Acyclic Nitrogen Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 546/308)
  • Patent number: 6313148
    Abstract: Compounds antagonistic of the pain enhancing effects of prostaglandins are disclosed. The compounds comprise an optionally-substituted A ring with a —CH(R3)N(R2)B—R1 and —OD groups positioned in a 1,2 relationship to one another on ring carbon atoms. The 3-position ring-atom is not substituted. B is an optionally-substituted pyridyl ring and the group R1 is positioned on B in a 1,3 or 1,4 relationship with the —CH(R3)N(R2)B- linking group. R1, R2 and R3 and D can be a number of different organic or halogen moieties. N-oxides of —NR2 and S-oxides of sulphur containing rings are disclosed as are processes for the preparation of the compounds, intermediates in their preparation, pharmaceutical compositions containing them, and their use as therapeutic agents.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: November 6, 2001
    Assignee: Zeneca Limited
    Inventor: Gloria Anne Breault
  • Patent number: 6303790
    Abstract: A process is described for preparing certain 4-alkyl- or 4-aryl-pyridine derivatives.
    Type: Grant
    Filed: November 20, 2000
    Date of Patent: October 16, 2001
    Assignee: Hoffman-La Roche Inc.
    Inventors: Hans Hilpert, Fabienne Hoffmann-Emery, Goesta Rimmler, Mark Rogers-Evans, Helmut Werner Stahr, Pius Waldmeier
  • Patent number: 6215024
    Abstract: The present invention provides a novel single step process for the production of amides from amines comprising reaction of amines with an acylating agent comprising of a carboxylic acid in a molar ratio of 1:3 to 1:10 in the presence of reusable natural montmorillonite/metal ion-exchanged clay catalysts, in a suitable solvent medium at a temperature in the range of 30-160° C. for a period of 0.02 to 6 hrs, and recovering the corresponding amides by a conventional simple work-up procedure.
    Type: Grant
    Filed: October 4, 1999
    Date of Patent: April 10, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Veldurthy Bhaskar, Mannepalli Lakshmi Kantam, Kottapalli Koteswara Rao, Kondapuram Vijaya Raghavan
  • Patent number: 6191150
    Abstract: A family of compounds having the general structural formula where W is a reverse hydroxamic acid group, and R1, R2, R3, R4, R5 and R6 are as described in the specification, or a pharmaceutically acceptable salt, solvate, biohydrolyzable ester, biohydrolyzable amide, affinity reagent, or prodrug thereof.
    Type: Grant
    Filed: August 25, 1999
    Date of Patent: February 20, 2001
    Assignee: Glaxo Wellcome Inc.
    Inventors: Robert Carl Andrews, Marc Werner Andersen, Dulce Garrido Bubacz, Joseph Howing Chan, David John Cowan, Michael David Gaul, Daryl Lynn McDougald, David Lee Musso, Michael Howard Rabinowitz, Jennifer Badiang Stanford, Robert William Wiethe
  • Patent number: 6031105
    Abstract: The present invention relates to certain compounds of the formula (I), ##STR1## which are useful in the synthesis of certian .beta.-adrenergic receptor agonists. The invention also relates to a process for synthesizing the compounds of formula (I) and to compounds of the formula (II), ##STR2## wherein R.sup.1, R.sup.2 and R.sup.4 are defined herein, which are useful in the synthesis of the compounds of formula (I). The invention also relates to a process for synthesizing a compound of formula (II). The invention further relates to processes for synthesizing compounds of formula (Z*), ##STR3## R.sup.1, R.sup.2 and Y.sup.2* are defined herein.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: February 29, 2000
    Assignee: Pfizer Inc
    Inventor: Steven W. Wright
  • Patent number: 6011039
    Abstract: A compound represented by the formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition for hyperphagia, obesity or diabetes, which comprises such a compound or salt as an active ingredient: ##STR1## wherein Ar.sup.1, Ar.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and W are as defined.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: January 4, 2000
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Takehiro Fukami, Toshiaki Mase, Yoshimi Tsuchiya, Akio Kanatani, Takahiro Fukuroda
  • Patent number: 6008361
    Abstract: The present invention relates to certain compounds of the formula (I), ##STR1## which are useful in the synthesis of certain .beta.-adrenergic receptor agonists. The invention also relates to a process for synthesizing the compounds of formula (I) and to compounds of the formula (II), ##STR2## wherein R.sup.1, R.sup.2 and R.sup.4 are defined herein, which are useful in the synthesis of the compounds of formula (I). The invention also relates to a process for synthesizing a compound of formula (II). The invention further relates to processes for synthesizing compounds of formula (Z*), ##STR3## R.sup.1, R.sup.2 and Y.sup.2* are defined herein.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: December 28, 1999
    Assignee: Pfizer Inc.
    Inventor: Steven W. Wright
  • Patent number: 5994377
    Abstract: Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.
    Type: Grant
    Filed: October 17, 1997
    Date of Patent: November 30, 1999
    Assignee: Gilead Sciences, Inc.
    Inventors: Choung U. Kim, Matthew A. Williams
  • Patent number: 5972975
    Abstract: Substituted 2-aminopyridine compounds of Formula (I) and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders.
    Type: Grant
    Filed: May 22, 1997
    Date of Patent: October 26, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Craig Esser, William Hagmann, William Hoffman, Shrenik Shah, Kenny Wong, Renee Chabin, Ravindra Guthikonda, Malcolm Maccoss, Charles Caldwell, Philippe Durette
  • Patent number: 5959115
    Abstract: A process for preparation of pure flupertine maleate and the pure A crystalline form of flupertine maleate by the use of water soluble alcohols during synthesis and/or purification.
    Type: Grant
    Filed: April 23, 1998
    Date of Patent: September 28, 1999
    Assignee: ASTA Medica Aktiengesellschaft
    Inventors: Alfred Olbrich, Peter Emig, Bernhard Kutscher, Karl-Friedrich Landgraf, Siegfried Pauluhn, Hans Stange
  • Patent number: 5919936
    Abstract: This invention provides 5-HT.sub.1F agonists of Formula I: ##STR1## where A-B, X, and R are as defined in the specification. The invention also encompasses pharmaceutical formulations employing compounds of Formula I as well as methods of treating conditions associated with 5-HT.sub.1F activation employing these compounds or compositions. The invention also provides intermediates useful for the preparation of the compounds of Formula I.
    Type: Grant
    Filed: July 9, 1998
    Date of Patent: July 6, 1999
    Assignee: Eli Lilly and Company
    Inventors: Sandra Ann Filla, Kirk W. Johnson, Lee A. Phebus, John Mehnert Schaus
  • Patent number: 5919792
    Abstract: This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as vitronectin receptor antagonists. The vitronectin receptor antagonist compounds of the present invention are .alpha.v.beta.3 antagonists, .alpha.v.beta.5 antagonists or dual .alpha.v.beta.3/.alpha.v.beta.5 antagonists useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation and tumor growth.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: July 6, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman, William F. Hoffman, Nathan C. Ihle
  • Patent number: 5863919
    Abstract: A lock unimolecular micelle includes at least one engineered acceptor specifically binding a ligand (or specifically a "key" unimolecular micelle) thereto. A key unimolecular micelle comprises a core molecule and a plurality of branches extending therefrom, at least one of the branches including a shank portion extending therefrom having a terminal moiety at an end thereof for binding to a complimentary acceptor of a lock unimolecular micelle. Together, the lock and key micelles form a unit, either irreversibly or reversibly bound wherein the lock micelles is a soluble receptor engineered to specifically bind to the specifically engineered key micelle.
    Type: Grant
    Filed: August 28, 1996
    Date of Patent: January 26, 1999
    Assignee: University of South Florida
    Inventors: George R. Newkome, Charles N. Moorefield, Gregory Baker
  • Patent number: 5760246
    Abstract: Novel compounds are provided which are inhibitors of MTP and thus are useful for lowering serum lipids and treating atherosclerosis and related diseases, and have the structure ##STR1## including pharmaceutically acceptable salts thereof or prodrug esters thereof, wherein q is 0, 1 or 2;R.sup.x is H, alkyl, aryl or halogen;A is(1) a bond;(2) --O--; or(3) ##STR2## B is: ##STR3## and wherein L.sup.2, L.sup.1, R.sup.1, R.sup.2, R.sup.3, R.sup.3', R.sup.3a, R.sup.3b, R.sup.4, R.sup.4', R.sup.5, X, ##STR4## are as defined herein.
    Type: Grant
    Filed: December 17, 1996
    Date of Patent: June 2, 1998
    Inventors: Scott A. Biller, John K. Dickson, R. Michael Lawrence, David R. Magnin, Michael A. Poss, Jeffrey A. Robl, William A. Slusarchyk, Richard B. Sulsky, Joseph A. Tino
  • Patent number: 5700938
    Abstract: The present invention provides an industrially advantageous process for preparing a 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo?4,5-b!pyridine derivative represented by the following formula (II) which is a precursor of an antagonist against an angiotensin II receptor useful as an antihypertensive drug, a biphenyl derivative which is a precursor of the substituent of the pyridine derivative, a process for the preparation thereof, and an intermediate useful for the preparation of the biphenyl derivative: ##STR1## The 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo?4,5-b!pyridine derivative can be prepared in a high yield according to the present invention from a 2-amino-5-halogeno-3-nitropyridine derivative through amidation, N-alkylation and reductive cyclization. The halogen atom introduced at the 5-position as a protective group against nitration can be eliminated simultaneously in the step which is conducted thereafter. Thus, this process is industrially advantageous.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 23, 1997
    Assignees: Eisai Co., Ltd., Eisai Chemical Co., Ltd.
    Inventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
  • Patent number: 5652251
    Abstract: The present invention relates to the new use of 6-amino-5-nitro- and -5-cyano-1,4-dihydropyridines of the general formula (I) ##STR1## in which A, D and R.sup.1 -R.sup.4 have the meaning given in the description, new 6-acylamino-dihydropyridines, processes for their preparation and their use as medicaments as selective potassium channel modulators, in particular for treatment of the central nervous system.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: July 29, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Urbahns, Siegfried Goldmann, Hans-Georg Heine, Bodo Junge, Rudolf Schohe-Loop, Henning Sommermeyer, Thomas Glaser, Reilinde Wittka, Jean-Marie-Viktor De Vry
  • Patent number: 5610304
    Abstract: Sulfonamide compounds of formula (I) or a pharmacologically acceptable salt thereof: ##STR1## exhibit excellent antitumor activity and low toxicity.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: March 11, 1997
    Assignee: Eisai Co., Ltd.
    Inventors: Hiroshi Yoshino, Norihiro Ueda, Hiroyuki Sugumi, Jun Niijima, Yoshihiko Kotake, Toshimi Okada, Nozomu Koyanagi, Tatsuo Watanabe, Makoto Asada, Kentaro Yoshimatsu, Atsumi Iijima, Takeshi Nagasu, Kappei Tsukahara, Kyosuke Kitoh
  • Patent number: 5583229
    Abstract: The present invention provides an industrially advantageous process for preparing a 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo[4,5-b]pyridine derivative represented by the following formula (II) which is a precursor of an antagonist against an angiotensin II receptor useful as an antihypertensive drug, a biphenyl derivative which is a precursor of the substituent of the pyridine derivative, a process for the preparation thereof, and an intermediate useful for the preparation of the biphenyl derivative: ##STR1##
    Type: Grant
    Filed: August 5, 1994
    Date of Patent: December 10, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
  • Patent number: 5559236
    Abstract: The present invention provides an industrially advantageous process for preparing a 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo[4,5-b]pyridine derivative represented by the following formula (II) which is a precursor of an antagonist against an angiotensin II receptor useful as an antihypertensive drug, a biphenyl derivative which is a precursor of the substituent of the pyridine derivative, a process for the preparation thereof, and an intermediate useful for the preparation of the biphenyl derivative: ##STR1## The 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo-[4,5-b]pyridine derivative can be prepared in a high yield according to the present invention from a 2-amino-5-halogeno-3-nitropyridine derivative through amidation, N-alkylation and reductive cyclization. The halogen atom introduced at the 5-position as a protective group against nitration can be eliminated simultaneously in the step which is conducted thereafter. Thus, this process is industrially advantageous.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 24, 1996
    Assignees: Eisai Co., Ltd., Eisai Chemical Co., Ltd.
    Inventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
  • Patent number: 5534528
    Abstract: The present invention relates to therapeutically active azacyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrain and hippocampus of mammals and especially in the treatment of Alzheimer's disease, severe painful conditions and glaucoma.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 9, 1996
    Assignee: Novo Nordisk A/S
    Inventors: Per Sauerberg, Preben H. Olesen
  • Patent number: 5532245
    Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, straight or branched chain alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2## wherein R.sub.9 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, mono- or dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano, carboxyl, chloro, bromo, fluoro or iodo; n is an integer from 0 to 6; R.sub.3 and R.sub.4, independent from each other, are hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, perfluoroalkyl, hydroxyalkyl, alkoxyalkyl, fluoro, or, when taken together, form a spirocyclic ring; R.sub.5 and R.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 2, 1996
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane, Bradford H. Hirth
  • Patent number: 5484930
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein each of R and R.sub.1 is a lower alkyl group having from 1 to 4 carbon atoms, which are useful as intermediates to make chiral ethyl (5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazin-7-yl)carbamate.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: January 16, 1996
    Assignee: Warner-Lambert Company
    Inventors: Om P. Goel, Sham S. Nikam
  • Patent number: 5470864
    Abstract: Compounds of the general formula: ##STR1## wherein m, X, Y, A, R.sub.2 and R.sub.3 are defined in the description.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: November 28, 1995
    Assignee: Adir et Compagnie
    Inventors: Muriel Duflos, Sylvie Robert-Piessard, Lucien Welin, Guillaume Le Baut, Daniel-Henri Caignard, Pierre Renard, Gerard Adam
  • Patent number: 5418245
    Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: May 23, 1995
    Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.
    Inventors: Alfred P. Spada, Paul E. Persons
  • Patent number: 5405856
    Abstract: There are described compounds of the formula ##STR1## where n is 0 or 1;X is O or NR.sub.2, R.sub.2 being hydrogen, loweralkyl or loweralkylcarbonyl;R is hydrogen, loweralkyl, arylloweralkyl or loweralkylcarbonyl; andR.sub.1 is ##STR2## wherein R.sub.3 is hydrogen, loweralkyl or loweralkylcarbonyl;m is 1 or 2;eachR.sub.4 is independently hydrogen or loweralkyl; andY is hydrogen, halogen, loweralkyl, loweralkoxy or trifluoromethyl;which compounds are useful as topical antiinflammatory agents for the treatment of various dermatoses.
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: April 11, 1995
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Richard C. Effland, Joseph T. Klein, Gordon E. Olsen, Larry Davis, Russell R. L. Hamer, Brian S. Freed
  • Patent number: 5384425
    Abstract: Diurea derivatives are provided which can be represented by the following general formula and salts thereof: ##STR1## wherein, R.sup.1 and R.sup.2 are the same or different, and each represents C.sup.1 -10 alkyl group, a C.sup.3 -18 cycloalkyl group, or a lower alkyl group substituted by cycloalkyl radical(s);R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different, and each represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, hydrocarbyl aralkyl group, a pyridyl group, or an unsubstituted or substituted phenyl group, the substituents of the phenyl group being selected from a group consisting of lower alkyl radical, halogen atom-substituted lower alkyl radical, halogen atom, nitro radical, amino radical, mono- or di-lower alkylamino radical, lower acylamino radical, hydroxyl radical, lower alkoxy radical and lower acyloxy radical;X represents an oxygen atom or a sulfur atom, and n.sup.1 and n.sup.2 represent an integer of 1 to 6; and wherein at least one of R.sup.3 -R.sup.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: January 24, 1995
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Noriki Ito, Tomoyuki Yasunaga, Yuichi Iizumi, Tomio Araki
  • Patent number: 5374733
    Abstract: The present invention relates to a novel sweetening agent and to its method of preparation. This novel sweetening agent is a 2-substituted acyl derivative of L-aspartic or L-glutamic acid and has the general formula ##STR1## R being an acyl group of the formula ##STR2## and R' being a group of the formula ##STR3## R.sub.1, R.sub.2, R.sub.3, X, Y and Z being variously defined. This novel sweetening agent is essentially characterized by a high sweetening potency and a high stability compatible with the conditions of industrial use, and is applied especially for sweetening soft drinks.
    Type: Grant
    Filed: January 11, 1993
    Date of Patent: December 20, 1994
    Inventors: Claude Nofre, Jean-Marie Tinti
  • Patent number: 5371086
    Abstract: An aminopyridine compound represented by the formula: ##STR1## wherein n represents 0 or 1; Z represents .dbd.S, .dbd.NCN or .dbd.CHNO.sub.2 ; R.sub.1 represents --NR.sub.3 R.sub.4, --NHNR.sub.3 R.sub.4, --NHCONHR.sub.3 or --NHSO.sub.2 R.sub.3 ; R.sub.2 represents H, or substituted or unsubstituted alkyl; R.sub.3 and R.sub.4, which may be the same or different, represent H, substituted or unsubstituted alkyl, aryl, substituted or unsubstituted acyl or alkoxycarbonyl group; and R.sub.3 and R.sub.4 may form a heterocyclic ring together with a nitrogen atom to which R.sub.3 and R.sub.4 are bound, through another heteroatom or without it; an optical isomer thereof or art acid salt thereof, which is excellent in pharmacological effect and repressed in side effects as a drug for circulatory diseases.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: December 6, 1994
    Assignee: The Green Cross Corporation
    Inventors: Tadahiro Takemoto, Masahiro Eda, Mitsuyoshi Hihara, Takehiro Okada, Hiroshi Sakashita, Miyuki Eiraku, Chikara Fukaya, Norifumi Nakamura, Masanori Sugiura, Sumio Matzno, Maki Goda, Yasumi Uchida
  • Patent number: 5367081
    Abstract: 1,4-dihydropyridine derivatives and optically active 1,4-dihydropyridine derivatives with the following formula, having vasodilating activity based on calcium antagonism, and PAF antaognism, and methods of producing the same are disclosed: ##STR1## wherein (*) indicates a chiral center in the case of the optically active 1,4-dihydropyridine derivatives.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: November 22, 1994
    Assignee: Fujirebio Inc.
    Inventors: Hiroshi Ikawa, Akiyoshi Kadoiri, Yasuko Konagai, Tetsuaki Yamaura, Noriko Kase
  • Patent number: 5348967
    Abstract: A diaminotrifluoromethylpyridine derivative of the formula (I) or its salt: ##STR1## wherein X is --CW.sup.1 R.sup.1, --COCOR.sup.2, --CW.sup.1 NHCOR.sup.2, --C(.dbd.W.sup.1)W.sup.2 R.sup.3 or --CW.sup.1 N(R.sup.4)R.sup.5, and Y is alkyl, --CW.sup.3 R.sup.6, --COCOR.sup.7, --NHCOR.sup.7, --C(.dbd.W.sup.3)W.sup.4 R.sup.8, --(NH).sub.m SO.sub.2 R.sup.9, --(NH).sub.m SO.sub.2 OR.sup.10 or --(NH).sub.m SO.sub.2 N(R.sup.11)R.sup.12, as defined herein.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: September 20, 1994
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Hideo Sugi, Itaru Shigehara, Shinji Odawara, Syuichi Yotsuya, Hirohiko Kimura, Kazuhiro Yamamoto
  • Patent number: 5334722
    Abstract: Fungicidal compounds of formula (I): ##STR1## in which X and Y are independently O or S, and A and R.sup.1 to R.sup.4 have various specified values.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: August 2, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Patrick J. Crowley, Alasdair T. Glen, Rosamund A. Spence, Kevin R. Lawson
  • Patent number: 5321137
    Abstract: The invention relates to a novel process for the preparation of imidazopyridines of formula I: ##STR1## in which R is an alkyl having 1-6 C atoms, characterized in that 3,4-diamino-2-chloropyridine (II) is reacted with an acid anhydride of the formula RCO--O--COR 40 (III), in which R is as defined and R' is R or can be another aliphatic or aromatic radical, to give a 4-amino-2-chloro-3-R-CO-aminopyridine (IV), this is converted with 4'-bromomethyl-2-cyanobiphenyl (V), in the presence of an alkali metal alcoholate in an inert solvent, to a 4-amino-2-chloro-3-R-CO-[N-(2'-cyano-biphenyl-4-ylmethyl)-amino]pyridine (VI) and this is treated with a strong acid, a 2-R-4-chloro-3-(2'-cyano-biphenyl-4-ylmethyl)-3H-imidazo[4,5-c]pyridine (VII) being formed as an intermediate.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: June 14, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Werner Mederski, Heinz-Hermann Bokel
  • Patent number: 5317021
    Abstract: Amino acid compounds of the formula: ##STR1## wherein the various symbols are as hereinafter described, which have inhibiting effect on enkephalinase.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: May 31, 1994
    Assignee: ONO Pharmaceutical Co., Ltd.
    Inventors: Masanori Kawamura, Yoshinobu Arai, Hideki Aishita
  • Patent number: 5238908
    Abstract: This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure ##STR1## wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R.sup.1, R.sup.2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: August 24, 1993
    Assignee: Rohm and Haas Company
    Inventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
  • Patent number: 5229403
    Abstract: A diaminotrifluoromethylpyridine derivative of the formula (I) or its salt: ##STR1## wherein X is --CW.sup.1 R.sup.1, --COCOR.sup.2, --CW.sup.1 NHCOR.sup.2, --C(.dbd.W.sup.1 (W.sup.2 W.sup.3 or --CW.sup.1 N(R.sup.4)R.sup.5, and Y is alkyl, --CW.sup.3 R.sup.6, --COCOR.sup.7, --NHCOR.sup.7, --C(.dbd.W.sup.3)W.sup.4 R.sup.8, --(NH).sub.m SO.sub.2 R.sup.9, --(NH).sub.m SO.sub.2 OR.sup.10 or --(NH).sub.m SO.sub.2 N R.sup.11)R.sup.12, wherein each of R.sup.1, R.sup.6 and R.sup.9, which are independent from one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted, each of R.sup.2 and R.sup.7, which are independent from each other, is alkyl which may be substituted, alkoxy which may be substituted, phenyl which may be substituted or phenoxy which may be substituted, each of R.sup.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: July 20, 1993
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Hideo Sugi, Itaru Shigehara, Shinji Odawara, Syuichi Yotsuya, Hirohiko Kimura, Kazuhiro Yamamoto
  • Patent number: 5227492
    Abstract: Diurea derivatives are provided which can be represented by the following general formula and salts thereof: ##STR1## Illustrative derivatives include 1,3-bis[[1-cycloheptyl-3-(3-pyridyl)ureido]-methyl]benzene, 1,3-bis[[1-cycloheptyl-3-(2-pyridyl)ureido]-methyl]benzene, and 1,3-bis[[1-cycloheptyl-3-(4-pyridyl)ureido]-methyl]benzene.The above compounds inhibit acyl-coenzyme A cholesterol acyltransferase (ACAT enzyme), and thereby control the accumulation of cholesterol ester to the smooth muscle of arterial wall in the blood vessel.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: July 13, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Noriki Ito, Tomoyuki Yasunaga, Yuichi Iizumi, Tomio Araki
  • Patent number: 5221682
    Abstract: There are described compounds of the formula ##STR1## where n is 0 or 1;X is O or NR.sub.2, R.sub.2 being hydrogen, loweralkyl or loweralkylcarbonyl;R is hydrogen, loweralkyl, arylloweralkyl or loweralkylcarbonyl; andR.sub.1 is ##STR2## wherein R.sub.3 is hydrogen, loweralkyl or loweralkylcarbonyl; m is 1 or 2; each R.sub.4 is independently hydrogen or loweralkyl; and Y is hydrogen, halogen, loweralkyl, loweralkoxy or trifluoromethyl;which compounds are useful as topical antiinflammatory agents for the treatment of various dematoses.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: June 22, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Richard C. Effland, Joseph T. Klein, Gordon E. Olsen, Larry Davis, Russell R. L. Hamer, Brian S. Freed
  • Patent number: 5217982
    Abstract: This invention relates to compounds which are derivatives of cyclopentane which are useful as antihypertensive agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: June 8, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Cynthia A. Fink, Alfred P. Spada
  • Patent number: 5212185
    Abstract: Compounds characterized generally as piperidinyl-terminated alkylamino ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; wherein X is selected from oxygen atom and methylene; wherein B is selected from a piperidinyl group, an isoindolyl group and an azabicyclononyl group; wherein R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; wherein R.sub.2 is phenylmethyl; wherein each of R.sub.3 and R.sub.5 is hydrido; wherein R.sub.4 is selected from ##STR2## wherein V is selected from hydrido and methyl; wherein R.sub.6 is cyclohexylmethyl; wherein R.sub.7 is selected from isobutyl, cyclopropyl and cyclopropylmethyl; wherein q is a number selected from zero through three, inclusive; and wherein n is a number selected from zero through three, inclusive; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: May 18, 1993
    Assignee: G. D. Searle & Co.
    Inventor: Gunnar J. Hanson
  • Patent number: 5204357
    Abstract: The invention relates to compounds of the formula I ##STR1## in which A represents a substituted thio-, sulfinyl- or sulfonyl-alkanoyl radical or a four- to eleven-membered heterocycle, B is an amino acid residue, R.sup.1 denotes hydrogen (substituted) alkyl, (substituted)cycloalkyl or aryl, R.sup.2 represents hydrogen, (substituted)alkyl or aryl, R.sup.3 denotes a radical of the formula --(CH.sub.2).sub.q --(X).sub.r --(CH.sub.2).sub.s --R.sup.6 with X denoting CF.sub.2, CO or CHR.sup.8, R.sup.6 denoting a (substituted)heteroaromatic, R.sup.8 denoting alkyl, alkoxy, alkylthio, alkylamino, hydroxyl, azide or halogen, q and s denoting 1 to 4, and r denoting 0 or 1, and R.sup.9 is hydrogen, (substituted)alkyl, alkanoyl, cycloalkanoyl, (substituted) aroyl or (substituted)aryl, and to the salts thereof. In addition, processes for the preparation of these compounds, and the use thereof as renin inhibitors are described.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: April 20, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
  • Patent number: 5177089
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: January 5, 1993
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5095017
    Abstract: 1,2-dihydropyrido[3,4-b]pyrazines are provided which possess antimitotic activity. The compounds have the structure: ##STR1## wherein R is a lower alkyl group and OR.sub.1 is a member selected from the group consisting of aryl-alkyl ethers having from seven to about 20 carbon atoms, alkyl carbamates having from one to about 12 carbon atoms, the alkyl portion of which may be substituted with a halogen atom, e.g., chlorine, fluorine, bromine or iodine; aryl-alkyl carbamates having from about seven to about 20 carbon atoms, aryl carbamates having from about six to about 20 carbon atoms, aryl-alkyl esters having from about 7 to about 20 carbon atoms, aryl esters having from about six to about 20 carbon atoms, alkylthiocarbamates having from about one to about 12 carbon atoms, aryl-alkylthiocarbamates having from about seven to about 20 carbon atoms, and arylthiocarbamates having from about six to about 20 carbon atoms.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: March 10, 1992
    Assignee: Southern Research Institute
    Inventor: Carroll G. Temple, Jr.
  • Patent number: 5057528
    Abstract: A series of novel aryloxyalkylamino - and arylaminoalkylamino-pyridine and imidazole compounds have been prepared, including their pharmaceutically acceptable salt, wherein the aryl moiety is further substituted by a sulphamoyl or sulphonylamino group or by a ureido or acylamino group located at the para-position of the ring with respect to the aforesaid alkylamino side chain. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Methods for preparing all these compounds from know starting materials are provided.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: October 15, 1991
    Assignee: Pfizer Inc.
    Inventors: Peter E. Cross, Roger P. Dickinson
  • Patent number: 5055582
    Abstract: This invention relates to a process for preparing useful thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)thioxomethyl]hydrazono]ethyl]-1.alpha. ,4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha.,7a.alpha.-4.alpha.,7.alpha.-meth ano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: October 8, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 4996218
    Abstract: Compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof, which have .beta..sub.2 -adrenoreceptor stimulant activity. They may be used in the treatment of diseases associated with reversible airways obstruction, such as asthma and chronic bronchitis.In preferred embodiments, Q represents a chlorine atom or a trifluoromethyl group, X represents a C.sub.3-4 alkylene chain, Y a C.sub.1-5 alkylene chain, R, R.sup.1 and R.sup.2 are each preferably a hydrogen atom or a methyl group and Het represents a pyrimidinyl pyrazinyl, triazinyl, thiazolyl, quinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl or pyridyl group.
    Type: Grant
    Filed: August 10, 1988
    Date of Patent: February 26, 1991
    Assignee: Glaxo Group Limited
    Inventor: Lawrence H. C. Lunts
  • Patent number: 4962113
    Abstract: Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group;R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group;l is 0 or 1;R.sup.5 is a phenylene group or an alkylene group which may be substituted;R.sup.11 is an alkyl group or aryl group;X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3;U is a group of the formula: ##STR4## wherein R.sup.
    Type: Grant
    Filed: July 26, 1988
    Date of Patent: October 9, 1990
    Assignee: Takeda Chemical Industries, Ltd
    Inventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
  • Patent number: RE37087
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I in which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: March 6, 2001
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: RE34137
    Abstract: The present invention relates to a method of manufacturing aromatic urethane, an aromatic mononitro-compound, an aromatic primary amine, and carbon monoxide being reacted using a catalyst containing a platinum group metal-containing compound as a major constituent to prepare N,N'-di-substituted urea. The resultant N,N'-di-substituted urea is reacted with a hydroxyl group-containing organic compound to prepare an aromatic primary amine and aromatic urethane, and the aromatic primary amine is separated to obtain aromatic urethane.
    Type: Grant
    Filed: October 12, 1989
    Date of Patent: December 1, 1992
    Assignee: NKK Corporation
    Inventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Itaru Sakai, Osamu Tajima