One Double Bond Between The Ring Members Of The Oxazole Ring Patents (Class 548/237)
  • Patent number: 5559133
    Abstract: A compound represented by formula I, Ar.sub.1 --O--M--O--Ar.sub.2, wherein Ar.sub.1 and Ar.sub.2 are independently substituted phenyl or substituted pyridinyl, the substituents on said phenyl or pyridinyl being independently selected from one, two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10) alkoxy, halogen, carbamyl, (C.sub.1 -C.sub.10) alkoxycarbonyl, oxazoyl, and (C.sub.1 -C.sub.10) alkyl substituted by halogen, (C.sub.1 -C.sub.10) alkoxy, hydroxy, or (C.sub.1 -C.sub.10) alkoxycarbonyl; ##STR1## O is oxygen; R' is (C.sub.1 -C.sub.3 alkyl or H; A is oxygen or sulfur; Q is selected from hydrogen, halogen, nitro, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 C.sub.6) perhaloalkyl, (C.sub.1 -C.sub.6) alkylthio (C.sub.1 -C.sub.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: September 24, 1996
    Assignee: Schering Corporation
    Inventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Richard W. Versace, Anil K. Saksena, Patrick A. Pinto
  • Patent number: 5557006
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth fire disclosed.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: September 17, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5554757
    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 10, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
  • Patent number: 5550247
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harner, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5527921
    Abstract: Peroxycarboxylic ester photoinitiators derived from aromatic nitrogen containing heterocyclic carboxylic acids are described. The heterocyclic aromatic ring may contain additional nitrogen atoms, be fused with another aromatic ring system, be substituted with an additional peroxycarboxylic ester group and/or be substituted with an electron group having a Hammett sigma value greater than 0.1. The peroxycarboxylic ester photoinitiators have been found to be useful in photopolymerizable compositions and photosensitive elements.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: June 18, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Jeanne E. Haubrich
  • Patent number: 5519062
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: May 21, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5510319
    Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: April 23, 1996
    Assignee: American Cyanamid Company
    Inventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
  • Patent number: 5506247
    Abstract: The present invention is directed to compounds which suppress immune responses and/or selectively inhibit complement. These compounds contain an aromatic ring and are substituted dihydrobenzofurans, spirobenzofuran-2(3H)-cycloalkanes, and their open chain intermediates. The compounds of the present invention, and the pharmaceutically acceptable salts thereof, interrupt the proteolytic processing of C5 to bioactive components, exhibit immunosuppressive activities, and have therapeutic utility in the amelioration of disease and disorders mediated by complement and/or immune activity.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: April 9, 1996
    Assignees: T Cell Sciences, Inc., The University of Mississippi
    Inventors: Robert D. Sindelar, Barton J. Bradbury, Teodoro S. Kaufman, Stephen H. Ip, Henry C. Marsh, Jr., Chew Lee
  • Patent number: 5491201
    Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: February 13, 1996
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5488063
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: January 30, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harmer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5478855
    Abstract: 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline. This compound is useful as miticide.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: December 26, 1995
    Assignee: Yashima Chemical Industry Co., Ltd.
    Inventors: Junji Suzuki, Yasuo Kikuchi, Kazuya Toda, Yoshiaki Itoh, Tatsuya Ishida, Tatsufumi Ikeda, Yokichi Tsukidate
  • Patent number: 5411979
    Abstract: An oxazoline derivative having the formula: ##STR1## which is useful for control of insects, mites and/or ticks. R.sub.1 is H, halo, (halo) alkyl, alkoxy alkyl, (halo) alkoxy alkyl, (halo) alkyl thio, (halo) cycloalkyl, alkylcycloalkyl, (halo) cycloalkoxy, alkylcycloalkoxy or (R.sup.5) phenyl, phenoxyl or phenylthio or (R.sup.5) pyridyl, pyridoxyl or pyridylthio, R.sub.3 is H or methyl, R.sub.4 is phenyl or mono or disubstituted phenyl.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: May 2, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Taro Hirose, Hirosi Kisida, Shigeru Saito, Hiroaki Fujimoto
  • Patent number: 5376683
    Abstract: The invention relates to .DELTA..sup.8 - and .DELTA..sup.9 -prostaglandin derivatives of formula I, ##STR1## in which means the radicals or , R.sup.1 means ##STR2## COOR.sup.4 or CONHR.sup.5, R.sup.2 and R.sup.3 respectively mean a hydrogen atom or a hydroxy group, and the OH group can be respectively in alpha- or beta- position,means a CH.sub.2 group, an O or S atom,W means hydrogen, --OR.sup.6, halogen, --CN--, --NO.sub.2, trifluoromethyl or COOR.sup.6, and if R.sup.4 means hydrogen, their salts with physiologically compatible bases, the alpha-, beta- or gamma- cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes, process for their production and their pharmaceutical use.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: December 27, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Ulrich Klar, Hartmut Rehwinkel, Helmut Vorbruggen, Karl H. Thierauch, Claus S. Sturzebecher
  • Patent number: 5374654
    Abstract: The invention relates to carbacyclin derivatives of Formula I ##STR1## wherein the various substituents are defined herein, including, inter alia,if R.sub.2 is a hydrogen atom, their salts with physiologically compatible bases, their cyclodextrin clathrates, and their use as medicinal agents.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
  • Patent number: 5366986
    Abstract: The present invention is directed to compounds which suppress immune responses and/or selectively inhibit complement. These compounds contain an aromatic ring and are substituted dihydrobenzofurans, spirobenzofuran-2(3H)-cycloalkanes, and their open chain intermediates. The compounds of the present invention, and the phamaceutically acceptable salts thereof, interrupt the proteolytic processing of C5 to bioactive components, exhibit immunosuppressive activites, and have therapeutic utility in the amelioration of disease and disorders mediated by complement and/or immune activity.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: November 22, 1994
    Assignees: T Cell Sciences, Inc., The University of Mississippi
    Inventors: Robert D. Sindelar, Barton J. Bradbury, Teodoro S. Kaufman, Stephen H. Ip, Henry C. Marsh, Jr., Chew Lee
  • Patent number: 5360577
    Abstract: Optically active compounds of the general formula ##STR1## wherein n stands for the number 0 or 1; R.sup.3 denotes a group R.sup.4 or a group of the general formula ##STR2## A.sup.1, A.sup.2 and A.sup.3 each independently represent 1,4-phenylene, which is unsubstituted or mono- or multiply-substituted with halogen, cyano and/or methyl and in which, where it is unsubstituted, 1 or 2 CH groups is/are optionally replaced by nitrogen, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, bycyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1 and Z.sup.4 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --; Z.sup.2 and Z.sup.3 each independently denote a single covalent bond, --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --C.tbd.C--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans form of --CH.dbd.CH--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: November 1, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Stephen Kelly
  • Patent number: 5359126
    Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventor: Charles A. McCombs
  • Patent number: 5354905
    Abstract: An N-alkoxymethyl benzamide derivative represented by Formula (I); ##STR1## (In the formula, reference X indicates a halogen atom, references Y.sub.1 and Y.sub.2 indicate hydrogen atoms or halogen atoms, and may be identical or different, and reference R indicates a lower alkyl group.) and a manufacturing method for this N-alkoxymethyl benzamide derivative in which a substituted benzamide and an .alpha.-haloacetal are reacted. Furthermore, a manufacturing method for benzamide derivatives in which the N-alkoxymethyl benzamide derivative represented by Formula (I) above and benzene or a derivative thereof are reacted, and a benzamide derivative is produced. The N-alkoxymethyl benzamide derivative of the present invention is a novel compound, and possesses utility as an intermediate in the manufacturing of oxazoline derivatives which possess insecticidal and anti-mite activity, and as a starting material for the synthesis of various organic compounds and the like.
    Type: Grant
    Filed: October 20, 1993
    Date of Patent: October 11, 1994
    Assignee: Yashima Chemical Industry Co., Ltd.
    Inventors: Yoshihiro Sato, Akihiro Koiso, Tohru Asada, Yasuhisa Miura, Yasuo Kikuchi, Yasuaki Hariya
  • Patent number: 5352832
    Abstract: The present invention comprises a process for the asymmetric synthesis of florfenicol, thiamphenicol or chloramphenicol, from a derivative of trans-cinnamic acid, comprising the steps:(a) converting the acid to an acid chloride using a chlorinating agent, and reducing the acid chloride to a trans allylic alcohol with a reducing agent;(b) asymmetrically epoxidizing the allylic alcohol of step (a), by reacting with t-butylhydroperoxide in the presence of a chiral epoxidation catalyst prepared from titanium (IV) isopropoxide and L-diisopropyltartaric acid, to form a chiral epoxide;(c) regioselectively opening the epoxide of step (b) by sequentially treating with sodium hydride, zinc chloride and dichloroacetonitrile to form an oxazoline;(d) stereoselective inversion/isomerization of the oxazoline of step (c) by sequentially treating with: (i) a lower alkylsulfonyl chloride and a tertiary amine base; (ii) sulfuric acid and water; (iii) an alkali metal hydroxide; to form an oxazoline;(e) optionally treating the ox
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: October 4, 1994
    Assignee: Schering Corporation
    Inventors: Guang-Zhong Wu, Wanda I. Tormos
  • Patent number: 5332835
    Abstract: Replacement with fluorine of the primary hydroxy group of 1-phenyl-2-amino-1,3-propanediol compounds wherein the secundary hydroxy group and the amino group have been suitably protected.The reaction is carried out with an inorganic fluoride in a polyglycol.New oxazoline compounds particularly useful in said-process.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: July 26, 1994
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino, Roberto Pagliarin
  • Patent number: 5314863
    Abstract: Compounds of the formula (I) ##STR1## and their use as antidotes against the phytotoxicity of many herbicides used on crops, without diminishing the effect of the herbicide against weeds.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: May 24, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz J. Loher, Wilfried Schwab, Klaus Bauer, Hermann Bieringer
  • Patent number: 5312826
    Abstract: Disclosed are a dicarboxylic acid compound represented by the formula (I): ##STR1## wherein R represents hydrogen atom, a lower alkyl group, phenyl group or hydroxyl group; R.sup.1 represents a straight or branched alkyl group having 1 to 10 carbon atoms or a lower alkyl group substituted by a group selected from aryl group, a sulfur- or nitrogen-containing heterocyclic monocyclic group and a cycloalkyl group having 4 to 8 carbon atoms; R.sup.2 represents a substituted or unsubstituted aryl group, a cycloalkyl group having 4 to 8 carbon atoms or a sulfur-containing or nitrogen-containing heterocylcic group; X represents sulfur atom, oxygen atom or a substituted or unsubstituted imino group; Y.sup.1 represents imino group, oxygen atom or sulfur atom and Y.sup.2 represents nitrogen atom, or Y.sup.1 represents a vinylene group and Y.sup.2 represents a group: --CH.dbd.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: May 17, 1994
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Ken-ichi Nunami, Tameo Iwasaki, Kazuo Matsumoto, Koji Yano, Isao Yamaguchi
  • Patent number: 5292756
    Abstract: A series of non-peptide derivatives of the formula ##STR1## that are antagonists of the fibrinogen IIb/IIIa receptor and thus are platelet anti-aggregation compounds useful in the prevention and treatment of diseases caused by thrombus formation.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: March 8, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, Melissa S. Egbertson, Wasyl Halczenko, George D. Hartman
  • Patent number: 5281716
    Abstract: A method is provided for preparing oxazole intermediates of the structure ##STR1## (wherein R is alkyl) wherein an oxazoline of the structure ##STR2## is oxidized employing an oxidizing agent such as cupric bromide, a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and a non-hydride donor amine base such as hexamethylenetetraamine (HMTA). The resulting oxazole may be hydrolyzed to the final anti-thrombotic - anti-vasospastic compounds.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: January 25, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Richard H. Mueller, Janak Singh
  • Patent number: 5276035
    Abstract: A disubstituted piperazine compound having the formula ##STR1## wherein R.sup.1 is halogen, methoxy, C.sub.1-6 -alkyl or trifluoromethyl, and R.sup.2 is methyl or substituted C.sub.1-8 -alkyl, C.sub.3-8 -alkenyl or C.sub.3-8 -cycloalkyl, where substituents may be hydroxy-, keto- or oximino-groups in any position leading to a stable tertiary amine; or R.sup.2 is a straight or branched C.sub.1-8 -alkyl or C.sub.3-8 -alkenyl, which in any position may be substituted as above, but is terminally substituted with one of the following groups: cyano, optionally C.sub.1-4 -alkoxy-substituted C.sub.1-4 -alkoxy, dimethoxy, optiontionally substituted phenoxy, phosphonic acid, thienyl, furyl, oxazoline, isoxazole, oxadiazole, where the optional substitution is represented by C.sub.1-6 -alkyl or phenyl, provided that when cyano is the only substituent in R.sup.2, R.sup.2 must contain at least four carbon atoms, and pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: January 4, 1994
    Assignee: Novo Nordisk A/S
    Inventors: Rolf Hohlweg, Erling Guddal, Erik B. Nielsen
  • Patent number: 5276037
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: January 4, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5276192
    Abstract: A process for preparing phenoxyethanamines from phenols and 2-oxazolines in quantitative yields was discovered. Phosphoric acid hydrolyzes the amide intermediate from the phenol/2-oxazoline reaction without cleaving the amide at the ether linkage and without undesired aromatic ring substitution. Thus, yield to the desired phenoxyethanamines is often 98% or better, requiring no subsequent purification. In contrast, sulfuric and hydrochloric acids give these undesired side reactions. Phenoxyethanamines are useful in thermosetting resins, pharmaceuticals and as surfactants.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: January 4, 1994
    Assignee: Texaco Chemical Company
    Inventors: Wei-Yang Su, George P. Speranza
  • Patent number: 5250546
    Abstract: Amino-alcohol derivatives of the formula, ##STR1## where R.sub.1 is a straight or branched alkyl group having 3 to 8 carbon atoms, R.sub.2 and R.sub.3 are each a lower alkyl group, or R.sub.2 and R.sub.3 form a 5- to 7-membered ring together with the adjacent nitrogen atom which may have an oxygen atom attached thereto, R.sub.4 is a hydrogen atom or a lower alkyl group, R.sub.5 is a hydrogen atom or a lower alkyl group, X is a hydrogen or halogen atom or a lower alkyl or lower alkoxy group, and n is an integer of 2 or 3, and acid addition salts thereof, are effectively useful as medicines and agricultural chemicals. Processes are also disclosed for preparing such compounds.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: October 5, 1993
    Assignee: Nippon Chemiphar Co., Ltd.
    Inventors: Mitsuo Masaki, Haruhiko Shinozaki, Masaru Satoh, Naoya Moritoh, Koichi Hashimoto, Toshiro Kamishiro
  • Patent number: 5244596
    Abstract: A mesomorphic compound represented by the following formula [I]: ##STR1## wherein R.sub.1 and R.sub.2 independently denote an alkyl group having 1-16 carbon atoms capable of having a substituent; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 independently denote a single bond ##STR2## A.sub.1, A.sub.2 and A.sub.3 independently denote ##STR3## X.sub.5 and X.sub.6 independently denote hydrogen atom, fluorine, chlorine, bromine, CH.sub.3, CN or CF.sub.3 ; n.sub.1 and n.sub.2 are 0 or 1, with provisos that (1) X.sub.2 cannot be a single bond when n.sub.1 is 0, (2) X.sub.3 cannot be a single bond when N.sub.2 is 1 and (3) at least one of X.sub.2 and X.sub.3 denotes ##STR4## when both n.sub.1 and n.sub.2 is O and A.sub.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: September 14, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5243056
    Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6 C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with X1 has the above mentioned meanings; orX2 together with R4 is --(CH.sub.2).sub.m --CH.dbd.CH--; --(CH.sub.2).sub.m --CH.sub.2 --CH.sub.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: September 7, 1993
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino
  • Patent number: 5227494
    Abstract: A novel process for regioselectively preparing oxazoline compounds is disclosed. The process utilizes an amino alcohol, a cyano compound, a base and a dihydric alcohol solvent, a polyhydric alcohol solvent or mixtures thereof.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: July 13, 1993
    Assignee: Schering Corporation
    Inventors: Doris P. Schumacher, Jon E. Clark, Bruce L. Murphy
  • Patent number: 5217973
    Abstract: The present invention relates to the derivatives of formula: ##STR1## as well as to their addition salts and to their use in therapy, in particular for the treatment of cardiovascular diseases, especially for the treatment of hypertension, cardiac insufficiency and diseases of the arterial wall.
    Type: Grant
    Filed: August 7, 1991
    Date of Patent: June 8, 1993
    Assignee: Laboratoires UPSA
    Inventors: Nicole Bru-Magniez, Eric Nicolai, Jean-Marie Teulon
  • Patent number: 5210206
    Abstract: The present invention relates to a process for the preparation of a compound of the formula: ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, loweralkyl, loweralkoxy-substituted loweralkyl, lower alkenyl, lower alkynyl, cycloalkyl and cycloalkylalkyl; R.sub.2 is selected from the group consisting of hydrogen, loweralkyl, loweralkoxy-substituted loweralkyl, halogen and loweralkoxy; R.sub.3 is selected from hydrogen, loweralkyl, and halogen; R* and R** are independently selected from loweralkyl and P.sub.1 is hydrogen or an nitrogen-protecting group; or an acid addition salt thereof.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: May 11, 1993
    Assignee: Abbott Laboratories
    Inventors: Howard E. Morton, Biswanath De, Daniel J. Kerkman
  • Patent number: 5201934
    Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, or one of the groups stated for R.sup.1 ;R.sup.3 and R.sup.4 are nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y.dbd.O,S);R.sup.6 is hydrogen, cycloalkyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkenyl or phenyl,phthalimido, tetrahydrophthalimido, succinimido, maleimido, benzotriazolyl ora group --N.dbd.CR.sup.7 R.sup.8, whereR.sup.7 and R.sup.8 are hydrogen or alkyl, and R.sup.8 may also be cycloalkyl, phenyl, or R.sup.7 and R.sup.8 together form a 4- to 7-membered alkylene chain;and if R.sup.
    Type: Grant
    Filed: October 3, 1990
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
  • Patent number: 5196544
    Abstract: This invention concerns polyiminoethers of general formula (I) in which A is an aliphatic, aromatic or araliphatic group containing 4 to 40 carbon atoms and n free valencies at various carbon atoms, x may assume values of 0 to 40, n has a value of 2, 3 or 4, Z is either a direct bond or the group CR.sup.5 R.sup.6, the substituents R.sup.1 to R.sup.6 independently of one another are H, alkyl or aryl containing up 8 carbon atoms, the substituent R.sup.7 is hydrogen, methyl or ethyl and Q is a phenylene group, which may be substituted by one or two methyl groups, or the group --CHR--M--, where R is selected from the group consisting of H, alkyl or alkenyl and M is selected from the group consisting of alkylene, alkenylene, arylene and alkarylene, and the parts R and M of the molecule independently of one another contain 0 to 12 carbon atoms and, in addition, may be substituted by a C.sub.1-3 alkoxy group. These compounds are made from polyisocyanates of formula A(NCO).sub.
    Type: Grant
    Filed: January 16, 1992
    Date of Patent: March 23, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Brigitte Hase, Horst-Juergen Krause, William Fristad
  • Patent number: 5190964
    Abstract: 5-fluorocarbacyclin derivatives of the Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH orA is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR2## in which the OH group can be in the .alpha.-- or .beta.-position, D is ##STR3## a C.sub.1-10 -aliphatic group (e.g., alkyl or alkenyl) which optionally can be substituted by fluorine atoms,n is 1, 2 or 3,E is a direct bond, --C.tbd.C-- or --CR.sub.6 .tbd.CR.sub.7 -- in which R.sub.6 represents a hydrogen atom or an alkyl group with 1-5 atoms and R.sub.7 represents a hydrogen atom, a halogen atom or an alkyl group with 1-5 C atoms,R.sub.4 is alkyl, cycloalkyl or optionally substituted aryl or a heterocyclic group,R.sub.5 is a free or functionally modified hydroxy groupand, when R.sub.2 is a hydrogen atom, its salts with physiologically compatible bases,have valuable pharmacological properties.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: March 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Martin Haberey, Claus-Steffen Sturzebecher, Michael-Harold Town
  • Patent number: 5182404
    Abstract: Novel biphenyl derivatives of the formula: ##STR1## wherein R.sup.1 is a substituted or unsubstituted aminocarbonyl group, aminothiocarbonyl group, a substituted or unsubstituted lower alkoxycarbonyl group, cyano group, or a group of the formula: ##STR2## one or two of R.sup.2 to R.sup.7 are hydrogen atom, and the remaining groups are the same or different and are each a lower alkoxy group, a phenyl-(lower)alkoxy group or hydroxy group, or the adjacent two groups thereof combine to form a lower alkylenedioxy group, and Alk.sup.1 is a lower alkylene group,or a pharmaceutically acceptable salt thereof, which are useful for the prophylaxis and treatment of hepatic diseases, and processes for preparing the same, and intermediates therefor.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: January 26, 1993
    Assignee: Tanabe Seiyake Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo, Yuzo Matsuoka, Mamoru Matsumoto, Masaki Sugiura
  • Patent number: 5169432
    Abstract: Substituted pyridines having at the 3 or 5 position a carbonyl oxy(thio)ester or a heterocyclocarbonyl and at the other a substituted alkyl group, herbicidal compositions and methods of use thereof.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: December 8, 1992
    Assignee: Monsanto Company
    Inventors: Susan M. Auinbauh, Len F. Lee, Karey A. Van Sant
  • Patent number: 5166361
    Abstract: This invention relates to novel methods for converting a diastereomeric mixture of S-protected derivatives of an orally active inhibitor of an angiotensin-converting enzyme (ACE) and its analogues into its separate optically resolved diastereomeric components. Specifically the invention relates to methods for the preparation of optically purified captopril and its analogs from racemic precursors. This resolution process is achieved through the fractional crystallization of S-protected derivatives of captopril and its precursors, which derivatives are useful for the reason that they are (1) easily prepared from novel precursors, (2) resolvable to their optically purified stereoisomeric species and (3) convertible to non-derivatized stereoisomeric species which correspond to the pharmacologically active inhibitor and its analogues. Novel methods for preparing the derivatives and their precursors are also noted herein. In addition, the novel derivatives and their precursors are also described herein.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: November 24, 1992
    Assignee: Sepracor, Inc.
    Inventor: Charles M. Zepp
  • Patent number: 5166153
    Abstract: Novel N-acylated 2-[4-(halophenoxy)-phenoxy]-ethylcarbamic acid esters of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.5 alkenyl,R.sub.2 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, --CO--R.sub.7 or --NR.sub.8 R.sub.9,R.sub.3 and R.sub.4 independently of one another are hydrogen or methyl,R.sub.5 is chlorine or fluorine,R.sub.6 is either the same substituent as R.sub.5 or is hydrogen,R.sub.7 is C.sub.1 -C.sub.8 alkoxy or --NR.sub.10 R.sub.11,R.sub.8 is C.sub.1 -C.sub.4 alkyl,R.sub.9 is C.sub.1 -C.sub.4 alkyl orR.sub.8 and R.sub.9 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.3 --,R.sub.10 is hydrogen or C.sub.1 -C.sub.4 alkyl andR.sub.11 is hydrogen or C.sub.1 -C.sub.4 alkyl, benzyl, phenyl, or phenyl substituted by halogen or by methyl, orR.sub.10 and R.sub.11 together form a C.sub.4 -C.sub.6 alkylene chain which may be interrupted by oxygen, sulfur or --NCH.sub.
    Type: Grant
    Filed: April 24, 1990
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5164371
    Abstract: The invention provides a series of novel heterocyclic ketones of formula I ##STR1## and pharmaceutically acceptable base-addition salts thereof, in which the values of R.sup.4, L, A, X and Q have the meanings defined in the following specification. The compounds of formula I are inhibitors of human leukocytic elastase. The invention also provides pharmaceutical compositions containing a compound of formula I, or a pharmaceutically acceptable base-addition salt thereof, and processes and intermediates for the manufacture of compounds of formula I.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: November 17, 1992
    Assignee: ICI Americas Inc.
    Inventors: Philip D. Edwards, Joseph J. Lewis, Charles W. Perkins, Diane A. Trainor, Richard A. Wildonger
  • Patent number: 5162353
    Abstract: The invention relates to carbacyclin derivatives with general formula I: ##STR1## in which Y.sub.1 stands for the radical --CH.sub.2 --X--(CH.sub.2).sub.n --R.sub.1 or the radical ##STR2## n, 1 or 3, R.sub.1, the radical ##STR3## the radical ##STR4## R.sub.9 stands for the radical --(CH.sub.2).sub.m --R.sub.6 or the radical --(CH.sub.2).sub.m-o --[Z.sub.1 --(CH.sub.2).sub.m-p ].sub.x --[Z.sub.2 --(CH.sub.2).sub.m-q ].sub.y --R.sub.6,m=2-20,o, p, and q are less than or equal to 19,x, y=0, 1 or 2,Z.sub.1 stands for a cis--CH.dbd.CH group, a trans--CH.dbd.CH group of a --C.dbd.C group, and each of these groups must be separated at least by a methylene group from the C-9 carbon atom of the carbacyclin bicyclic compound,Z.sub.2 stands for oxygen, sulfur, an NH or an N methyl group,R.sub.6 stands for amino, methylamino, hydroxy, carboxy or mercapto,X an oxygen atom or a methylene group,Y.sub.2 hydrogen or fluorine,A a --CH.sub.2 --CH.sub.2, trans--CH.dbd.CH or --C.dbd.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
  • Patent number: 5159084
    Abstract: The present invention discloses novel optically active oxazoline compounds represented by the formula (I): ##STR1## wherein R.sup.1 represents an alkoxy group having not more than 20 carbon atoms and R.sup.2 represents a low grade alkyl group, as well as liquid crystal compositions containing said compound and a switching mode of high reponse speed using them. Furthermore, the invention discloses that the devices using said liquid crystal compositions can suitably be used in the opto-electronics field not only for display device but also as various electro-optic devices.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: October 27, 1992
    Assignee: Ricoh Company, Ltd.
    Inventor: Masayuki Shoshi
  • Patent number: 5153327
    Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasospastic disease have the structural formula ##STR1## wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or ##STR2## wherein Y is O, a single bond or vinyl, with the proviso that when n is O, if Z is ##STR3## then Y cannot be O, and when Z is --CH.dbd.CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=; R is CO.sub.2 H, CO.sub.2 lower alkyl, CH.sub.2 OH, CO.sub.2 alkali metal, CONHSOR.sup.3 m CONHR.sup.3a or --CH.sub.2 -5-tetrazolyl, X is O, S or NH; and where R.sup.1, R.sup.2, R.sup.3 and R.sup.3a are as defined herein.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: October 6, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Raj N. Misra, Philip M. Sher, Philip D. Stein, Steven E. Hall, David Floyd, Joel C. Barrish
  • Patent number: 5153328
    Abstract: Intermediates having the formula ##STR1## wherein R is --NO.sub.2, CH.sub.3 S--, CH.sub.3 SO--, or CH.sub.3 SO.sub.2 --, X.sub.1 is hydrogen, alkyl, haloalkyl, (substituted) phenyl or phenylalkyl and Y is F or --OSO.sub.2 R.sub.6 wherein R.sub.6 is methyl, trifluoromethyl, (substituted) phenyl naphthyl or pyridyl are disclosed.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: October 6, 1992
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino, Roberto Pagliarin
  • Patent number: 5141948
    Abstract: 2-Substituted phenyl-2-oxazoline derivatives or 2-substituted phenyl-2-thiazoline derivatives represented by the general formula (I) ##STR1## in which R.sub.1 and R.sub.2 may be same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a lower haloalkyl group or a lower haloalkoxy group, with a proviso that R.sub.1 and R.sub.2 do not simultaneously represent hydrogen atoms;R.sub.3 represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group;R.sub.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: August 25, 1992
    Assignee: Yashima Chemical Industrial Co., Ltd.
    Inventors: Satoshi Miyamoto, Junji Suzuki, Yasuo Kikuchi, Kazuya Toda, Yoshiaki Itoh, Tatsufumi Ikeda, Tatsuya Ishida, Tasuaki Hariya, Yokichi Tsukidate, Chiharu Morikawa
  • Patent number: 5141955
    Abstract: Anti-inflammatory benzylselanobenzamides made from anilines and benzylamines have the formula I ##STR1## are disclosed wherein R is hydrogen, methyl or ethyl;R.sup.1 and R.sup.2 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, amino, dimethylamino or nitro; andR.sup.3 and R.sup.4 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, or nitro and, taken together, represent methylenedioxy; andn is 0.1 or 2.
    Type: Grant
    Filed: November 8, 1990
    Date of Patent: August 25, 1992
    Assignee: A. Nattermann & Cie. GmbH
    Inventors: Michel Evers, Hartmut Fischer, Jurgen Biedermann, Rolf Terlinden, Sigurd Leyck
  • Patent number: 5130440
    Abstract: A process for the production of 2-alkyl- or alkenyl-2-oxazolines, in which the alkyl or alkenyl group may be a hydroxy-, dihydroxy- or hydroxy, C.sub.1 -C.sub.2 -alkoxy-substituted hydrocarbon radical containing at least 7 carbon atoms, produces the subject compounds in high yields when C.sub.8 -C.sub.22 fatty acids or esters thereof are reacted with 2-amino-ethanol or ethanolamides of these fatty acids in the presence of titanium or zirconium compounds corresponding to the formula M(OR.sup.2).sub.4 wherein M=Ti or Zr.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: July 14, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Horst-Juergen Krause, Peter Neumann
  • Patent number: 5128478
    Abstract: Optically active oxazoline-carboxylic acid derivatives of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkykl group which is substituted and has 1 to 20 carbon atoms, a cycloalkyl group, a cycloalkyl group which is substituted, a phenyl group, a phenyl group which is substituted, a vinyl group, a vinyl group which is substituted, an ethynyl group or an ethynyl group which is substituted;R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms or a benzyl group;R.sup.3 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group or a benzyl group,and a method for preparing the above compounds and derivatives thereof involving a reaction between an aldehyde and an isocyano-carboxylate in the presence of a catalyst mixture.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: July 7, 1992
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yoshihiko Ito, Tamio Hayashi
  • Patent number: 5124343
    Abstract: The invention relates to carbacyclins of general Formula I ##STR1## wherein R.sub.1 is the residue CH.sub.2 OH or ##STR2## with R.sub.2 meaning a hydrogen atom, an alkyl, cycloalkyl, aryl residue, a ##STR3## or heterocyclic residue, or R.sub.1 is the residue ##STR4## with R.sub.3 meaning an alkanoyl or alkanesulfonyl residue of respectively 1-10 carbon atoms or the residue R.sub.2, orR.sub.1 is the residue ##STR5## wherein m is the number 1 or 2, X is an oxygen atom or a CH.sub.2 -group,A is a trans--CH.dbd.CH- or --.tbd.C--group,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,n is the number 1, 2, or 3,D is a straight-chain alkylene group of 1-5 carbon atoms,E is a --C.tbd.C---bond or a --CR.sub.6 =CR.sub.7 --group wherein R.sub.6 and R.sub.7 are different from each other and mean a hydrogen atom or an alkyl group of 1-5 carbon atoms or a hydrogen atom or a halogen atom, preferably chlorine,R.sub.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: June 23, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Hernd Raduechel, Werner Skuballa, Norbert Schwarz, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town