ring having a substituent selected from the group consisting of a sulfonic group, a carboxyl group, an hydroxyl group, a halogen atom, a cyano group, an amino group and a C.sub.1 -C.sub.5 alkyl group connected to the ring directly or through a divalent connection group, with a proviso that R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, Z.sup.1 and Z.sup.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: April 21, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigeru Ohno, Yuji Mihara, Keiichi Adachi
  • Patent number: 5087704
    Abstract: The present invention provides a cyanine compound represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is an optionally substituted lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom, Z is an acidic residue, and n is 2 or 3. This cyanine compound is suitable for use as a near infrared light-absorbing organic dye useful as an optical disc recording medium for semiconductor laser recording.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: February 11, 1992
    Assignee: Asahi Chemical Co., Ltd.
    Inventors: Osamu Manabe, Shigeo Fujita, Shizuo Iwata, Morihiro Kamiyama
  • Patent number: 5075455
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: December 24, 1991
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 5071853
    Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: December 10, 1991
    Inventors: Christopher F. Bigge, Sheryl J. Hays, Graham Johnson, Perry M. Novak, Daniel F. Ortwine
  • Patent number: 5055589
    Abstract: The present invention provides an indolenine derivative represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom. This indolenine derivative is useful as an intermediate for synthesizing a cyanine compound suitable for use as an organic near infrared light-absorbing dye useful as an optical disc recording medium adapted for semiconductor laser recording.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: October 8, 1991
    Assignee: Asahi Chemical Co., Ltd.
    Inventors: Osamu Manabe, Shigeo Fujita, Shizuo Iwata, Morihiro Kamiyama
  • Patent number: 5039821
    Abstract: Preparation of novel symmetrical and unsymmetrical chromogenic di-[bis-(indolyl)ethylenyl]tetrahalophthalides is disclosed. Specifically these compounds are chromogenic di-[bis-(indolyl)ethylenyl]tetrahalophthalides of the formula ##STR1## wherein L and X are as hereinafter defined. The process disclosed involves condensing bis(indolyl)ethylenes with tetrahalophthalic anhydride in acetic anhydride, in the presence of an electron acceptor or preferably an acetate of Group I or II of the Periodic Table. Optionally, and preferably, where unsymmetrical di-[bis-(indolyl)ethylenyl]tetrahalophthalides are desired, indoles are reacted with an acylindole in the presence of a Vilsmeier reagent to form the starting bis(indolyl)ethylene.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: August 13, 1991
    Assignee: Appleton Papers Inc.
    Inventor: Ponnampalam Mathiaparanam
  • Patent number: 4996328
    Abstract: Novel bis-(indolyl)ethylenes, process for their production and record systems utilizing such bis-(indolyl)ethylene chromogens are described.Bis-(indolyl)ethylenes of the following general formula are prepared: ##STR1## wherein each L.sup.1 and L.sup.2 is the same or different and is each independently selected from indole moieties (J1) through (J4) (L.sup.1 need not be the same as L.sup.2), ##STR2## wherein in (J1) through (J4) above, each of R.sup.5, R.sup.6, R.sup.13, R.sup.14, R.sup.21, R.sup.22, R.sup.29 and R.sup.30 need not be the same and is each independently selected from hydrogen, alkyl (C.sub.1 -C.sub.8), cycloalkyl, alkylaroxy, alkylalkoxy, and substituted or unsubstituted aryl, such as phenyl, naphthyl, or heterocyclyl.Each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.23, R.sup.24, R.sup.25, Rphu 26, R.sup.27, and R.sup.
    Type: Grant
    Filed: March 8, 1989
    Date of Patent: February 26, 1991
    Assignee: Appleton Papers Inc.
    Inventor: Ponnampalam Mathiaparanam
  • Patent number: 4959479
    Abstract: Disclosed are new indole derivatives of the following general formula (I): ##STR1## and a process for producing the derivatives (I) by irradiating a solution of a triazolylnaphthalene derivative of the following general formula (II) in a solvent with light: ##STR2## wherein R' represents a hydrogen atom, a halogen atom, an alkyl group, a nitro group or a ##STR3## group, n represents a number of 1 or 2, and when n is 2, two R groups may be either the same or different from each other and R.sub.n is the same as R'.sub.n or represents a ##STR4## group ortho-condensed with the naphthalene ring: W and Z each represent a hydrogen atom, a halogen atom, an alkyl group, a carboxyl group or an ester group thereof, n represents a number of 1 or 2, and when n is 2, two W groups and two Z groups may be either the same or different from each other, respectively.
    Type: Grant
    Filed: October 26, 1989
    Date of Patent: September 25, 1990
    Assignee: Agency of Industrial Science & Technology
    Inventors: Yoshinobu Nagawa, Koichi Honda, Hiroshi Nakanishi
  • Patent number: 4910314
    Abstract: There is provided a fluorescent adduct which is amenable to detection by fluorometric and electrochemical techniques. The adduct is of the formula: ##STR1## wherein X is a radical derived from a primary amine of the formula X--NH.sub.2 and where R.sub.1 --R.sub.6 are selected from various organic or inorganic substituents.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: March 20, 1990
    Assignee: Oread Laboratories, Inc.
    Inventors: Pierre M. R. de Montigny, Larry A. Sternson, Arnold J. Repta, John F. Stabaugh, Takeru Higuchi, deceased, by Martin B. Dickinson, Jr., co-executor, by Kenji W. Higuchi, co-executor
  • Patent number: 4877807
    Abstract: A 5-phenyl-1,3,3a,4,5,9b-hexahydro-3H-benz(e)indole compound of the formula I: ##STR1## wherein R.sup.1 is hydrogen or C.sub.1-6 alkyl, R.sup.2 is hydrogen or C.sub.1-3 alkyl in the 3a- or 4-position, R.sup.3 and R.sup.4 are each hydrogen, hydroxyl, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or trifluoromethyl, acetylamino or amino and R.sup.5 is hydrogen or C.sub.1-3 alkyl, or a salt thereof with a physiologically tolerated acid. The compounds and compositions are useful for treating depression or trating convulsions and which exhibit a sedative and tranquilizing effect when administered to a patient.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: October 31, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Steiner, Walter Himmele, Ernst Buschmann, Hans-Juergen Teschendorf, Harald Weifenbach
  • Patent number: 4876181
    Abstract: A dye useful for absorbing infrared radiation in photographic elements, having the structure: ##STR1## is disclosed. In this formula R.sub.1 and R.sub.2 each independently represents sulfoalkyl, carboxyalkyl, or sulfatoalkyl of from 3 to 6 carbon atoms, having at least 3 carbon atoms in the alkyl chain between the nitrogen atom of each Z ring and the sulfo or sulfato group, and at least 2 carbon atoms in the alkyl chain between the nitrogen atom of each Z ring and the carboxy group.R.sub.3 and R.sub.5 are each hydrogen or together represent the atoms necessary to complete 5- or 6-membered carbocyclic ring, and R.sub.4 represents hydrogen, alkyl of 1 to 4 carbon atoms, aryl, cyano, halogen, or ##STR2## where R.sub.6 and R.sub.7 each independently represents alkyl of from 1 to 6 carbon atoms or aryl, or together represent the non-metallic atoms necessary to form a 5- or 6-membered ring.X.sym. represents a cation.Z.sub.1 and Z.sub.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: October 24, 1989
    Assignee: Eastman Kodak Company
    Inventors: Gary S. Proehl, Anthony D. Gingello, David J. Collett, Richard L. Parton, David A. Stegman, Anthony Adin
  • 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: 4634705
    Abstract: Disclosed herein are adrenergic compounds represented by the formula ##STR1## wherein m is 0, 1 or 2; R.sub.1, R.sub.2, R.sub.3 and R.sub.7 are taken from the group consisting of hydrogen, hydroxy, loweralkyl, loweralkoxy, halo, amino, acetamido or NHSO.sub.2 R wherein R is taken from the group consisting of hydrogen or loweralkyl, provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.7 cannot simultaneously be hydrogen or halo, and provided that when one of R.sub.1, R.sub.2, R.sub.3 and R.sub.7 is halo, the others cannot simultaneously be hydrogen and when two of R.sub.1, R.sub.2, R.sub.3 and R.sub.7 are halo, the other two cannot simultaneously be hydrogen and provided that R.sub.1 and R.sub.7 cannot simultaneously be methoxy each when R.sub.2 and R.sub.3 are hydrogen; R.sub.1 and R.sub.2 or R.sub.2 and R.sub.3 or R.sub.3 and R.sub.7 taken together can form a methylenedioxy or ethylenedioxy bridge; or R.sub.1 and R.sub.2 or R.sub.2 and R.sub.3 or R.sub.3 and R.sub.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: January 6, 1987
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Fatima Z. Basha
  • Patent number: 4622405
    Abstract: Disclosed herein are 1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrroles represented by the formula ##STR1## wherein R.sub.1 is hydrogen, loweralkyl of 1 to 5 carbon atoms, arylalkyl, loweracyl or benzoalkylenedioxy; R.sub.2 and R.sub.3 may be the same or different and are hydroxy, loweralkoxy, halo, thiomethyl, loweracyl, NR.sub.4 R.sub.5, NHSO.sub.2 R.sub.6 or arylalkoxy or R.sub.2 and R.sub.3 taken together may form a methylenedioxy or ethylenedioxy bridge; R.sub.4 and R.sub.5 may be the same or different and are hydrogen, loweralkyl of 1 to 2 carbon atoms or loweracyl; and R.sub.6 is hydrogen or loweralkyl of 1 to 2 carbon atoms.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: November 11, 1986
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Martin Winn
  • Patent number: 4618683
    Abstract: Disclosed herein are tetrahydro-benzo[e]isoindolines represented by the formula ##STR1## wherein R, R.sub.1 and R.sub.2 are independently selected from hydrogen, loweralkyl of 1 to 4 carbon atoms, hydroxy, loweralkoxy of 1 to 3 carbon atoms, allyloxy, benzyloxy, benzoyloxy, thiomethyl, halo, ##STR2## wherein t is 0 or 1, n is 0 to 5 and R.sub.11 and R.sub.14 are independently selected from hydrogen, halo, hydroxy, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 3 carbon atoms or amino; orR and R.sub.1, or R.sub.1 and R.sub.2 can be taken together to form a methylenedioxy or ethylenedioxy bridge; with the proviso that at least one of R, R.sub.1 or R.sub.2 must be other than hydrogen and the proviso that two of R, R.sub.1, or R.sub.2 must be other than methoxy in the 7 and 8 positions when the remaining one of R, R.sub.1 or R.sub.2 is hydrogen; andR.sub.
    Type: Grant
    Filed: November 20, 1984
    Date of Patent: October 21, 1986
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Daniel J. Kerkman, William J. McClellan