Plural Ring Oxygens In The Hetero Ring Patents (Class 549/430)
  • Patent number: 6383521
    Abstract: The present invention provides Wondonin A of general formula (I), which is extracted from a two-sponge association of phylum Porifera (sponge) and has antiangiogenic activity, and a process for preparing the same. Wondonin A has no cytotoxicity, but has an inhibitory activity against angiogenesis which is one of the crucial mechanisms of cancer cell metastasis, thus, it can be applied not only as an anticancer drug but also as a therapeutic agent of angiogenesis-associated diseases such as cardiac ischemia, rheumatoid arthritis, and diabetes mellitus.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: May 7, 2002
    Assignee: Korea Ocean Research and Development
    Inventors: Jong-Heon Shin, Ki-Woong Cho, Young-Wan Seo, Jung-Rae Rho, Hyi-Seung Lee, Ho-Jeong Kwon
  • Patent number: 6376683
    Abstract: The present invention relates to an improved, efficient and enantio-selective process for the synthesis of (4R, 6S)-4-hydroxy-6-hydroxymethyl tetrahydropyran-2-one, employing the Sharpless asymmetric dihydroxylation and regiospecific nucleophilic hydride opening of the cyclic sulfite/sulfate as the key steps. The invention also resides in the intermediates used in the process.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: April 23, 2002
    Assignee: Council of Scientific & Industrial Research
    Inventors: Pradeep Kumar, Rodney Agustinho Fernandes
  • Publication number: 20020042524
    Abstract: This invention provides an improved process for cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine which is an intermediate for the preparation of (−)cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydronaphthalene-2-ol which is useful for the treatment of osteoporosis.
    Type: Application
    Filed: October 9, 2001
    Publication date: April 11, 2002
    Inventor: Charles K.F. Chiu
  • Patent number: 6369099
    Abstract: A method of modifying or altering the structure of a 1&agr;-hydroxylated vitamin D compound to increase its biological activity by altering the conformational equilibrium of the A-ring to favor a chair conformation that presents the 1&agr;-hydroxyl in the axial orientation. This is accomplished by either locking the A-ring chair conformation in a geometry having an axially orientated 1&agr;-hydroxyl, or by the addition of one or more substituents to the A-ring which interact with other substituents in the molecule or on the A-ring to provide a driving force to the A-ring to adopt a chair conformation which presents the 1&agr;-hydroxyl in the axial orientation.
    Type: Grant
    Filed: April 20, 2000
    Date of Patent: April 9, 2002
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Rafal R. Sicinski
  • Patent number: 6358980
    Abstract: Compounds of the formula: useful in the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: March 19, 2002
    Assignee: American Cyanamid Company
    Inventors: Jeremy I. Levin, Aranapakam M. Venkatesan, James M. Chen, Arie Zask, Vincent P. Sandanayaka, Mila T. Du, Jannie L. Baker
  • Publication number: 20020032339
    Abstract: The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitabIe base. The invention also provides useful arylboron intermediates.
    Type: Application
    Filed: December 18, 1998
    Publication date: March 14, 2002
    Inventors: SEBASTIAN MARIO MARCUCCIO, MARY RODOPOULOS, HELMUT WEINGOLD
  • Patent number: 6355812
    Abstract: The invention relates to improved methods of producing aryl dioxoalkanoic acid compounds and derivatives useful as intermediates for diarylpyrrole therapeutic agents by the alcoholysis of benzoylcyclohexanone ketal compounds.
    Type: Grant
    Filed: May 5, 2000
    Date of Patent: March 12, 2002
    Assignee: Orth-McNeil Pharmaceutical, Inc.
    Inventors: Michael P. Ferro, Kathleen A. McCoy
  • Patent number: 6348606
    Abstract: The claimed invention relates to cyclic dienol ethers of formula (III). wherein R3 is hydrogen and R4 is C1-4 alkoxy or R3 and R4 together form an optionally substituted methylenedioxy group —O—C(R5)(R6)—O—, wherein R5 and R6 are each independently hydrogen, C1-4 alkyl or phenyl.
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: February 19, 2002
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, August Rüttimann
  • Publication number: 20020015804
    Abstract: There can be provided a liquid crystalline compound expressed by the general formula (1): 1
    Type: Application
    Filed: July 22, 1999
    Publication date: February 7, 2002
    Inventors: YASUHIRO HASEBA, SHUICHI MATSUI, KAZUTOSHI MIYAZAWA, NORIHISA HACHIYA, ETSUO NAKAGAWA
  • Patent number: 6342612
    Abstract: The present invention is directed to indanyl derivatives and the use of the indanyl derivatives in creating fragrances, and scents in items such as perfumes colognes and personal care products.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: January 29, 2002
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Robert P. Belko, Ellen Ann Molner
  • Patent number: 6342613
    Abstract: The present invention regards a three-step process for the synthesis of 5-(&agr;-hydroxyalkyl) benzo[1,3]dioxols. The process comprises: (i) the reaction of pyrocatechin (1,2-dihydroxybenzene) with a dihalo or di-alkoxyalkane, with the formation of a benzo[1,3]dioxol derivative; (ii) 5-selective catalytic acylation of the benzo[1,3]dioxol, with formation of a 5-alkanoylbenzo[1,3]dioxol and its subsequent (iii) reduction to 5-(&agr;-hydroxyalkyl) benzo[1,3]dioxol. Also described are new benzodioxols obtainable using the above-mentioned process. The process of the invention is industrially simple and has low environmental impact; it allows to obtain in high yields derivatives of considerable interest, in particular for the perfumery industry, and in the sector of insecticides.
    Type: Grant
    Filed: May 23, 2001
    Date of Patent: January 29, 2002
    Assignee: Endura S.p.A.
    Inventors: Valerio Borzatta, Dario Brancaleoni
  • Patent number: 6313322
    Abstract: A process for preparing acetals of the formula I where a) the Rs are, independently of one another, a C1-C20-alkyl or C3-C20-alkenyl radical, or b) the two R radicals together form the members of an unsubstituted or C1-C10-alkyl-substituted 5- to 7-membered cyclic acetal, by reacting 3-methyl-2-butenal in the presence of sulfamic acid, of a N-(C1-C8-alkyl)sulfamic acid or of a N,N-di(C1-C8-alkyl)sulfamic acid as catalyst with: an alcohol of the formula R—OH (IIa), or an orthoester of the formula HC—(OR)3 (III) or a mixture of an alcohol of the formula (IIa) and an orthoester of the formula (III), or an alcohol of the formula HO—(CH2)m—OH (IIb), where m is a number from 2 to 4, and (CH2)m group in the alcohol IIb may be substituted by a C1-C10-alkyl group.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: November 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gisela Hieber, Klaus Ebel
  • Patent number: 6307069
    Abstract: The decomposition reactive emulsifier of this invention is a compound of formula (I): wherein R1 and R2 are the same or different and each represents an alkyl or alkenyl group of from 1 to 20 carbon atoms or a hydrogen atom and both R1 and R2 are not concurrently a hydrogen; R3 is a hydrogen atom or a methyl group; A is an alkylene or substituted alkylene group of 2 to 4 carbon atoms; n is an integer of from 1 to 100 when X is a hydrogen atom or n is an integer of from 0 to 100 when X is an ionic hydrophilic group, said ionic hydrophilic group being anionic, cationic or amphoteric and when n is 2 or greater (AO)n is a homopolymer or a block copolymer or a random copolymer.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: October 23, 2001
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Masayuki Hashimoto, Toshiyuki Nishitani
  • Patent number: 6294568
    Abstract: The present invention provides compounds represented by the general formula (I): and a salt thereof, and anti-inflammatory agents and antitumor agents containing the compounds as the active ingredients.
    Type: Grant
    Filed: June 26, 2000
    Date of Patent: September 25, 2001
    Assignee: Nissin Food Products Co., Ltd.
    Inventors: Toshihiro Yamada, Yoichi Nobuhara, Kazuhiro Kobayashi, Satoshi Hirano, Takanobu Sakurai, Hiroshi Mikami, Ayako Miyake
  • Publication number: 20010004457
    Abstract: The sensory properties of the diastereomeric enantiomer pairs and of the pure enantiomers of the compound 2-methyl-4-phenyl-1,3-dioxolane are described. The cis compounds (2 S,4 R)-2-methyl-4-phenyl-1,3-dioxolane and (2 S,4 R)-2-methyl-4-phenyl-1,3-dioxolane are the most sensorially valuable. These enantiomers and mixtures thereof are particularly suitable for use as a sensorially active substance, for example as a fragrance.
    Type: Application
    Filed: December 15, 2000
    Publication date: June 21, 2001
    Inventors: Wilhelm Pickenhagen, Dietmar Schatkowski
  • Patent number: 6232476
    Abstract: This invention provides an improved process for cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine which is an intermediate for the preparation of (-)cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydronaphthalene-2-ol which is useful for the treatment of osteoporosis.
    Type: Grant
    Filed: May 19, 2000
    Date of Patent: May 15, 2001
    Assignee: Pfizer Inc.
    Inventor: Charles K. F. Chiu
  • Patent number: 6187963
    Abstract: Processes are disclosed for the conversion of propylene to an acrolein derivative by converting propylene to acrolein and converting acrolein to the acrolein derivative. The processes utilize oxygen and recycle propane to the acrolein reactor. Process feeds can comprise, propane, propylene or mixtures thereof. The presence of propane in the propylene-to-acrolein reaction can enhance the efficiency of the processes.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: February 13, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: William George Etzkorn, Richard A. Galley, Thomas E. Snead, Jonathan Lester Brockwell, Mark Anderson Young, John Michael Maher, Barbara Knight Warren
  • Patent number: 6177400
    Abstract: The compounds according to the general formula in which formula the dotted lines indicate a single or a double bond, n and m are 0 or 1, R1 is hydrogen or an acyl group —C(O)R3, R3 being a linear or branched alkyl or alkylene group from C1 to C8, the oxygen atom being bound to the adjacent &agr;-carbon atom by a double bond in the case where n is 0 and by a single bond in the case where n is 1, R2 is hydrogen or a linear or branched alkyl, alkenyl or alkoxy group from C1 to C8, or R2 is an alkenoxy group which is linked to the group R1 to form a 1,3-dioxolane cycle having 5 to 7 ring members, are useful perfuming ingredients. The most preferred compounds according to the invention are those which have a damascone- or damascenone-like structure, with the methyl substituent being in 4-position of the ring instead of the 2-position, as is the case in damascones and damascenones.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Wolfgang Klaus Giersch
  • Patent number: 6153769
    Abstract: A process for the manufacture of polyene aldehydes comprises reacting a polyene O,O-ethylene acetal with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or Bronsted acid, hydrolyzing the resulting condensation product and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel polyene O,O-ethylene acetals as well as the likewise novel condensation products in this process form further aspects of the invention. The final products are primarily carotenoids which find corresponding use, e.g. as colorants and pigments for foodstuffs, animal products etc.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: November 28, 2000
    Assignee: Roche Vitamins Inc.
    Inventor: August Ruttimann
  • Patent number: 6150532
    Abstract: The present invention relates to novel protein tyrosine phosphatase modulating compounds having the general structure shown in Formula (A1), to methods for their preparation, to compositions comprising the compounds, to their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention relates to modulation of the activity of molecules with phosphotyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganism, eukaryoic cells, whole animals and human being. R' and R" are independently selected from the group consisting of hydrogen, halo, cyano, nitro, trihalomethyl, alkyl, arylalkyl. R'" is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, arylalkyl. X is aryl. Y is selected from hydrogen or ##STR1## wherein (*) indicates a potential point of attachment to X.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: November 21, 2000
    Inventors: Adnan Mjalli, Sepehr Sarshar, Xiaodong Cao, Farid Bakir
  • Patent number: 6127407
    Abstract: The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof, which are specific, potent and safe inhibitors of mammalian cell proliferation. The compounds can be used to inhibit mammalian cell proliferation in situ as a therapeutic approach towards the treatment or prevention of diseases characterized by abnormal cell proliferation, such as cancer.
    Type: Grant
    Filed: November 20, 1997
    Date of Patent: October 3, 2000
    Assignees: Ion Pharmaceuticals, Inc., President and Fellows of Harvard College, Children's Medical Center Corporation
    Inventors: Carlo Brugnara, Jose Halperin, Rudolf Fluckiger, Emile M. Bellott, Jr., Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
  • Patent number: 6120859
    Abstract: Polymerisable optically active compounds have the general formula: ##STR1## where: W.sup.1 denotes a polymerisable residue,S.sup.1 denotes a spacer unit,Y.sup.1 denotes a single bond, or one of the groups --O--, --COO--, --OOC--, --OCOO--, --S--, --CONH-- or --NHCO--,M denotes a divalent mesogenic group, andR.sup.1 and R.sup.2 denote straight chain, branched or cyclic alkyl groups with up to 8 carbon atom.
    Type: Grant
    Filed: December 1, 1999
    Date of Patent: September 19, 2000
    Assignee: Rolic AG
    Inventors: Richard Buchecker, Teodor Lukac, Klaus Schmitt, Alois Villiger
  • Patent number: 6099751
    Abstract: Chiral compounds of the formula I ##STR1## where: R.sup.1,R.sup.2,R.sup.3,R.sup.4 are hydrogen or aromatic, aliphatic or araliphatic radicals having 1 to 40 carbon atoms,R.sup.5,R.sup.6,R.sup.7,R.sup.8 are aromatic or aliphatic radicals having 1 to 20 carbon atoms,with the proviso that at least one of the radicals R.sup.1 to R.sup.8 contains a polymerizable group,are used as dopes in liquid crystals, in compositions for coating substrates and in the preparation of interference pigments which can be used in printing inks and surface coatings.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: August 8, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Meyer, Karl Siemensmeyer, Hans-Georg Kuball, Bernhard Weiss, Dieter Seebach
  • Patent number: 6075155
    Abstract: Disclosed are compounds of the formulas ##STR1## which are useful as monomers in photopolymerizable compositions. Also disclosed are methods of polymerizing these monomers, and polymers produced thereby.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: June 13, 2000
    Assignee: Rensselaer Polytechnic Institute
    Inventor: James V. Crivello
  • Patent number: 6071861
    Abstract: The dihalopropene compounds of the general formula [I ] have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Grant
    Filed: December 2, 1998
    Date of Patent: June 6, 2000
    Assignee: Sumitomo Chemical Company, Inc.
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 6054476
    Abstract: Iminoacetamides of the formula (I) ##STR1## in which A represents a single bond or optionally substituted alkylene,Q represents oxygen or sulphur,R.sup.1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl,R.sup.2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl,R.sup.3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl,R.sup.4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyla process for their preparation, pesticidal compositions containing them, and their use for controlling pests.
    Type: Grant
    Filed: April 15, 1998
    Date of Patent: April 25, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Seitz, Klaus Stenzel
  • Patent number: 6043272
    Abstract: The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof, which are specific, potent and safe inhibitors of mammalian cell proliferation. The compounds can be used to inhibit mammalian cell proliferation in situ as a therapeutic approach towards the treatment or prevention of diseases characterized by abnormal cell proliferation, such as cancer.
    Type: Grant
    Filed: November 20, 1997
    Date of Patent: March 28, 2000
    Assignees: Ion Pharmaceuticals, Inc., President and Fellows of Harvard College, Children's Medical Center Corporation
    Inventors: Carlo Brugnara, Jose Halperin, Rudolf Fluckiger, Emile M. Bellott, Jr., Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
  • Patent number: 6037482
    Abstract: A process for the catalytic addition of nucleophilic agents to alkynes or allenes to form alkenes substituted by the nucleophile which may further react with the nucleophile and/or isomerize comprises using a catalyst comprising a wholly or partly ionized complex of univalent gold.
    Type: Grant
    Filed: June 15, 1998
    Date of Patent: March 14, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Schulz, Joaquim Henrique Teles
  • Patent number: 5969154
    Abstract: A liquid crystalline compound of formula ##STR1## wherein B and D are each independently of the other C.sub.6 -C.sub.24 alkyl, ##STR2## L is ##STR3## methyl or C.sub.10 -C.sub.18 alkyl, wherein R.sub.1 is C.sub.4 -C.sub.18 alkyl, with the proviso that when L is methyl, at least one of B and D is C.sub.6 -C.sub.24 alkyl;R2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano or nitro,R3, R4 and R5 are each independently of one another hydrogen, OR6, SR6, SeR6, --NHR6, --NR6R7, ##STR4## with the proviso that at least one of R3, R4 and R5 is not hydrogen, R6 is C.sub.7 -C.sub.37 alkyl, C.sub.7 -C.sub.37 alkylene or C.sub.5 -C.sub.18 alkyl which is interrupted by 1 to 6 hetero atoms selected from the group consisting of O, S and N,R7 is hydrogen or R9,R8 is hydrogen or C.sub.1 -C.sub.4 alkyl, andR9 is C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkylene or C.sub.3 -C.sub.12 alkyl which is interrupted by 1 to 6 hetero atoms selected from the group consisting of O, S and N.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: October 19, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, Abul Iqbal, Nancy Tebaldi, Klaus Praefcke
  • Patent number: 5916995
    Abstract: There are disclosed an aromatic hydroxy compound or polymer substituted with acetal of Formula (I), (II) or (III), and a negative photoresist composition prepared therefrom. The pattern formed of the negative photoresist composition has good cross sections in addition to being superior in transmissivity to deep uv light and excimer laser and in thermal resistance and storage stability after exposure.
    Type: Grant
    Filed: September 17, 1997
    Date of Patent: June 29, 1999
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ji-Hong Kim, Sun-Yi Park
  • Patent number: 5917059
    Abstract: Cyclic acetals or ketals are prepared by reacting a polyol with the appropriate aldehydes or ketones, with part of the aldehyde or ketone being distilled out during the reaction.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: June 29, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Karl Haberle, Helmut Gruner, Michael Hirn
  • Patent number: 5912366
    Abstract: .alpha.,.alpha.-Difluoro-.beta.-hydroxy thiol esters of Formula (III): ##STR1## wherein: R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, S-tert-butyl difluorothioacet-2-yl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkenyl, substituted C.sub.3 -C.sub.8 cycloalkyl, substituted C.sub.3 -C.sub.8 cycloalkenyl, aryl, substituted aryl, C.sub.6 -C.sub.10 fused aromatic rings, and substituted C.sub.6 -C.sub.10 fused aromatic rings; orR.sup.c and R.sup.d together make up a ring selected from the group consisting of C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkenyl, substituted C.sub.3 -C.sub.8 cycloalkyl and substituted C.sub.3 -C.sub.8 cycloalkenyl;R.sup.e is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, substituted C.sub.1 -C.sub.10 alkyl, aryl, substituted aryl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkenyl, substituted C.sub.3 -C.sub.8 cycloalkyl and substituted C.sub.3 -C.sub.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: June 15, 1999
    Assignee: Eli Lilly and Company
    Inventor: John A. Weigel
  • Patent number: 5886198
    Abstract: Cyclic formal is manufactured by cyclic reaction of an alkylene glycol and an aldehyde in a reactor, producing formal mixed with unreacted aldehyde as an impurity, which impurity is reduced in amount by connecting the reactor to a distillation tower and continuously supplying alkylene glycol to the distillation tower from which unreacted formaldehyde and a cyclic formal are being distilled, and continuously reacting them with supplied raw formaldehyde by countercurrent flow during distillation; water content in azeotropic admixture with cyclic formal can be removed by azeotropic distillation with a hydrocarbon azeotropic mixture with water, distilling water from the cyclic formal.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: March 23, 1999
    Assignee: Toray Industries, Inc.
    Inventors: Daisuke Ogawa, Masahiro Koike, Yoshiyuki Yamamoto
  • Patent number: 5880301
    Abstract: The present invention provides a novel optically active bidentate phosphine ligand palladium complex of formula (I) or (II) which can be used for the preparation of optically active .beta.-hydroxyketones: ##STR1## ?wherein Y.sup.- represents an anion pair which may form salt; X represents ##STR2## {wherein R.sup.1 represents hydrogen atom, C.sub.1-6 alkyl group, C.sub.1-6 alkoxyl group, cyano group, nitro group, halogen atom or phenyl group, etc.; m represents 1 or 2; when m is 2, two R.sup.1 s may be same or different}; andA and B each independently represents phenyl group or cyclohexyl group {said phenyl group and cyclohexyl group each is unsubstituted or substituted by R.sup.2 (R.sup.2 has the same meaning as defined in R.sup.1)}).
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: March 9, 1999
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Kazuhiko Ohrai
  • Patent number: 5876570
    Abstract: A purification process for cyclic formals, in which water is efficiently removed from a crude cyclic formal, namely, a mixture of a cyclic formal and water which is difficult to be separated from the mixture, thereby obtaining a cyclic formal of high purity which contains only a very small amount of water.The purification process for cyclic formals is characterized by the steps of supplying a mixture of a cyclic formal and water into a distillation tower, effecting distillation while supplying a hydrophilic solvent (A) having a boiling point from 180.degree. to 250.degree. C. into the distillation tower at a position higher than the supply position of the mixture, and taking out a purified cyclic formal as a distillate.
    Type: Grant
    Filed: January 18, 1996
    Date of Patent: March 2, 1999
    Assignee: Hoechst Celanese Corporation
    Inventor: Hubert H. Thigpen
  • Patent number: 5773635
    Abstract: A process for preparing polyenecarbonyl compounds having a high all-E content and their acetals or ketals by aldol condensation or Horner-Emmons reaction comprises carrying out the reaction, for the purposes of the preferred formation of a double bond of E configuration and in order to maintain the E configuration of the double bonds in the stating compounds as completely as possible, in the presence of oxygen or an oxygen-inert gas mixture or nitric oxide or a nitric oxide-inert gas mixture and/or in the presence of specific stable radicals and/or in the presence of quinones or quinone derivatives.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Dobler, Wolfgang Krause, Joachim Paust, Otto Worz, Udo Rheude, Wolfram Burst, Gunter Dauwel, Armin Bertram, Bernhard Schulz, Gunter Wegner, Peter Munster, Hansgeorg Ernst, Arno Kochner, Heinz Etzrodt
  • Patent number: 5756804
    Abstract: A process for preparing polycyclic aromatic compounds, which comprises reactinga) an aromatic boron compound withb) an aromatic halogen compound or an aromatic perfluoroalkylsulfonate in the presence ofc) a base,d) a nickel or palladium catalyst,e) a phosphorus-containing ligand andf) a polyhydric alcohol, a sulfoxide or sulfone.The process gives high yields, in particular also in the coupling of chloroaromatics.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: May 26, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Hans-Jerg Kleiner
  • Patent number: 5756775
    Abstract: A process to make .alpha.,.alpha.-difluoro-.beta.-hydroxy thiol esters of formula (IIIA) ##STR1## comprising reacting a difluoroethanethioate of formula (IVA) ##STR2## with a second reactant selected from the group consisting of aldehydes, ketones, acid halides and esters; in a solvent and in the presence of a strong base; with the proviso that the process is conducted in the absence of a catalyst and in the absence of a silyl containing compound. These thiol esters are useful as intermediates in organic syntheses of pharmaceutical products.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: May 26, 1998
    Assignee: Eli Lilly and Company
    Inventor: John A. Weigel
  • Patent number: 5739336
    Abstract: Heterocyclic compounds of Formula I: ##STR1## in which n is 2, 3, 4, 5 or 6; t is 1, 2, 3 or 4; u is 0 or 1 (provided that t is not 1 when u is 0); X is O or N(R.sup.4); Y and Z are independently C(O), C(S) or CH.sub.2 (provided that Y and Z are not both CH.sub.2); R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are as defined in the specification; and their pharmaceutically acceptable salts and N-oxides, formulations containing them, their uses as therapeutic agents, and their synthesis.
    Type: Grant
    Filed: June 20, 1996
    Date of Patent: April 14, 1998
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Klaus K. Weinhardt, Jacob Berger, David S. Carter, Lee A. Flippin
  • Patent number: 5717113
    Abstract: Novel acetogenins isolated from Asimina triloba and Goniothalamus giganteus of the family Annonaceae and derivatives of those and other acetogenins are described. Bioactive cyclic formaldehyde acetal derivatives are prepared from Annonaceous acetogenins having 1,2-, 1,4- or 1,5-diols. A non-adjacent bis-tetrahydrofuran (THF) acetogenin is prepared from an unsaturated mono-THF acetogenin earlier isolated from Goniothalamus giganteus. The substantially pure acetogenins and acetogenin derivatives of the invention exhibit cytotoxicity to human solid tumor cell lines equipotent to adriamycin or orders of magnitude more potent than adriamycin, and they exhibit effective pesticidal activities.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: February 10, 1998
    Assignee: Purdue Research Foundation
    Inventors: Jerry L. McLaughlin, Zhe-ming Gu, Geng-xian Zhao
  • Patent number: 5698715
    Abstract: A process for the preparation of unsaturated cyclic ethers of the general formula I ##STR1## in which Z denotes --(CHR.sup.4).sub.q or --(CHR.sup.4).sub.q --O--q is 0, 1, 2 or 3 andR.sup.1, R.sup.2, R.sup.3, and R.sup.4 denote hydrogen or C.sub.1 -C.sub.4 alkyl from diols of the general formula II ##STR2## in which, R.sup.1, R.sup.2, and R.sup.3 have the aforementioned meanings, in the presence of a cobalt-containing supported catalyst, wherein the cobalt-containing supported catalyst used contains cobalt and a noble metal--selected from the group consisting of platinum, palladium, rhodium, iridium, ruthenium, osmium, rhenium, or mixtures thereof--in an atomic ratio of from 0.5:1 to 70000:1 on an inert support and optionally basic alkali metal and alkaline earth metal salts, scandium, vanadium, chromium, manganese, iron, nickel, copper, zinc, germanium, tin, lead, antimony, bismuth, or mixtures thereof and the reaction is carried out in the liquid phase at temperatures ranging from 150.degree. to 300.degree.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: December 16, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Schroeder, Thomas Fetzer, Christopher William Rieker, Klaus Ebel
  • Patent number: 5695615
    Abstract: A purification process for cyclic formals, in which water is efficiently removed from a crude cyclic formal, namely, a mixture of a cyclic formal and water which is difficult to be separated from the mixture, thereby obtaining a cyclic formal of high purity which contains only a very small amount of water.The purification process for cyclic formals is characterized by the following two purification steps:(1) Supplying a mixture of a cyclic formal and water into a distillation tower at a supply position, and effecting distillation while supplying a hydrophilic solvent (A) having a boiling point from 180.degree. to 250.degree. C. at a position higher than the supply position of the mixture to take out a cyclic formal (X) containing 100 to 5000 ppm of water as a distillate, and(2) Distilling the cyclic formal (X) obtained in step (1) or treating it with a dehydrant to obtain a purified cyclic formal (Y) which contains less water than in the cyclic formal (X).
    Type: Grant
    Filed: August 1, 1995
    Date of Patent: December 9, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: Hubert H. Thigpen
  • Patent number: 5690793
    Abstract: A purification process for cyclic formals, in which water is efficiently removed from a crude cyclic formal, namely, a mixture of a cyclic formal and water which is difficult to be separated from the mixture, thereby obtaining a cyclic formal of high purity which contains only extremely small amounts of water and impurities.The purification process for cyclic formals is characterized by the steps of supplying a mixture of a cyclic formal and water into a distillation tower, effecting distillation while supplying a hydrophilic solver (A) having a boiling point from 180.degree. to 250.degree. C. and a purified cyclic formal (X) containing not more than 200 ppm of water into the distillation tower at positions higher than the supply position of the mixture and higher than the supply position of the hydrophilic solvent (A), respectively, and taking out a purified cyclic formal from the top of the tower as a distillate.
    Type: Grant
    Filed: August 1, 1995
    Date of Patent: November 25, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: Hubert H. Thigpen
  • Patent number: 5688972
    Abstract: A process for the preparation of acetals by reacting one or more ethylenically unsaturated compounds with carbon monoxide, hydrogen and a liquid or dissolved organic nucleophilic compound containing at least two vicinal hydroxy groups in the presence of a catalyst system comprising:a) a source of plantinum;b) a source of anions; andc) a bidentate ligand of the formulaR.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 (I)wherein M.sup.1 and M.sup.2 independently represent a phosphorus, arsenic or antimony atom, R represents a bivalent organic bridging group containing from 1 to 4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent substituted or non-substituted cyclic group whereby the two free valencies are linked to M.sup.1 and R.sup.3 and R.sup.4 independently represent a substituted or non-substituted hydrocarbyl group, or together represent a bivalent substituted or non-substituted cyclic group whereby the two free valencies are linked to M.sup.2.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: November 18, 1997
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Dennis Humphrey Louis Pello
  • Patent number: 5688973
    Abstract: Process for the production of 2-vinyl-1,3-dioxolane reacting acrolein with ethylene glycol in the presence of a solid, acidic catalyst and recovery of the reaction mixture. Selectivity may be increased in comparison with known prior art processes by performing the reaction in the presence of a solid acidic catalyst at a temperature of below 50.degree. C.; the reaction mixture, from which the catalyst has been removed, is treated by extraction using an organic solvent which substantially does not dissolve ethylene glycol and has a boiling point of above 130.degree. C.; the two phases obtained on extraction are treated for recovery by distillation and recovered educts and the organic solvent are recycled.
    Type: Grant
    Filed: September 5, 1995
    Date of Patent: November 18, 1997
    Assignee: Degussa Aktiengesellschaft
    Inventors: Mathias Hoepp, Dietrich Arntz, Wolfgang Boeck, Andreas Bosse-Plois, Klaus Raible
  • Patent number: 5681504
    Abstract: A chiral dopant of the formula ##STR1## wherein ring A is 1,4-phenylene which is optionally substituted with one or more fluorine atoms, chlorine atoms, bromine atoms, cyano groups, or methyl groups, and in which one or two CH groups can be replaced by nitrogen, or is trans-1,4-cyclohexylene;Z is a single covalent bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 --; X.sup.1,X.sup.2,X.sup.3,X.sup.4 each independently are hydrogen or fluorine;R.sup.1 is hydrogen, is alkyl with 1 to 12 carbon atoms which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --0--, is alkenyl with 2 to 12 carbon atoms, which is optionally substituted with one or more fluorine or chlorine atoms and in which one or two non-adjacent CH.sub.2 groups can be replaced by --O--, is a group of the formula ##STR2## and when R.sup.1 is bonded to an aromatic ring, can also be fluorine, chlorine, cyano, CF.sub.3, OCHF.sub.2 or --OCF.sub.3 ;R.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: October 28, 1997
    Assignee: Rolic AG
    Inventors: Richard Buchecker, Guy Marck, Martin Schadt
  • Patent number: 5672708
    Abstract: N-arylaminoacrylic acid derivatives are obtained in good yields and in high purities when benzoylacetic acid derivatives are reacted with N-arylimino ethers. The products thus prepared are used, in particular, for the preparation of 4-quinolone-3-carboxylic acid derivatives, which have an outstanding bactericidal action.
    Type: Grant
    Filed: August 31, 1995
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Rauchschwalbe, Bernhard Beitzke, Wolfgang Eymann, Helmut Fiege
  • Patent number: 5663320
    Abstract: The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity and intermediates useful in those processes.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: September 2, 1997
    Assignee: BioChem Pharma, Inc.
    Inventors: Tarek Mansour, Haolun Jin, Allan H.L. Tse, M. Arshad Siddiqui
  • Patent number: 5635608
    Abstract: The invention relates to caged compounds for the study of biological processes, where the caged compound has a photoremoveable .alpha.-carboxy-substituted o-nitrobenzyl group. Covalent attachment of the substituted o-nitrobenzyl to a parent compound yields a caged compound with biological and/or physical properties that are significantly altered from the original properties of the parent compound. Illumination of the caged compounds to cleave the photoremoveable group yields the parent compound with its original properties restored.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: June 3, 1997
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, Kyle R. Gee
  • Patent number: 5616736
    Abstract: A method of preparing cyclic formals which contain only small amounts of by-product impurities and unreacted starting materials, and which are ready to be purified.In preparing a cyclic formal by reacting alkylene glycol with formaldehyde in the presence of a catalyst, a reaction vessel provided with a vapor-liquid contact zone at the upper part thereof is used. Vapor generated from the reaction mixture and containing a cyclic formal goes up and passes through the vapor-liquid contact zone to be condensed. While part of the condensate is returned to the vapor-liquid contact zone, the remainder of the condensate is taken out as a distillate.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: April 1, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: Hubert H. Thigpen