Chalcogen Attached Indirectly To The Ring System By Nonionic Bonding Patents (Class 549/445)
  • Patent number: 5723489
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1.These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.
    Type: Grant
    Filed: May 7, 1996
    Date of Patent: March 3, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Philip M. Sher, William N. Washburn, Kathleen M. Poss
  • Patent number: 5686633
    Abstract: Inks, particularly inks for ink jet printing, contain at least one compound of the formula I ##STR1## as a stabilizer. The symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.3 ' and R.sub.4 ' are as defined in claim 1. The compounds are in part novel and are suitable for use as light stabilizers for organic materials.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: November 11, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Eric Vieira, Hugh Stephen Laver
  • Patent number: 5686460
    Abstract: The present invention relates to the carbocyclic diarylmethylene derivatives of formula (I): ##STR1## and to their use in therapeutics, especially as drugs with anti-inflammatory and analgesic properties.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: November 11, 1997
    Assignee: Laboratoires UPSA
    Inventors: Eric Nicolai, Michele Launay, Dominique Potin, Jean-Marie Teulon
  • Patent number: 5612381
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 18, 1997
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5599952
    Abstract: Methods of producing carboxylic acid ester derivatives of formulae (I) and (II), which are useful, for instance, as intermediates for producing an anti-hypercholesterolemic agent having an inhibitory effect on HMG-CoA Reductase: ##STR1## wherein R.sup.1 and R.sup.2 are independently a protective group for hydroxyl group, or R.sup.1 and R.sup.2 integrally constitute a protective group for hydroxyl groups; R.sup.3 is an alkyl group, or an aryl group; and R.sup.4 is a substituted aryl group, a substituted heterocyclic group, a substituted vinyl group, or a substituted cycloalkenyl group; and ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are respectively the same as defined in the above formula (I), are disclosed. In addition, intermediates for use in these methods of producing the carboxylic acid ester derivatives are disclosed.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: February 4, 1997
    Assignee: Fujirebio Inc.
    Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Eiko Mori, Hisako Kobayashi, Hiroshi Ikawa
  • Patent number: 5559105
    Abstract: A compound of formula: ##STR1##
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: September 24, 1996
    Assignee: SmithKline Beecham Corporation
    Inventors: Deborah L. Bryan, John D. Elliott
  • Patent number: 5541204
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: July 30, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: Philip M. Sher, William N. Washburn, Kathleen M. Poss
  • Patent number: 5536853
    Abstract: Compounds of Formula 1 bind opioid receptors: ##STR1## wherein X and Y are each independently ##STR2##
    Type: Grant
    Filed: April 11, 1994
    Date of Patent: July 16, 1996
    Assignee: Chiron Corporation
    Inventors: David C. Spellmeyer, Walter H. Moos, Eric J. Martin, Ronald N. Zuckermann, Gregory Stauber, Kevin R. Shoemaker, Dane Goff
  • Patent number: 5508461
    Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: April 16, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
  • Patent number: 5472984
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: December 5, 1995
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5420301
    Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: May 30, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
  • Patent number: 5420273
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Hoffman-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5387593
    Abstract: Novel piperazinyl- and piperidinyl-cyclohexanols of the following formula are useful as anxiolytic agents and have other psychotropic properties ##STR1##
    Type: Grant
    Filed: February 17, 1994
    Date of Patent: February 7, 1995
    Assignee: Briston-Myers Squibb
    Inventors: Ronald J. Mattson, John D. Catt
  • Patent number: 5369127
    Abstract: Compounds of the formula ##STR1## where W is (CH.sub.2).sub.n where n is 1 or 2, or n is O and W represents lower alkyl groups attached to each oxygen;m is an integer between 1 and 8;R.sub.1 is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.4, CONR.sub.5 R.sub.6, CONR.sub.5 SO.sub.2 R.sub.7, CH.sub.2 OH, CH.sub.2 OR.sub.7, CH.sub.2 O--COR.sub.7, CH.sub.2 O--CONR.sub.5, R.sub.7, CH.sub.2 OCOOR.sub.7, CH.sub.2 NH.sub.2, CH.sub.2 NR.sub.5 R.sub.6, CH.sub.2 NR.sub.5 COR.sub.7, CHO, CH(OR.sub.8).sub.2, CHOR.sub.9 O, --COR.sub.10, CR.sub.10 (OR.sub.8).sub.2, or CR.sub.10 OR.sub.9 O, where R.sub.4 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.4 is phenyl or lower alkylphenyl, R.sub.5 and R.sub.6 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.7 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.8 is lower alkyl, and R.sub.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: November 29, 1994
    Assignee: Allergan, Inc.
    Inventors: Robert M. Burk, David F. Woodward
  • Patent number: 5315018
    Abstract: The present invention relates to the hydroxymethylation of aromatic compounds and the subsequent transformation of the hydroxymethylated aromatic compounds to the polyalkoxyalkylene derivative thereof.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: May 24, 1994
    Assignee: Roussel-Uclaf
    Inventors: Stuart J. Penny, Roy H. Valentine
  • Patent number: 5276205
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 carboalkoxy, C.sub.2 -C.sub.5 alkylcarbonyl, nitro or cyano;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 haloalkenoxy, nitro, cyano, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 carboalkoxy;R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy;provided that:R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen; orR.sub.1 and R.sub.2 taken together are C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy;R.sub.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: January 4, 1994
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • Patent number: 5270301
    Abstract: The present invention relates to certain fluoro-amide derivatives, as described herein, which are human leukocyte elastase (HLE) inhibitors making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated, including treatment of tissue degenerative diseases such as pulmonary emphysema. The invention also includes intermediates useful in the synthesis of these fluoro-amide derivatives, processes for preparing them, pharmaceutical compositions containing such peptide derivatives and methods for their use.
    Type: Grant
    Filed: May 7, 1990
    Date of Patent: December 14, 1993
    Assignee: ICI Americas Inc.
    Inventor: Donald J. Wolanin
  • Patent number: 5258529
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## where R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallycarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5250574
    Abstract: An aromatic compound of the formula: ##STR1## wherein R.sup.1 is, the same or different, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; R.sup.2 is a hydrogen atom or a methyl group; R.sup.3 is, the same or different, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.2 alkoxy group or a C.sub.1 -C.sub.2 haloalkoxy group, or two adjacent R.sup.3 s may be combined together to represent a C.sub.1 -C.sub.2 alkylenedioxy group optionally bearing one or two substituents selected from halogen and methyl; p is an integer of 2 to 5; q is an integer of 0 to 5, which is useful for control of insect pests.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: October 5, 1993
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Noriyasu Sakamoto, Akira Shuto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda
  • Patent number: 5248834
    Abstract: Pesticidal compounds of formula II: R.sub.A CR.sub.3 .dbd.CR.sub.4 CHDR.sub.Bin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 - in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 alkyl groups.R.sub.3 and R.sub.4 which may be identical or differ, represent hydrogen halogen or C.sub.1 -C.sub.6 alkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [1R, cis] 2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal,the configuration of R.sub.A and CHDR.sub.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: September 28, 1993
    Assignee: British Technology Group Limited
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay, Ahmet Baydar
  • Patent number: 5194628
    Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 l in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: March 16, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
  • Patent number: 5153182
    Abstract: Insecticided compositions comprising (a) a mixture of methylenedioxybenzene derivative compounds having in the benzene ring one, two and three substituents of the formula --CH.sub.2 O--(CH.sub.2 CH.sub.2 O).sub.2 --R.sub.1 wherein R.sub.1 is hydrogen or an alkyl group having from 1 to 4 carbon atoms and (b) an insecticide selected from the group consisting of synthetic pyrethroids, carbamates, organic phosphorates, avermentines and insect growth regulators.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: October 6, 1992
    Assignee: Endura S.p.A.
    Inventor: Antonio Tozzi
  • Patent number: 5024743
    Abstract: The present invention provides compounds of the general formula: ##STR1## where R.sub.1 is a hydrogen atom or a methoxy or ethoxy radical and R.sub.2 and R.sub.3 are hydrogen atoms or R.sub.2 and R.sub.3 together represent an aromatic carbon-carbon bond and R.sub.1 is a hydrogen atom, a hydroxyl group or an ethoxy radical; and the pharmaceutically acceptable salts thereof.The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them, as well as their use in therapy.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: June 18, 1991
    Assignee: Madaus GmbH & Co.
    Inventors: Klaus Gorler, Gunter Krumbiegel, Michael Hanack, Lakshmina R. Subramanian
  • Patent number: 5011950
    Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: April 30, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4988826
    Abstract: The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ --CH.sub.2 --Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: January 29, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robin A. E. Carr, Lyn Powell
  • Patent number: 4940806
    Abstract: Novel substituted 2-(1H-1,2,4-triazolyl)-1-phenylethan-1-one ketals of the general formula ##STR1## wherein one of the two phenyl substituents is in 2-position and the other is in 4-position, and wherein R.sub.a is halogen, methyl or C.sub.1 -C.sub.3 haloalkoxy, and U and V are each independently of the other C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.6 alkoxy, or together are an alkylene bridge selected from ##STR2## wherein R.sub.1 to R.sub.5 are as defined herein, and the acid addition salts and metal complex salts, have microbicidal properties and are especially suitable for controling phytopathogenic microorganisms. They can be used in the form of plant protective or seed dressing agents for preventing or controlling plant pathogens.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: July 10, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4918092
    Abstract: Compounds having the formula I: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: April 17, 1990
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Richard Frenette, Robert N. Young, Masatoshi Kakushima
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4876270
    Abstract: Novel substituted .alpha.,.alpha.-diphenylethylene derivatives of formula I ##STR1## in which R.sub.1 and R.sub.4 independently of one another each represents hydrogen, hydroxy, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.3 -alkoxy substituted by from 1 to 7 halogen atoms, alkoxyalkoxy having a total of from 2 to 6 carbon atoms, C.sub.3 -C.sub.5 -alkenyloxy or C.sub.3 -C.sub.5 -alkynyloxy;R.sub.2 and R.sub.3 independently of one another each represents hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.5 -alkoxy or nitro; orR.sub.1 and R.sub.2 together represent a radical --O--CH.sub.2 --O-- or --O--CH.sub.2 --CH.sub.2 --O--;R.sub.5 and R.sub.6 independently of one another each represents hydrogen, halogen or methyl;R.sub.7 and R.sub.
    Type: Grant
    Filed: February 10, 1988
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Rudolf Waespe
  • Patent number: 4840971
    Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4838924
    Abstract: This invention relates to novel compounds of formula [I], a process for their production, and their use as a herbicide. ##STR1## wherein A represents the bond ##STR2## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group;B represents a hydrogen atom, a methyl group or a methoxy group; andAr represents one member selected from the group consisting of ##STR3## in which R.sup.1 to R.sup.38, are as defined hereinafter.
    Type: Grant
    Filed: April 1, 1987
    Date of Patent: June 13, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Takematsu, Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 4837327
    Abstract: Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: June 6, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4803290
    Abstract: Substituted 5'-nonanol/5'-nonene compounds which exhibit important antimicrobial and antifungal activity, compositions and methods of delivery against pathovars and pathogens, and methods of synthesis from commonly available reactants. The antimicrobial composition active ingredient is one or more substituted 1,2-alkylidenedioxybenzene compounds of the formula: ##STR1## where R.sub.3 is selected from 5'-nonanol and 5'-nonene, and R.sub.1 and R.sub.2 are selected from H and C.sub.1 -C.sub.5 alkyl, alkenyl and alkynyl groups. The preferred compounds are 5-(5'-hydroxy- 5'- nonanyl)-1,1-methylenedioxybenzene and 4-(5'-non-4'-enyl)-1,2-methylenedioxybenzene. Compositions including these compounds exhibit antimicrobial activity against a variety of pathogens and pathovars, e.g., Xanthomonas campestris spp. bacteria, antifungal activity against a variety of fungi and bacteria, and are highly specific, e.g.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: February 7, 1989
    Assignee: PCRI, Inc.
    Inventors: Basil A. Burke, Muraleedharan Nair
  • Patent number: 4789743
    Abstract: The invention relates to a process for the preparaton of compounds of the formula I by reacting an alkali metal alcoholate with a compound of the formula II in the presence of an aliphatic ester such as methyl formate, and then condensing guanidine with the resulting compound of the formula III.The compound of the formula II can be prepared by reacting the corresponding benzaldehyde with acrylonitrile in the presence of diazabicyclo-2,2,2,-octane.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: December 6, 1988
    Assignee: Societe Anonyme: Sanofi Pharma S.A. - Succursale de Carouge
    Inventor: Abram Becker
  • Patent number: 4778935
    Abstract: Fluorinated nitroalcohols of the formula (I) ##STR1## process for their preparation by reaction of fluoronitroalkane of the formula (II) ##STR2## with a carbonyl compound of the formula (III) ##STR3## fluorinated aminoalcohols of the formula (IV) ##STR4## and a process for their preparation by hydrogentation of compounds of the formula (I).
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: October 18, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert K. Beck, Dieter Seebach
  • Patent number: 4777185
    Abstract: Pesticidal compounds of formula IR.sub.A CR.sub.3 .dbd.CR.sub.4 CHDR.sub.B Iin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 --in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 alkyl groups.R.sub.3 and R.sub.4 which may be identical or differ, represent hydrogen halogen or C.sub.1 -C.sub.6 alkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [1R, cis]2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal,the configuration of R.sub.A and CHDR.sub.
    Type: Grant
    Filed: April 5, 1985
    Date of Patent: October 11, 1988
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. Singh Khambay, Ahmet Baydar
  • Patent number: 4772633
    Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
  • Patent number: 4721795
    Abstract: Compounds suitable for being used as lubricants, having general formula:(I) RO--(C.sub.3 F.sub.6 O).sub.m --(CFXO).sub.n --CFX--L, or(II) R"CFXO--(C.sub.3 F.sub.6 O).sub.x (CFXO).sub.y --(C.sub.2 F.sub.4 O).sub.z --(CFX--L, whereR=--CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7X=F, --CF.sub.3R"=F, --CF.sub.3, --C.sub.2 F.sub.5m=an integer from 3 to 100n=a finite integer, or=zero, wherefore m+n ranges from 3 to 100, provided that, if n is finite, m/n ranges from 5 ro 20 and R is preferably=CF.sub.3, if n=zero, R is preferably --C.sub.2 F.sub.5 or --C.sub.3 F.sub.7x=a finite integer, or=zeroy, z=finite integers, such that x+y+z ranges from 5 to 200, while x+z/y ranges from 5 to 0.5, provided that when x=zero, z/y ranges from 1 to 0.5 and y+z ranges from 5 to 200 n while X is preferably F, and R"=LL=group A--Y, whereA=--CH.sub.2 O--, --CH.sub.2 --O--CH.sub.2, --CF.sub.2, CF.sub.2 O--,Y=an organic radical covered by one of the following formulas: ##STR1## where R.sub.1, R.sub.2 =alkyls C.sub.1 -C.sub.3,E=CHR.
    Type: Grant
    Filed: December 31, 1984
    Date of Patent: January 26, 1988
    Assignee: Montedison S.p.A.
    Inventors: Gerardo Caporiccio, Ezio Strepparola, Mario A. Scarati
  • Patent number: 4611004
    Abstract: 3-Phenoxybenzyl-(2-phenyl-2,2-alkylene-ethyl) ethers and -thioethers of the formula ##STR1## wherein A is oxygen or sulfur,R.sub.1 is hydrogen, methyl, cyano or ethinyl,R.sub.2 and R.sub.3 are hydrogen, halogen or C.sub.1 -C.sub.5 -alkyl,n is 2 to 4,X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.5 -alkoxy or C.sub.1 -C.sub.5 -haloalkoxy,X.sub.2 is hydrogen, halogen or C.sub.1 -C.sub.5 -alkyl, or together with X.sub.1 in the adjacent position is methylenedioxy, andX.sub.3 and X.sub.4 are each hydrogen or halogen.A process for producing these compounds and their use for controlling pests are described.
    Type: Grant
    Filed: March 27, 1985
    Date of Patent: September 9, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell
  • Patent number: 4599362
    Abstract: The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R.sup.1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R.sup.2 stands for a hydrogen atom, or a methyl or ethyl group, R.sup.3 stands for a halogen atom, or a methyl or methoxyl group, R.sup.4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R.sup.4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or thioethers and a use of these ethers or thioethers.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
    Type: Grant
    Filed: November 18, 1983
    Date of Patent: July 8, 1986
    Assignee: Mitsuitoatsu Chemicals, Inc.
    Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Akira Hosono, Kengo Oda, Yutaka Kubota, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
  • Patent number: 4570005
    Abstract: 2-Arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different,are produced by reacting a compound represented by the following formula (V): ##STR4## with a compound represented by the following formula (VI):B--CH.sub.2 --D (VI)wherein Ar, R and B are defined above, A is a halogen atom and D is Y--H in which Y is as defined above,in the presence of a base in dimethylsulfoxide or sulfolane.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: February 11, 1986
    Assignee: Mitsuitoatsu Chemicals Inc.
    Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Kenji Kodaka, Tsutomu Ishii, Teruhiko Toyama, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
  • Patent number: 4552894
    Abstract: A 2-fluoroethoxy-substituted benzene derivative represented by the general formula ##STR1## wherein X represents an oxygen or sulfur atom, R.sup.1 and R.sup.2 represent a hydrogen atom or a lower alkyl group, n represents 0 or 1, and A represents a group of the general formula ##STR2## in which R.sup.3 and R.sup.4 represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkylthio group or a methylenedioxy group, R.sup.5 and R.sup.6 represent a hydrogen atom or a lower alkyl group, and p and m represent 0 or 1.This compound is useful as an active ingredient of insecticidal and acaricidal agents, and can be produced by reacting a compound of the general formula ##STR3## with a compound of the general formulaA--D (IV)wherein in general formulae (III) and (IV), A, R.sup.1, R.sup.
    Type: Grant
    Filed: January 24, 1984
    Date of Patent: November 12, 1985
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsuneo Inoue, Kiyoshi Nakatani, Kengo Oda, Tutomu Ishii, Takatoshi Udagawa, Shiro Shiraishi
  • Patent number: 4546183
    Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group --NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and di-lower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: October 8, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
  • Patent number: 4526993
    Abstract: Conjugated dienols for providing cure sites to air-drying acrylic finishes are prepared from conjugated dienoic acids by conversion to an activated ester followed by sodium borohydride reduction thereof.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: July 2, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Chaucer C. Tang
  • Patent number: 4508925
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 9, 1983
    Date of Patent: April 2, 1985
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4503033
    Abstract: A cosmetic composition for the treatment of the oily appearance of hair and skin so as to reduce or eliminate said oily appearance comprises in a suitable cosmetic vehicle at least one compound of the formula ##STR1## wherein R.sub.1 is either ##STR2## wherein r' and r" can be hydrogen, 2-hydroxy ethyl, 2-hydroxy propyl or 2,3-dihydroxy propyl, R.sub.2 is ##STR3## wherein R.sub.4 is ##STR4## wherein R.sub.5 is --OH, --OCH.sub.3, --OC.sub.4 H.sub.9 or --OCH.sub.2 COOH and R.sub.3 is hydrogen or methyl, or R.sub.2 and R.sub.3 together form ##STR5## wherein m is 3-5 and n is 2-5.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: March 5, 1985
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Claude Bouillon, Jean Maignan
  • Patent number: 4482728
    Abstract: Certain polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes are useful for insect control especially as insect chemosterilants and oviposition inhibitors. The benzyl-3,4-methylenedioxybenzenes also find utility as growth inhibitors for mosquito larvae.
    Type: Grant
    Filed: April 20, 1982
    Date of Patent: November 13, 1984
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Leonard Jurd
  • Patent number: 4481142
    Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and dilower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.
    Type: Grant
    Filed: October 27, 1982
    Date of Patent: November 6, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser