Plural Six-membered Hetero Rings Patents (Class 549/415)
  • 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: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5110949
    Abstract: An improved method for synthesizing leukotriene B.sub.4 and derivatives thereof is disclosed, as are novel intermediates used in the process. Unlike prior art processes, the method of this invention involves a step in which 2(R)-[[(1,1-dimethylethyl)diphenylsilyl]oxy]dec-4 (Z)-ene-1-ol or a related compound is coupled with methyl-[5(S)-[[1,1dimethylethyl)-diphenylsilyl]oxy]-dec-8 (E)-10-(dimethylphosphono)-6-ynoate.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: May 5, 1992
    Assignee: University of Pennsylvania
    Inventors: Yoshihiro Abe, Kyriacos C. Nicolaou
  • Patent number: 5104861
    Abstract: The invention relates to 7-oxoprostacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is the residue OR.sub.3 wherein R.sub.3 can mean hydrogen or alkyl of 1-10 carbon atoms optionally substituted by halogen, phenyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -dialkylamino, or the residue NHR.sub.4 meaning an alkanoyl or alkanesulfonyl residue of respectively 1-10 carbon atoms,W is a hydroxymethylene or a ##STR2## group wherein the OH-group can be respectively esterified with a benzoyl or alkanoic acid residue of 1-4 carbon atoms or etherified with a tetrahydropyranyl, tetrahydrofuranyl, (C.sub.1 -C.sub.4 -alkoxy)-C.sub.1 -C.sub.4 -alkyl or tri-(C.sub.1 -C.sub.4 -alkyl)-silyl residue, wherein the free or modified OH-group can be in the .alpha.- or .beta.- position,D is a straight-chain or branched alkylene group of 1-5 carbon atoms,R.sub.2 is a straight-chain or branched alkyl group of 1-6 carbon atoms,R.sub.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: April 14, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Manfred Maas, Helmut Vorbruggen, Claus-Steffen Sturzebecher
  • Patent number: 5096905
    Abstract: The invention relates to elaiophylin derivatives of the formulae (I), (I'), (III) and (III') ##STR1## in which the C.dbd.C double bonds in the 2,3 and 4,5 position may also be hydrogenated and in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X have the meanings indicated. The invention furthermore relates to a process for the preparation of these elaiophylin derivatives, and the use thereof as pharmaceuticals, in particular as anthelmintic pharmaceuticals.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: March 17, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Kretzschmar, Peter Hammann, Dieter Duwel, Gerhard Wohner, Rudiger Marquardt, Klaus Kuhlein
  • Patent number: 5093370
    Abstract: A quaternary ammonium having a muscle relaxation activity compound represented by the formula (I): ##STR1## wherein R.sub.1 represents a methylene, a lower alkylenoxy, a lower alkenylene, a lower alkynylene, --CO--, --COO--, a lower alkylene carbonyloxy, --CH(OR.sub.5)--, a lower alkylenecarbonyl, a hydroxy lower alkylene, --O--, --S--, --SO--, or --SO.sub.2 --; R.sub.2 represents a hydrogen atom, a hydroxy lower alkyl, an aldehyde, a lower alkyl carbonyl, --NO.sub.2, or --NHR.sub.6 ; R.sub.3 represents a hydrogen atom of a group --R.sub.1 --(CH.sub.2).sub.a --[CH(CH.sub.2 A)--CH.sub.2 ].sub.b --A; R.sub.4 represents an anion; R.sub.5 and R.sub.6 represent a hydrogen atom or a acetyl; A represents a quaternary ammonium group; a represents an integer of 1 to 8; b represents 0 or 1; m represents an integer of 1 to 4; and (Z) represents a trivalent benzene ring, a trivalent naphthalene ring, a trivalent diphenyl or a trivalent ethane radical.
    Type: Grant
    Filed: April 9, 1990
    Date of Patent: March 3, 1992
    Assignee: Tobishi Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Masayasu Kimura, Kenji Naito, Osamu Sakuma, Tadashi Morita
  • Patent number: 5079259
    Abstract: A 9-chloroprostane of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha. or .beta.-position and R.sub.1, R.sub.4, R.sub.5, A, B, W, D and E are as described hereinafter which are useful as medical agents.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: January 7, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
  • Patent number: 5077037
    Abstract: Methods and compositions for enhancing magnetic resonance imaging in at least a portion of a warm-blooded animal.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: December 31, 1991
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: Rebecca A. Wallace
  • Patent number: 5068364
    Abstract: Chalcone derivatives having at least one tetrahydropyranyloxy group is disclosed. Typically, the compounds are represented by general formula (I) ##STR1## wherein X and X' each represent a tetrahydropyranyl group, R and R', which are then same or different, each represent an alkyl group or a hydrogen atom, n and n' each are an integer of from 0 to 5, m and m' each are integers of from 0 to 5, provided that n+n' is 1 or more, and that n+m is an integer of from 0 to 5 and n'+m' is an integer of from 0 to 5. Also, disclosed are processes for producing the chalcone derivatives starting from acetophenone or its derivative and benzaldehyde or its derivative at least one of which has at least one tetrahydropyranyloxy group. Further, disclosed is 2,3,4,2',4'-pentahydroxychalcone.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: November 26, 1991
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hidetsugu Takagaki, Shigenori Nakanishi, Masayoshi Abe, Hiromi Ohki, Yoshiyuki Sano
  • Patent number: 5049681
    Abstract: A novel optically active allyl alcohol derivative represented by the following general formulae (I), (II), (III) and (IV): ##STR1## The novel optically active allyl alcohol can be used effectively for producing leucotrienes B.sub.4 by the process of reacting an optically active halogen substituted allyl alcohol and a novel optically active acetylene-substituted allyl alcohol.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: September 17, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 5049673
    Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • Patent number: 5045302
    Abstract: This invention concerns novel bidentate ligands L having two phosphorus or arsenic atoms. Cationic complexes of the ligands with Technetium-99m, e.g. having the formula [TcO.sub.2 L.sub.2 ].sup.+, are useful for body imaging, particularly myocardial imaging. The ligands have the general formulaY.sub.2 QZQY.sub.2where Q is phosphorus orZ is a --CC-- or --CCC-- or --COC-- groups,the four groups Y are all C1-C8 saturated hydrocarbon or fluorohydrocarbon with 1-3 ether oxygen atoms.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: September 3, 1991
    Assignee: Amersham International plc
    Inventors: James D. Kelly, Kwok W. Chiu, Ian A. Latham
  • Patent number: 4971987
    Abstract: The invention also relates to carbacyclin derivatives of general formula I' ##STR1## wherein R.sub.9 is an alkyl group of 1-10 carbon atoms or the group --C.dbd.C--(CH.sub.2).sub.m --R.sub.6 whereinm is 1 to 16 andR.sub.6 is hydroxy on amino.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: November 20, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
  • Patent number: 4952710
    Abstract: This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula ##STR1## wherein R.sub.1 is hydrogen, --COCH.sub.3, --COCF.sub.3, --CO--phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl;wherein R.sub.2 is --CH.sub.2 OR.sub.1, --COOH, --COOR, --CHO, --CH.sub.2 --OSi(R.sub.12).sub.3, ##STR2## wherein R is lower alkyl and each R.sub.12 is independently lower alkyl or aryl; andwherein Y is ethylene, cis-vinylene, trans-vinylene, or acetylene.Also disclosed is a novel process for preparation of the above-defined cyclopenteneheptenoic acid derivative. This process involves coupling of a higher order cuprate complex with a chiral cyclopentene compound. The resultant product is particularly useful as a starting compound for high yield synthesis of optically active prostaglandins.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: August 28, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Kevin A. Babiak, Arthur L. Campbell
  • Patent number: 4929740
    Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower akoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: May 29, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Gary F. Cooper
  • Patent number: 4925590
    Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: May 15, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
  • Patent number: 4894392
    Abstract: Disclosed are specific aminoalkyl naphthalenediol derivatives that enhance host resistance to infectious organisms. Such agents are administered prophylactically to individuals whose resistance to infection is comprised by chemotherapy, surgery, burns or other forms of severe stress.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Philippe L. Durette, Timothy F. Gallagher
  • Patent number: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4883887
    Abstract: A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: November 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
  • Patent number: 4876275
    Abstract: 3,4-dihydro-2H-pyrans of the formula I ##STR1## where R.sup.1 is C.sub.4 -C.sub.20 -alkyl, C.sub.4 -C.sub.20 -alkoxyalkyl, aryl or C.sub.7 -C.sub.20 -arylalkyl, or is aryl or C.sub.7 -C.sub.20 -arylalkyl which bears from one to three substituents selected from the group consisting of halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -haloalkyl, C.sub.1 -C.sub.8 -alkoxy or C.sub.1 -C.sub.8 -haloalkoxy, R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sup.3 is aryl, or aryl bearing from one to three substituents selected from the group consisting of halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -haloalkyl, C.sub.1 -C.sub.8 -alkoxy or C.sub.1 -C.sub.8 -haloalkoxy, or the radical ##STR2## where R.sup.4, R.sup.5 and R.sup.6 are hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sup.7 is phenyl or benzoyl, or phenyl or benzoyl bearing from one to three substituents selected from the group consisting of halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -haloalkyl, C.sub.1 -C.sub.8 -alkoxy and C.sub.1 -C.sub.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: October 24, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Himmele, Hans Theobald, Franz Merger, Ernst Hofmann, Christoph Kuenast, Peter Hofmeister
  • Patent number: 4870207
    Abstract: Known compound, optically active arphamenine A can now be synthesized in an optically active pure form and in a favorable yield by a new process comprising consecutive steps with starting from L-arginine, wherein racemization of intermediate reaction products can be minimized.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: September 26, 1989
    Assignee: Zaiden Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, deceased, Takaaki Aoyagi, Kuniaki Tatsuta, Takeshi Nakamura, Shunzo Fukatsu
  • Patent number: 4861922
    Abstract: There is disclosed a method of hydroformylating 3-methyl-3-buten-1-ol and analogs thereof with carbon monoxide and hydrogen in the presence of a rhodium compound free from modification by a ligand containing an element belonging to the group V of the periodic table as well as a method of producing 3-methylpentane-1,5-diol and .beta.-methyl-.delta.-valerolactone using such hydroformylation product.
    Type: Grant
    Filed: February 11, 1987
    Date of Patent: August 29, 1989
    Assignee: Kuraray Company, Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4842638
    Abstract: Tetrahydro(thio)pyran-2,4-dione derivatives of the formula ##STR1## where R.sup.1 is hydrogen, a cation, alkylcarbonyl, C.sub.2 -C.sub.10 -alkenylcarbonyl, or benzoyl which is unsubstituted or substituted by alkyl, R.sup.2 is alkyl, R.sup.3 is a non-aromatic, unsubstituted or alkyl-substituted heterocyclic compound of 5 to 7 ring members and having at most one double bond in the heterocyclic ring, X is oxygen or sulfur, and Z is oxygen or the radical NO--R.sup.4, R.sup.4 denoting alkyl, alkenyl, alkynyl, haloalkyl, hal oalkenyl, alkoxyalkyl or the radical CH.sub.2 --R.sup.5, where R.sup.5 is a he terocyclic compound of 5 ring members and containing from 1 to 3 hetero-atoms and from 0 to 2 double bonds and bearing either no substituents or one or two substituents selected from the group consisting of alkyl, alkoxy, halogen, trifluoromethyl, alkoxymethyl, alkylthiomethyl and vinyl, or R.sup.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: June 27, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung
  • Patent number: 4822909
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: June 9, 1987
    Date of Patent: April 18, 1989
    Assignee: Asashi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4822804
    Abstract: Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl-.omega.-homo PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl-.omega.-homo PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl-.omega.-homo PGI.sub.2,5,6, 7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16-p ropoxy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-et ho xy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-pr op oxy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16-phenoxy PGI.sub.2 and methyl esters thereof.5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16 -phenoxy PGI.sub.
    Type: Grant
    Filed: September 29, 1987
    Date of Patent: April 18, 1989
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
  • Patent number: 4818431
    Abstract: New tetrahydropyran derivatives of the formula I ##STR1## in which G is H.sub.2 or .dbd.O, R.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH.sub.2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R.sup.2 is also H, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A.sup.1 and, when n is 2 or 3, for the groups A.sup.2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: April 4, 1989
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
  • Patent number: 4812582
    Abstract: This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 14, 1989
    Assignee: The Upjohn Company
    Inventor: Stephen J. Nelson
  • Patent number: 4810805
    Abstract: There are disclosed a (2-chloro-3-oxo-1-alkenyl)-bicyclo[3.3.0 octene derivative represented by the formula: ##STR1## wherein R.sup.1 represents --CH.sub.2 CH.sub.2 CH.sub.2 COOR.sup.5, --CH.sub.2 CH.sub.2 --O--CH.sub.2 COOR.sup.5, --CH.dbd.CHCH.sub.2 COOR.sup.5 or --CH.sub.2 CH.sub.2 C.tbd.C--COOR.sup.5 group where R.sup.5 in the groups represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom, an acyl group having 1 to 7 carbon atoms, a tri(1 to 7 carbon atoms)-hydrocarbylsilyl group or a group forming an acetal bonding with an oxygen atom of a hydroxy group; R.sup.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: March 7, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Masakatsu Shibasaki, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Aoki, Yoshio Hayashi
  • Patent number: 4808590
    Abstract: This invention relates to novel compositions which are useful as antitumor, antiviral and antifungal compositions, a process of producing the compositions and a method for inhibiting tumors, viruses and fungi utilizing the composition. More particularly, the novel compositions are derived from marine sponge Theonella sp.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: February 28, 1989
    Assignee: Harbor Branch Oceanographic Institution, Inc.
    Inventors: Tatsuo Higa, Shinichi Sakemi, Sue S. Cross
  • Patent number: 4808736
    Abstract: In this process of the invention a compound of the formula ##STR1## wherein R is a leaving group, is reacted with a compound of the formula ##STR2## wherein R.sup.1 is an ether protecting group, and, if desired a thus-obtained compound of the formula ##STR3## is converted in a known manner into d-.alpha.-tocopherol.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: February 28, 1989
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4783480
    Abstract: A 6-keto-prostaglandin E.sub.1 derivative of the formula: ##STR1## (wherein R.sup.1 represents an amino acid or amino alcohol residue, R.sup.2 represents a single bond or an alkylene group of from 1 to 4 carbon atoms, R.sup.3 represents (i) an alkyl group of from 1 to 8 carbon atoms, (ii) a cycloalkyl group of from 4 to 7 carbon atoms, which may be unsubstituted or substituted by at least one alkyl group of from 1 to 8 carbon atoms or (iii) a phenyl or phenoxy group, which may be unsubstituted or substituted by chlorine, trifluoromethyl or alkyl of from 1 to 3 carbon atoms, provided that when R.sup.2 represents a single bond R.sup.3 does not represent phenoxy)cyclodextrin clathrates thereof and non-toxic salts thereof possess selective cytoprotective activity.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: November 8, 1988
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hirohisa Wakatsuka, Tadao Okegawa, Yoshinobu Arai
  • Patent number: 4778904
    Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower alkoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.
    Type: Grant
    Filed: January 9, 1987
    Date of Patent: October 18, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Gary F. Cooper
  • Patent number: 4777184
    Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: October 11, 1988
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
  • Patent number: 4751317
    Abstract: An antibiotic has been isolated from fermentation of a new Streptomyces culture. The new ionophore is active as an antibacterial and anticoccidial agent.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: June 14, 1988
    Assignee: Pfizer Inc.
    Inventors: Walter P. Cullen, John R. Oscarson, Junsuke Tone, Hiroshi Maeda
  • Patent number: 4721729
    Abstract: Carbacyclins of Formula I ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl, aryl, aralkyl, or heterocyclic group,Y is a keto group or a hydroxymethylene group,X is a --CH.sub.2 -- group or an oxygen atom,A is a --CH.sub.2 --CH.sub.2 --, a trans--CH.dbd.CH-- or a --C.tbd.C-- group,W is a hydroxymethylene group or a ##STR2## D is the group ##STR3## a straight-chain or branched, saturated alkylene group or unsaturated alkylene group of up to 5 carbon atoms which can optionally be substituted by 1-2 fluorine atoms,n is 1, 2 or 3,E is a direct bond, a --C.tbd.C-- group or a --CR.sub.4 .dbd.CR.sub.5 -- group wherein R.sub.4 is hydrogen or an alkyl group and R.sub.5 is hydrogen, halogen or an alkyl group,R.sub.2 is an alkyl, cycloalkyl, aryl, or heterocyclic group, andR.sub.3 is a hydroxy group,are valuable, e.g., as cytoprotective agents.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: January 26, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
  • Patent number: 4709055
    Abstract: There is described a novel process for producing hydroquinone derivatives of the formula ##STR1## wherein R is an ether protecting group, and their conversion into d-.alpha.-tocopherol, starting from compounds of the formula ##STR2## wherein R is an ether protecting group and R.sup.1 is hydrogen or an ether protecting group.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: November 24, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4707554
    Abstract: A new method has been disclosed for obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.dbd.-dihydroxy-3,3a.beta.,4,5,6,6a.beta.- hexahydro-2H-cyclopenta [b] furane useful in the synthesis of prostaglandins or their analogs, and a method for obtaining new sulphonyl initial compounds of the general formula 4, in which Z denotes a hydrogen atom or a protective group, Y denotes a group of the formula .dbd.CHOZ.sup.1, in which Z.sup.1 has the meaning stated for Z, whereby protective groups Z and Z.sup.1 may be the same or different, and Ar denotes optionally a substituted aryl group.In the method according to the invention the new sulphonyl derivative of the general formula 4 is alkylated with an electrophilic agent comprising: carbonyl derivatives, oxiranes and halohydrins or their derivatives; the alkylation product is transformed into derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.alpha.-dihydroxy-3,3a.beta.,4,5,6,6a.beta .
    Type: Grant
    Filed: November 27, 1985
    Date of Patent: November 17, 1987
    Assignee: Polska Akademia Nauk-Instytut Chemii Organicznej
    Inventors: Barbara Achmatowicz, Andrzej R. Daniewski, Stanislaw Marczak, Jacek Pankowski, Jerzy Wicha
  • Patent number: 4703127
    Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.
    Type: Grant
    Filed: September 2, 1983
    Date of Patent: October 27, 1987
    Assignee: The Australian National University
    Inventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
  • Patent number: 4699989
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 13, 1987
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4699920
    Abstract: The invention relates to 9-halo-.DELTA..sup.2 -prostane derivatives of general Formula I ##STR1## wherein Hal is a fluorine or chlorine atom in the .alpha.- or .beta.-position,R.sub.1 is the residue OR.sub.2 with R.sub.2 meaning a hydrogen atom, alkyl, cycloalkyl, aryl or a heterocyclic residue; or the residue NHR.sub.3 wherein R.sub.3 means an acid residue or the residue R.sub.2 andA is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or --C.tbd.C--group,W is a free or functionally modified hydroxymethylene or ##STR2## wherein the respective OH-groups can be in the .alpha.- or .beta.-position,D and E jointly mean a direct bond orD is a straight- or branched-chain alkylene group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 --group wherein R.sub.6 is a hydrogen atom or an alkyl group and R.sub.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: October 13, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge
  • Patent number: 4680307
    Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: July 14, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
  • Patent number: 4659844
    Abstract: The invention relates to new cyclic ethers which are substituted in the .alpha.-position by an isocyanide-dichloride group, of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the meaning indicated in the description, and to a process for their preparation.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
  • Patent number: 4658044
    Abstract: Compounds of formula (C) ##STR1## where either R.sup.D represents a hydroxymethyl group and R.sup.E represents a hydroxyl group or R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.E represents a hydroxyl group and R.sup.D represents an ethenyl group and R.sup.F represents a hydroxyl or protected hydroxyl group or a leaving group with the proviso that either R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.F represents a protected hydroxyl group, which compounds are of use as intermediates in the preparation of compounds having antiviral activity.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 14, 1987
    Assignee: Glaxo Group Limited
    Inventor: Paul Ravenscroft
  • Patent number: 4649156
    Abstract: The present invention provides a novel 6-nitroprostaglandin derivatives of the formula (I) ##STR1## wherein A, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.The 6-nitroprostaglandin derivatives is useful as medicines because of its excellent pharmacological activities including platelet aggregation inhibiting activity, blood pressure lowering activity and anti-ulcerous activity, and useful as intermediate for other pharmaceutically active compounds such as 6-oxoprostaglandin derivatives, prostaglandin E.sub.1 derivatives, etc.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: March 10, 1987
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4638002
    Abstract: The invention relates to new 2,3,4-trinor-1,5-inter-m-phenylene-PGI.sub.2 derivatives of the formula (I) ##STR1## wherein A stands for carboxy, cyano, tetrazolyl or --COOR.sup.3 or --CONR.sup.1 R.sup.2 ;R.sup.3 is C.sub.1-4 alkyl or an equivalent of a pharmacologically acceptable cation:R.sup.1 and R.sup.2 each stands for hydrogen, phenyl; C.sub.1-5 alkyl, optionally substituted by carboxy, hydroxy, phenyl or C.sub.2-5 alkoxycarbonyl; or C.sub.1-4 alkylsulfonyl; orR.sup.1 and R.sup.2 together form an .alpha.,.omega.-alkylene chain containing 3-6 carbon atoms;B stands for oxygen or methylene;Y is optionally bromo-substituted vinylene or a --C.tbd.C-- group:R.sup.4 stands for hydrogen or tetrahydro-pyran-2-yl;R.sup.5 represents an alkyl group containing 5-9 carbon atoms, which can be optionally interrupted by one or more oxygen atom(s) or --CH.dbd.CH-- or --C.tbd.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: January 20, 1987
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Szekely, Sandor Botar, Krisztina Dolgos nee Kekesi, Bela Bertok, Antal Gajary, Tamas Szabolcsi, Gabor Kovacs, Marianna Lovasz nee Gaspar
  • Patent number: 4632997
    Abstract: A method for preparing a cis-bicyclo[3.3.0]octylidene derivative represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group; R.sup.2 is a hydrogen atom or a protective group for hydroxyl group; and Y is ##STR2## where R.sup.3 is a hydrogen atom or a protective group for hydroxyl group; R.sup.4 is a hydrogen atom or a straight, branched or cyclic alkyl group, alkenyl group or alkynyl group; and X is a group represented by CH.dbd.CH or C.tbd.C,comprises carrying out the catalytic hydrogenation reaction of a (1-alkenyl)-cis-bicyclo[3.3.0]octene derivative represented by the formula: ##STR3## wherein R.sup.1, R.sup.2 and Y have the same meanings as defined above, in the presence of a metal carbonyl compound or its complex represented by the formula:Mw(CO)x(H)y(R)zwherein M is a metal element of the group VIB; R is a .pi. ligand or a phosphine ligand; w is 1 or 2; x is an integer of 3 to 6; y is 0 or 1; and z is 0 or an integer of 1 to 3.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: December 30, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4612380
    Abstract: The prostacyclins 7-fluoro-6,9-epoxy-16-substituted-15-hydroxyprost-[4 or 5,13]-dienoic acids and esters useful as anti-secretory agents, blood pressure lowering agents, anti-ulcerogenic agents, anti-hypertensive agents, bronchodilation agents and for combating gastro-hyperacidity and as anti-blood platelet aggregating agents.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: September 16, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Perry Rosen, Hans Maag
  • Patent number: 4608435
    Abstract: New benzo-1,4-quinones and salts thereof with organic or inorganic acid and bases have the formula I ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## wherein Q is selected from the residues --CO.sub.2 R.sub.4, --CON(R.sub.4)(R.sub.5), --OR.sub.5, --OCOR.sub.7, --N(R.sub.8)(R.sub.9), --PO(OR.sub.10)([O].sub.x R.sub.11), --SO.sub.2 R.sub.12, --CN, Halogen, --NO.sub.2 or --COR.sub.13, n is an integer from 1 to 20, k is 1 or 2 and x is 0 or 1, and R.sub.1 to R.sub.5 and R.sub.7 to R.sub.13 are as defined in the specification.The compounds of formula I are useful in photographic materials such as bleaching inhibitors in films of photographic silver dye bleach materials.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: August 26, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4606753
    Abstract: Novel oxabicycloalkane ether of the formula ##STR1## wherein X is a single bond or --C(CH.sub.3).sub.2 -- and Y is a single bond or --CH.sub.2 -- with the proviso that both X and Y are not a single bond; R is H or --C(O)R.sup.3 in which R.sup.3 is H or certain hydrocarbyl groups; R.sup.1 is certain hydrocarbyl groups, or certain derivatives thereof, such as esters or carbamoyl compounds; and R.sup.2 is cyano or certain unsaturated, aromatic, heterocyclic, cycloalkyl, cycloalkenyl or secondary alkyl group, are useful as herbicides or plant growth regulators.
    Type: Grant
    Filed: June 15, 1984
    Date of Patent: August 19, 1986
    Assignee: Shell Oil Company
    Inventor: James E. Powell
  • Patent number: 4603144
    Abstract: Kojic acid ether-ester derivatives of formula I ##STR1## are useful pharmacological agents for the prevention, management or alleviation of elastase mediated diseases or conditions.
    Type: Grant
    Filed: August 16, 1984
    Date of Patent: July 29, 1986
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, Masateru Miyano