Chalcogen Attached Indirectly To The Bicyclo Ring System By Acyclic Nonionic Bonding Patents (Class 548/509)
  • Patent number: 5969155
    Abstract: The present invention is directed to the synthesis of useful products from the explosive trinitrotoluene. This substance has a limited shelf life as a reliable explosive and large quantities of it have and will become surplus. Ecologically safe, and preferably commercially useful ways of disposing of it are therefore much to be desired. In the present invention the end products are nitroindoles of the general formula 4-Z.sup.1,6-Z.sup.2 indole wherein Z.sup.1 and Z.sup.2 are the same or different and are halo or nitro provided at least one of said groups is nitro.
    Type: Grant
    Filed: April 9, 1998
    Date of Patent: October 19, 1999
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Sreenivasa R. Eturi, Abdollah Bashir-Hashemi, Sury Iyer
  • Patent number: 5948808
    Abstract: Provided in the present invention are compounds and compositions of substituted indole-3-carbinols and diindolylmethane suitable for treating estrogen-dependent tumors. Also provided are methods of treating such cancerous-conditions.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: September 7, 1999
    Assignee: The Texas A&M University System
    Inventor: Stephen H. Safe
  • Patent number: 5939451
    Abstract: The present invention is concerned with compounds of formula ##STR1## wherein Z is a substituted indolyl group of formula ##STR2## R.sup.1 is hydrogen, amino, lower alkylamino, lower dialkylamino, lower alkyl, halogen, or trifluoromethyl;R.sup.2 is hydrogen or lower alkyl;R.sup.11 is hydrogen or halogen;R.sup.12 is hydrogen or lower alkyl; anda is a single or double bond;or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: June 4, 1997
    Date of Patent: August 17, 1999
    Assignee: Hoffmann-la Roche Inc.
    Inventors: Michael Bos, Claus Riemer, Andrew Sleight
  • Patent number: 5932743
    Abstract: The present invention relates to novel substituted indole compounds of formula (I) ##STR1## having pharmacological activity, to processes for their preparation, to solid phase methods for preparing libraries of the compounds, to utilizing libraries of the compounds for drug discovery, and to pharmaceutical compositions thereof.
    Type: Grant
    Filed: July 29, 1998
    Date of Patent: August 3, 1999
    Assignee: American Home Products Corporation
    Inventors: Michael D. Collini, John W. Ellingboe
  • Patent number: 5919947
    Abstract: The present invention relates to a traceless solid phase process for the preparation of an indole derivative, which comprises the following steps:(1) reaction of an optionally substituted 2-iodoaniline derivative via the nitrogen atom of the NH.sub.2 moiety thereof with a dihydropyran-functionalized polymeric resin under conditions effective to form an aminal linkage;(2) reaction of the tetrahydropyran aminal derivative thereby obtained with an acetylene derivative in the presence of a transition metal catalyst under conditions effective to promote indole formation;(3) treatment of the product thereby obtained with acid, whereby the aminal linkage is cleaved and the desired indole derivative is liberated from the resin; and(4) isolation of the desired indole derivative thereby obtained.
    Type: Grant
    Filed: September 2, 1998
    Date of Patent: July 6, 1999
    Assignee: Merck Sharp & Dohme Ltd.
    Inventor: Adrian Leonard Smith
  • Patent number: 5869692
    Abstract: A composition for the oxidation dyeing of keratinous fibers containing at least one coupler selected from N-substituted 4-hydroxyindole compounds and acid addition salt thereofs and at least one oxidation base, N-substituted 4-hydroxyindole compounds, a process for synthesizing these substituted compounds, their use as couplers for the oxidation dyeing of keratinous fibers in combination with at least one oxidation base, as well as dyeing processes employing them.
    Type: Grant
    Filed: September 18, 1997
    Date of Patent: February 9, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5856517
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.1' are independently alkyl, aryl, alkenyl or alkynyl;R.sup.2 and R.sup.2' are independently hydrogen or alkyl;R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently are ##STR2## CH.sub.2 OR.sup.10, CHO, CH.sub.2 NR.sup.11 R.sup.12, hydrogen, halogen, cyano, alkyl, hydroxy, alkoxy, aryloxy, haloalkyl, nitro, amino, acylamino, aralkyloxy, monoalkylamino, dialkylamino, alkylthio, alkylsulphinyl or alkylsulphonyl, provided that at least one of R.sup.4, R.sup.5, R.sup.6 or R.sup.7 is cyano, ##STR3## CH.sub.2 OR.sup.10, CH.sub.2 NR.sup.11 R.sup.12, or CHO ; R.sup.8 is alkyl, aralkyl or aryl;R.sup.10 is hydrogen, alkyl, aralkyl or aryl;R.sup.11 and R.sup.
    Type: Grant
    Filed: July 24, 1997
    Date of Patent: January 5, 1999
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Donna Mary Huryn, Dennis Dalton Keith
  • Patent number: 5789440
    Abstract: The present invention relates to novel 5,6-dihydropyrone derivatives and related structures which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The 5,6-dihydropyrone derivatives are useful in the development of therapies for the treatment of bacterial and viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of multifunctionalized 5,6-dihydropyrones and of related structures.
    Type: Grant
    Filed: October 12, 1994
    Date of Patent: August 4, 1998
    Assignee: Warner-Lambert Company
    Inventors: Edmund Lee Ellsworth, Elizabeth Lunney, Bradley Dean Tait
  • Patent number: 5767141
    Abstract: Substituted propane derivatives, a process for their preparation and the use of the compounds for treating diseasesPropane derivatives of the formula I ##STR1## in which the radicals have the meanings stated in the description, a process for the preparation of these compounds, their use as pharmaceuticals, and pharmaceutical products are described. Also described are novel intermediates for preparing the compounds of the formula I.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: June 16, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerrit Schubert, Horst Hemmerle, Peter Below, Andreas Herling, Hans-Jorg Burger
  • Patent number: 5756531
    Abstract: The present invention provides a class of substituted indole and indene iminoxy derivatives of the formula ##STR1## which inhibit leukotriene biosynthesis and are useful in the treatment of allergic and inflammatory disease states.
    Type: Grant
    Filed: April 30, 1996
    Date of Patent: May 26, 1998
    Assignee: Abbott Laboratories
    Inventors: Clint D. W. Brooks, Richard A. Craig, David E. Gunn, Teodozyji Kolasa, Jimmie L. Moore, Andrew O. Stewart
  • Patent number: 5739353
    Abstract: This invention relates to substituted N-arylindoles, a process for producing them and their use as herbicides. In particular, this invention relates to substituted N-arylindoles of the formula ##STR1## wherein R, R.sup.3, X, Z, n and k are defined herein.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: April 14, 1998
    Assignee: Zeneca Limited
    Inventors: Ferenc M. Pallos, Christopher J. Mathews
  • Patent number: 5728712
    Abstract: 3,4-Disubstituted-phenylsulphonamides have therapeutic utility via TNF or phosphodiesterase inhibition.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: March 17, 1998
    Assignee: Chiroscience Limited
    Inventors: John Gary Montana, Hazel Joan Dyke, Robert James Maxey, Christopher Lowe
  • Patent number: 5726063
    Abstract: A colorimetric assay of enaldehydes or of malonic dialdehyde as lipid peroxidation indices in an aqueous medium includinga) addition to the medium of a reagent of a compound of general formula I and their optional addition salts with organic or inorganic bases or with organic or inorganic acids. ##STR1## in which formula: A and C, which may be identical or different, each represent H, ##STR2## wherein A and C cannot simultaneously represent H, with:R.sup.1 =H; alkyl; aralkyl; aryl substituted on the aryl ring; alkyl sulfonate Y.sup.+ ; alkyl phosphonate, Y.sup.+ ; or alkyl carboxylate, Y.sup.+ ;R.sup.2 =H; --OR.sup.4 ; F; Cl; Br; I; --NO.sub.2 ; SO.sub.3.sup.31 Y.sup.+ ; --CN; --COOR.sup.4 ; or --CONR.sup.5 R.sup.6 ;R.sup.3 =H; --OR.sup.4 ; --NR.sup.5 R.sup.6 ; --SR.sup.4 ; F; Cl; Br; I; --NO.sub.2 ; --SO.sub.3 --Y.sup.+ ; --CN; --COR.sup.5 ; --COOR.sup.4 ; or --CONR.sup.5 R.sup.6 ;R.sup.4 =H; alkyl; aralkyl; or aryl substituted on the aryl ring;R.sup.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: March 10, 1998
    Assignee: Oxis Isle of Man, Limited
    Inventors: Dominique Gerard-Monnier, Irene Erdelmeier, Jean Chaudiere, Jean-Claude Yadan
  • Patent number: 5719144
    Abstract: Fibrinogen receptor antagonists having the formula ##STR1## where L is L is (CH.sub.2).sub.p, where p is 1 or 2; and Z is --CR.sup.1 .dbd.CR.sup.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: February 17, 1998
    Assignee: Merck & Co., Inc.
    Inventors: George D. Hartman, John H. Hutchinson, Wasyl Halczenko
  • Patent number: 5688822
    Abstract: Compounds of the formula: ##STR1## Formula I and the pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising a therapeutically-effective amount of the compounds or salts in combination with a pharmaceutically-acceptable carrier and methods for treating 5-lipoxygenase mediated conditions, inflammation-associated disorders and allergies.
    Type: Grant
    Filed: February 7, 1996
    Date of Patent: November 18, 1997
    Assignee: G.D. Searle & Co.
    Inventors: Ish Kumar Khanna, Michael Allan Stealey, Richard Mathias Weier
  • Patent number: 5676884
    Abstract: Nonlinear optical (NLO) compositions are disclosed which contain polar disulfone-functionalized molecules (PDFMs) incorporated in a polymeric material. when aligned noncentrosymmetrically in the polymeric material, the PDFMs generate a second-order NLO response. There is also disclosed: a method of preparing a NLO composition; novel PDFMs and novel polymers; and a new process for preparing PDFMs.
    Type: Grant
    Filed: November 20, 1996
    Date of Patent: October 14, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: George V. Tiers, Robert J. Koshar, Louis M. Leichter
  • Patent number: 5672706
    Abstract: A process is disclosed for the preparation of the substantially pure compound of the formula: ##STR1## comprising catalytic hydrogenation of a compound of the formula: ##STR2## wherein R.sub.6 and R.sub.7 are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR5## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl; or an acid addition salt thereof.
    Type: Grant
    Filed: April 17, 1996
    Date of Patent: September 30, 1997
    Assignee: Abbott Laboratories
    Inventors: Anthony R. Haight, Owen J. Goodmonson, Shyamal I. Parekh, Timothy A. Robbins, Lou S. Seif
  • Patent number: 5618821
    Abstract: Compounds of the formula ##STR1## wherein Q is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substituents;Y is an alkylene bridge of 3-9 carbon atoms;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano;R.sub.3 is alkoxycarbonyl, alkyltetrazolyl, substituted or unsubstituted phenyl or heterocyclyl, the N-oxide thereof, or a pharmaceutically acceptable acid addition salt thereof is an effective antipicornaviral agent.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: April 8, 1997
    Assignee: Sanofi, S.A.
    Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz
  • Patent number: 5604253
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: February 18, 1997
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Cheuk K. Lau, Cameron Black, Daniel Guay, Jacques Y. Gauthier, Yves LeBlanc, Patrick Roy, Yves Ducharme, Pierre Hamel
  • Patent number: 5599774
    Abstract: Substituted N-arylindoles, a process for producing them and their use as herbicides. In particular, substituted N-arylindoles of the formula ##STR1## are disclosed in which: R is hydrogen; halogen; nitro; cyano; alkyl; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; carbonylalkoxy; alkyloxyalkoxy; cyanoalkoxy; benzyloxy; alkoxycarbonylalkoxy; alkylcarbonylalkoxy; haloalkyl; hydroxalkyl; formyl; azido; carboxy or its salts; COOalkyl; amino; substituted amino wherein the substituents are alkyl, alkoxy, hydroxy, formyl, alkylcarbonyl, substituted alkylcarbonyl substituted with carboxy or alkoxycarboxy, alkylsulfonyl, haloalkylsulfonyl, aminocarbonyl, (di)alkylaminocarbonyl, alkoxycarbonyl, alkoxyalkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, amino or (di)alkyl amino; carboxyamido; substituted carboxyamido wherein said substituents can be selected from alkyl, alkylsulfonyl, and haloalkylsulfonyl; sulfonamido wherein the N is substituted with hydrogen and/or alkyl; YR.sup.4 wherein Y is O or S(O).sub.m and R.sup.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ferenc M. Pallos, Christopher J. Mathews
  • Patent number: 5583149
    Abstract: A series of novel serotonergic indolyl derivatives of cycloalkanyl- and cycloalkenyl-amines of Formula I are intended for use in the alleviation of vascular headaches.
    Type: Grant
    Filed: August 21, 1995
    Date of Patent: December 10, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: Joseph A. Cipollina, Jonas A. Gylys, Ronald J. Mattson, Charles P. Sloan
  • Patent number: 5556981
    Abstract: This invention provides novel heterocyclic derivatives, their pharmaceutical formulations, and their use for antagonizing angiotensin II receptors in mammals.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: September 17, 1996
    Assignee: Eli Lilly and Company
    Inventors: Donald B. Boyd, Sherryl L. Lifer, Winston S. Marshall, Alan D. Palkowitz, William Pfeifer, Jon K. Reel, Richard L. Simon, Mitchell I. Steinberg, K. Jeff Thrasher, Venkatraghaven Vasudevan, Celia A. Whitesitt
  • Patent number: 5516916
    Abstract: A process for preparing dye compositions which comprises hydrolyzing an O-protected 5,6-dihydroxyindole with an alkaline material under anaerobic condition and the products made by such process.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: May 14, 1996
    Assignee: Clairol Incorporated
    Inventors: Bryan P. Murphy, Keith C. Brown, Thomas M. Schultz, Alice A. Meyer
  • Patent number: 5496844
    Abstract: The present invention provides indole derivatives of the general formula: ##STR1## The indole derivatives of the invention have potent antiestrogen activity and are useful as drugs for the treatment of estrogen-dependent diseases, such as anovulatory infertility, prostatic hypertrophy, osteoporosis, breast cancer, endometrial cancer and melanoma.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: March 5, 1996
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Masatoshi Inai, Tadanao Shibutani, Jun Kanaya, Masako Moritake, Akie Tanaka
  • Patent number: 5468768
    Abstract: A series of novel serotonergic indolyl derivatives of cycloalkanyl- and cycloalkenyl-amines of Formula I are intended for use in the alleviation of vascular headaches.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: November 21, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventors: Joseph A. Cipollina, Jonas A. Gylys, Ronald J. Mattson, Charles P. Sloan
  • Patent number: 5451605
    Abstract: Compounds of the formula ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: September 19, 1995
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. Chandraratna, Richard L. Beard
  • Patent number: 5288761
    Abstract: Open chain enediyne dihydroperoxides having eight carbons between the hydroperoxide groups that cleave DNA are disclosed, as are methods of making and using the same.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: February 22, 1994
    Assignee: The Scripps Research Institute
    Inventors: Kyriacos C. Nicolaou, Erik Sorensen, Chan-Kou Hwang, Robert Discordia, Robert G. Bergman, Robert E. Minto
  • Patent number: 5229413
    Abstract: Compositions containing certain indole-2-carboxylate compounds and derivatives are described as being therapeutically effective in treatment of CNS disorders resulting from neurotoxic damage or neurodegenerative diseases, particularly those CNS disorders resulting from ischemic events. Preferred compounds are of the formula ##STR1## wherein each of R.sup.5 and R.sup.6 is independently selected from hydrido, bromo, chloro and fluoro, and wherein each of R.sup.10 and R.sup.12 is independently selected from hydrido and lower alkyl, and pharmaceutically-acceptable salts thereof.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: July 20, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Nancy M. Gray, Brian K. Cheng, William F. Hood, Michael S. Dappen, Alex A. Cordi
  • Patent number: 5210214
    Abstract: A process for preparing indolenines of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are independently of one another hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -alkylphenyl, C.sub.7 -C.sub.20 -phenalkyl, or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 together are an unsubstituted or C.sub.1 -C.sub.12 -alkyl-substituted C.sub.3 -C.sub.8 -alkylene chain,X and Y are independently of one another hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.2 -C.sub.8 -alkoxyalkyl, C.sub.2 -C.sub.8 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, halogen, nitro or cyano,by reacting a 4-methylene-1,3-dioxolan-2-one of the formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, with an aniline of the formula III ##STR3## where X and Y are each as defined above, in the presence of a Lewis acid and in the presence or absence of a halide of main group 1 or 2 of the Periodic Table at from 100.degree.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Diehl, Martin Fischer, Manfred Dimmler
  • Patent number: 5206380
    Abstract: A chromogenic compound for use in pressure- or heatsensitive record material has the general formula (I):R.sub.1 --CH.dbd.CH--CR.sub.3 (OR.sub.4)--CH.dbd.CH--R.sub.2 (I)in which:R.sub.1 and R.sub.2 are the same or different and each is a group of one of the formulae (II): ##STR1## in which the benzene ring of the group of formula (IIa) is optionally further substituted, and in which:R.sub.10 and R.sub.11 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group, orR.sub.10 and R.sub.11 together with the nitrogen atom to which they are attached form an optionally-substituted heterocyclic ring, which may include one or more further hetero atoms;R.sub.12, R.sub.13 and R.sub.14 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group;R.sub.3 is an optionally-substituted aryl group; andR.sub.4 is hydrogen or an optionally-substituted alkyl, aryl or aralkyl group.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: April 27, 1993
    Assignee: The Wiggins Teape Group Limited
    Inventor: Kenneth J. Shanton
  • Patent number: 5202500
    Abstract: Arylacetaldehyde-dialkylacetals are prepared with high yields and selectivity from the corresponding chloromethylaromatics in the presence of hydrogen chloride acceptors and methyl carbonyl compounds as catalysts and in the presence of orthoesters as water-binding agents by hydroformylation with carbon monoxide and hydrogen.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: April 13, 1993
    Assignee: Huels Aktiengesellschaft
    Inventors: Christoph Theis, Wilfried Latz
  • Patent number: 5183894
    Abstract: The present invention relates to 2-substituted-1-hydroxyindoles of the following formula: ##STR1## wherein, R.sup.1 is an electron withdrawing group,R.sup.2 is an alkenyl having 2-10 carbon atoms, and N-substituted .alpha.-iminobenzyl group wherein the substituents are selected from the group consisting of phenyl, anilino and dimethylamino, an unsubstituted aromatic group, and an aromatic group having meta or para substituents which are nitro, trifluoromethyl, fluoro, formyl, hydroxyiminomethyl and carbamoyl,R.sup.3 is a halogen atom, andn is 0, 1, or 2,provided that when R.sup.2 is either phenyl or nitro substituted phenyl and n is 0, then R.sup.1 is not cyano.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: February 2, 1993
    Assignee: Eastman Kodak Company
    Inventors: William R. Schleigh, Thomas R. Welter
  • Patent number: 5180728
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, lower alkyl, lower alkenyl, aryl or ar(lower)alkyl,R.sup.4 is imidazolyl, which may have alkyl or imino-protective group as substituents, or pyridyl,A is lower alkylene, andis single bond or double bond, and pharmaceutically acceptable salts thereof, having 5-HT antagonism.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: January 19, 1993
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masayuki Kato, Shigetaka Nishino, Kiyotaka Ito, Hisashi Takasugi
  • Patent number: 5128363
    Abstract: Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a trifluoromethoxy substituent in the 5-, 6-, 7-, or 8-position, and methods for their preparation and use, are disclosed. The derivatives are useful anti-inflammatory and analgesic agents.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: July 7, 1992
    Assignee: American Home Products Corporation
    Inventor: Amedeo A. Failli
  • Patent number: 5118695
    Abstract: 1-Hydroxyindoles of the following formula are useful in controlling fungi: ##STR1## wherein: R.sup.1 is hydrogen or an electron withdrawing group;R.sup.2 is selected from the group consisting of alkenyl having 2-10 carbon atoms, N-substituted-.alpha.-iminobenzyl, an unsubstituted or substituted aromatic group and acyl of 2-16 carbon atoms,R.sup.3 is selected from the group consisting of halogen atoms, andn is 0 to 4.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: June 2, 1992
    Assignee: Eastman Kodak Company
    Inventors: William R. Schleigh, Thomas R. Welter
  • 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: 5091379
    Abstract: Topical polyethylene glycol based formulations for the delivery of 2-substituted-1-naphthols and indoles and particularly, 2-phenylmethyl-1-naphthol are provided. Said topical formulations exert excellent localized antiinflammatory activity while demonstrating low levels of skin penetration in vitro and in vivo thereby reducing unwanted side effects and reducing systemic toxicity associated with the active drug compounds.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: February 25, 1992
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Bruce J. Aungst
  • Patent number: 5082938
    Abstract: Enhanced branched chain hydroxyl compounds are provided of formulaY--(Z).sub.1-6wherein Y is the residue of a nucleophile devoid of conjugated divalent linking moieties, and each Z is a poly(oxyalkylene) moiety having a molecular weight of from about 200-10,000 and containing at least one glycidol residue, wherein at least one of the primary oxy sites of said glycidol residue is linked preferably directly to a first epoxide residue of three or more carbons, and wherein said first epoxide residue is linked through a secondary oxy site preferably directly to a second epoxide reside having a primary terminal hydroxyl.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: January 21, 1992
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, David J. Moody
  • Patent number: 5021430
    Abstract: Disclosed are compound of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and R.sub.o independently represent lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by aryl-lower alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl, by acylamino-lower alkyl, by guanidino-lower alkyl, by (C.sub.3 -C.sub.7)-cycloalkyl, by (C.sub.3 -C.sub.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: June 4, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Gary M. Ksander
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • 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: 4977274
    Abstract: The invention relates to new 4-hydroxyindole derivatives of general formula: ##STR1## in which R represents a labile protective group and R.sub.1 can represent hydrogen, a C.sub.1 -C.sub.6 alkyl radical, a C.sub.3 -C.sub.6 cycloalkyl radical, a lower alkoxy radical, a lower hydroxyalkyl radical, a lower (lower alkoxy) alkyl radical, a phenyl radical optionally substituted with a halogen atom or a lower alkyl or lower alkoxy radical, a cyano radical, a radical of formula ##STR2## in which R.sub.2 and R.sub.3, which may be identical or different, each represent hydrogen or a lower alkyl radical, R.sub.4 represents a hydroxy group, a lower alkyl or lower alkoxy radical or a radical ##STR3## in which R.sub.2 and R.sub.3 have the same meaning as above, R.sub.5 represents a lower alkyl radical and Alk represents a single bond or a straight- or branched-chain alkylene radical having from 1 to 4 carbon atoms.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: December 11, 1990
    Assignee: Sanofi
    Inventors: Marcel Descamps, Walter Verstraeten
  • Patent number: 4904799
    Abstract: Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1-, 4-, 5-, 6-, 7- and 8- are disclosed. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: February 27, 1990
    Assignee: American Home Products Corp.
    Inventors: Brian A. McKittrick, Alan H. Katz
  • Patent number: 4897493
    Abstract: Process for the production of substituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acids having useful analgesic and anti-inflammatory activity.
    Type: Grant
    Filed: January 31, 1989
    Date of Patent: January 30, 1990
    Assignee: American Home Products Corporation
    Inventors: Chia-Cheng Shaw, Karel Pelz
  • Patent number: 4882339
    Abstract: Disclosed are compounds of the formula ##STR1## wherein R.sub.1 represents unsubstituted or lower alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, unsubstituted or lower alkyl substituted C.sub.7 -or C.sub.8 -bicycloalkyl, unsubstituted or lower alkyl-substituted adamantyl, 4-piperidinyl or N-lower alkyl or aryl-lower alkyl-substituted piperidinyl, 1- or 2-indanyl, 1- or 2-tetrahydronaphthyl, 1- or 2-perhydroindanyl, 1- or 2-perhydronaphthyl; R.sub.2 represents hydrogen, lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, aryl-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl, lower alkanoyl or aryl-lower alkanoyl; or R.sub.1 and R.sub.2 combined with the nitrogen to which they are attached represent pyrrolidino, piperidino, perhydroazepino, morpholino, thiomorpholino, tetrahydro- or perhydro-(isoquinolinyl or quinolinyl), dihydro- or perhydroindolyl, piperazino or N-lower alkyl-piperazino; R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 21, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Jan W. F. Wasley
  • Patent number: 4871656
    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, from 2 to 4 carbon atoms, having 2 carbon atoms in the alkyl chain linking the nitrogen atom of each Z ring and the sulfo or sulfato group, and 1 carbon atom in the alkyl chain linking 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 a 5- or 6-membered carbocyclic ring, and R.sub.4 represents hydrogen, alkyl of 1 to 4 carbon atoms, halogen, cyano, 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 heterocyclic ring.X.sup..sym. represents a cation.Z.sub.1 and Z.sub.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: October 3, 1989
    Assignee: Eastman Kodak Company
    Inventors: Richard L. Parton, ANthony D. Gingello, David J. Collett, David A. Stegman, ANthony Adin
  • Patent number: 4843081
    Abstract: A and A' are each hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or aryloxy;X is cyano, nitro, COOR, SR, SOR or SOOR;R is H, C.sub.1-6 alkyl or aryl;n n' and n" are each 0 to 4; andm, m' and m" are each 1 to 4, have calcium channel blocking activity.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: June 27, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles
  • Patent number: 4837327
    Abstract: Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: June 6, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4831156
    Abstract: The disclosure relates to compounds of the formula ##STR1## and pharmaceutically acceptable addition salts thereof wherein X represents a substituted or unsubstituted alkylene chain containing 1 to 4 carbon atoms, wherein R.sub.5 is a lower alkyl group, wherein R.sub.6 is either hydrogen or methyl, R.sub.9 is hydrogen or lower alkyl, wherein Am is selected from the class consisting of amino, lower mono and dialkylamino, piperidino, piperazino, N-lower alkyl piperazino, pyrrolidino, and morpholino groups, wherein Y.sub.1 and Y.sub.2 are identical and are hydrogen, halogen, methyl or ethyl and n is an integer in the range of 1-5.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: May 16, 1989
    Assignee: The University of Tennessee Research Corp.
    Inventors: Thomas P. Kennedy, George W. Kabalka
  • Patent number: 4826994
    Abstract: Production of indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1 and 4. The nucleus may be optionally substituted at positions 5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.
    Type: Grant
    Filed: February 26, 1988
    Date of Patent: May 2, 1989
    Assignee: American Home Products Corporation
    Inventors: Alan H. Katz, Christopher A. Demerson, Leslie G. Humber