Plural Six-membered Hetero Rings Patents (Class 549/415)
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Patent number: 5162353Abstract: 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: GrantFiled: August 21, 1990Date of Patent: November 10, 1992Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
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Patent number: 5116869Abstract: 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: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5110949Abstract: 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: GrantFiled: September 13, 1989Date of Patent: May 5, 1992Assignee: University of PennsylvaniaInventors: Yoshihiro Abe, Kyriacos C. Nicolaou
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Patent number: 5104861Abstract: 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: GrantFiled: February 20, 1991Date of Patent: April 14, 1992Assignee: Schering AktiengesellschaftInventors: Manfred Maas, Helmut Vorbruggen, Claus-Steffen Sturzebecher
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Patent number: 5096905Abstract: 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: GrantFiled: September 14, 1989Date of Patent: March 17, 1992Assignee: Hoechst AktiengesellschaftInventors: Gerhard Kretzschmar, Peter Hammann, Dieter Duwel, Gerhard Wohner, Rudiger Marquardt, Klaus Kuhlein
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Patent number: 5093370Abstract: 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: GrantFiled: April 9, 1990Date of Patent: March 3, 1992Assignee: Tobishi Yakuhin Kogyo Kabushiki KaishaInventors: Masayasu Kimura, Kenji Naito, Osamu Sakuma, Tadashi Morita
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Patent number: 5079259Abstract: 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: GrantFiled: September 8, 1987Date of Patent: January 7, 1992Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 5077037Abstract: Methods and compositions for enhancing magnetic resonance imaging in at least a portion of a warm-blooded animal.Type: GrantFiled: August 3, 1990Date of Patent: December 31, 1991Assignee: Mallinckrodt Medical, Inc.Inventor: Rebecca A. Wallace
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Patent number: 5068364Abstract: 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: GrantFiled: November 21, 1989Date of Patent: November 26, 1991Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Hidetsugu Takagaki, Shigenori Nakanishi, Masayoshi Abe, Hiromi Ohki, Yoshiyuki Sano
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Patent number: 5049681Abstract: 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: GrantFiled: July 8, 1988Date of Patent: September 17, 1991Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 5049673Abstract: 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: GrantFiled: October 30, 1987Date of Patent: September 17, 1991Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Akwasi Minta
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Patent number: 5045302Abstract: 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: GrantFiled: March 28, 1989Date of Patent: September 3, 1991Assignee: Amersham International plcInventors: James D. Kelly, Kwok W. Chiu, Ian A. Latham
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Patent number: 4971987Abstract: 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: GrantFiled: March 7, 1988Date of Patent: November 20, 1990Assignee: Schering AktiengesellschaftInventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
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Patent number: 4952710Abstract: 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: GrantFiled: October 7, 1988Date of Patent: August 28, 1990Assignee: G. D. Searle & Co.Inventors: Kevin A. Babiak, Arthur L. Campbell
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Patent number: 4929740Abstract: 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: GrantFiled: July 11, 1988Date of Patent: May 29, 1990Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4925590Abstract: 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: GrantFiled: March 9, 1989Date of Patent: May 15, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
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Patent number: 4894392Abstract: 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: GrantFiled: May 12, 1988Date of Patent: January 16, 1990Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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Patent number: 4894181Abstract: 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: GrantFiled: May 16, 1988Date of Patent: January 16, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
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Patent number: 4883887Abstract: 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: GrantFiled: July 1, 1988Date of Patent: November 28, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
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Patent number: 4876275Abstract: 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: GrantFiled: April 1, 1988Date of Patent: October 24, 1989Assignee: BASF AktiengesellschaftInventors: Walter Himmele, Hans Theobald, Franz Merger, Ernst Hofmann, Christoph Kuenast, Peter Hofmeister
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Patent number: 4870207Abstract: 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: GrantFiled: July 30, 1987Date of Patent: September 26, 1989Assignee: Zaiden Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, deceased, Takaaki Aoyagi, Kuniaki Tatsuta, Takeshi Nakamura, Shunzo Fukatsu
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Patent number: 4861922Abstract: 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: GrantFiled: February 11, 1987Date of Patent: August 29, 1989Assignee: Kuraray Company, Ltd.Inventors: Yasuo Tokitoh, Noriaki Yoshimura
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Patent number: 4842638Abstract: 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: GrantFiled: January 12, 1988Date of Patent: June 27, 1989Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung
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Patent number: 4822909Abstract: 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: GrantFiled: June 9, 1987Date of Patent: April 18, 1989Assignee: Asashi Glass Company Ltd.Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
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Patent number: 4822804Abstract: 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: GrantFiled: September 29, 1987Date of Patent: April 18, 1989Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
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Patent number: 4818431Abstract: 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: GrantFiled: November 24, 1986Date of Patent: April 4, 1989Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
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Patent number: 4812582Abstract: 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: GrantFiled: May 6, 1987Date of Patent: March 14, 1989Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4810805Abstract: 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: GrantFiled: December 19, 1986Date of Patent: March 7, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Masakatsu Shibasaki, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Aoki, Yoshio Hayashi
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Patent number: 4808590Abstract: 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: GrantFiled: July 15, 1988Date of Patent: February 28, 1989Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Tatsuo Higa, Shinichi Sakemi, Sue S. Cross
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Patent number: 4808736Abstract: 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: GrantFiled: August 10, 1987Date of Patent: February 28, 1989Assignee: Hoffmann-LaRoche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4783480Abstract: 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: GrantFiled: January 28, 1987Date of Patent: November 8, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Tadao Okegawa, Yoshinobu Arai
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Patent number: 4778904Abstract: 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: GrantFiled: January 9, 1987Date of Patent: October 18, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4777184Abstract: 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: GrantFiled: April 29, 1986Date of Patent: October 11, 1988Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
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Patent number: 4751317Abstract: An antibiotic has been isolated from fermentation of a new Streptomyces culture. The new ionophore is active as an antibacterial and anticoccidial agent.Type: GrantFiled: August 29, 1986Date of Patent: June 14, 1988Assignee: Pfizer Inc.Inventors: Walter P. Cullen, John R. Oscarson, Junsuke Tone, Hiroshi Maeda
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Patent number: 4721729Abstract: 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: GrantFiled: February 8, 1985Date of Patent: January 26, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Robert Nickolson, Martin Haberey, Olaf Loge, Claus-Steffen Stuerzebecher
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Patent number: 4709055Abstract: 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: GrantFiled: January 13, 1986Date of Patent: November 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4707554Abstract: 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: GrantFiled: November 27, 1985Date of Patent: November 17, 1987Assignee: Polska Akademia Nauk-Instytut Chemii OrganicznejInventors: Barbara Achmatowicz, Andrzej R. Daniewski, Stanislaw Marczak, Jacek Pankowski, Jerzy Wicha
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Patent number: 4703127Abstract: 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: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4699989Abstract: 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: GrantFiled: February 11, 1985Date of Patent: October 13, 1987Assignee: Asahi Glass Company Ltd.Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
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Patent number: 4699920Abstract: 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: GrantFiled: September 17, 1985Date of Patent: October 13, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge
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Patent number: 4680307Abstract: 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: GrantFiled: January 26, 1984Date of Patent: July 14, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
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Patent number: 4659844Abstract: 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: GrantFiled: July 25, 1985Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
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Patent number: 4658044Abstract: 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: GrantFiled: October 24, 1985Date of Patent: April 14, 1987Assignee: Glaxo Group LimitedInventor: Paul Ravenscroft
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Patent number: 4649156Abstract: 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: GrantFiled: July 19, 1985Date of Patent: March 10, 1987Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
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Patent number: 4638002Abstract: 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: GrantFiled: December 30, 1983Date of Patent: January 20, 1987Assignee: 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
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Patent number: 4632997Abstract: 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: GrantFiled: February 8, 1985Date of Patent: December 30, 1986Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
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Patent number: 4612380Abstract: 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: GrantFiled: September 9, 1985Date of Patent: September 16, 1986Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Perry Rosen, Hans Maag
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Patent number: 4608435Abstract: 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: GrantFiled: April 28, 1983Date of Patent: August 26, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4606753Abstract: 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: GrantFiled: June 15, 1984Date of Patent: August 19, 1986Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4603144Abstract: 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: GrantFiled: August 16, 1984Date of Patent: July 29, 1986Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Masateru Miyano