Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/434)
  • Patent number: 5554772
    Abstract: N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives, their N-oxide forms and pharmaceutically acceptable salts having gastrointestinal motility stimulating properties, compositions containing these compounds as active ingredient and methods of treating warm-blooded animals suffering from the decreased peristalsis of the gastrointestinal system.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: September 10, 1996
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Frans M. A. Van den Keybus
  • 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: 5525739
    Abstract: According to the invention, a new process has been found for the preparation of 2,2-difluoro-benzo[1,3]-dioxole-cabaldehydes of the formula (I) ##STR1## in which benzo[1,3]dioxole-carbaldehydes are chlorinated, the 2,2-dichloro-dichloromethylbenzo[1,3]dioxoles formed, which are likewise new, are partly fluorinated to give the 2,2-difluoro-dichloromethyl-benzo[1,3]dioxoles, which are likewise new, and these are then reacted with urotropin to give the desired compounds.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: June 11, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • Patent number: 5514816
    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 C1 or Br, or is --COOR.sup.2, --SiR.sup.2.sub.3 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 alkylphenyl, 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: May 12, 1995
    Date of Patent: May 7, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
  • 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: 5496848
    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.sup.2.sub.3 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: May 12, 1995
    Date of Patent: March 5, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Ka/ nel, Bruno Schaub
  • Patent number: 5493032
    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.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: February 20, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
  • Patent number: 5488167
    Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: January 30, 1996
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5488166
    Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: January 30, 1996
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5432290
    Abstract: A process for the preparation of 2,2-difluoro-1,3-benzodioxole from 2,2-dichlorol,3-benzodioxole. 2,2-Difluoro-1,3-benzodioxole is prepared by reaction of 2,2-dichloro-1,3-benzodioxole with potassium fluoride in the presence of an effective quantity of a catalyst selected from potassium hydrogen fluoride, sodium hydrogen fluoride, cesium hydrogen fluoride, rubidium hydrogen fluoride, and quaternary ammonium hydrogen fluoride. 2,2-Difluoro-1,3-benzoxodiole is an intermediate compound which is used particularly for the preparation of products for agricultural chemistry and for the synthesis of pharmaceutical products.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: July 11, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Casado, Michel Crochemore, Bernard Langlois
  • Patent number: 5420308
    Abstract: According to the invention, a new process has been found for the preparation of 2,2-difluoro-benzo[1,3]-dioxole-carbaldehydes of the formula (I) ##STR1## in which benzo[1,3]dioxole-carbaldehydes are chlorinated, the 2,2-dichloro-dichloromethylbenzo[1,3]dioxoles formed, which are likewise new, are partly fluorinated to give the 2,2-difluoro-dichloromethyl-benzo[1,3]dioxoles, which are likewise new, and these are then reacted with urotropin to give the desired compounds.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: May 30, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • 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: 5416112
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of ##STR2## Z.sub.1 and Z.sub.2 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN and alkyl of 1 to 3 carbon atoms, R.sub.3 is hydrogen or alkyl of 1 to 3 carbon atoms, m is an integer from 0 to 6, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are individually selected from the group consisting of hydrogen, halogen, --CN, --NO.sub.2, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.10, --(CH.sub.2).sub.n --CX.sub.3, --O--(CH.sub.2).sub.n CX.sub.3 and --S--(CH.sub.2).sub.n --CX.sub.3, R.sub.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: May 16, 1995
    Assignee: Roussel Uclaf
    Inventor: Elizabeth A. Kuo
  • Patent number: 5384415
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: January 24, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5380883
    Abstract: A compound of the formula ##STR1##
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: January 10, 1995
    Assignee: Roussel-Uclaf
    Inventors: Marc Benoit, Sylvain Laugraud, Jean-Louis Brayer
  • Patent number: 5350865
    Abstract: A novel process for the preparation of benzodioxoles of the formula (I) ##STR1## in which Hal represents a chlorine atom or a fluorine atom, from dichlorobenzodioxole using stoichiometric quantities of anhydrous hydrofluoric acid.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: September 27, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Erwin Schnalke, Josef Heinrich, Fritz Doring
  • 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: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5298661
    Abstract: Charge transporting materials having general formula (I): ##STR1## R.sup.1 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; an aralkyl group; a nitro group; an unsubstituted or substituted aryl group; a halogen; an amino group; an unsubstituted or substituted dialkylamino group; R.sup.2 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; or a halogen; R.sup.3 represents hydrogen; an alkyl group having 1 to 4 carbon atoms; an alkoxyl group having 1 to 4 carbon atoms; a halogen; a dialkylamino group; an amino group; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; a methylenedioxy group; an aralkyl group; or an unsubstituted or substituted aryl group; R.sup.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 29, 1994
    Assignee: Ricoh Company, Ltd.
    Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
  • Patent number: 5292962
    Abstract: Intermediates to 1-phenyl-3-naphthalenyloxypropanamines which selectively inhibit serotonin uptake and are useful for treating a variety of disorders linked to decreased neurotransmission of serotonin in mammals.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: March 8, 1994
    Assignee: Eli Lilly and Company
    Inventors: Charles A. Alt, Roger L. Robey, Eldon E. Van Meter
  • Patent number: 5281725
    Abstract: New 2,2-dihalogeno-benzo[1,3]dioxoles substituted in the 4-position, of the general formula (I) ##STR1## in which R represents fluorine, chlorine, bromine or nitro andHal represents chlorine or fluorine, and their use as starting substances for the synthesis of highly active compounds, for example in the field of plant protection and pharmaceuticals.The compounds of the formula (I) can be prepared by analogous processes, for example by chlorination from corresponding benzo[1,3]dioxoles substituted in the 4-position, and these substances according to the invention can be further reacted with hydrogen fluoride to give substances to which the invention likewise relates.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: January 25, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • Patent number: 5260460
    Abstract: According to the invention, a new process for the preparation of fluorine-substituted aminobenzodioxoles and -benzodioxanes of the formula (I) ##STR1## in which n represents an integer 1 or 2, has been found, in which fluorine-substituted nitrohalogeno-benzodioxoles and -benzodioxanes, which are likewise new, are hydrogenated. The novel intermediates are obtained from fluorine-substituted benzodioxoles and benzodioxanes by halogenation and subsequent nitration. The amino compounds are important starting materials for highly active biocides.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: November 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Andres, Albrecht Marhold
  • Patent number: 5241086
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: August 31, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5223539
    Abstract: The present invention relates to compounds of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Z can be: ##STR2## wherein R.sup.3 is alkyl having 1 to 6 carbon atoms and, when n is greater than 1, each R.sup.3 can be the same or different; and n is an integer from 1 to 3;R.sup.1 and R.sup.2 can each independently be hydrogen, straight or branched chain alkyl, or cycloalkyl having 3 to 8 carbon atoms which can optionally be substituted at one or more positions by alkyl of 1 to 6 carbon atoms; X is oxygen, sulfur, NR.sup.4, wherein R.sup.4 is hydrogen or alkyl having 1 to 4 carbon atoms, C.dbd.O, CHOH, or CH.sub.2 ; Y is hydrogen, alkoxy, halogen, alkyl, or hydroxy; and m is an integer from 0 to 3. The compounds are antagonists of platlet-activating factor (PAF).
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: June 29, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Roger A. Nosal, Michael A. Stealey, Richard M. Weiser
  • Patent number: 5212173
    Abstract: Pharmacologically active compounds corresponding to the formula I ##STR1## in which n represents 2-5,m represents 2-6,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 represents an OR.sup.4 group in which R.sup.4 denotes lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.2 represents a ##STR2## group in which R.sup.5 and R.sup.6 independently of one another each denote hydrogen, lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a saturated 5- or 6-membered heterocycle,R.sup.3 represents a saturated monocyclic or bicyclic hydrocarbon group which is derived from terpenes and has 10 or 11 carbon atoms, andZ represents oxygen or, if R.sup.3 is a dihydronopyl group, Z may also represent sulfur,and salts thereof.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
  • Patent number: 5202351
    Abstract: A novel 1-phenylalkyl-3-phenylurea derivative represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.5 represent independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; R.sup.2 represents hydrogen or C.sub.1 -C.sub.15 alkyl; R.sup.3 represents C.sub.1 -C.sub.15 alkyl or R.sup.3 represents together with R.sup.2 C.sub.2 -C.sub.9 alkylene; R.sup.4 and R.sup.5 represent independently C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; X represents oxygen or sulfur; Y represents --O--(CH.sub.2).sub.l --O-- wherein l is an integer of 1 to 3 or --(CH.sub.2).sub.p -- wherein p is an integer of 3 to 5; m is 0 or an integer of 1 to 5; and n is 0 or an integer of 1 to 3, is provided. The 1-phenylalkyl-3-phenylurea derivative (I) have the action of reducing cholesterol in blood by ACAT inhibition, and therefore, useful for treating hyperlipemia and atherosclerosis.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: April 13, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Sekiya, Shinya Inoue, Chiaki Hyodo, Hiromi Okushima, Kohei Umezu, Kazuo Suzuki
  • Patent number: 5164518
    Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: November 17, 1992
    Assignee: Iowa State University Research Fondation Inc.
    Inventor: Richard C. Larock
  • Patent number: 5106867
    Abstract: The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: April 21, 1992
    Assignee: American Cyanamid Company
    Inventors: Jonathan D. Bloom, Thomas H. Claus, Vern G. DeVries, Jo A. Dolan, Minu D. Dutia
  • 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: 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: 4975451
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; and Ar.sup.1 is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 2-methyl[1-1'-biphenyl]-3-yl, or 6-phenoxy-2-pyridyl, exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively nontoxic to fish.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: December 4, 1990
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
  • Patent number: 4940807
    Abstract: Electron-rich aromatic compounds are selectively brominated in good yield in the presence of water using potassium tribromide as the brominating agent. In this way monobromination is favored and dibromination is suppressed as compared to the use of elemental bromine as the brominating agent.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: July 10, 1990
    Assignee: Ethyl Corporation
    Inventor: Robert N. DePriest
  • Patent number: 4904775
    Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof and possessing antibacterial activity, and intermediates to compounds of formula I having the formula
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: February 27, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, Peter H. Ermann
  • Patent number: 4889870
    Abstract: There are provided new 2-(2,2-difluorocyclopropyl)alkyl esters of general formula I ##STR1## in which Y, R.sub.1-7 and n have the meanings given in the description and processes for their preparation. The new compounds can be used to combat insects and mites.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: December 26, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Peter Wegner, Hans-Rudolf Kruger, Dietrich Baumert, Hartmut Joppien
  • 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: 4885368
    Abstract: Novel radical ion salts of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each hydrogen, methyl, ethyl, phenyl, methoxy, ethoxy, fluorine, chlorine or bromine, or R.sup.1 or R.sup.1 and R.sup.3 may furthermore be tert-butyl and/or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 together may in each case form a radical of the formula ##STR2## where z is 0, 1, 2 or 3, and the fused aromatic rings are unsubstituted or monosubstituted or disubstituted by chlorine, bromine, methyl and/or methoxy, M.sup.m.sym. is an m-valent alkali metal, alkaline earth metal, transition metal, tin, lead, thallium, ammonium, phosphonium, arsonium or stibonium ion, k is from 1 to 5, l is from 0.1 to 4, m is from 1 to 3, n is from 0.1 to 4, x is from 0 to 2 and y is from 0 to 6, and k, l, n, x and y may furthermore be non-integral numbers and (l+x)=n.m, are electrically conductive in the crystalline state. A number of the salts are stable at 300.degree. C. and above.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: December 5, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegfried Huenig, Alexander Aumueller, Peter Erk
  • 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: 4861903
    Abstract: A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula ##STR1## in which the substituents have the meaning given in the description of the invention.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: August 29, 1989
    Assignee: Zambon spa
    Inventors: Claudio Giordano, Graziano Castaldi
  • 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: 4791139
    Abstract: 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: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • 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: 4780550
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R hu d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: October 25, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Carter
  • 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: 4761491
    Abstract: 2-Substituted-1,3-dioxacycloalkanes (also known as acetonides) (such as ##STR1## (4-hydroxy-2,2-dimethyl-1,3-benzodioxole)) are prepared by reacting a diol (such as 1,2,3-trihydroxybenzene) and a diunsaturated ether (such as diisopropenyl ether). The reaction is exothermic and produces a ketone as the only by-product. The invention has utility in hydroxyl moiety "protection" and in pesticide synthesis.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: August 2, 1988
    Assignee: The Dow Chemical Company
    Inventor: Robert H. Heistand, II
  • Patent number: 4736057
    Abstract: This invention concerns novel (4-substituted-2-phenylcyclohexyl)alkenoic and alkanoic acid derivatives of the formula I wherein one of Ra and Rb is hydrogen, hydroxy, (1-6C)alkyl, (1-6C)alkoxy, (3-6C)alkenyloxy or phenyl(1-4C)alkoxy and the other of Ra and Rb is hydrogen, (1-6C)alkyl, (1-6C)alkoxy or (3-6C)alkenyloxy; or Ra and Rb together form a (2-4C)alkylenedioxy or oxo group; benzene ring X optionally bears a substituent selected from halogeno, (1-6C)alkyl, (1-6C)alkoxy, hydroxy, (2-6C)alkanoyloxy, (1-6C)alkanoylamino, trifluoromethyl and nitro; n is 3-5; Y is ethylene or vinylene; and in the cyclohexane ring, the substituents at positions 1 and 2 have cis- or trans-relative stereochemistry; and the pharmaceutically acceptable salts, (1-6C)alkyl esters and (1-6C)alkanesulphonamides thereof. The compounds of formula I possess valuable pharmacological properties of use in medicines.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: April 5, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Allen J. Guildford, Ralph W. Turner
  • Patent number: 4730060
    Abstract: New agents of carbacyclin derivatives are disclosed, which are represented by the following formula: ##STR1## wherein A is a --CH.dbd.CH-- or --C.tbd.C-- group. B is a substituted or unsubstituted indanyl group, substituted or unsubstituted benzodioxanyl group, substituted or unsubstituted benzodioxolanyl group or 2,3,5,6,7, 8-hexahydrobenzodioxanyl group. D is --CH.sub.2 -- or --O--. .about.OH group represents .alpha. or .beta. configuration of OH group; and ##STR2## These compounds are useful as anit-ulcer, anti-hypertensive or anti-thrombotic agents.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: March 8, 1988
    Assignee: Kotobuki Seiyaku Co. Ltd.
    Inventors: Tsuyoshi Tomiyama, Akira Tomiyama, Takashi Yanagisawa, Masayuki Yokota
  • Patent number: 4713458
    Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.
    Type: Grant
    Filed: August 21, 1984
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Kevin A. Frazier, James M. Renga
  • Patent number: 4692166
    Abstract: Use for dyeing keratinous fibres, and especially human hair, on a compound corresponding to the formula: ##STR1## in which X denotes a bromine or chlorine atom.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: September 8, 1987
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Herve Andrean, Jean Cotteret