Chalcogen Bonded Directly To The Ring Carbon Para To The Ring Oxygen (e.g., Chromones, Etc.) Patents (Class 549/401)
  • Patent number: 5659051
    Abstract: There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro or a group of the RCONH wherein R is C.sub.1 -C.sub.20 alkyl, phenyl, phenyl-substituted (C.sub.1 -C.sub.20) alkyl, phenyl (C.sub.1 -C.sub.20)alkoxyphenyl or (C.sub.1 -C.sub.20) alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): ##STR3## wherein A.sup.1 and A.sup.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Hideki Ushio, Yukari Fujimoto, Tsutomu Matsumoto, Masayoshi Minai, Katsuichi Yasunaga, Hiroshi Sogabe, Takahiro Kotera
  • Patent number: 5605896
    Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: February 25, 1997
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
  • Patent number: 5591772
    Abstract: The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiatherogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: January 7, 1997
    Assignee: Lipogenics, Inc.
    Inventors: Ronald H. Lane, Asaf A. Qureshi, Winston A. Salser
  • Patent number: 5571844
    Abstract: The invention relates to amidinophenylalanine derivatives, to the synthesis of these compounds, to their use and to pharmaceutical compositions which contain these compounds which act as thrombin inhibitors.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: November 5, 1996
    Assignee: Behringwerke Aktiengesellschaft
    Inventors: Werner St uber, Rainer Koschinsky
  • Patent number: 5550152
    Abstract: The invention relates to benzopyran leukotriene B.sub.4 (LTB.sub.4) antagonists and pharmaceutical compositions containing the compounds. The compounds inhibit the action of LTB.sub.4 and are therefore useful in the treatment of LTB.sub.4 induced illnesses such as inflammatory disorders.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: August 27, 1996
    Assignee: Pfizer Inc.
    Inventors: Kevin Koch, Lawrence S. Melvin, Jr., Lawrence A. Reiter, Sally G. Ruggeri
  • Patent number: 5539128
    Abstract: Processes, and intermediates, for use in preparing the compound of the formula ##STR1## The compounds of formula II are useful in the preparation of cis (+) N-trifluoromethylsulfonyl-3-[4-hydroxy-6-ArO-chroman-3-ylmethyl]-4-methoxy aniline compounds wherein Ar is defined below. The cis (+) N-trifluoromethylsulfonyl-3-[4-hydroxy-6-ArO-chroman-3-ylmethyl]-4-methoxy aniline compounds are useful for inhibiting the production of leukotrienes and/or blocking leukotriene receptors and in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 23, 1996
    Assignee: Pfizer Inc.
    Inventor: George J. Quallich
  • Patent number: 5491152
    Abstract: The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: February 13, 1996
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
  • Patent number: 5480858
    Abstract: Cyclohexanedione derivatives of the formula (I), ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, R.sup.2 is a C.sub.1 -C.sub.4 alkyl group, each of R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl group, and n is an integer of 0 to 2, or salts thereof exhibit high selectivity for corn, wheat and barley, and can control gramineous weeds and broad-leaved weeds at low dosages.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: January 2, 1996
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Masashi Sakamoto, Mitsuru Shibata, Ichiro Nasuno, Kazuyoshi Koike
  • Patent number: 5474994
    Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: December 12, 1995
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
  • Patent number: 5466813
    Abstract: Imine dyes useful in photographic materials have the formula ##STR1## wherein R.sup.1, E.sup.1, E.sup.2, L.sup.1, L.sup.2, L.sup.3,D and m are defined as in the specification.Solid particle dispersions of dyes of formula (I) that contain at least one base-ionizable functional group such as carboxy, sulfonamido, or sulfamoyl are useful as filter dyes in photographic elements.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: November 14, 1995
    Assignee: Eastman Kodak Company
    Inventors: Donald R. Diehl, Margaret J. Helber, Hugh Williamson
  • Patent number: 5457124
    Abstract: The invention relates to compounds selected from the group consisting of the formulas: ##STR1## wherein R.sup.2 and Ph are as described herein. These compounds are potent leukotriene B.sub.4 antagonists and are therefore useful in the treatment of inflammatory diseases.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: October 10, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Andrzej R. Daniewski, Ferdinand K. Lee, Keith A. Yagaloff
  • Patent number: 5455267
    Abstract: The present invention relates to a chromone derivative and an aldose reductase inhibitor comprising said compound as efective component, which is represented by the following formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent a lower alkyl group, etc., R.sub.3 represents an oxygen atom, a sulfur atom, etc., R.sub.7 represents a phenyl group substituted or not substituted, etc., and R represents a hydrogen atom or a lower alkoxy group. The present compounds exhibit superior inhititory action on aldose reductase and are useful for the treatment of various complications of diseases in diabetes, such as cataract, retinopathy, keratopathy, nephropathy, and neuropathy.
    Type: Grant
    Filed: October 12, 1994
    Date of Patent: October 3, 1995
    Assignee: Tsumura & Co.
    Inventors: Yasushi Igarashi, Takuji Yamaguchi, Yoshimitsu Ogawa, Mika Tomita, Hiroko Hayashi, Toshitsugu Sato, Kunio Hosaka
  • Patent number: 5420307
    Abstract: 2-Amino-4-oxo-4H-benzopyrans I ##STR1## (m=0, 1 or 2; R.sup.1 -R.sup.4 have the meanings stated in the description) and the salts of I, and herbicides which contain 2-(4-hetaryloxy)- and 2-(4-aryloxy)-phenoxyacetic acid derivatives and/or cyclohexenone derivatives as herbicidal active ingredients and 2-amino-4-oxo-4H-benzopyrans I' as antidotes.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: May 30, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Gerhard Nilz, Helmut Walter, Andreas Landes, Wolfgang Freund
  • 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: 5407961
    Abstract: The present invention is concerned with antiretroviral (e.g. anti HIV-1) compounds having the formula ##STR1## Pharmaceutical compositions containing said compounds of formula (I-a) or (I-b), and processes of preparing said compounds and compositions.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: April 18, 1995
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Frans M. A. Van den Keybus, Karin J. M. M. Nuyens, Paul A. J. Janssen
  • Patent number: 5359098
    Abstract: Sigma binding site agents having the formula ##STR1## wherein A.sup.1, A.sup.2, A.sup.3, B, y and 2 are defined in the specification, W is halogen, which are novel intermediates useful in preparing the presently binding site agents.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: October 25, 1994
    Assignee: Guilford Pharmaceuticals Inc.
    Inventors: Ronald H. Erickson, Kenneth J. Natalie, Jr., Michael J. Pontecorvo, Waclaw J. Rzeszotarski
  • Patent number: 5326784
    Abstract: New cycloalkylalkylamines which are sigma-receptor ligands of formule (I) ##STR1## in which: R.sub.1 is H or lower alkyl; X and Y are H, OH, lower alkyl, lower alkoxy, halogen or nitrile; V.sub.1 and V.sub.2 together form a double bond attached to an oxygen atom or to a hydroxyimino radical, or are linked as an ethylenedioxy chain; A represents a valency bond, an oxygen atom, a methylene or an ethylene group; m is equal to 0, 1 or 2; n has the value of an integer from 1 to 5. Psychotropic drug which is also useful in gastroenterology.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: July 5, 1994
    Assignee: Institut de Recherche Jouveinal
    Inventors: Jean-Louis Junien, Alain Calvet, Henri Jacobelli, Francois Roman
  • Patent number: 5324743
    Abstract: This invention provides certain 1,2,4,5 substituted benzene derivatives containing "acid" substituents derived from cyclic or heterocyclic moieties. These unique compounds are leukotriene B.sub.4 antagonists and formulations of these derivatives, and a method of using these derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: June 28, 1994
    Assignee: Eli Lilly and Company
    Inventors: Robert D. Dillard, J. Scott Sawyer, Michael J. Sofia
  • Patent number: 5314918
    Abstract: This invention relates to alkanoic acid compounds having phenyl and heteroarylthio substituents which are useful as leukotriene antagonists, processes for the preparation thereof, and pharmaceutical compositions containing such compounds.This invention also relates to methods of treating diseases in which leukotrienes are a factor by administration of an effective amount of the above compounds or compositions.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: May 24, 1994
    Assignee: SmithKline Beecham Corporation
    Inventors: James S. Frazee, John G. Gleason, Ralph F. Hall
  • Patent number: 5312820
    Abstract: Carbamoyl and oxycarbonyl derivatives of biphenylmethylamines of structure I are angiotensin-II antagonists with balanced AT.sub.1 and AT.sub.2 activity useful in the treatment of hypertension and related disorders and ocular hypertension. ##STR1## where X is --O-- or --N(R.sup.7)--.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: May 17, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Wallace T. Ashton, Linda L. Chang, William J. Greenlee, Steven M. Hutchins, Ralph A. Rivero
  • Patent number: 5310952
    Abstract: A novel process for the preparation of aminochromans of the general formula: ##STR1## wherein R is a C.sub.1 -C.sub.4 alkyl group. In the process, a nitrochromanone of the general formula: ##STR2## is hydrogenated with hydrogen in the presence of a hydrogenation catalyst. The resultant aminochromanone (III) is reduced using zirconium oxide/isopropanol to the aminochromene (IV). The latter is finally hydrogenated with hydrogen in the presence of a hydrogenation catalyst to give the final product. The aminochromans are useful intermediates for the preparation of hypolipidaemic pharmaceuticals.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: May 10, 1994
    Assignees: Lonza Ltd., Sankyo Company Ltd.
    Inventor: Josef Heveling
  • Patent number: 5288749
    Abstract: The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: February 22, 1994
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, John F. DeBernardis, Rajnandan Prasad, Kevin B. Sippy, Karin R. Tietje
  • Patent number: 5278174
    Abstract: Sigma binding site agents having the formula ##STR1## which are useful to inhibit sigma binding site-induced activity, pharmaceutical compositions including these agents, and methods of using these agents to inhibit sigma binding site-induced activity in mammals. Also disclosed are novel intermediates useful in preparing the presently invented agents.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: January 11, 1994
    Assignee: Scios Nova, Inc.
    Inventors: Ronald H. Erickson, Kenneth J. Natalie, Jr., Michael J. Pontecorvo, Waclaw J. Rzeszotarski
  • Patent number: 5273999
    Abstract: Compounds of the formula ##STR1## wherein X is O or CH.sub.2 ;Y is O, --CH.sub.2 --CH.sub.2, --CH.dbd.CH--, --C.tbd.C--, or --OCH.sub.2 C.sub.6 H.sub.4 --;Z is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--;f, h, k, m and t, independently, are 0 or 1;n is an integer from 1 to 12;R.sup.1 is hydrogen, lower alkyl, lower alkenyl, cycloalkyl, or aralkyl; andA is B or --O--B, wherein B is a mono-, di- or tricyclic aromatic or heteroaromatic moiety substituted by the group --COR.sup.2, --(O).sub.t --(W).sub.s --COR.sup.2 or --(CH.dbd.CH).sub.p COR.sup.2 and which may also contain up to 4 additional substituents selected, independently, from the group consisting of halogen, cyano, lower alkyl, lower alkoxy, sulfonamido, alkanoyl, aroyl, --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, provided that no more than one of said substituents is --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, and wherein E is COR.sup.2 or R.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Ferdinand K. Lee, Keith A. Yagaloff
  • Patent number: 5268386
    Abstract: A novel heterocyclic compound capable of lowering the uric acid levels in plasma and urine having the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, lower alkyl, phenyl or substituted phenyl, or R.sup.1 and R.sup.2 may form a four- to eight-membered carbon ring together with the carbon atom to which they are attached; R.sup.3 is hydrogen or lower alkyl; R.sup.4 is one or two radicals selected from a group consisting of hydrogen, halogen, nitro, lower alkyl, phenyl, substituted phenyl, --OR.sup.5 and --SO.sub.2 NR.sup.6 R.sup.6' ; R.sup.5 is hydrogen, lower alkyl, phenyl-substituted lower alkyl, carboxymethyl or ester thereof, hydroxyethyl or ether thereof, or allyl; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; R.sup.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: December 7, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiroshi Harada, Eiichi Ohsugi, Yukio Yonetani, Toshihiro Shinosaki
  • Patent number: 5241101
    Abstract: Pesticidal substituted oxime ethers of the formula ##STR1## in which R represents in each case unsubstituted or substituted alkyl, cycloalkyl, aryl or heterocyclyl andX represents nitrogen or a CH group.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: August 31, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Wolfgang Kramer, Stefan Dutzmann
  • Patent number: 5239090
    Abstract: The (3S,4R)-isomer of a compound of formula (E) is disclosed.
    Type: Grant
    Filed: February 24, 1992
    Date of Patent: August 24, 1993
    Assignee: Beecham Group p.l.c.
    Inventor: Erol A. Faruk
  • Patent number: 5234900
    Abstract: The present invention relates to novel oxabicyclo ether derivative compounds, compositions containing these ether derivative compounds, and methods of using these compounds or compositions to control the growth of undesired vegetation. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals or broadleaf crops.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: August 10, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Jr., Wendy S. Taylor
  • Patent number: 5232944
    Abstract: Novel chroman derivatives of the formula I ##STR1## in which X is O or NR.sup.11,Z is CH.sub.2, O, S or CHHal,R.sup.1 and R.sup.5 are each A,R.sup.2 is H or A,R.sup.1 and R.sup.2 together are also alkylene having 3-6 C atoms,R.sup.3 is OH or OAc,R.sup.4 is H,R.sup.3 and R.sup.4 together are also a bond,R.sup.6 and R.sup.7 are each H, A, HO, AO, CHO, ACO, ACS, HOOC, AOOC, AO--CS, ACOO, A--CS--O, hydroxyalkyl, NO.sub.2, NH.sub.2, NHA, NA.sub.2, CN, F, Cl, Br, I, CF.sub.3, ASO, ASO.sub.2, AO--SO, AO--SO.sub.2, AcNH, AO--CO--NH, H.sub.2 NSO, HANSO, A.sub.2 NSO, H.sub.2 NSO.sub.2, HANSO.sub.2, A.sub.2 NSO.sub.2, H.sub.2 NCO, HANCO, A.sub.2 NCO, H.sub.2 NCS, HANCS, A.sub.2 NCS, ASONH, ASO.sub.2 NH, AOSONH, AOSO.sub.2 NH, ACO-alkyl, nitro-alkyl, cyanoalkyl, A--C(.dbd.NOH) or A--C(.dbd.NNH.sub.2),R.sup.8 and R.sup.9 are each H or A or together are .dbd.O or .dbd.S,R.sup.10 is H, Hal, CHO or CH.sub.2 OH,R.sup.11 is H, A, Ac or CH.sub.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: August 3, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Ingeborg Lues, Jacques De Peyer, Rolf Bergmann
  • Patent number: 5223532
    Abstract: Non-peptidyl compounds characterized generally as chromonyl/chromonylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.7 are taken together to form a partially saturated or fully saturated heterocyclic ring containing five to eight ring members with one or two ring members being oxygen atoms and the remaining ring members being carbon atoms, and which heterocyclic ring may be optionally substituted with lower alkyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: June 29, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5223629
    Abstract: A process is disclosed for the preparation of (.+-.)-6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrol idino)-2H-1-benzopyran-3-ol of the Formula (VI) ##STR1## from 4-cyanophenol of the Formula (I) ##STR2## which comprises reacting 4-cyanophenol of the Formula (I) with isoprene, followed with bromination and dehydrobromination steps with formation of intermediates to react with 2-pyrrolidone resulting in obtaining the compound of the Formula (VI).
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: June 29, 1993
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Tibor Timar, Tibor Eszenyi, Peter Sebok, Vilmos Galamb, Julia Fazekas, Terezia Istvan, Eva Kovach, Erika Nagy
  • Patent number: 5219883
    Abstract: This invention relates to LTD.sub.4 antagonists of the formula: ##STR1## or pharmaceutically acceptable salts thereof, wherein R.sup.1 is methyl, phenyl, ##STR2## wherein X.sub.1 and X.sub.2 may be the same or different and are members of the group consisting of hydrogen, --Cl, --Br, --CF.sub.3, --NH.sub.2, --NO.sub.2, or alkyl of 1-3 carbon atoms; m is 1 to 9; n is 1 to 5; V is --CH(OH)--, or --CH.sub.2 --; W is hydrogen or alkyl of 1-6 carbon atoms; Y is hydrogen or --COCH.sub.3 provided that when W is hydrogen Y is not hydrogen; both Z moieties are --CHO, --COOR.sup.2, --COR.sup.3, --CH(OR.sup.4)--CH.sub.2 OR.sup.4, or CH.sub.2 OR.sup.4 with the exception that when one Z moiety of Formula I is COOR.sup.2, the other Z moiety may be COR.sup.3 ;R.sup.2 is hydrogen, a pharmaceutically acceptable cation, straight or branched chain alkyl having 1-6 carbon atoms, --CH.sub.2 --CH(OR.sup.5)--CH.sub.2 --OR.sup.5, CH(CH.sub.2 OR.sup.5).sub.2 with the proviso that when Z is --COOR.sup.2, the R.sup.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: June 15, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Francis J. Koszyk, James R. Deason
  • Patent number: 5210234
    Abstract: A compound of the following formula: ##STR1## wherein: R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 polymethylene; R.sub.3 is hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 alkylcarbonyloxy; R'.sub.4 is ethyl, isopropyl, t-butyl or cyclopentyl, and R.sup.1.sub.6 is hydrogen or C.sub.1-6 alkyl.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: May 11, 1993
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Geoffrey Stemp, Frederick Cassidy
  • Patent number: 5210095
    Abstract: Non-peptidyl compounds characterized generally as chromonyl/chromonylalkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: May 11, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5202433
    Abstract: A polysaccharide derivative prepared by replacing a part or the whole of hydrogen atoms of hydroxyl and/or amino groups of a polysaccharide with one or more atomic groups represented by the following formula (1), (2) or (3) is new and useful for the separation of optical isomers: ##STR1## wherein the number of carbon atoms constituting R is 1 to 30 and R is a group having at least one asymmetric center.
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: April 13, 1993
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshio Okamoto, Koichi Hatada
  • Patent number: 5192799
    Abstract: Amine represented by the following formula (1), or their acid addition salts or their quaternary ammonium salts. ##STR1## The amines of formula (1) or their pharmaceutically acceptable acid addition salts or quaternary ammonium salts are useful for the treatment and prevention of heart diseases of animals, particularly arrhythima, myocardial infarction, angina pectoris and heart failure and psychoneurological diseases.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: March 9, 1993
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Ikuo Tomino, Masaharu Ishiguro, Takumi Kitahara, Keiichi Yokoyama, Noriaki Kihara, Joji Kamiya, Kanji Yoshihara, Masaaki Ishii, Akira Mizuchi, Kazutoshi Horikomi, Akira Awaya, Takuo Nakano
  • 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: 5179092
    Abstract: A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, --O--, or --S--; R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy or carboxy which may be optionally esterized or amidated; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: January 12, 1993
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
  • Patent number: 5162553
    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 diastereometric 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: June 19, 1991
    Date of Patent: November 10, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Shinro Setoguchi, Mineo Tsuruda, Chiaki Kitami, Tsutomu Yamanaka
  • Patent number: 5151442
    Abstract: Compounds of the formula ##STR1## in which: Z represents a halogen or a cyano, acetyl, trifluoroacetyl, nitro, C.sub.1 -C.sub.4 alkylthio, carboxyl, phosphono, dialkoxyphosphonyl or alkoxycarbonyl group, the alkylthio and alkoxy groups containing from 1 to 3 carbon atoms;R.sub.1 denotes a hydroxyl group and R.sub.2 represents hydrogen, or R.sub.1 and R.sub.2 taken together form an additional bond between the carbon atoms by which they are carried; andR.sub.3 representsa group NH--X--R.sub.4, in which X denotes a direct bond or an SO.sub.2 group and R.sub.4 represents a phenyl group which is unsubstituted or monosubstituted or disubstituted by a halogen, a nitro group, a C.sub.1 -C.sub.4 group, a trifluoromethyl group, an amino group, a group --N(Alk).sub.2, a group --COOAlk or a group OAlk, Alk denoting a C.sub.1 -C.sub.4 Alkyl group;a group --S--R.sub.5, in which R.sub.5 represents a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: September 29, 1992
    Assignee: Sanofi
    Inventors: Georges Garcia, Alain Di Malta, Philippe Soubrie
  • Patent number: 5143924
    Abstract: Novel chroman derivatives of the formula I ##STR1## in which R.sup.1 to R.sup.6 and Z have the meanings given in Patent Claim 1, and their salts show effects on the cardiovascular system and can be used for the treatment or prophylaxis of cardiac insufficiency, angina pectoris, high blood pressure, incontinence and alopecia.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: September 1, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Ingeborg Lues, Rolf Bergmann, Jacques De Peyer
  • Patent number: 5130322
    Abstract: The invention relates to chroman derivatives of the formula I ##STR1## in which R.sup.1 is A,R.sup.2 is OA,R.sup.3 is OH,R.sup.4 is H, orR.sup.3 and R.sup.4 together are a bond,R.sup.5 is a 2-oxo-1,2-dihydro-1-pyridyl or 2-oxo-2,3-dihydro-4-pyrodyl radical which is optionally monosubstituted by A,R.sup.6 is CN,R.sup.7 and R.sup.8 are each H,Z is O, NH or a bond, andA is alkyl having 1-6 C atoms,or a physiologically acceptable salt thereof.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: July 14, 1992
    Inventors: Rolf Gericke, Manfred Baumgarth, Ingeborg Lues, Rolf Bergmann, Jacques De Peyer
  • Patent number: 5125954
    Abstract: The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: June 30, 1992
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Richard B. Phillips
  • Patent number: 5116954
    Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: May 26, 1992
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
  • Patent number: 5097046
    Abstract: Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: March 17, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna, Charles E. J. Beck, Salvatore M. Brucato
  • Patent number: 5071871
    Abstract: New benz[b]pyranes and pyranopyridines of formula I, ##STR1## wherein the significances of substituents V, T, W, R.sub.3 to R.sub.5, R.sub.9, R.sub.10, m, X, Y and Z are given in claim 1 and their N-oxides and their salts and their use in the treatment of raised blood pressure in the treatment of vascular disorders and other disorders in which a reduction in tension of the smooth muscles is therapeutically useful, as well as in the treatment of hair loss and baldness. Further the compounds are useful in the treatment of asthma and obstructive disorders of the respiratory system as well as in the prophylactic treatment of obstructive or inflammatory airways disease, for example asthma, as well as novel pharmaceutical compositions comprising said K.sup.+ channel activators suitable for such use.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: December 10, 1991
    Assignee: Sandoz Ltd.
    Inventors: Stefan Blarer, John Morley, Ian D. Chapman
  • 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: 5045541
    Abstract: Fused pyridazine compounds ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and respectively hydrogen, a halogen, hydroxy, nitro, amino, cyano, trifluoromethyl, and alkyl, an alkoxy or an alkanoylamino; one of R.sub.a and R.sub.b is a group of the formula--O--Y--NR.sup.5 R.sup.6wherein R.sup.5 and R.sup.6 are the same or different and respectively hydrogen, an alkyl, a phenylalkyl or a substituted phenylalkyl or a group forming a heterocycle together with the adjacent nitrogen atom and Y stands for a straight- or branched-chain alkylene which may have hydroxy group as a substituent on the chain, and the other is hydrogen, or both of R.sub.a and R.sub.b are the same or different and respectively a group of the formula--O--Y--NR.sup.5 R.sup.6wherein R.sup.5 and R.sup.6 are of the same meanings as defined above; W is .dbd.CH-- or .dbd.N; X is CH.sub.2, S, SO, SO.sub.
    Type: Grant
    Filed: July 2, 1989
    Date of Patent: September 3, 1991
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Toru Nakao, Minoru Kawakami, Masao Hisadome, Tetsuya Tahara
  • Patent number: 5023352
    Abstract: Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.6 cycloalkyl moiety; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powder and perfumed polymers.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: June 11, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna, Charles E. J. Beck, Salvatore M. Brucato
  • 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