Cyclopropyl In Acid Moiety Patents (Class 560/124)
  • Publication number: 20020010361
    Abstract: There is provided a process for producing 3,3-dimethyl-2-formylcyclopropanecarboxylic ester of formula (1): 1
    Type: Application
    Filed: January 26, 2001
    Publication date: January 24, 2002
    Inventors: Koji Hagiya, Ichiro Komoto, Akio Kurihara
  • Patent number: 6333428
    Abstract: The present invention provides fluorobicyclo[3.1.0]hexane derivatives represented by the formula [wherein R1 and R2 are the same or different and each represents a hydrogen atom, a C1-10 alkyl group, a C3-8 cycloalkyl group or a C3-8 cycloalkyl-C1-5 alkyl group: Y1 and Y2 are the same or different and each represents a hydrogen atom, a C1-10 alkylthio group, a C3-8 cycloalkylthio group, a C3-8 cycloalkyl-C1-5 alkylthio group, a C1-5 alkoxy group, a C3-8 cycloalkoxy group or a C3-8 cycloalkyl-C1-5 alkoxy group; or one represents a hydrogen atom and the other represents a hydroxyl group, a C1-5 alkoxy group, a C3-8 cycloalkoxy group or a C3-8 cycloalkyl-C1-5 alkoxy group; or Y1 and Y2 together represent an oxygen atom or —X(CH2)nX— (X represents an oxygen atom or a sulfur atom: N is 2 or 3)], pharmaceutically acceptable salts thereof, or hydrates thereof.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: December 25, 2001
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Atsuro Nakazato, Toshihito Kumagai, Kazunari Sakagami, Kazuyuki Tomisawa
  • Publication number: 20010037036
    Abstract: There is disclosed chiral copper complex catalyst composition, which is obtained by contacting an optically active N-salicylideneaminoalcohol compound of formula (1): 1
    Type: Application
    Filed: January 23, 2001
    Publication date: November 1, 2001
    Inventors: Gohfu Suzukamo, Makoto Itagaki, Michio Yamamoto
  • Patent number: 6297410
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, cyclopropane carboxaldehyde is condensed with malonic acid to form 3-cyclopropylacrylic acid; 3-cyclopropylacrylic acid is halogenated to form (E,Z)-1-halo-2-cyclopropylethylene; and (E,Z)-1-halo-2-cyclopropylethylene is dehydrohalogenated to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
    Type: Grant
    Filed: January 12, 2000
    Date of Patent: October 2, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
  • Patent number: 6291409
    Abstract: A process for modifying an unsaturated polyol fatty acid ester stock, such as an unsaturated triacylglycerol oil, to enhance its fluidity and/or oxidative stability is provided. The method includes reacting the unsaturated polyol fatty acid ester stock with cyclopropanating agent. Lubricants containing cyclopropanated polyol fatty acid ester and methods for their production and use are also provided.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: September 18, 2001
    Assignee: Cargill, Inc.
    Inventors: Dharma R. Kodali, Keqiang Li
  • Publication number: 20010014755
    Abstract: An ester compound, which is a production intermediate of a pyrethroid compound, given by formula 1
    Type: Application
    Filed: December 22, 2000
    Publication date: August 16, 2001
    Inventor: Tomonori Yoshiyama
  • Patent number: 6268525
    Abstract: The present invention provides an advantageous method for producing an optically active chrysanthemic acid. Disclosed is a method for producing an optically active chrysanthemic acid whose trans isomer ratio and optical purity are improved, which comprises reacting chrysanthemic acid having a trans isomer ratio of not less than 50% and an optical purity of not less than 10% e.e. with an optically active organic amine to optically resolve said chrysanthemic acid.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: July 31, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Itagaki, Goufu Suzukamo, Kazuaki Sasaki, Kunihiko Fujita
  • Patent number: 6262298
    Abstract: The invention relates to a process for the C-alkylation of dialkyl malonates, in which a dialkyl malonate is reacted with an alkyl halide in the presence of potassium carbonate as a hydrogen halide acceptor in an inert solvent, and a phase-transfer catalyst is not added until from 50 to 80% of the dialkyl malonate has reacted. The phase-transfer catalyst may be, for example, a tetraalkylammonium salt or a tetraalkylammonium hydroxide, a tetraalkylphosphonium salt or a tetraalkylphosphonium hydroxide or a crown ether.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: July 17, 2001
    Assignee: Huels Aktiengesellschaft
    Inventors: Josef Metz, Clemens Osterholt
  • Patent number: 6258975
    Abstract: Provided is an industrially useful process for producing an optically active 2-hydroxy-4-arylbutyric acid or its ester. An optically active acyloxysuccinic anhydride is reacted with an aromatic compound in the presence of a Lewis acid to produce an optically active 2-acyloxy-4-oxo-4-arylbutyric acid. The 2-acyloxy-4-oxo-4-arylbutyric acid is converted to an optically active 2-acyloxy-4-arylbutyric acid through catalytic reduction. The 2-acyloxy-4-arylbutyric acid is hydrolyzed in the presence of an acid or an alkali to produce an optically active 2-hydroxy-4-arylbutyric acid. The 2-hydroxy-4-arylbutyric acid is reacted with an alcohol in the presence of an acid to produce an optically active 2-hydroxy-4-arylbutyric acid ester.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: July 10, 2001
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masahiko Kurauchi, Yoshimasa Hagiwara, Hiroyuki Matsueda, Takashi Nakano, Kunisuke Izawa
  • Publication number: 20010007040
    Abstract: 1,1-cyclopropanedicarboxylic diesters are prepared from malonic diesters, 1,2-dihaloethane and alkali metal carbonate in the presence of a mixture of available or in situ-produced phase transfer catalyst and polyalkylene glycol or derivatives thereof which are capped at one or both ends, in particular those with ether end groups, where the molar ratio of malonic diester: 1,2-dihaloethane: alkali metal carbonate is 1:(1 to 7):(1 to 1.4).
    Type: Application
    Filed: December 19, 2000
    Publication date: July 5, 2001
    Inventors: Andreas Harthun, Manfred Neumann, Christoph Theis
  • Patent number: 6245919
    Abstract: A cyclopropylglycine derivative having the following formula: and an intermediate compound for the synthesis of the cyclopropylglycine derivative are novel compounds. The cyclopropylglycine derivative shows a selectivity higher than that of the known agonists to metabotropic L-glutamate receptors, and therefore is a metabotropic type agonist to L-glutamate which has excellent characteristics.
    Type: Grant
    Filed: December 28, 1998
    Date of Patent: June 12, 2001
    Assignees: Nippon Chemiphar Co., Ltd.
    Inventors: Haruhiko Shinozaki, Takeo Taguchi, Michiko Ishida
  • Patent number: 6245922
    Abstract: A photoactive compound that is the reaction product of an alkenyl azlactone compound and a nucleophilic aromatic ketone is described. Mer units derived from this compound can be used, for example, to crosslink via a hydrogen abstracting mechanism acrylic polymers in which they are incorporated.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: June 12, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Steven M. Heilmann, Gaddam N. Babu, Larry R. Krepski, Howell K. Smith, II, Daniel E. Mickus
  • Patent number: 6225495
    Abstract: Ester compounds shown by the formula: wherein R1 represents a hydrogen atom, halogen atom, C1-C3 alkyl group optionally substituted by halogen atom(s), C2-C3 alkenyl group optionally substituted by halogen atom(s), C1-C3 alkoxy group optionally substituted by halogen atom(s), C1-C3 alkylthio group optionally substituted by halogen atom(s) or (C1-C3 alkoxy)methyl group optionally substituted by halogen atom(s), n represents an integer of 1 to 4 and X represents a hydrogen atom or C1-C3 alkyl group, have excellent pesticidal activity.
    Type: Grant
    Filed: February 24, 1999
    Date of Patent: May 1, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ujihara, Tomonori Iwasaki
  • Patent number: 6207854
    Abstract: Disclosed a process for preparing substantially enantiomerically pure 3-amino-3-cyclopropylpropanoate esters, i.e., esters of 3-amino-3-cyclopropylpropanoic acid (3-cyclopropylalanine esters or 3-CPA esters) by a 5-step process wherein cyclopropanecarboxaldehyde (CPCA) is reacted with malonic acid and a source of ammonia to obtain 3-cyclopropylalanine (3-CPA); esterifying the 3-CPA; contacting the 3-CPA ester with a substantially enantiomerically pure acid selected from tartaric acid, dibenzoyltartaric acid and mandelic acid to obtain a diastereomeric salt of the 3-CPA ester and the acid; recrystallization of the salt to substantial diastereomeric purity; and neutralizing the salt to afford the substantially enantiomerically pure 3-CPA ester.
    Type: Grant
    Filed: December 15, 1999
    Date of Patent: March 27, 2001
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Virginie Falque, Ronald Michael Scott
  • Patent number: 6191306
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an &agr;-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: February 20, 2001
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Gruman, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
  • Patent number: 6162926
    Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the C.sub.n fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by .sup.3 He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: December 19, 2000
    Assignee: Sphere Biosystems, Inc.
    Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
  • Patent number: 6153650
    Abstract: Novel gamma aminobutyric acids of formula (I) are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, inflammation, and gastrointestinal damage. Processes for the preparation and intermediates useful in the preparation are also disclosed.
    Type: Grant
    Filed: March 1, 1999
    Date of Patent: November 28, 2000
    Assignee: Warner-Lambert Company
    Inventors: Justin Stephen Bryans, David Christopher Horwell, Clare Octavia Kneen, Andrew John Thorpe, David Juergen Wustrow
  • Patent number: 6136887
    Abstract: The invention relates to vinylcyclopropane derivatives according to the formula ##STR1## in which A is --[--Y--CO--C(.dbd.CH.sub.2)R.sup.4 ].sub.m or --C(.dbd.CH.sub.2)CO--O--C.sub.1-4 -alkyl, U and X, independently of each other, stand for CO, COO or CONH; Y and Z stand for O or NH or are absent, but Y and Z cannot be absent at the same time; n, m stand for a whole number from 0 to 4, but n and m are not 0 at the same time; R.sup.1 is H, CH.sub.3 or Cl; R.sup.2, R.sup.3 stand for H, a C.sub.1 - to C.sub.10 -alkyl or alkylene radical, which can be interrupted by O, S or NH, for a C.sub.6 - to C.sub.14 -aryl or arylene, C.sub.7 - to C.sub.14 -alkylaryl or alkylarylene or a C.sub.5 - to C.sub.8 -cycloalkyl or cycloalkylene radical; and R.sup.4 is H or a C.sub.1 - to C.sub.10 -alkyl radical, and to processes for their production. The compounds are suitable in particular for the production of adhesives, cements, composites and mouldings.
    Type: Grant
    Filed: March 11, 1999
    Date of Patent: October 24, 2000
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Volker Rheinberger, Thomas Voelkel, Urs Karl Fischer
  • Patent number: 6130350
    Abstract: Cyclopropanecarboxylic acid derivatives are prepared by reacting halogenocyclopropanecarboxylic acid derivatives with metals in the presence of bases and with or without addition of hydrogen in an advantageous manner if the base is added during the reaction. By means of the process according to the invention, good yields and selectivities and a high proportion of cis isomers in the reaction product may be achieved.
    Type: Grant
    Filed: November 16, 1998
    Date of Patent: October 10, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Wolters, Norbert Lui, Nikolaus Muller
  • Patent number: 6118019
    Abstract: A 3-alkoxypropionic ester derivative, an olefin polymerization solid catalyst component using the same, an olefin polymerization catalyst using the same, and a process for the preparation of a polyolefin using the same. The 3-alkoxypropionic ester derivative is represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrocarbon group having from 1 to 10 carbon atoms; R.sup.2 represents a hydrocarbon group having from 1 to 20 carbon atoms; R.sup.3 represents a hydrocarbon group having from 1 to 20 carbon atoms; and R.sup.4 represents a branched hydrocarbon group having 3 or more carbon atoms.
    Type: Grant
    Filed: December 29, 1998
    Date of Patent: September 12, 2000
    Assignee: Showa Denko K.K.
    Inventors: Masaki Fushimi, Shintaro Inazawa
  • Patent number: 6111130
    Abstract: The present invention relates to a process for the preparation of trifluoromethylated derivatives of the formula CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)R, wherein R is unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R', a phenyl group unsubstituted or substituted with R'; R' is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl; and wherein where R and/or R' are substituted each is substituted with R', by reaction of HCFC-353 with carboxylic acid salts. The trifluoromethylated derivatives, particularly CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)CH.sub.3, are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds, which find utility as pharmaceuticals, agricultural chemicals, and materials such as liquid crystals.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: August 29, 2000
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 6107339
    Abstract: The derivatives of esters of carboxylic acids represented by the general formula I: ##STR1## wherein: R.sub.1 is an alkyl group having a chain or branched chain of 1 to 4 carbon atoms; andR.sub.2 is a group represented by the following general formulae II, III or IV; ##STR2## wherein: R.sub.3 is a hydrogen atom or a methyl group;X is an oxygen atom or a methylidene group;R.sub.4 is an hydrogen atom or an ethynyl group;R.sub.5 and R.sub.6 are alike or differently selected from the group consisting of hydrogen, fluorine, chlorine atoms or methyl group;R.sub.7 is a hydrogen atom or a trifluoromethyl group;R.sub.8 is selected from the group consisting of propargyl, methoxymethyl or methylthio groups; orR.sub.7 and R.sub.8 may combine with each other to form a methylenedioxy chain; and the process for manufacturing the same, and the insecticides and the insect proofing agents containing the same as an active ingredient.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: August 22, 2000
    Assignee: Dainihon Jochugiku Co., Ltd.
    Inventors: Yoshio Katsuda, Koji Nakayama, Yoshihiro Minamite
  • Patent number: 6100424
    Abstract: Aminoacetic acid esters of formula I in which R.sup.1, R.sup.2 and R.sup.3 are identical or different hydrocarbon radicals, or any two of these radicals form a carbon ring with the carbon atom to which they are attached and R.sup.4 is hydrogen or an alkyl radical having 1-4 carbon atoms, are prepared by reacting an .alpha.-substituted malonic acid monoamide ester of formula II ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings above, by the Hofmann degradation reaction, with a hypohalite in an amount of up to 1.5 equivalents in an aqueous-basic medium containing base in an amount of 0.8-1.5 equivalents per mol. of starting malonic acid monoamide ester II.
    Type: Grant
    Filed: July 9, 1999
    Date of Patent: August 8, 2000
    Assignee: Degussa-Huels Aktiengesellschaft
    Inventor: Wolfgang Kleemiss
  • Patent number: 6072074
    Abstract: A propynyl compound shown by the formula: ##STR1## wherein R represents a lower alkyl group or a hydrogen atom, is an intermediate for producing 3-Z-(1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid esters advantageously in industry.
    Type: Grant
    Filed: May 5, 1999
    Date of Patent: June 6, 2000
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Tatsuya Mori, Noritada Matsuo
  • Patent number: 6051539
    Abstract: A process for modifying an unsaturated polyol fatty acid ester stock, such as an unsaturated triacylglycerol oil, to enhance its fluidity and/or oxidative stability is provided. The method includes reacting the unsaturated polyol fatty acid ester stock with cyclopropanating agent. Lubricants containing a modified unsaturated polyol fatty acid ester and methods for their production and use are also provided.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: April 18, 2000
    Assignee: Cargill, Inc.
    Inventors: Dharma R. Kodali, Keqiang Li
  • Patent number: 6049001
    Abstract: Novel fluorine-containing carboxylic acid compounds of formula (II) are provided that can be reacted together with a base to produce industrially useful 3-(2-chloro-2-fluorovinyl)-2,2-dimethyl cyclopropanecarboxylic acid compounds of formula (I). The fluorine-containing containing carboxylic acid compounds of formula (II), if so desired, can be produced by reacting together a carboxylic acid compound of formula (III) and trichlorofluoromethane. In each of the formulas (I), (II), and (III), R is a lower alkyl group or a hydrogen atom.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: April 11, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ken Otaka, Noritada Matsuo
  • Patent number: 6049019
    Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, cyclopropane carboxaldehyde is condensed with malonic acid to form 3-cyclopropylacrylic acid; 3-cyclopropylacrylic acid is halogenated to form (E,Z)-1-halo-2-cyclopropylethylene; and (E,Z)-1-halo-2-cyclopropylethylene is dehydrohalogenated to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
    Type: Grant
    Filed: July 30, 1998
    Date of Patent: April 11, 2000
    Assignee: DuPont Pharmaceuticals
    Inventors: Joseph M. Fortunak, Zhe Wang, Jianguo Yin
  • Patent number: 6034128
    Abstract: An ester compound represented by the formula: ##STR1## wherein R is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group unsubstituted or substituted with one or more halogen atoms, an allyl group unsubstituted or substituted with one or more halogen atoms, or a propargyl group unsubstituted or substituted with one or more halogen atoms; and X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group unsubstituted or substituted with one or more halogen atoms, a C.sub.2 -C.sub.3 alkenyl group unsubstituted or substituted with one or more halogen atoms, a C.sub.2 -C.sub.3 alkynyl group unsubstituted or substituted with one or more halogen atoms, a C.sub.1 -C.sub.3 alkoxy group unsubstituted or substituted with one or more halogen atoms, a C.sub.1 -C.sub.3 alkylthio group unsubstituted or substituted with one or more halogen atoms, or a C.sub.1 -C.sub.3 alkoxymethyl group containing a C.sub.1 -C.sub.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: March 7, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kazuya Ujihara
  • Patent number: 6024973
    Abstract: The present invention provides a fabric protectant having an excellent effect in preventing the hatching of eggs of fabric pest insects. The fabric protectant comprises a paper or paper-like sheet carrying 2, 3, 5, 6-tetrafluorobenzyl 1R-trans-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropanecarboxylate (Transfluthrin) and 1-ethynyl-2-methyl-2-pentenyl 1R-cis, trans-chrysanthemate (Empenthrin).
    Type: Grant
    Filed: February 20, 1998
    Date of Patent: February 15, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Takao Ishiwatari
  • Patent number: 6017957
    Abstract: A method is disclosed for the treatment of neuropsychopharmacological disorders which are associated with or result from excessive activation of the N-methyl-D-aspartate receptor complex, which method comprises administering an effective neuropsychopharmacological disorder-treating amount of a compound possessing partial agonist properties for the strychnine insensitive glycine modulatory sites of N-methyl-D-aspartate receptors. Exemplary of partial agonists which are useful in the method of the invention are 1-aminocyclopropanecarboxylic acid, and associated derivates thereof. Novel injectable pharmaceutical compositions are also disclosed.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: January 25, 2000
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Phil Skolnick, Anita Lewin, Juan-Carlos Marvizon, James Monn, Kenner Rice
  • Patent number: 6011169
    Abstract: A process for producing an optically active cyclopropanecarboxylic acid ester which is characterized by reacting a prochiral olefin with a diazoacetic acid ester in the presence of a copper complex obtained by reacting an optically active bisoxazoline ligand with a copper compound.
    Type: Grant
    Filed: July 10, 1998
    Date of Patent: January 4, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Itagaki, Gohfu Suzukamo
  • Patent number: 5986130
    Abstract: The compounds 3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethyl-(1R,cis)-cyc lopropane carboxylic acid, cis-3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethyl-cyclopro pane carboxylic acid and (1R,5S)-4-(1,1-dichloro-2,2,2-trifluoroethyl)-6,6-dimethyl-3-oxabicyclo[3. 1.0]hexan-2-one occur as intermediates in a process for the preparation of insecticidally active cyclopropane carboxylate esters, said process starting from 6,6-dimethyl-4-hydroxy-3-oxabicyclo[3.1.0]hexan-2-one (Biocartol) which is reacted with the compound CF.sub.3 --CC1X.sub.2 (X=halogen) in the presence of zinc.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: November 16, 1999
    Assignee: Cheminova Agro A/S
    Inventors: Per Dausell Klemmensen, Hans Kolind-Andersen, Ib Winckelmann
  • Patent number: 5986095
    Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: November 16, 1999
    Assignee: E.R. Squibb & Sons, Inc.
    Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
  • Patent number: 5955627
    Abstract: According to the present invention, a process for the preparation of a cyclopropylacetylene derivative represented by the following formula (III): ##STR1## is provided, which comprises reacting a cyclopropylacrylic acid derivative represented by the following formula (I): ##STR2## with a halogenating agent to obtain a halogenocyclopropylpropionic acid derivative represented by the following formula (II): ##STR3## and reacting the halogenocyclopropylpropionic acid derivative with a base.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: September 21, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Makoto Nakazawa, Toshimichi Mitani, Yoichi Satake, Shigeo Oozono, Goro Asanuma, Manzo Shiono
  • Patent number: 5952521
    Abstract: Surfactants useful as dispersing aids in the preparation of compositions comprising a hydrophilic colloid having hydrophobic particles dispersed therein have the structure ##STR1## wherein M is a cation; X represents a group having the structure ##STR2## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represents hydrogen or alkyl; or R.sup.1 and R.sup.2 taken together represent cycloalkyl; or R.sup.3 and R.sup.4 taken together represent cycloalkyl; and, n represents 0 or 1; provided that the total number of carbon atoms in each X group is 3 or 4, and when R.sup.1 is hydrogen R.sup.2 is other than methyl. Such surfactants offer coating and photographic property advantages when incorporated in multilayer photographic materials comprising a support bearing a plurality of hydrophilic colloid layers.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: September 14, 1999
    Assignee: Eastman Kodak Company
    Inventors: Alan Robert Pitt, Trevor John Wear, Danuta Gibson
  • Patent number: 5925676
    Abstract: An ester compound represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 may be the same or different and each represent a C.sub.1 -C.sub.6 alkyl group, or other specified groups, which may be optionally substituted with one or more halogen atoms; and R.sub.3 represents a pyrethroid acid residue (a group resulting from elimination of the carboxyl group from pyrethroid acid), and a pesticidal composition containing the ester compound as an active ingredient.
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: July 20, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Kazunori Tsushima, Masayo Sugano
  • Patent number: 5900492
    Abstract: A method for resolving optically impure 3-oxa-2-oxobicyclo?3.1.0!hexane-1-carboxylic acid esters. A method is provided for producing a 1-alkoxycarbonyl-2-hydroxymethylcyclopropane-1-carboxylic acid.N-benzyl-.alpha.-phenylethylamine diastereomer salt. An enantiomer of N-benzyl-.alpha.-phenylethylamine is reacted with a 1-alkoxycarbonyl-2-hydroxymethylcyclopropane-1-carboxylic acid to produce a precipitate that is enriched in one diastereomer of the salt. After isolating the optically active salt, the N-benzyl-.alpha.-phenylethylamine may be separated to produce the corresponding 1-alkoxycarbonyl-2-hydroxymethylcyclopropane-1-carboxylic acid. Under acidic conditions, the carboxylic acid and hydroxyl groups undergo ring closure to afford the optically active 3-oxa-2-oxobicyclo?3.1.0!hexane-1-carboxylic acid ester.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: May 4, 1999
    Assignee: Ajinomoto Co., Inc.
    Inventors: Katsutoshi Sakata, Takashi Tsuji, Noriyasu Kataoka, Masanobu Yatagai
  • Patent number: 5886212
    Abstract: Multifunctional polymerizable vinyl cyclopropane derivatives are described which have at least two vinyl cyclopropane units and are suitable in particular as a constituent of dental materials.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: March 23, 1999
    Assignee: Ivoclar AG
    Inventors: Volker Rheinberger, Frank Zeuner, Norbert Moszner
  • Patent number: 5869737
    Abstract: A cyclopropane-1,1-dicarboxylic acid compound is prepared by reacting a malonic acid compound and a 1,2-dihalogeno compound with an alcoholate as a condensation agent which is gradually added to a mixture of said malonic acid compound and said 1,2-chloro compound as a solution or suspension is an alcohol.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: February 9, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Klaus-Dieter Steffen
  • Patent number: 5863931
    Abstract: Amidino derivatives of formula (I) and salts, and pharmaceutically acceptable esters and amides thereof, in which: R.sup.1 is a C.sub.1-6 straight or branched chain alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.3-6 cycloalkyl group or a C.sub.3-6 cycloalkylC.sub.1-6 alkyl group; Q is an alkylene, alkenylene or alkynylene group having 3 to 6 carbon atoms and which may optionally be substituted by one or more C.sub.1-3 alkyl groups; a group of formula --(CH.sub.2).sub.p X(CH.sub.2).sub.q -- where p is 2 or 3, q is 1 or 2 and X is S(O).sub.x where x is 0, 1 or 2, O or NR.sup.2 where R.sup.2 is H or C.sub.1-6 alkyl; or a group of formula --(CH.sub.2).sub.r A(CH.sub.2).sub.s -- where r is 0, 1 or 2, s is 0, 1 or 2 and A is a 3 to 6 membered carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C.sub.1-6 alkyl, amino, C.sub.1-6 alkylamino or diC.sub.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: January 26, 1999
    Assignee: Glaxo Wellcome Inc.
    Inventors: Richard Mansfield Beams, Harold Francis Hodson, Richard Michael John Palmer
  • Patent number: 5859283
    Abstract: 4-Substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meanings defined in the description, which possess valuable herbicidal properties and intermediates useful in their preparation.
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: January 12, 1999
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventor: Susan Mary Cramp
  • Patent number: 5840958
    Abstract: This invention relates to a process for preparing certain isomers of 2,2-dimethyl-3-(2,2-disubstitutedvinyl)cyclopropanecarboxylic acid or derivatives thereof. More specifically it relates to the epimerization of the 1S cyclopropanecarboxylic acid and its derivatives into the corresponding 1R isomers.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: November 24, 1998
    Assignee: FMC Corporation
    Inventors: Ronald E. Montgomery, Leland A. Smeltz
  • Patent number: 5808134
    Abstract: An intermediate for the production of (3-oxo-2-oxobicyclo?3,1,0!hexan-1-yl) methanol represented by formula (II): ##STR1## selected from the group of compounds (9)-(11) as shown below, wherein R.sup.1 represents a lower alkyl group, R.sup.3 and R.sup.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: September 15, 1998
    Assignee: Ajinomoto Co., Ltd.
    Inventors: Tomoyuki Onishi, Takashi Tsuji, Toshihiro Matsuzawa
  • Patent number: 5780669
    Abstract: A compound represented by the following formula (1) or (3): ##STR1## is subjected to a catalytic hydrogenolysis reaction in the presence of a base and thus a compound represented by the following formula (2): ##STR2## wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and X represents a chlorine atom or a bromine atom;is easily produced. This compound is usable as an intermediate for the preparation of drugs.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: July 14, 1998
    Assignee: Daiichi Pharmaceutical Co., Ltd.
    Inventors: Toshifumi Akiba, Takanobu Ikeya, Hirofumi Kawanishi, Yusuke Yukimoto, Shinji Kamihara, Tsutomu Ebata
  • Patent number: 5767305
    Abstract: Described are cyclopropyl carboxylic acid esters defined according to the structure: ##STR1## or the structure: ##STR2## wherein R.sub.1 is cis-3-hexenyl or cyclohexyl methyl and R.sub.2 is one of n-hexyl, cis-3-hexenyl, cyclohexyl methyl or n-heptyl and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles. The compounds having the structure: ##STR3## are novel compounds.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: June 16, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Gail I. Malcolm, Marie R. Hanna, Marc D. Evans
  • Patent number: 5723649
    Abstract: The invention provides an improved process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid in which the corresponding lower alkyl ester of a carboxylic acid selected from 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-2-enoic acid and 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-2-enoic acid is treated with an alkali metal lower alkoxylate in the presence of an aromatic hydrocarbon solvent under conditions under which the lower alcohol of the alkoxylate is removed from the reaction mixture by distillation with the aromatic solvent. The products are useful as intermediates in the manufacture of pyrethroid insecticides.
    Type: Grant
    Filed: January 31, 1997
    Date of Patent: March 3, 1998
    Assignee: Zeneca Limited
    Inventors: Martin Charles Bowden, Stephen Martin Brown
  • Patent number: 5710324
    Abstract: The present invention is directed to a new class of compound which are useful as inhibitors of the biosynthesis of nitric oxide.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: January 20, 1998
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Jeffrey P. Whitten, Ian A. McDonald, Laurie E. Lambert, Niall S. Doherty
  • Patent number: 5670697
    Abstract: There is disclosed a process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid which comprises the steps of(a) reacting a compound of formula:CF.sub.3 --CXCl--CH(OH)--CH.dbd.C(CH.sub.3).sub.2 (I)wherein X is chloro or bromo, with a tri-lower-alkyl orthoacetate containing up to four carbon atoms in each alkyl groups in the presence of at least a catalytic amount of an acid catalyst at an elevated temperature for a sufficient time to obtain a compound of formula:CF.sub.3 --CXCl--CH.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 CO.sub.2 R(III)wherein R is an alkyl group containing up to four carbon atoms, and(b) treating said compound of formula (III) with at least one molar equivalent of a base to obtain said alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid. The products are useful as intermediates for insecticides.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: September 23, 1997
    Assignee: Zeneca Limited
    Inventors: Martin Charles Bowden, Michael Drysdale Turnbull
  • Patent number: 5663418
    Abstract: Disclosed is a process for the preparation of cyclopropanecarboxylic acid by the non-catalytic, oxidation of cyclopropanecarboxaldehyde using molecular oxygen as the oxidant. Also disclosed are processes for the preparation of amides, esters and acid chlorides from cyclopropanecarboxylic acid.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: September 2, 1997
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price
  • Patent number: RE37188
    Abstract: Disclosed is a process for the preparation of cyclopropanecarboxylic acid by the non-catalytic, oxidation of cyclopropanecarboxaldehyde using molecular oxygen as the oxidant. Also disclosed are processes for the preparation of amides, esters and acid chlorides from cyclopropanecarboxylic acid.
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: May 22, 2001
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price