Five-membered Alicyclic Ring Containing Patents (Class 568/838)
  • Patent number: 5545665
    Abstract: The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.
    Type: Grant
    Filed: December 28, 1993
    Date of Patent: August 13, 1996
    Assignee: Allergan
    Inventor: Robert M. Burk
  • Patent number: 5516929
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: May 14, 1996
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
  • Patent number: 5504066
    Abstract: The invention concerns pentene derivatives of the general formula (I), in which, independently of each other, R.sup.1 is hydrogen or a methyl group, R.sup.2 and R.sup.3 are hydrogen or an alkyl group with 1 to 5 C-atoms, R.sup.4 is hydrogen or a CHR.sup.5 R.sup.6 group (R.sup.5 and R.sup.6 being hydrogen or an alkyl group with 1 to 6 C-atoms) and X is a CO or CHOH group, with the provision that (a) at least one of the groups R.sup.2 and R.sup.3 is an alkyl group and (b) 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-1-ol is excluded. Such compounds are odoriferous substances with interesting fragrances and high diffusion power.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: April 2, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Thomas Markert, Volker Porrmann, Klaus Bruns
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5498802
    Abstract: A process for preparing 6-chloro-2-hexanone which comprises the steps of (a) dehydrating cyclohexanol in the presence of a suitable catalyst and at a suitable temperature and for a sufficient period of time to form cyclohexene; (b) rearranging said cyclohexene at a higher temperature than in step (a) in the presence of a suitable catalyst and for a sufficient period of time to form 1-methylcyclopentene; (c) hydrating said 1-methylcyclopentene at a temperature lower than step (b) and in the presence of a resin catalyst for a sufficient period of time to form 1-methylcyclopentanol; (d) reacting said 1-methylcylcopentanol with a suitable amount of an alkali metal hypochlorite in the presence of a carboxylic acid to form 1-methylcyclopentyl hypochlorite; and (e) heating said 1-methylcyclopentyl hypochlorite for a sufficient period of time to form 6-chloro-2-hexanone.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: March 12, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Diane E. Allen, Ramakrishnan Chidambaram
  • Patent number: 5491265
    Abstract: A process for preparing 6-chloro-2-hexanone which comprises the steps of (a) oxidizing methylcyclopentane with ozone in the presence of a carboxylic acid and for a sufficient period of time to form 1-methylcyclopentanol; (b) reacting said 1-methylcyclopentanol with a suitable amount of an alkali metal hypochlorite in the presence of a carboxylic acid to form 1-methylcyclopentyl hypochlorite; and (c) heating said 1-methylcyclopentyl hypochlorite for a sufficient period of time to form 6-chloro-2-hexanone.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: February 13, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Diane E. Allen, Charles E. Tucker, Charles C. Hobbs, Ramakrishnan Chidambaram
  • Patent number: 5489716
    Abstract: The invention provides novel methods for the oxidation of hydrocarbons with oxygen-containing gas to form hydroxy-group containing compounds and for the decomposition of hydroperoxides to form hydroxygroup containing compounds. The catalysts used in the methods of the invention comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The catalyst compositions are prepared by halogenating a transition metal complex of a porphyrin.
    Type: Grant
    Filed: September 7, 1994
    Date of Patent: February 6, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Paul E. Ellis, Jr., James E. Lyons
  • Patent number: 5475158
    Abstract: A process for the preparation of cycloalkanols by the hydrolysis of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, which comprises the following steps:a) reaction of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters with water at a temperature of from 30.degree. to 250.degree. in the liquid phase yielding a reaction mixture consisting of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, cycloalkanol, C.sub.1 -C.sub.4 fatty acids, and water.b) separation of the reaction mixture obtained in stage a) at a temperature of from 0.degree. to 200.degree. C. into a top phase consisting substantially of cycloalkanol and cycloalkyl C.sub.1 -C.sub.4 fatty acid esters and a bottom phase consisting substantially of water and C.sub.1 -C.sub.4 fatty acids.c) separation of cycloalkanol from the top phase obtained in stage b) by distillation and recycling unconverted cycloalkyl C.sub.1 -C.sub.4 fatty acid esters to stage a).
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: December 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
  • Patent number: 5434312
    Abstract: 1,3-Butadiene is hydroformylated at 60.degree. to 150.degree. C. and 1 to 20 MPa in the presence of an aqueous solution which contains, as catalyst, at least one water-soluble rhodium compound and at least one water-soluble organic phosphine. A pH of 8 to 11 is maintained in the aqueous catalyst solution to increase the selectivity of the reaction with respect to the formation of n-five carbon aldehydes and their secondary products. The latter, in particular, can be hydrogenated to 2-propylheptanol, useful as the alcohol component of phthalic ester plasticizers.
    Type: Grant
    Filed: September 2, 1994
    Date of Patent: July 18, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Fell, Peter Hermanns
  • Patent number: 5426246
    Abstract: Disclosed are a catalyst for directly reducing a carboxylic acid, the catalyst comprising a tin compound and a ruthenium compound supported on a carrier, the catalyst being prepared by the steps of calcining the tin compound in the presence of oxygen after deposition of the tin compound alone on the carrier, and activating the obtained product after deposition of the ruthenium compound on said carrier, a process for preparing the catalyst, and a process for preparing an alcohol compound using the catalyst.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: June 20, 1995
    Assignee: Arakawa Chemical Industries, Ltd.
    Inventors: Eiji Nagahara, Yasushi Itoi
  • Patent number: 5414016
    Abstract: Leukotriene-B.sub.4 derivatives of formula I ##STR1## are described, in which R.sup.1 means CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sup.5, CONR.sup.6 R.sup.7, orR.sup.1 together with R.sup.2 means a carbonyl group,R.sup.4 symbolizes H, C.sub.1 -C.sub.10 alkyl optionally substituted, C.sub.3 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl radical optionally substituted, or a 5-6-membered aromatic heterocyclic ring,A symbolizes a trans, trans-CH.dbd.CH--CH.dbd.CH, a --CH.sub.2 CH.sub.2 --CH.dbd.CH-- or a tetramethylene group,B symbolizes a C.sub.1 -C.sub.10 alkylene group, which optionally can be substituted by fluorine or the group ##STR2## D can mean a direct bond, oxygen, sulfur, --C.tbd.C--, --CH.dbd.CR.sup.6 or together withB can also mean a direct bond, their salts with physiologically compatible bases and their cyclodextrin clathrates.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: May 9, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5382709
    Abstract: Substituted (1.alpha., 2.beta., 3.alpha. or .beta.,4.alpha.,5.alpha. or .beta.)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclopentylamines are inhibitors of alphamannosidase and alpha-fucosidase and are useful immunostimulants, antiviral and antimetastatic agents.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: January 17, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Robert A. Farr, Norton P. Peet
  • Patent number: 5349097
    Abstract: A process for the catalytic isomerization of secondary .alpha.-alkenols of formula I ##STR1## in which R.sup.1 is a C.sub.1 -C.sub.20 alkyl group or a C.sub.2 -C.sub.2 alkenyl group and in which R.sup.2 stands for hydrogen, a halogen atom, a C.sub.1 -C.sub.10 alkoxy group, a carbonyl group, or a C.sub.1 -C.sub.20 alkyl group and in which R.sup.1 and R.sup.2 can be joined together to complete a five-membered or six-membered carbocyclic ring, to primary .alpha.-alkenols of formula II ##STR2## or for the isomerization of primary .alpha.-alkenols of formula II to secondary .alpha.-alkenols of formula I, wherein the isomerization is carried out in the presence of organotrioxorhenium(VII) compounds of formula III ##STR3## in which R.sup.3 is a C.sub.1 -C.sub.10 alkyl group, a cyclopentadienyl group substituted by from one to five C.sub.1 -C.sub.4 alkyl groups, an unsubstituted cyclopentadienyl group, a C.sub.6 -C.sub.10 aryl group, or a C.sub.7 -C.sub.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: September 20, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Thome, Michael Roeper, Heinz-Josef Kneuper
  • Patent number: 5336815
    Abstract: Preparation of vinyl glycols (I) ##STR1## (R.sup.1 to R.sup.6 =H, a carbo-organic radical, optionally substituted) in which an unsaturated diol of formula II ##STR2## is isomerized in the presence of a rhenium catalyst under neutral conditions. The compounds (I) serve as intermediates for the preparation of active substances and for the preparation of polymers.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: August 9, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Walter Gramlich, Michael Huellmann, Hans-Ulrich Scholz
  • Patent number: 5332814
    Abstract: Process for the preparation of racemic compounds of the formula I ##STR1## or enantiomers thereof, in which B is the radical of a nucleic base from the series comprising purine, a purine analogue or a pyridine analogue, and R is H or a protective group R.sub.1, by reactinga) a compound of the formula II or enantiomer thereof ##STR2## with a compound of the formulae X--CO--X, X--CS--X, X--SO--X, X--SO.sub.2 --X, R.sub.2 --NCO, R.sub.3 R.sub.4 N--C(O)--R.sub.5, X.sub.2 P--R.sub.6 or X.sub.2 P(O)--R.sub.6, in which X is a leaving group, R.sub.2 is, for example, C.sub.1 -C.sub.18 alkyl, R.sub.3 and R.sub.4 are, for example, H or C.sub.1 -C.sub.18 alkyl, R.sub.5 is, for example, H or C.sub.1 -C.sub.12 alkyl, and R.sub.6 is, for example, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, to give a compound of the formula III or enantiomers thereof ##STR3## in which Y is the groups --C(O)--, --C(S)--, --SO--, --SO.sub.2 --, R.sub.2 NH--CH.dbd., R.sub.3 R.sub.4 N--CR.sub.5 .dbd., R.sub.6 P.dbd. and R.sub.6 (O)P.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: July 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Heinz Moser
  • Patent number: 5288701
    Abstract: The invention concerns novel odorants, namely derivatives of dihydrocampholenic aldehyde having the formula ##STR1## wherein R is ##STR2## one of the dotted lines in each of (a) and (b) represents an additional bond, and,R.sup.1, R.sup.2 and R.sup.3 are selected from the group consisting of hydrogen and alkyl groups of from one to four carbon atoms, with the proviso that R.sup.3 is present only when the additional bond is between the carbon atoms designated as .beta. and .gamma..The invention also concerns odorant compositions containing the dihydrocampholenic aldehyde derivatives and methods for making same.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: February 22, 1994
    Assignee: Givaudan-Roure Corporation
    Inventor: Josianne Baudin
  • Patent number: 5264638
    Abstract: A process for the extraction and purification of the diterpene alcohol Plaunotol from the leaves of the medicinal plant, Croton sublyratus Kurz. The process involves extracting firstly with a lower aliphatic alcohol followed by extracting from the alcohol solution with a chlorinated hydrocarbon. Then impurities are hydrolysed and the required Plaunotol separated by extraction with a hydrocarbon. This process is simple and gave much better yields than prior processes.
    Type: Grant
    Filed: January 28, 1992
    Date of Patent: November 23, 1993
    Assignee: Chulalongkorn University
    Inventor: Naline Nilubol
  • Patent number: 5262571
    Abstract: A process of synthesizing enantiomerically pure compounds defined by Formula V, ##STR1## which are useful as chiral auxiliaries is disclosed. The process comprises, first, combining a base of Formula Y.sup.- Z.sup.+ (Formula I), wherein Y.sup.- is an organic anion and Z.sup.+ is an inorganic cation, with a compound of Formula II, ##STR2## wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group and R.sub.2 is the same as R.sub.1, or wherein R.sub.1 and R.sub.2 together form cyclopentane or cyclohexane, and wherein R.sub.3 is a substituted or unsubstituted aryl group, to form a compound defined by Formula III, ##STR3## then: (b) reacting the compound of Formula III with a cyclic epoxide defined by Formula IV, ##STR4## wherein n is 1, 2, or 3, to form a racemic mixture of a compound defined by Formula V.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: November 16, 1993
    Assignee: North Carolina State University
    Inventors: Daniel L. Comins, James M. Salvador
  • Patent number: 5225579
    Abstract: There is provided a method with which vitamin D.sub.2, vitamin D.sub.3, activated type vitamin D.sub.2, activated type vitamin D.sub.3 and their derivatives are prepared from 7,8 -dihyroxy vitamin D.sub.2, D.sub.3 or any of their derivatives by means of a reducing elimination technique involving as cyclic orthoester of a 7,8-dihydroxy compound or a thiocarbonate compound as an intermediate compound or an elimination technique utilizing a reducing metal such as titanium. The method according to the invention ensures a practical and simple synthetic process and a high yeild as compared with any existing methods for manufacturing these chemicals.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: July 6, 1993
    Assignee: Hoxan Corporation
    Inventor: Yuji Tahara
  • Patent number: 5206229
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: April 27, 1993
    Assignee: Leo Pharmaceutical Products LTD
    Inventors: Martin J. Calverley, Lise Binderup, Ernst T. Binderup
  • Patent number: 5202502
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5149843
    Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5149889
    Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: September 22, 1992
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Jurgen Deberitz, Wilfried Weiss
  • Patent number: 5126452
    Abstract: This invention relates to new process for preparing certain optically active purine substituted cyclopentene derivatives and novel intermediates used in this process. In particular, the invention concerns the synthesis of the 1R-cis isomer of carbovir, (1R-cis)-amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-6H-pur in-6-one, an antiviral agent, and certain intermediates.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: June 30, 1992
    Assignee: Glaxo Inc.
    Inventors: Robert Vince, Mark L. Peterson, John W. Lackey, Robert A. Mook, Jr., John J. Partridge
  • Patent number: 5107039
    Abstract: Optically active cyclopentenols are here disclosed which are represented by the formula (I) ##STR1## (wherein R is a hydrogen atom or an acyl group having 2 to 15 carbon atoms, and the sign * denotes a chiral carbon atom).The optically active cyclopentenols can be prepared by a process which comprises the step of carrying out a transesterification between (.+-.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: April 21, 1992
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Kazutoshi Miyazawa
  • Patent number: 5087775
    Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
  • Patent number: 5068368
    Abstract: A process for the preparation of ethynyl carbinols of the formula: ##STR1## wherein R" is hydrogen, a substituted or unsubstituted aliphatic or aromatic hydrocarbon, R'" is a substituted or unsubstituted aliphatic or aromatic hydrocarbon or R" and R'" together to the carbon atom to which they are joined represent a steroid, which comprises the steps ofA. reacting in a solvent system comprising an aromatic hydrocarbon, at least one lithium alkylamide selected from the group consisting of: ##STR2## wherein R is a hydrogen or lower alkyl, R' is hydrogen, lower alkyl, a substituted or unsubstituted aliphatic, alicyclic or aromatic hydrocarbon, x is an integer of 2 to 8, y and z are each 0 to 1, with acetylene to form a monolithium acetylideB. reacting in a solvent system comprising an aromatic hydrocarbon, the monolithium acetylene from Part A with a ketone of the formula R"R'"C.dbd.O, wherein R" and R'" are as hereinbefore defined, and thenC.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: November 26, 1991
    Assignee: Cyprus Foote Mineral Company
    Inventors: W. Novis Smith, Christopher Louer
  • Patent number: 5066815
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 19, 1991
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 5057630
    Abstract: This invention relates to a new process for preparing certain optically active purine substituted cyclopentene derivatives including the antiviral agent, carbovir, and novel intermediates used in this process. In particular, this invention concerns a synthesis of (1R-cis)-4-hydroxymethyl-2-cyclopenten-1-ol, an intermediate in this process.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: October 15, 1991
    Assignee: Glaxo Inc.
    Inventors: John W. Lackey, Robert A. Mook, Jr., John J. Partridge
  • Patent number: 5043495
    Abstract: A process of separation and purification of a propargyl alcohol which comprises treating a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each other, and is selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a phenyl group; a halophenyl group, a phenyl group having at least one methyl substituent, an aralkyl group and a cycloalkyl group,which is chemically or optically impure,with a tertiary diamine represented by Formula (II): ##STR2## wherein each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and R.sub.3, R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: August 27, 1991
    Assignee: Ube Industries, Ltd.
    Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
  • Patent number: 5030772
    Abstract: This invention relates to hydroxylated derivatives of vitamin D.sub.2 and a process for preparing such compounds. In particular, a process for preparing the 24-epimer of vitamin D.sub.2 and the corresponding 1.alpha.-hydroxylated derivative thereof is disclosed. The vitamin D.sub.2 derivatives would find application in the treatment of or prophylaxsis for various disease states characterized by calcium and phosphorous imbalances.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: July 9, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Shigeya Okada
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4999454
    Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: March 12, 1991
    Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.
    Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
  • Patent number: 4990693
    Abstract: Novel physiologically active substances KS-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 5, 1991
    Assignee: Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
  • Patent number: 4987236
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom, R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: January 22, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4983775
    Abstract: Novel physiologically active substances Ks-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: January 8, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
  • Patent number: 4968848
    Abstract: A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyl-trimethylsilane of the general formula (CH.sub.3).sub.3 Si-C.sub.n F.sub.2n+1 (I), wherein the group C.sub.n F.sub.2n+1 represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula F.sup.1 --CO--R.sup.2 (II), wherein R.sup.1 represents a hydrocarbon group or hydrogen and R.sup.2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R.sup.1 and R.sup.2 together may also be part of an alicyclic ring system, in the presence of a salt-like fluoride--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR1## and isolating this compound or hydrolyzing it to yield an alcohol of the formula IV ##STR2## The invention also relates to pentafluoroethyl trimethylsilane (CH.sub.3).sub.3 Si--CF.sub.2 CF.sub.3 and a process for the preparation of this compound.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: November 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfred Kruse, Gunter Siegemund, Axel Schumann
  • Patent number: 4958033
    Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
  • Patent number: 4935560
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: June 19, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4933508
    Abstract: A method for producing a cycloalkanol, which comprises oxidizing a cycloalkane with a molecular oxygen-containing gas in a liquid phase in the presence of a catalyst, wherein an aromatic nitro compound is present in the oxidation reaction system.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: June 12, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Haruo Habu, Kouji Watanabe, Takeshi Matsuoka
  • Patent number: 4933511
    Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: June 12, 1990
    Assignee: ICI Australia Limited
    Inventors: Matthew Gredley, Colin Wilshire
  • Patent number: 4916252
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4902812
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: February 20, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4886919
    Abstract: A process for the gas phase hydrogenation of unsaturated trisubstituted monoesters to the saturated trisubstituted alcohols using a Zn.sub.a Cu.sub.b X.sub.c Ni.sub.d O.sub.e reduced catalyst.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: December 12, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Ernesto Vera-Castaneda, John E. Logsdon
  • Patent number: 4870104
    Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: September 26, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4866181
    Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 12, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4849550
    Abstract: A industrially excellent method for producing a cycloalkanol by the hydration of a cycloalkene having from 4 to 8 carbon atoms with an aromatic sulfonic acid as a catalyst which comprises carrying out said hydration in the presence of a phenol.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: July 18, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Itaru Kawata
  • Patent number: 4835278
    Abstract: A process is described for the preparation of a compound of formula (2) ##STR1## (wherein R is a C.sub.1-6 alkyl or a C.sub.7-20 aralkyl group) and the salts thereof, which comprises reducing a compound of formula (3) ##STR2## (or a salt thereof), using a reducing system comprising borohydride ions and metal ions selected from lanthanide ions, alkaline earth metal ions or yttrium ions in solution. The reduction system may be provided by a borohydride (e.g. NaBH.sub.4) and a metal salt (e.g. CeCl.sub.3).The ester (2) may then if desired be hydrolyzed to give the parent acid.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: May 30, 1989
    Assignee: Glaxo Group Limited
    Inventors: Roger Barrett, Clive A. Meerholz, Brian D. Judkins
  • Patent number: 4820879
    Abstract: The present invention provides a process for making hydrocarbyloxy magnesium halides by reacting in an inert atmosphere under anhydrous conditions activated magnesium metal with an oxygen containing compound of 1 to 20 carbon atoms and an anhydrous hydrogen halide to produce a hydrocarbyloxy magnesium halide.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: April 11, 1989
    Assignee: Lithium Corporation of America
    Inventor: Vijay C. Mehta