Plural Ring Oxygens In The Tricyclo Ring System Patents (Class 549/387)
  • Patent number: 5702645
    Abstract: Described herein are photochromic compounds or a structural isomer of the photochromic compound, the photochromic compounds represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.8, A, B, C, and D are each selected from the group consisting essentially of hydrogen, a stable organic radical, a heterocyclic group, halogen, a nitrogen-substituted radical, and a nitrogen-substituted ring radical.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: December 30, 1997
    Assignee: Vision-Ease Lens, Inc.
    Inventor: Frank J. Hughes
  • Patent number: 5686485
    Abstract: The present invention relates to EI-1941 compounds having interleukin-1 production inhibitory activity which are represented by the formula: ##STR1## wherein either of R.sup.1 and R.sup.2 is hydrogen and the other is hydroxy, or R.sup.1 and R.sup.2 together represent oxygen; and R.sup.3 is hydroxy and R.sup.4 is hydrogen, or R.sup.3 and R.sup.4 together represent --0--.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: November 11, 1997
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Takeo Tanaka, Hidemasa Kondo, Fumito Koizumi, Hiroki Ishiguro, Mayumi Yoshida, Katsuhiko Ando, Yuzuru Matsuda
  • Patent number: 5646175
    Abstract: Novel carbamoyloxylabdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure and treating cardiac failure utilizing compounds and compositions thereof are disclosed.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: July 8, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Raymond W. Kosley, Jr., Robert Joseph Cherill, Gerard O'Malley
  • Patent number: 5639889
    Abstract: A process for producing an optically active benzopyran compound of the formula [I] or [II]: ##STR1## in which an olefin compound of the formula [V] or [VI]: ##STR2## is subjected to asymmetric epoxidation reaction, using, as a catalyst, an optically active manganese complex of the formula [III] or [IV]: ##STR3##
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: June 17, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tsutomu Katsuki, Naoki Hosoya, Akira Hatayama
  • Patent number: 5428027
    Abstract: Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: June 27, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John P. Daub, George P. Lahm, Bradford S. Marlin
  • Patent number: 5418232
    Abstract: A compound of formula (I) possesses excellent potassium channel opening activity and is effective on various diseases arising from contractions of blood vessels, bronchial smooth muscles, etc., for example, ischemic heart diseases exemplified by angina pectoris, asthma, pollakisuria, sequela of subarachnoid hemorrhage, peripheral arterioinfarct, and so on. The compound has potent and long-lasting antihypertensive activity, with the onset of the action being slow, excellent activity in increasing renal blood flow, and high safety, and is therefore particularly useful as an antihypertensive. ##STR1## The substituents are as defined in the specification.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 23, 1995
    Assignee: Daiichi Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Mimura, Hideo Kubo
  • Patent number: 5409952
    Abstract: A compound of the formula (I) ##STR1## in which: R.sub.1 represents a hydrogen atom, a lower alkyl group, a hydroxy group or a lower alkoxy group,R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.11 are as defined in the description.Medicaments.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: April 25, 1995
    Assignee: Adir et Compagnie
    Inventors: Jean D. Brion, Guillaume Le Baut, Francoise Zammatio, Alain Pierre, Ghanem Atassi, Larbi Belachmi
  • Patent number: 5387700
    Abstract: A process for producing chlorosulfate and sulfamate esters of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol is disclosed. The process involves a two step procedure involving in the first step reacting of an alcohol with sulfuryl chloride in the presence of a tertiary or heterocyclic amine base in a solvent selected from the group consisting of toluene, t-butyl methyl ether or tetrahydrofuran to produce a chlorosulfate intermediate, which is preferably stabilized by an aqueous wash and/or treatment with a base, and in the second step reacting of the resulting intermediate with an amine in a solvent selected from the group consisting of t-butyl methyl ether, tetrahydrofuran and lower alkanol.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: February 7, 1995
    Assignee: McNeilab, Inc.
    Inventors: Cynthia A. Maryanoff, Lorraine Scott, Kirk L. Sorgi
  • Patent number: 5374650
    Abstract: Novel carbamoyloxylabdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure and treating cardiac failure utilizing compounds and compositions thereof are disclosed.
    Type: Grant
    Filed: March 25, 1993
    Date of Patent: December 20, 1994
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Raymond W. Kosley, Jr., Robert J. Cherill, Gerard O'Malley
  • Patent number: 5356866
    Abstract: Furobenzopyran derivatives of the general formula (I): ##STR1## in which R.sup.1 is a lower alkyl group, R.sup.2 is a lower alkyl group, lower alkoxy group, halogen atom or lower alkyl group substituted by a halogen atom, R.sup.3 is a lower alkyl group, lower alkoxy group, halogen atom, lower alkyl group substituted by a halogen atom, phenoxy group or benzyloxy group, R.sup.4 is a hydrogen atom or lower alkyl group and m and n are any integers between 0 and 4, have an excellent herbicidal activity on weeds and are completely selective to crops such as paddy rice, soybeans and cotton.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: October 18, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Kiyoshi Arai, Masayuki Ooka, Fumiaki Koizumi, Sadafumi Koda, Yasunaga Iwasaki, Yoshiro Kanemoto
  • Patent number: 5356929
    Abstract: The invention features phototherapeutic compositions comprising Type 1, Type 2, or Type 3 psoralens and methods of using such compounds for treatment of proliferative diseases of skin, blood and bone marrow.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: October 18, 1994
    Assignee: Lehigh University
    Inventors: Ned D. Heindel, Jeffrey D. Laskin
  • Patent number: 5318988
    Abstract: Aminomethyl-chromans are obtained by alkylation of correspondingly substituted amines or by reductive amination of correspondingly substituted aldehydes. The aminomethyl-chromans can be used as active compounds in medicaments, in particular for the treatment of diseases of the central nervous system.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: June 7, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Schohe-Loop, Hans-Georg Heine, Bodo Junge, Thomas Glaser, Jean M. Viktor De Vry, Wolfgang Dompert, Henning Sommermeyer
  • Patent number: 5276054
    Abstract: Substituted hexahydrobenzopyran derivatives of the Formulae A, B, or C are useful as angiotensin II antagonists: ##STR1##
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: January 4, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Maria T. Diez, Michael A. Goetz, Robert A. Giacobbe, Otto D. Hensens, Leeyan Huang, Isabel Martin, E. Tracy T. Jones, Siobhan Stevens-Miles, Yu L. Kong
  • Patent number: 5273998
    Abstract: The present invention provides an industrially valuable method for preparing an optically active 3,4-dihydro-3,4-epoxy-2H-1-benzopyran compound which is useful as a starting material for an optically active benzopyran compound with antihypertensive, coronary blood flow-increasing activities and the like, provides a diastereomeric ester compound which is useful as an intermediate for said epoxy compound and also provides a use of said diastereomeric ester compound in making of said epoxy compound, and further an optically active benzopyran compound which is useful as medicine.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: December 28, 1993
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventor: Tsutomu Yamanaka
  • Patent number: 5258402
    Abstract: Imidate derivatives of sulfamates having the following formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and X are as herein defined have been found to be useful prodrug and exhibit anticonvulsant activity when converted to the active agent upon administration to a mammal and are thus useful in the treatment of conditions such as epilepsy. Further, the present invention encompasses pharmaceutical compositions containing a compound of formula (I) as well as methods for their use.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: November 2, 1993
    Assignee: McNeil-PPC, Inc.
    Inventor: Bruce E. Maryanoff
  • Patent number: 5254595
    Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: October 19, 1993
    Assignee: Elf Sanofi
    Inventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
  • Patent number: 5189183
    Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: February 23, 1993
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 5180717
    Abstract: Bivalent ligand compounds synthesized from a tether composition joining two heterocyclic groups comprising furochromones, furobenzoxazinones, and benzobisdifurans. These compounds show pharmacological activity in blocking ACAT enzymes which are major regulators of cholesterol metabolism. The compounds also show activity in lowering plasma triglycerides and elevating HDL cholesterol. They are useful in the prevention or treatment of the constriction or obstruction of arterial vessels, atherosclerosis, hyperlipidemia, hypertriglyceridemia, chylomicronemia, and pancreatitis.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: January 19, 1993
    Assignee: The Upjohn Company
    Inventors: Ronald B. Gammill, Frank P. Bell
  • Patent number: 5176919
    Abstract: Pharmaceutical and cosmetic compositions comprising extracts of Ammi visnaga and Ammi majus or the vasoactive agents contained therein are described.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: January 5, 1993
    Assignee: Indena, S.p.A.
    Inventors: Sergio Bertini Curri, Ezio Bombardelli
  • Patent number: 5137911
    Abstract: An isochromane derivative having the general formula I ##STR1## in which each of R.sub.1, R.sub.2, and R.sub.3 is one to four substituents independently selected from hydrogen, hydroxy, alkyl (1-4 C), alkoxy (1-4 C), halogen, or CF.sub.3, or represents a methylenedioxy group;R.sub.4 is selected from hydrogen or alkyl (1-4 C);Alk is an alkylene group with 1-4 carbon atoms;Alk' is an alkylene group with 2-4 carbon atoms, when R.sub.5 is selected from hydrogen or alkyl (1-4 C) and X is O or S; orAlk' is an alkylene group with 1-4 carbon atoms or a bond, when R.sub.5 is an alkyl (1-4 C) group and X is CH.sub.2 or a bond;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: August 11, 1992
    Assignee: Akzo N.V.
    Inventors: Michael Combourieu, Jean-Claude Laigle
  • Patent number: 5103025
    Abstract: The invention relates to a process for the resolution of enantiomers of 3,4-epoxy-3,4-dihydro-2,2-dimethyl-3-R-2H-1-benzopyran-6-carbonitriles (I), in which R is H or CH.sub.3, characterized in that racemic I is dissolved in an inert solvent or solvent mixture together with a small amount of (-)-I [or (+)-I], the solution is seeded with (-)-I [or (+)-I], the precipitated (-)-I [or (+)-I] is isolated, further racemic I is dissolved in the filtrate, seeded with (+)-I [or (-)-I], the precipitated (+)-I [or (-)-I] is isolated and, if desired, this crystallization cycle is repeated one or more times.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ralf Devant, Rolf Gericke
  • Patent number: 5075460
    Abstract: A compound of the formula ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 polymethylene; and R'.sub.4 is ethyl, isopropyl, t-butyl or cyclopentyl.
    Type: Grant
    Filed: December 6, 1989
    Date of Patent: December 24, 1991
    Assignee: Beecham Group plc
    Inventors: John M. Evans, Geoffrey Stemp, Frederick Cassidy
  • Patent number: 5066816
    Abstract: The present invention provides an industrially valuable method for preparing an optically active 3,4-dihydro-3,4-epoxy-2H-1-benzopyran compound which is useful as a starting material for an optically active benzopyran compound with antihypertensive, coronary blood flow-increasing activities and the like, and also provides a diastereomeric ester compound with a 3-halo-4-hydroxy-2H-1-benzopyran compound which is useful as an intermediate for said epoxy compound.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: November 19, 1991
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Shinro Setoguchi, Mineo Tsuruda, Chiaki Kitami, Tsutomu Yamanaka
  • Patent number: 5028711
    Abstract: Benzopyran derivatives of the general formula I ##STR1## are disclosed. The compounds are therapeutic active compounds.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 2, 1991
    Assignee: Beiersdorf Aktiengesellschaft
    Inventors: Wolfgang Stenzel, Theo Schotten, Ben Armah
  • Patent number: 5013853
    Abstract: A compound of the formula: ##STR1## where in x-y is --CO--CH.sub.2 --, --COCR.sup.10-, --CHOHCHR.sup.8-, --CH.dbd.CR.sup.8 -- or ##STR2## and R.sup.9 is various, R.sup.1 and R.sup.8 are alkyl, R.sub.2 is H or alkyl and R.sup.1 and R.sup.2 are alkylene, are disclosed as useful as intermediates for cardiovascular agents.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: May 7, 1991
    Assignee: Merck Patent Gesellschaft MIT Beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Ingeborg Lues, Rolf Bergmann, Jacques De Peyer
  • Patent number: 5011950
    Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: April 30, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 4994584
    Abstract: The present invention provides new compound, 10-substituted-5,9-dioxatricyclo[6.4.0.0.sup.2,6 ]dodecane-4-one, which is very useful as an intermediate for prostaglandin synthesis.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: February 19, 1991
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
  • Patent number: 4990668
    Abstract: Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group.The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: February 5, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Khuong H. X. Mai, Ghanshyam Patil, William L. Matier
  • Patent number: 4963537
    Abstract: Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: April 26, 1989
    Date of Patent: October 16, 1990
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
  • Patent number: 4822803
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 4, 1988
    Date of Patent: April 18, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
  • Patent number: 4814346
    Abstract: Isoflavans of the formula I ##STR1## wherein the groups OR, R', R" and ring B are as defined in the specification, exhibit valuable pharmacological properties, especially for the treatment of vascular diseases. They are prepared by methods known per se.
    Type: Grant
    Filed: November 4, 1987
    Date of Patent: March 21, 1989
    Assignee: Zyma SA
    Inventors: Alban I. Albert, Friedrich W. Zilliken
  • Patent number: 4812160
    Abstract: Cyclohexenone derivative of the formula ##STR1## where A is oxygen or NOR.sup.8, where R.sup.8 is alkyl, alkenyl, alkynyl, haloalkyl or haloalkenyl, chlorothienyl or alkoxyalkylB is O, S, SO or SO.sub.2,X is hydrogen or methoxycarbonyl,R.sup.1 is hydrogen, carbonylalkyl, benzoyl or a cation,R.sup.2 is alkyl,R.sup.3 and R.sup.4 are hydroxyl, chlorine, bromine, thioalkylcarboxyl, thiocarbonylalkyl, alkylcarbonyloxy, alkoxy, or alkylthio, or R.sup.3 and R.sup.4 together epoxy,R.sup.5 and R.sup.6 are hydrogen or methyl or R.sup.5 and R.sup.6 are together methyleneoxyethylene, andR.sup.7 is hydrogen or methyl,and herbicides containing these compounds.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: March 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Johann Jung, Wilhelm Rademacher
  • Patent number: 4758677
    Abstract: 2,2-Dimethyl-3,4-dihydro-2H-benzo[b]pyran-3-ols bearing an amino group in the 4-position and a cyano group in the benzo ring, their salts, esters and ethers, demonstrate excellent vasodilatory activity. The compounds, of which trans-2,2-dimethyl-4-isopropylamino-6-cyano-3,4-dihydro-2H-benzo[b]pyran-3 -ol is a representative embodiment, can be prepared from the corresponding 3,4-epoxy derivative upon treatment with an amine.
    Type: Grant
    Filed: November 17, 1982
    Date of Patent: July 19, 1988
    Assignee: Beecham Group p.l.c
    Inventor: John M. Evans
  • Patent number: 4745127
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: January 7, 1987
    Date of Patent: May 17, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
  • Patent number: 4661595
    Abstract: A method for preparing a compound of formula I ##STR1## in which X is O or S;both groups R together with the two carbon atoms to which they are attached form a fused aromatic group;R.sub.1 is an organic radical; andn is 0, 1, 2 or 3comprising reacting a compound of formula II ##STR2## where R, R.sub.1 and n are defined above and where each R.sub.3, independently, is C.sub.1-12 alkoxy or one R.sub.3 is C.sub.1-12 alkoxy and the other R.sub.3 is halogen,with elemental sulphur in an alkaline medium, a metal sulphide or a metal hydrosulphide.Compounds of formula I and formula II are useful as photoinitiators.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: April 28, 1987
    Assignee: Sandoz Ltd.
    Inventor: Lajos Avar
  • Patent number: 4654362
    Abstract: Derivatives of 2,2'-iminobisethanol having useful properties in the treatment and/or the prevention of disorders of the coronary-vascular system.
    Type: Grant
    Filed: October 12, 1984
    Date of Patent: March 31, 1987
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Guy R. E. Van Lommen, Marcel F. L. De Bruyn, Marc F. J. Schroven
  • Patent number: 4614809
    Abstract: The present invention particularly provides novel furochromones and intermediates for their preparation.
    Type: Grant
    Filed: April 25, 1984
    Date of Patent: September 30, 1986
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4582916
    Abstract: Sulfamates of the following formula (I): ##STR1## wherein X is O or CH.sub.2 and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as herein defined have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and intermediates form part of the present invention.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: April 15, 1986
    Assignee: McNeilab, Inc.
    Inventors: Bruce E. Maryanoff, Joseph F. Gardocki
  • Patent number: 4563458
    Abstract: The invention relates to substituted 4-aminomethylene-chromans and chromens of Formula (I) infra, as well as methods for making of said chromans and chromens, compositions containing said chromans and chromens and methods for the use of said chromans, chromens and compositions containing said chromans and chromens. The compounds and compositions of the invention are useful for their circulation influencing activity.
    Type: Grant
    Filed: December 13, 1983
    Date of Patent: January 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Arno Widdig, Hans-Joachim Kabbe, Andreas Knorr, Ulrich Benz
  • Patent number: 4542228
    Abstract: The present specification provides intermediates for novel analogs of khellin, a natural product, which are useful in the treatment and prevention of atherosclerosis. Particularly, the present disclosure provides novel 5H-furo[3,2-g]-benzopyran-5-ones substituted at the nine position by methoxy and substituted at the four position by hydroxy.
    Type: Grant
    Filed: January 3, 1984
    Date of Patent: September 17, 1985
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4540798
    Abstract: The present invention provides certain novel aminoethanyl furochromones which are useful for antiatherosclerotic purposes.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: September 10, 1985
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4513006
    Abstract: Sulfamates of the following formula (I): ##STR1## wherein X is O or CH.sub.2 and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as herein defined have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and intermediates form part of the present invention.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 23, 1985
    Assignee: McNeil Lab., Inc.
    Inventors: Bruce E. Maryanoff, Joseph F. Gardocki
  • Patent number: 4503066
    Abstract: The invention provides various medical compositions for use in treating or preventing certain of the side effects of diabetes or galactosemia. The active ingredients are selected from a series of novel aldose reductase inhibitory spiro-linked pyrrolidine-2,5-diones of the general formula: ##STR1## or a pharmaceutically acceptable salt, or a non-toxic, biodegradable precursor thereof. Processes for the production of these compounds are also provided. A particular compound suitable for use as an active ingredient is spiro[pyrrolidine-3,9'-xanthene]-2,5-dione.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: March 5, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventors: David R. Brittain, Robin Wood
  • Patent number: 4490547
    Abstract: The present invention provides certain novel benzopyrans which are useful for antiatherosclerotic purposes.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: December 25, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4487774
    Abstract: Amino derivatives of isochromans are described. These compounds exhibit antipsychotic and hypotensive activity.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: December 11, 1984
    Assignee: The Upjohn Company
    Inventor: John M. McCall
  • Patent number: 4459420
    Abstract: The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: July 10, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4438274
    Abstract: The present specification provides novel analogs of khellin, a natural product, which are useful in the treatment and prevention of atherosclerosis. Particularly, the present disclosure provides novel 5H-furo[3,2-g]-benzopyran-5-one substituted at the four and nine positions by methoxy or optionally substituted at the four position by hydroxy or alkoxy groups other than methoxy, certain 7-(N,N-dialkylaminoethen-2-yl substituted compounds. Also provided are certain novel antiatherosclerotic 7H-furo[3,2-g][1]benzopyrans.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: March 20, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4434296
    Abstract: The present specification provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof. 3-Furoic acid is treated with succinic anhydride and diesterified to 3-carboxy-.delta.-oxo-2-furanbutanoic acid bis (alkyl ester). Following amination, cyclization and bis methylation, 6-formyl-4,7-dimethoxy-5-benzofurancarboxcyclic acid alkyl ester is prepared. This compound is then converted to known intermediates in the synthesis of khellin and analogs. Further, the present invention provides numerous novel anti-atherosclerotic 4,9-di-(C.sub.2 -C.sub.4)-alkoxyfurochromones.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: February 28, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4434295
    Abstract: The present specification provides novel analogs of khellin. These analogs are all useful as antiatherosclerotic agents. Particularly, the present specification provides 4-methoxy, 9-methoxy, or 4,9-dimethoxy-6,7-dihydro-7,7-disubstituted-5H-furo[3,2-g][1]benzopyran-5- ones.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: February 28, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4424389
    Abstract: A process for producing chroman, a compound of the formula, ##STR1## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, which comprises reacting a compound of the formula, ##STR2## or an optically active compound thereof wherein A is an aryl group and R.sub.5 is a C.sub.1 -C.sub.4 alkyl group, with a compound of the formula, ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.3 alkyl group, X is a halogen atom and R.sub.2, R.sub.3 and R.sub.4 are as defined above, to obtain a compound of the formula, ##STR4## or an optically active compound thereof wherein A, R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: January 3, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yoji Sakito