Halogen Containing Patents (Class 568/812)
  • Patent number: 6194606
    Abstract: The present invention provides compounds having the formula: in which R is hydrogen or C1-C4alkyl, preferably hydrogen and Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, CF3, halogen (F, Cl, Br or I) or SO3M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C1-C4alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C1-C4alkyl and C1-C4hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: February 27, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
  • Patent number: 6187966
    Abstract: A process for preparing optically active alcoholic compounds wherein a carbonyl compound is assymmetrically reduced in an economical and practical manner. The process comprises treating a prochiral carbonyl compound represented by the general formula (1) with an optically active organoaluminum compound represented by the general formula (2) to conduct asymmetric reduction, thereby preparing an optically active alcoholic compound represented by the general formula (3).
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: February 13, 2001
    Assignee: Kaneka Corporation
    Inventors: Tadashi Sugawa, Kenji Inoue, Kazunori Kan
  • Patent number: 6156940
    Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.
    Type: Grant
    Filed: April 8, 1998
    Date of Patent: December 5, 2000
    Assignees: Sumika Fine Chemicals Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 6046354
    Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.
    Type: Grant
    Filed: August 31, 1998
    Date of Patent: April 4, 2000
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
  • Patent number: 6043400
    Abstract: This invention is a process for preparing chlorohydrins by reacting a chlorinating species, such as hypochlorous acid, with at least one unsaturated organic compound, such as propylene or butylene, at a pH of greater than 6.0. The chlorinating species is formed in a first step by reacting a source of chlorine, such as Cl.sub.2 gas, with an aqueous pH adjusting source, such as aqueous NaOH.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: March 28, 2000
    Assignee: The Dow Chemical Company
    Inventor: Edward M. Jorge
  • Patent number: 6037505
    Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6025531
    Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.
    Type: Grant
    Filed: June 3, 1998
    Date of Patent: February 15, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
  • Patent number: 6020517
    Abstract: A process for producing a fluorinated benzonitrile comprising hydrogenolyzing a fluorinated dicyanobenzene substituted with 1 to 4 fluorine atoms and having the remainder which may be substituted with a chlorine atom in the presence of a catalyst to cause hydrodecyanation of only the cyano group of one side and a process for producing a fluorinated benzyl alcohol comprising reducing the fluorinated benzonitrile and hydrolyzing the fluorinated benzonitrile and reducing the resultant corresponding fluorinated benzoic acid to convert the cyano group to a hydroxymethyl group.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: February 1, 2000
    Assignee: Showa Denko K.K.
    Inventors: Hiroyuki Monzen, Katsutoshi Morinaka, Hideo Miyata, Tsutomu Nozawa, Haruaki Ito, Kohei Morikawa
  • Patent number: 6015926
    Abstract: An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2-trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.
    Type: Grant
    Filed: May 11, 1998
    Date of Patent: January 18, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Cheng Yi Chen, Lushi Tan, Richard D. Tillyer
  • Patent number: 6002052
    Abstract: A compound having the formula: ##STR1## wherein: R is fluorine, hydrogen, an unsubstituted or substituted aliphatic or unsubstituted or substituted aromatic radical;R.sub.1 is an unsubstituted or substituted aliphatic radical, or unsubstituted or substituted aromatic radical; andR.sub.2 is hydrogen, an unsubstituted or substituted aliphatic radical, or unsubstituted or substituted aromatic radical.
    Type: Grant
    Filed: January 6, 1999
    Date of Patent: December 14, 1999
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5993780
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I ##STR1## (wherein n is 0 or 1, and where n is 1 each C.sub.6 R.sub.5 moeity may be the same or different; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M.sub.1, two or three non-adjacent R groups in each C.sub.6 R.sub.5 moiety being iodine and at least one, and preferably two or three, R groups in each C.sub.6 R.sub.5 moiety being M or M.sub.1 moieties; X denotes a bond or a group providing a 1 to 7 atom chain linking two C.sub.6 R.sub.5 moieties or, where n is 0, X denotes a group R; each M independently is a non-ionic hydrophilic moiety; and each M.sub.1 independently represents a C.sub.1-4 alkyl group substituted by at least one hydroxyl group and optionally linked to the phenyl ring via a carbonyl, sulphone or sulphoxide group, at least one R group being an M.sub.1 moiety; with the proviso that where n is zero either at least one M.sub.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: November 30, 1999
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Goran Andersson, Lars-Goran Wistrand, Klaes Golman, .O slashed.yvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, H.ang.kan Wikstrom, Tomas Klingstedt, Ib Leunbach, Arne Berg, Harald Dugstad
  • 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: 5981807
    Abstract: A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: November 9, 1999
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Hiroki Kodama, Takuya Motokawa, Hiroshi Yamaguchi, Masanori Yoshida
  • Patent number: 5902909
    Abstract: The present invention provides compounds having the formula: ##STR1## in which R is hydrogen or C.sub.1 -C.sub.4 alkyl, preferably hydrogen and Y is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, halogen (F, Cl, Br or I) or SO.sub.3 M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C.sub.1 -C.sub.4 alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: May 11, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
  • Patent number: 5900502
    Abstract: According to the present invention there is provided a process for the selective introduction of one or more fluorine atoms into a disubstituted aromatic compound in an acid medium with fluorine gas characterized in that the acid medium has a dielectric constant of at least 20 and a pH of less than 3. The present process provides a cost effective means of selectively introducing one or more fluorine atoms into an aromatic compound in good overall yield.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: May 4, 1999
    Assignee: BNFL Fluorochemicals Limited
    Inventors: Christopher John Skinner, John Hutchinson, Julie Thomson, Richard Dickinson Chambers
  • Patent number: 5849958
    Abstract: Pesticidal 1,4-diaryl-2-fluoro-2-butene compounds having the structural formula I ##STR1## and compositions and methods comprising those compounds for the control of insect and acarid pests.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: December 15, 1998
    Assignee: American Cyanamid Company
    Inventors: Keith D. Barnes, Yulin Hu
  • Patent number: 5841001
    Abstract: The present invention provides an industrially advantageous process for the preparation of an optically active 2-halo-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or as intermediates thereof; and a simple process for the preparation of an optically active substituted styrene oxide or 2-amino-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or intermediates thereof. A 2-halo-1-(substituted phenyl)ethanol represented by the following general formula (I) is allowed to contact, in the presence of a carboxylic anhydride, with an enzyme stereoselectively catalyzing ester interchange to produce an optically active 2-halo-1-(substituted phenyl)ethanol: ##STR1## (wherein X represents a chlorine atom or a bromine atom, and R.sup.1, R.sup.2 and R.sup.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a C.sub.1-5 alkyl group, a C.sub.1-5 haloalkyl group, a C.sub.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: November 24, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ken Tanaka, Mari Yasuda, Makoto Ueda
  • Patent number: 5831132
    Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral keytone with an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: November 3, 1998
    Assignees: Sumika Fine Chemicals Company, Ltd., Sumitomo Chemical Company, Ltd.
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 5780692
    Abstract: A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: July 14, 1998
    Assignee: Takasago International Corporation
    Inventors: Minzo Sakaguchi, Takashi Imai, Takashi Miura, Tetsuro Yamazaki
  • Patent number: 5777181
    Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: July 7, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 5756849
    Abstract: The invention relates to a process and a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, characterized in that it comprises:a) a fluorocarboxylic acid of formula Ew--CF.sub.2 --COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, andb) a polar aprotic solvent;and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 5756862
    Abstract: A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: ##STR1## wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: May 26, 1998
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Hiroki Kodama, Takuya Motokawa, Hiroshi Yamaguchi, Masanori Yoshida
  • Patent number: 5731479
    Abstract: Optically active alcohols are prepared by reducing optically active carboxylic acids with hydrogen in the presence of ruthenium catalysts.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: March 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Stefan Antons
  • Patent number: 5696299
    Abstract: A process for producing an optically active alcohol comprising carrying out interesterification between a racemic alcohol and an ester selected from the group consisting of (a) a diester between a lower monohydric alcohol and a saturated dicarboxylic acid having 14 or more carbon atoms, (b) a triglyceride of a saturated fatty acid having 16 or more carbon atoms, and (c) a monoester between a lower monohydric alcohol and a saturated fatty acid having 18 or more carbon atoms in the presence of lipase, preferably heat-resistant lipase, and in the presence or absence of a solvent, preferably in the absence of a solvent, under a substantially water-free condition, separating an optically active alcohol rich in either one of R- and S-forms from the reaction mixture, and adding an optically inactive non-racemic alcohol to the residue of the previous step to carry out interesterification under the same conditions as in the previous reaction to separate the other enantiomer.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: December 9, 1997
    Assignee: The Nisshin Oil Mills, Ltd.
    Inventors: Satoshi Negishi, Seiichi Shirasawa, Junko Suzuki, Yukie Masuda
  • Patent number: 5663448
    Abstract: Compounds of general formula (I), stereosiomers and pharmaceutically acceptable salts thereof, wherein each of Z and Z' are independently H or F; Q is (a), CH(OH), (b); X is H, Br, Cl, F or CF.sub.3 ; Y is H, Br, Cl, F, OH, OR.sub.5, OC(O)R.sub.4, N.sub.3, CN, NO.sub.2, SO.sub.3 H, CO.sub.2 R.sub.4, NH.sub.2, NHR.sub.9, NR.sub.9 R'.sub.9, C(R.sub.6)(R.sub.7)(V'R.sub.8) or C(O)R.sub.7, provided that when both Z and Z' are F, then Y is H or F; V and V' are each independently CH.sub.2 or O; R.sub.1 is H or CH.sub.3 ; R.sub.2, R.sub.9 and R'.sub.9 are each independently (C.sub.1-6)alkyl, or R.sub.2 and V--R.sub.3 taken together with the carbon atom to which they are attached form a 3-6 membered ring; R.sub.3, R.sub.6, R.sub.7 and R.sub.8 are each independently H, (C.sub.1-6)alkyl, or (C.sub.3-6)cycloalkyl; R.sub.4 is H, (C.sub.1-10)alkyl, (C.sub.0-4)alkylene aryl or (C.sub.3-8)cycloalkyl; and R.sub.5 is (C.sub.1-10)alkyl, benzyl, phenethyl or (C.sub.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: September 2, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Jean-Noel Collard, Jean-Marie Hornsperger, Daniel Schirlin
  • Patent number: 5663453
    Abstract: Compounds of the formula ##STR1## in which: n is 0, 1 or 2, and, if n is 2, the two radicals R.sub.3 are identical or different;R.sub.2 is methyl, fluorine, chlorine or bromine;R.sub.3 is C.sub.1 -C.sub.3 -alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy, fluorine, chlorine or bromine:R.sub.5 is hydrogen or C.sub.1 -C.sub.9 alkyl andX is methylene, O, S or C(.dbd.O):can be used as intermediates for agrochemical active ingredients.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geiby Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5637719
    Abstract: The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 10, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5574194
    Abstract: The compound 2,6-bis-(trifluoromethyl)-benzyl alcohol which is useful as an intermediate to compounds having pesticidal properties.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: November 12, 1996
    Assignee: Roussel Uclaf
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute
  • Patent number: 5510491
    Abstract: This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H or COZ;X.sub.1 and X.sub.2 are independently H, lower alkyl,aryl, aryl lower-alkyl or polystyrene orR and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; andZ is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: April 23, 1996
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5486627
    Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: January 23, 1996
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
  • Patent number: 5414158
    Abstract: It has surprisingly now been discovered that alkoxy-magnesium halides of the general formula ROMgX wherein R is an alkyl having from about 1 to 18 carbon atoms and X is a halide can be synthesized in an inert hydrocarbon in just one step process by reacting magnesium which has been preliminarily activated with small quantities (approximately 5 mol %) of magnesium alkyl with a substantially equimolar mixture of an alkyl halide and an alkanol. That is, the present invention provides a one step reaction process for preparing alkoxy-magnesium halides. This one step reaction process involves reacting magnesium metal which has been previously activated with a magnesium-alkyl compound, with an equimolar mixture of an alkyl halide and an alkanol. Yields in excess of 90% can be obtained by employing the inventive one step reaction process.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: May 9, 1995
    Assignee: Witco GmbH
    Inventor: Stefan Gurtzgen
  • Patent number: 5364993
    Abstract: Fullerenes are selectively functionalized by adsorbing fullerene molecules on molecular sieves such as zeolites as the first step in a desired functionalizing reaction and then adding functional groups or compounds to the fullerenes within the molecular sieves. An improved reactor for fullerene material is thereby available. Selectively functionalized fullerenes formed in accordance with the invention can also serve as precursors for further selectively functionalized products.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: November 15, 1994
    Assignee: Inrad, Inc.
    Inventors: Zhenyu Zhang, Warren Ruderman, James R. Fehlner
  • Patent number: 5356893
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: October 18, 1994
    Assignee: Glaxo Group Limited
    Inventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
  • Patent number: 5334776
    Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: August 2, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Fumio Toda
  • Patent number: 5326898
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: July 5, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5288908
    Abstract: Compounds of the formula ##STR1## in which X represents hydrogen, --NO.sub.2 or --NH.sub.2 and Y represents --CH.sub.3, --COOH, --CONH.sub.2, --NH.sub.2 or --N.dbd.N--Z, in which the group --Z is ##STR2## with the proviso that if Y represents the group --N.dbd.N--Z, X is only --NO.sub.2, and if Y represents the group --CH.sub.3, X is only hydrogen, are described. A compound of the formula ##STR3## the preparation of which in a multi-stage process, in which the compounds of the general formula (I) are also obtained, is described, is preferred.The resulting 3,4'-diamino compound is suitable for the preparation of polycondensates and shaped articles, films and fibers of high heat resistance.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
  • Patent number: 5288928
    Abstract: There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula ##STR1## wherein R.sub.1 is as defined herein, to give compounds of formula ##STR2## The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: February 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Emil A. Broger, Yvo Crameri, Hans P. Isenring, Albert Pfiffner
  • 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: 5254752
    Abstract: The invention provides a process for the preparation of a 4-halobenzyl alcohol of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 - to C.sub.20 -alkyl, C.sub.2 - to C.sub.20 -alkoxyalkyl, C.sub.3 - to C.sub.20 -cycloalkyl, or C.sub.4 - to C.sub.30 -cycloalkylalkyl,R.sup.2 is C.sub.1 - to C.sub.20 -alkyl, C.sub.2 - to C.sub.20 -alkoxyalkyl, C.sub.3 - to C.sub.20 -cycloalkyl or C.sub.4 - to C.sub.30 -cycloalkylalkyl,X is halogen andm is 0 to 2,by reacting a haloaromatic carbonyl compound of the formula ##STR2## where R.sup.1, R.sup.2, X and m are as defined above, with hydrogen on a hydrogenation catalyst consisting essentially of copper oxide (I), copper oxide (II) and mixtures thereof in the presence of at least one primary, secondary or tertiary amine selected from the group consisting of acyclic, cyclic and heterocyclic aliphatic amines, in the presence or absence of an inert solvent, at from 50.degree. to 130.degree. C. and at from 10 to 200 bar.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: October 19, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Brudermueller, Martin Schmidt-Radde
  • 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: 5245091
    Abstract: The invention relates to a process for the synthesis of 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol in (dicofol) from chlorol and chlorobenzene, in which process the acid by-products formed during the condensation reaction of the chloral and the chlorobenzene are used as reaction medium in the final step for synthesis of dicofol.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: September 14, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Jaume Castella Sola, Jaime Palencia Adrubau, Raymond Commandeur, Bernard Gorny
  • Patent number: 5227540
    Abstract: A process is described for the preparation of fluoroalcohols of the formula below ##STR1## in which R.sub.f is a perfluoroalkyl radical having 1 to 20 carbon atoms and R is hydrogen or an alkyl radical having 1 to 5 carbon atoms, by reaction of a perfluoroalkylethylene, R.sub.f --CH.dbd.CH.sub.2, and an n-C.sub.1 to C.sub.6 -alkanol in the presence of a free radical initiator, the perfluoroalkylethylene, the alkanol and the free radical initiator being used in the molar ratio of 1 to 20-50 to 0.002-0.2. In the novel process, in addition, the reaction is carried out in a specific manner and under specific reaction conditions. The fluoroalcohols given are obtained in high yield.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: July 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Wolfgang Knaup
  • Patent number: 5212301
    Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: May 18, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5202506
    Abstract: A process for the formation of perfluoroalkylethyl alcohols from perfluoroalkylethyl iodides is disclosed. The process involves treatment of the perfluoroalkylethyl iodide with oleum.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: April 13, 1993
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Jack R. Kirchner, Leonard H. Beck, James E. Dowd
  • Patent number: 5169993
    Abstract: The invention provides cyclohexenol derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; and R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group, with the provisos that when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom then n is not 0 and, when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom and n is 1, R does not represent a fluorine atom substituted at the 4-position of the phenyl ring; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidal active cyclopentane derivatives.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 5151548
    Abstract: Benzene derivatives of the general formula ##STR1## where Hal is halogen, R.sup.1 is a hydrocarbon radical of 1 to 18 carbon atoms, R.sup.2 is hydrogen or alkyl of 1 to 6 carbon atoms and X is hydrogen or halogen, are prepared by a process in which a toluene derivative of the general formula ##STR2## is electrochemically oxidized in the presence of an acid of the formula R.sup.2 --COOH (III). Novel benzene derivatives of the general formula ##STR3## where R.sup.3 is hydrogen or an R.sup.2 --CO-- radical but R.sup.1 cannot be methyl if X is hydrogen, and of the general formula ##STR4## where R.sup.4 is a branched or cyclic alkyl radical of 3 to 12 carbon atoms, but R.sup.4 cannot be isopropyl if X is hydrogen. The compounds of formulas IV and VI are intermediates for crop protecting agents, e.g. pyrethroids.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: September 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Hermeling, Dieter Degner, Albrecht Harreus, Norbert Goetz, Jochen Wild, Hans Theobald, Bernd Wolf
  • Patent number: 5146011
    Abstract: Described herein is a process for the preparation of chlorohydrins by reacting a concentrated, aqueous solution of hypochlorous acid with at least one unsaturated organic compound having from 2 to about 10 carbon atoms and selected from the group consisting of substituted or unsubstituted olefins and cyclic olefins.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: September 8, 1992
    Assignee: Olin Corporation
    Inventors: Ming Shen, John A. Wojtowicz
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5132469
    Abstract: 4-Haloalkenyl-2,3,5,6-tetrafluorobenzyl alcohols of formula (III): ##STR1## are intermediates to insecticidally active fluorobenzyl esters of formula (I): ##STR2## wherein X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol, and R, R.sup.6 and R.sup.7 are each selected from hydrogen, halogen and alkyl of up to four carbon atoms, provided that at least one of R, R.sup.6 and R.sup.7 represents halogen, and further provided that R and R.sup.6 are not both bromine when R.sup.7 is hydrogen.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: July 21, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael J. Robson