Chalcogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding (e.g., Sulfato Betaines, Etc.) Patents (Class 546/339)
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Patent number: 4889865Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.Type: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4889953Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.Type: GrantFiled: July 22, 1987Date of Patent: December 26, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
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Patent number: 4886622Abstract: An optically liquid crystalline compound having an extremely large spontaneous polarization value and a chiral smectic liquid crystal composition containing the compound are provided, the compound being expressed by the formula ##STR1## wherein m represents an integer of 2 to 18; l represents an integer of 0 to 12; n represents 0 or 1; R represents an alkyl group or an alkoxy group each of 2 to 20 carbon atoms, a halogen atom or cyano group; and A and B each represent a single bond, ##STR2## wherein X represents hydrogen atom, a halogen atom or cyano group, and a chiral smectic liquid crystal composition containing at least one kind of the above compound.Type: GrantFiled: August 18, 1987Date of Patent: December 12, 1989Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Takashi Inukai, Hiromichi Inoue, Shinichi Saito, Kouji Ohno
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Patent number: 4880936Abstract: An optically active compound represented by formula (I): ##STR1## wherein R represents a straight chain alkyl group having from 2 to 12 carbon atoms; R' represents a straight chain alkyl or alkoxy group having from 1 to 20 carbon atoms; C represents an asymmetric carbon atom; A represents ##STR2## and X and Y each represents a hydrogen atom or a fluorine atom, provided that X and Y do not simultaneously represent a fluorine atom. The compound (I) reduces a temperature dependence of the threshold voltage of a nematic liquid crystal composition when added thereto in a small amount.Type: GrantFiled: March 25, 1988Date of Patent: November 14, 1989Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Makoto Sasaki, Kiyohumi Takeuchi, Haruyoshi Takatsu
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Patent number: 4879060Abstract: 2-phenylpyridine derivatives represented by the general formula: ##STR1## wherein when Y is R--, Z is one of R--, RO--, ##STR2## when Y is RO--, Z is one of straight chain pentyl, ##STR3## and when Y is one of Z is one of R--, RO-- and --CN; when Y is --CN, Z is one of RO--, ##STR4## and R is a straight chain alkyl group from 1 to 12 carbon atoms, are disclosed. The 2-phenylpyridine derivatives in accordance with the invention are particularly well-suited for use in nematic liquid crystal compositions for reducing the steepness and response time of the liquid crystal compositions in a liquid crystal display device.Type: GrantFiled: May 22, 1987Date of Patent: November 7, 1989Assignee: Seiko Epson Kabushiki KaishaInventors: Yoshio Shionozaki, Hiroshi Mukai, Tsuyoshi Obikawa, Shuhei Yamada
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Patent number: 4876026Abstract: An optically active-2-methylbutyrate capable of imparting a spontaneous polarization value to achiral smectic compositions and also constituting ferroelectric liquid crystal compositions exhibiting a fast response at room temperature, and a liquid crystal composition containing the same, and further a light-switching element therefrom, are provided, which optically active-2-methylbutyrate is expressed by the formula ##STR1## wherein R represents a linear or branched alkyl group or alkoxy group, each of 1 to 18 carbon atoms; A represents ##STR2## wherein X represents any one of F, Cl, Br or cyano group; and * indicates an optically active carbon atom.Type: GrantFiled: December 15, 1987Date of Patent: October 24, 1989Assignee: Chisso CorporationInventors: Shinichi Saito, Hiromichi Inoue, Kazutoshi Miyazawa, Kouji Ohno, Makoto Ushioda
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Patent number: 4865763Abstract: A novel liquid crystalline, halogen-containing heterocyclic compound having a characteristic that even when its S.sub.c * phase is supercooled, no other smectic phases appear, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group of 2 to 18 carbon atoms; X represents --N.dbd. or --CH.dbd.; Y represents F or Cl; n represents an integer of 0 to 10; and a symbol * represents an asymmetric carbon atom.Type: GrantFiled: June 6, 1988Date of Patent: September 12, 1989Assignee: Chisso CorporationInventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Kazutoshi Miyazawa, Shinichi Saito
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Patent number: 4866066Abstract: Thiomethylpyridine derivatives having bronchosecretolytic and mucolytic activity according to the formula: ##STR1## wherein R is a group attached in the 2-, 3- or 4-position of the pyridine ring which corresponds to the following general formula:Q--S--CH.sub.2 -- (II)wherein Q is a substituted or unsubstituted aryl group or a 5- or 6-membered heterocyclic group which may optionally contain one or more substituents and/or which may be condensed with an optionally substituted phenyl group or with an optionally substituted heterocycle; R' is a lower alkyl group, a halogen atom or an aminoalkyl group; and n is 0 or an integer of from 1 to 4; and the therapeutically-acceptable acid addition salts thereof.The new compounds are distinguished by surprising activity compared with known compounds, such as "Ambroxol".Type: GrantFiled: February 17, 1987Date of Patent: September 12, 1989Assignee: Ludwig Heumann & Co. GmbHInventors: Helmut Schickaneder, Heidrun Engler, Istvan Szelenyi
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Patent number: 4859687Abstract: The described novel pyridine derivatives are those of the general formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3, or benzyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3,R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy,R.sub.3, R.sub.4 and R.sub.5 independently of one another are each hydrogen, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, NO.sub.2 and/or CF.sub.3,U and V independently of one another are each C.sub.1 -C.sub.6 -alkyl, or alkyl substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or together form one of the following alkylene bridges: ##STR2## R.sub.a is hydrogen, C.Type: GrantFiled: February 20, 1986Date of Patent: August 22, 1989Assignee: Ciba-Giegy CorporationInventor: Peter Riebli
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Patent number: 4855423Abstract: Sulfatobetaines are prepared by reacting an addition compound of sulfur trioxide and a tertiary amine with an alkylene carbonate.Type: GrantFiled: October 13, 1987Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Gerold Braun, Chung-Ji Tschang, Christos Vamvakaris, Klaus Glaser
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Patent number: 4851413Abstract: Quinone derivatives represented by the general formula ##STR1## (wherein, R.sup.1 and R.sup.2, the same or different, refer to a hydrogen atom, methyl or methoxymethyl group, or R.sup.1 and R.sup.2 bind together to form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or methyl group; R.sup.4 is a nitrogen-containing heterocyclic group which may be substituted; R.sup.Type: GrantFiled: January 16, 1987Date of Patent: July 25, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Kohei Nishikawa
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Patent number: 4845219Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.Type: GrantFiled: July 23, 1987Date of Patent: July 4, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
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Patent number: 4845228Abstract: The present invention relates to cyclohexanone derivatives represented by general formula: ##STR1## wherein R represents a hydrogen atom or an acetyl group. The cyclohexanone derivatives are important intermediates for producing isoquinoline derivatives which are useful as drugs, especially for heart drugs.Type: GrantFiled: January 26, 1988Date of Patent: July 4, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsuneji Suzuki, Sannohe, Kunio, Toshihiko Ito, Masahiko Maruyama, Joji Kamiya, Makoto Hirayama, Takafumi Kitano, Akira Awaya
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Patent number: 4837236Abstract: A heterocyclic compound of the formula: ##STR1## wherein A is an oxygen atom or a sulfur atom;B is either one of the groups: --CH.sub.2 --CHR.sup.1 -- or --CH.dbd.CR.sup.1 -- (in which R.sup.1 is a hydrogen atom or a methyl group);W is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group;X is either one of the following groups: ##STR2## (in which R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy(lower)alkyl group, a hydroxyl group or a hydroxy(lower)alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group and n is an integer of 0 or 1);Z is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a halo(lower)alkyl group, a halo(lower)alkoxy group, a nitro group, a methylenedioxy group or a cyano group;p is an integer of 0 to 5; andq is an integer of 0 or 1, or its salt, which is useful as a fungicide.Type: GrantFiled: September 24, 1987Date of Patent: June 6, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Meki, Hirotaka Takano
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Patent number: 4837330Abstract: Sulfatobetaines are prepared by reacting an adduct of a base having a tertiary N atom and sulfur trioxide with an alkylene oxide in the presence of an alkylene carbonate as a solvent.Type: GrantFiled: March 15, 1988Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Gerold Braun, Chung-Ji Tschang, Christos Vamvakaris, Klaus Glaser
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Patent number: 4834904Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: December 24, 1986Date of Patent: May 30, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 4826531Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.Type: GrantFiled: April 17, 1987Date of Patent: May 2, 1989Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 4820839Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.Type: GrantFiled: January 23, 1987Date of Patent: April 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
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Patent number: 4810715Abstract: Thiomethylpyridine derivatives having bronchosecretolytic and mucolytic activity according to the formula: ##STR1## wherein R is a group attached in the 2-, 3- or 4-position of the pyridine ring which corresponds to the following general formula:Q--S--CH.sub.2 -- (II)wherein Q is a substituted or unsubstituted aryl group or a 5- or 6-membered heterocyclic group which may optionally contain one or more substituents and/or which may be condensed with an optionally substituted phenyl group or with an optionally substituted heterocycle;R' is a lower alkyl group, a halogen atom or an aminoalkyl group; andn is 0 or an integer of from 1 to 4;and the therapeutically-acceptable acid addition salts thereof.The new compounds are distinguished by surprising activity compared with known compounds, such as "Ambroxol".Type: GrantFiled: March 16, 1987Date of Patent: March 7, 1989Assignee: Ludwig Heumann & Co. GmbHInventors: Helmut Schickaneder, Heidrun Engler, Istvan Szelenyi
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Patent number: 4797411Abstract: The invention relates to cycloalkyl-substituted 4-pyridyl derivatives of formula (I) ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl;each of R.sub.1 and R.sub.2 is, independently, hydrogen or C.sub.1 -C.sub.4 alkyl;n is an integer of 1 to 5; and either(a) A is >C.dbd.O and B is --O--, --NH-- or --CH.sub.2 --; or(b) A is --CH.sub.2 --and B is --O--, --NH--, --CH.sub.2 -- or >C.dbd.O; or(c) A is --O-- and B is >C.dbd.O or --CH.sub.2 --; or(d) A is --NH-- and B is >C.dbd.O or --CH.sub.2 --,and their pharmaceutically acceptable salts.The compounds of the invention show aromatase inhibiting activity and can be useful, e.g., in treating hormone-dependent tumors and prostatic hyperplasia.Type: GrantFiled: July 13, 1987Date of Patent: January 10, 1989Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Angelo Crugnola, Enrico di Salle, Paolo Lombardi
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Patent number: 4797490Abstract: 6-Fluoro-7-pyridylquinolone carboxylic esters and acids having antibacterial activity are prepared by coupling of a 2-fluorophenyl-metallic compound with a pyridyl bromide or iodide in the presence of a transition metal catalyst, nitrating and hydrogenating the pyridyl-2-fluorophenyl compound formed, introducing a substituent on the nitrogen of the amine formed, and cyclizing after reacting with a dialkyl or dibenzyl ethoxymethylene malonate to form a 6-fluoro-7-pyridyl-1,4-dihydroquinol-4-one 3-carboxylate, and hydrolyzing to the corresponding acid.Type: GrantFiled: September 15, 1986Date of Patent: January 10, 1989Assignee: Pfizer Inc.Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
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Patent number: 4795587Abstract: A novel liquid crystal compound exhibiting SC phase which, when added to an optically active liquid crystal, makes the resulting chiral smectic liquid crystal material exhibit superior performances in liquid crystal display elements utilizing the ferroelectricity of the material, and a chiral smectic C composition using the compound, which compound is expressed by the formula ##STR1## wherein R.sup.1 l represents an alkyl group of 7 to 12 carbon atoms and R.sup.2 represents an alkyl group of 5 to 12 carbon atoms.Type: GrantFiled: March 20, 1987Date of Patent: January 3, 1989Assignee: Chisso CorporationInventors: Kouji Ohno, Hiromichi Inoue, Takashi Inukai, Shinichi Saito, Kazutoshi Miyazawa
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Patent number: 4794188Abstract: Compounds of the formula:Ar.sub.1 -X-Ar-Z-(R).sub.n'and salts thereof, whereinAr.sub.1 is a nitrogen, sulfur or oxygen heterocyclic ring;Ar is a phenyl ring or a nitrogen, oxygen or sulfur heterocyclic ring;Ar and Ar.sub.1 may be fully substituted or less than fully substituted with H, CH.sub.3, lower alkyl, aryl, aralkyl, halo, hydroxy, lower alkoxy, CF.sub.Type: GrantFiled: December 19, 1985Date of Patent: December 27, 1988Assignee: USV Pharmaceutical CorporationInventors: John H. Musser, Utpal R. Chakraborty
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Patent number: 4792563Abstract: Insecticidally active compounds of the formula (I): ##STR1## wherein R.sup.4 represents a group selected from those groups represented by R.sup.5 in insecticidally active compounds of formula: ##STR2## R.sup.3 is selected from fluoromethyl and difluoromethyl, and either (a) R.sup.1 and R.sup.2 represent alkyl of one, two, three or four carbon atoms, or (b) R.sup.1 and R.sup.2 taken together with the adjacent carbon atom form a cycloalkyl ring of four, five or six carbon atoms.Type: GrantFiled: October 6, 1987Date of Patent: December 20, 1988Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4791139Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.Type: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4784792Abstract: A ferroelectric pyridine compound suitable as a liquid crystal for display mode utilizing ferroelectric properties and exhibiting SC* phase at a temperature somewhat higher than room temperature and a liquid crystal composition are provided, which compound is expressed by the formula ##STR1## wherein n represents an integer of 0 to 8, R.sub.1 represents an alkyl group of 2 to 18 carbon atoms, R.sub.2 represents an alkyl group of 1 to 18 carbon atoms and the symbol * indicates that C having the symbol attached thereon is an optically active carbon atom.Type: GrantFiled: December 16, 1986Date of Patent: November 15, 1988Assignee: Chisso CorporationInventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Kazutoshi Miyazawa, Shinichi Saito
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Patent number: 4781857Abstract: A novel liquid crystal compound exhibiting SC phase which, when added to an optically active liquid crystal, makes the resulting chiral smectic liquid crystal material exhibit superior performances in liquid crystal display elements utilizing the ferroelectricity of the material, and a chiral smectic C composition using the compound. The compound is expressed by the formula ##STR1## wherein X represents F or Cl and R.sub.1 and R.sub.2 each represent a straight chain alkyl group of 1 to 18 carbon atoms.Type: GrantFiled: March 20, 1987Date of Patent: November 1, 1988Assignee: Chisso CorporationInventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Shinichi Saito, Kazutoshi Miyazawa
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Patent number: 4776880Abstract: Disclosed are diphenoxymethylpyridines, their preparation and their use as herbicides.Type: GrantFiled: February 1, 1988Date of Patent: October 11, 1988Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Ingrid L. Knox
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Patent number: 4772416Abstract: A novel phenylpyridine derivative which exhibits a positive dielectric anisotropy and is useful as a component of liquid crystal materials and also has a broad temperature range of liquid crystal phases, a high clearing point and a superior compatibility with other liquid crystal compounds or liquid crystal compositions, and a composition containing the derivative are provided. The phenylpyridine derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbon atoms, X represents H or F; Y represents F, --CN or an alkyl group or an alkoxy group of 1 to 10 carbon atoms; and m represents 0 or 1.Type: GrantFiled: March 20, 1987Date of Patent: September 20, 1988Assignee: Chisso CorporationInventors: Yasuyuki Goto, Kazunori Nigorikawa, Toyoshiro Isoyama
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Patent number: 4767865Abstract: The present invention provides novel 3'-pyridinylalkenylindole-2-carboxylic acids and derivatives thereof of the formula I and II ##STR1## which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.Type: GrantFiled: June 29, 1987Date of Patent: August 30, 1988Assignee: The Upjohn CompanyInventors: Roy A. Johnson, Chiu-Hong Lin
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Patent number: 4765924Abstract: A novel liquid crystalline, halogen-containing heterocyclic compound having a characteristic that even when its S.sub.c * phase is supercooled, no other smectic phases appear, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group of 2 to 18 carbon atoms; X represents --N.dbd. or --CH.dbd.; Y represents F or Cl; n represents an integer of 0 to 10; and a symbol * represents an asymmetric carbon atom.Type: GrantFiled: January 14, 1987Date of Patent: August 23, 1988Assignee: Chisso CorporationInventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Kazutoshi Miyazawa, Shinichi Saito
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Patent number: 4758573Abstract: Compounds of the general formula ##STR1## and pharmaceutically acceptable salts thereof have antithrombotic activity. Het represents 1-[1H-imidazolyl], 1-N-morpholinyl or pyridyl. A representative compound is 6-[2-(1H-Imidazol-1-yl)-1-yl-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]he xanoic acid.Type: GrantFiled: February 3, 1986Date of Patent: July 19, 1988Assignee: G. D. Searle & Co.Inventors: Paul W. Manley, Lai M. Fook
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Patent number: 4753947Abstract: Novel pyridine and pyrazine derivatives of the formula ##STR1## wherein R.sup.4 is 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl-4-oxide or 2-pyrazinyl-1,4-dioxide, and R, R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, processes for their preparation, fungicidal compositions containing said compounds, and methods for the use of such compounds or compositions for combatting fungi in agriculture and in horticulture are disclosed. Novel starting materials and fungicidal active substances of the formula ##STR2## wherein R.sup.4' is 3-pyridyl or 2-pyrazinyl, and R and R.sup.1" as hereinafter set forth, which are used for the preparation of the compounds of formula I, and their N-oxides, as well as fungicidal compositions containing these compounds as the active substance, are also described.Type: GrantFiled: August 26, 1985Date of Patent: June 28, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Franz Dorn, Francois Montavon, Milos Suchy
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Patent number: 4754043Abstract: There are disclosed compounds of the formula ##STR1## wherein X is --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## Z is CR or N, where n=1; or Z is O,S, or NR, when n=0; R is hydrogen or loweralkyl;n is 0 or 1;R.sup.1 is hydroxy, amino, loweralkyl sulfonamido, perfluoro loweralkyl sulfonamido or OR;R.sup.2 is hydrogen or loweralkyl;R.sup.3 is hydrogen or loweralkyl; orR.sup.2 and R.sup.3 taken together form a benzene ring; andthe dotted line represents an optional double bond;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like.Type: GrantFiled: October 6, 1986Date of Patent: June 28, 1988Assignee: American Home Products CorporationInventors: Anthony F. Kreft, III, John H. Musser, Thomas W. Pattison, John P. Yardley
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Patent number: 4752413Abstract: A novel liquid crystal compound exhibiting smectic phases and useful for display elements and a chiral smectic liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 each represent an alkyl group of 1 to 20 carbon atoms and X represents H atom or F atom, and which composition comprises at least one kind of the compounds of the formula (I) and an optically active compound.Type: GrantFiled: May 26, 1987Date of Patent: June 21, 1988Assignee: Chisso CorporationInventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Shinichi Saito, Kazutoshi Miyazawa
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Patent number: 4751225Abstract: A nitrogen-containing heterocyclic compound of the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and R.sub.17 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, a trifluoromethyl group or a nitro group, R.sub.18, R.sub.19, R.sub.20 and R.sub.21 are, the same or different, each a hydrogen atom or a methyl group, k is an integer of 0 to 1 and l is an integer of 0 to 3);R.sub.2 and R.sub.3 are, the same or different, each a hydrogen atom, a halogen atom or a methyl group;R.sub.4 is a halogen atom or a methyl group;R.sub.5 and R.sub.6 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.1 -C.sub.Type: GrantFiled: April 21, 1987Date of Patent: June 14, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Sumio Nishida, Noritada Matsuo, Makoto Hatakoshi, Hirosi Kisida
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Patent number: 4745120Abstract: The present invention relates to new pyridines substituted in the 3-position, of the formula ##STR1## and to a process for their preparation. The compounds bring about specific inhibition of thromboxane synthetase and can thus be used as medicaments.Type: GrantFiled: August 21, 1985Date of Patent: May 17, 1988Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Wilhelm Bartmann, Gerhard Beck, Hans-Hermann Lau
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Patent number: 4743622Abstract: The invention relates to new aromatic alkane derivatives of the general formula ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 alkyl, halo-C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, halo-C.sub.2-4 alkynyl, phenyl-C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, halo-C.sub.1-4 alkoxy, phenyl-C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, halo-C.sub.2-4 alkenyloxy, phenyl-C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo-C.sub.2-4 alkynyloxy, phenyl-C.sub.2-4 alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or these groups substituted by one or more of C.sub.1-6 alkyl, halo-C.sub.1-6 alkyl, phenyl-C.sub.1-6 alkyl, C.sub.1-6 alkyl interrupted by an O-, N- or S- atom, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.Type: GrantFiled: February 11, 1986Date of Patent: May 10, 1988Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
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Patent number: 4739079Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: March 27, 1986Date of Patent: April 19, 1988Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4731373Abstract: Glycerine derivatives of the formula ##STR1## wherein the residues R.sup.1, R.sup.2 and R.sup.3 have the significance given in the description,and their hydrates, which inhibit blood platelet activating factor (PAF), are descried.Type: GrantFiled: December 10, 1984Date of Patent: March 15, 1988Assignee: Hoffman-La Roche Inc.Inventors: Richard Barner, Kasper Burri, Jean-Marie Cassal, Paul Hadvary, Georges Hirth, Klaus Muller
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Patent number: 4725373Abstract: New compositions of matter are disclosed which are the products resulting from reacting an alkyl substituted aromatic heterocyclic nitrogen-containing compound such as 2,4,6-trimethylpyridine or 2,3,5,6-tetramethylpyrazine with a dicarboxylic acid monoanhydride such as 2-dodecen-1-yl succinic anhydride. These compositions are useful in preventing corrosion of metallic articles in corrosive environments. They are particularly useful in down hole oil and gas well applications.Type: GrantFiled: February 24, 1986Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventors: Duane S. Treybig, James L. Potter
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Patent number: 4723018Abstract: 2-phenylpyridine derivatives having the general formula: ##STR1## wherein Y is ##STR2## and Z is a straight chain alkyl group having from 1 to 16 carbon atoms, ##STR3## R' is a straight chain alkyl group having from 2 to 12 carbon atoms, R.sup.2 is a straight chain alkyl group having from 1 to 12 carbon atoms, n is an integer from 1 to 10 and * is an asymmetric carbon are provided. The derivatives are stable, have low viscosity, excellent electro-optical response properties and broaden the ferroelectric temperature range when added to ferroelectric liquid crystal compositions.Type: GrantFiled: January 21, 1987Date of Patent: February 2, 1988Assignee: Seiko Epson CorporationInventors: Yoshio Shionozaki, Hiroshi Mukai, Tsuyoshi Obikawa, Shuhei Yamada, Rei Miyazaki
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Patent number: 4713456Abstract: A process for the preparation of a 5-acylpyrimidine of the formula ##STR1## in which R is an organic radical comprising reacting a methyl ketone of the formulaR--CO--CH.sub.3in a first stage with a formylating reagent in the presence of a base to form an enolketone of the formulaR--CO--CH.dbd.CH--OR.sup.10in which R.sup.10 represents hydrogen or a base radical, thereafter reacting the enolketone in 2nd and 3rd stages with formamidine or a formamidine salt, and with an amino-formylating agent, and, in a 4th stage heating to cyclize the compound formed.The end products, some of which are new, are intermediates for making herbicides.Type: GrantFiled: August 26, 1985Date of Patent: December 15, 1987Assignee: Bayer AktiengesellschaftInventors: Hans-Ludwig Elbe, Graham Holmwood
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Patent number: 4692183Abstract: Disclosed are diphenoxymethyl pyridines, their preparation and their use as herbicides.Type: GrantFiled: December 30, 1985Date of Patent: September 8, 1987Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Ingrid L. Evoy
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Patent number: 4692528Abstract: Process for preparing analgesic and narcotic antagonistic isoquinolines comprising:(a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol;(b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine;(c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone;(d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]-octane-6-propanol;(e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of --Cl, --Br, --I, p-MeC.sub.6 H.sub.4 SO.sub.3 and MeSO.sub.3 --.Type: GrantFiled: June 11, 1985Date of Patent: September 8, 1987Assignee: E. I. Du Pont De Nemours and CompanyInventor: Ashokkumar B. Shenvi
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Patent number: 4692450Abstract: Polycyclic salts of the formulaA.sup.- XN.sup.+ CH.sub.2 --(Y).sub.n --(CH.sub.2).sub.p --(Z).sub.q --L--(T).sub.r --M IwhereinA.sup.- is the anion of a strong organic or inorganic acid;XN.sup.+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R.sup.1, R.sup.2 and R.sup.3 ;n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15;Y is CH.sub.2, C(H,OH) or C(O);Z is O, S, CH.sub.2, C(O), NQ.sup.1, SO.sub.2, C(O)O, OC(O), C(O)N(Q.sup.1) or N(Q.sup.1)C(O);L is p-phenylene substituted by R.sup.4 ; andM is phenyl substituted by R.sup.5 and R.sup.6,T has one of the meanings given above, for Z or is C(CH.sub.3).sub.2, C.sub.2 H.sub.4, C(Q.sup.2).dbd.C(Q.sup.3), C.tbd.C, CH.sub.2 C(O), C(O)CH.sub.2, CH.sub.2 O or OCH.sub.2,R.sup.1 is a group Ar, Ar--C.sub.1-4 -alkyl, ArO or Arc(O),Ar is phenyl substituted by R.sup.7, R.sup.8 and R.sup.9 ;R.sup.2 and R.sup.3 individually are H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.6 H.sub.Type: GrantFiled: January 10, 1986Date of Patent: September 8, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Jean-Marie Cassal, Albrecht Edenhofer, Henri Ramuz
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Patent number: 4684220Abstract: 2-phenylpyridine derivatives represented by the general formula: ##STR1## wherein when Y is R--, Z is one of R--, RO--, ##STR2## when Y is RO--, Z is one of straight chain pentyl, ##STR3## and --CN; and when Y is one of ##STR4## Z is one of R--, RO-- and --CN; when Y is --CN, Z is one of RO--, ##STR5## and R is a straight chain alkyl group from 1 to 12 carbon atoms, are disclosed. The 2-phenylpyridine derivatives in accordance with the invention are particularly well-suited for use in nematic liquid crystal compositions for reducing the steepness and response time of the liquid crystal compositions in a liquid crystal display device.Type: GrantFiled: July 11, 1985Date of Patent: August 4, 1987Assignee: Seiko Epson Kabushiki KaishaInventors: Yoshio Shionozaki, Hiroshi Mukai, Tsuyoshi Obikawa, Shuhei Yamada
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Patent number: 4665174Abstract: A process for preparing cyclopentenone derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted ar(lower)alkyl and A is the residue of a nucleophilic agent from which a hydrogen atom is excluded, which comprises reacting a 3-hydroxy-4-cyclopentenone compound of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above with a nucleophilic agent of the formulaA--H (III)wherein A is as defined above.The cyclopentenone derivatives of the formula (I) are useful as pharmaceuticals, agricultural chemicals, perfumes and as intermediates for the preparation of agricultural chemicals, pharmaceuticals and perfumes.Type: GrantFiled: May 11, 1982Date of Patent: May 12, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4661596Abstract: There are disclosed compounds of the formula ##STR1## wherein X is --Ch.sub.2 CH.sub.2 --, --CH=CH--, ##STR2## Z is CR or N, when n=1; or Z is O, S, or NR, when n=0; R is hydrogen or loweralkyl;n is 0 or 1;R.sup.1 is hydroxy, amino, loweralkyl sulfonamido, perfluoro loweralkyl sulfonamido or OR;R.sup.2 is hydrogen or loweralkyl;R.sup.3 is hydrogen or loweralkyl; orR.sup.2 and R.sup.3 taken together form a benzene ring; andthe dotted line represents an optional double bond;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like.Type: GrantFiled: October 3, 1985Date of Patent: April 28, 1987Assignee: American Home Products CorporationInventors: Anthony F. Kreft, III, John H. Musser, Thomas W. Pattison, John P. Yardley
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Patent number: 4645771Abstract: The disclosure concerns novel 1-benzyl-1,2,3,6-tetrahydropyridine derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or a (1-4C)-alkyl radical, and benzene ring A bears one or two substituents selected from combinations of halogeno, (1-4C)-alkyl, (1-4C)-alkoxy, hydroxy, nitro, cyano, carboxamido, carboxyl, [(1-4C)-alkoxy]carbonyl, hydroxymethylene, amino, (1-4C)-alkanoylamino, (1-4C)-alkylsulphonamido, [(1-4C)-alkoxy]carbonyloxy, (1-4C)-alkanoyloxy and optionally substituted benzoyloxy radicals, and their pharmaceutically acceptable salts; pharmaceutical compositions thereof; analogy processes for their manufacture; and methods of medical treatment employing such derivatives.The compounds of formula I are inhibitors of the aggregation of blood platelets and are of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease.Type: GrantFiled: September 30, 1982Date of Patent: February 24, 1987Assignee: Imperial Chemical Industries PLCInventor: Stuart D. Mills