Unsaturated Carbocyclic Ring Or Acyclic Carbon To Carbon Unsaturation Containing Patents (Class 549/80)
  • Patent number: 5856560
    Abstract: A process and intermediates for preparing .alpha.
    Type: Grant
    Filed: December 10, 1996
    Date of Patent: January 5, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Bayer, Heinz Isak, Horst Wingert, Hubert Sauter, Michael Keil, Markus Nett, Remy Benoit, Ruth Muller
  • Patent number: 5856323
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i. e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: January 5, 1999
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5824661
    Abstract: Compounds of the formula ##STR1## where m and n are integers 0 to 10 and m+n equals 0 to 10, (a) X is O or S(b) Z is a covalent bond; a monocyclic or polycyclic carbocycle ring moiety; or a monocyclic or polycyclic heterocyclic ring moiety containing one or more heteroatoms selected from O, S, or N;(c) Q is covalent bond; O; or S;(d) R is COOH, SO.sub.3 H, PO.sub.3 H.sub.2, or P(O)(OH)R.sup.4, wherein R.sup.4 is C.sub.1 -C.sub.8 alkyl;(e) R.sup.1, R.sup.2 and R.sup.5 are as defined in the claims.are useful in the treatment of calcium and phosphate elated disorders, such as arthritis and the like.
    Type: Grant
    Filed: September 7, 1994
    Date of Patent: October 20, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Marion David Francis, Susan Mary Kaas, Frank Hallock Ebetino
  • Patent number: 5808112
    Abstract: The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.
    Type: Grant
    Filed: June 17, 1997
    Date of Patent: September 15, 1998
    Assignee: Hoechst Marion Roussel Inc.
    Inventors: Timothy T. Curran, David A. Hay, Jonathan C. Evans
  • Patent number: 5808083
    Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification, have retinoid-like biological activity.
    Type: Grant
    Filed: May 12, 1997
    Date of Patent: September 15, 1998
    Assignee: Allergan
    Inventors: Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Roshantha A. Chandraratna
  • Patent number: 5789600
    Abstract: An electrolytically polymerizable macromolecular compound which is advantageously usable as a surface modifier for a polar surface, as a compatibilizing agent for polymer alloys, as an adhesive primer, as an electrochromic substance, etc., a polymerizable monomer to be used for the production thereof, and a method for the production of an electrolytically polymerized film thereof are disclosed. The macromolecular compound has a repeating unit represented by the following general formula (2): ##STR1## wherein R.sub.1 represents a hydrogen atom or an alkyl group, A represents an electrolytically polymerizable group, and B represents a divalent group.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: August 4, 1998
    Assignee: YKK Corporation
    Inventors: Makoto Sakai, Masaki Wakabayashi, Akira Ishibashi
  • Patent number: 5747542
    Abstract: Compounds of the formula ##STR1## where the symbols have the meaning described in the application, have retinoid-like or retinoid antagonist-like biological activity.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: May 5, 1998
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Alan T. Johnson, Richard L. Beard, Min Teng, Tae K. Song, Harold N. Wong, Roshantha A. Chandraratna
  • Patent number: 5739140
    Abstract: Novel compounds of Formula I and methods of making and using the compounds which are useful as fungicides, particularly in the agricultural field: ##STR1## wherein C.sub.1 and C.sub.2 are carbon atoms which are part of an aromatic ring; W is alkoxyimino, alkoxymethylene or alkylthiomethylene; R.sub.1 is independently selected from the group consisting of halogen, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, wherein the alkyl or alkoxy are optionally substituted by halogen, and p is 0, 1, or 2; Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, NR.sub.2 wherein R.sub.2 is hydrogen or a lower aliphatic group, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 S(O)--, --OCH.sub.2 --, --SCH.sub.2 --, --S(O)CH.sub.2 --, --CH.sub.2 ON.dbd.C(R.sub.3)-- or --CH.dbd.NB wherein B is --O--CO--, --N.dbd.CR.sub.3, or --CR.sub.3 R.sub.4 -- wherein R.sub.3 and R.sub.4 are independently hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: October 23, 1996
    Date of Patent: April 14, 1998
    Assignee: Monsanto Company
    Inventors: William P. Clinton, Jim I. McLoughlin, Anita E. Otal, John J. Parlow, Dennis P. Phillion, Ajit S. Shah
  • Patent number: 5723499
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(i): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: March 3, 1998
    Assignee: C.I.R.D. Galderma
    Inventors: Bruno Charpentier, Jean-Michel Bernardon
  • Patent number: 5663367
    Abstract: Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R.sub.4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.4 groups, the divalent Y radical being substituted by the Z and --CR.sub.1 .dbd.CR.sub.1 --CR.sub.1 .dbd.CR.sub.1 groups on adjacent carbons; X is S, O, or NR.sub.5 ; n is 1 or 2; R.sub.1 and R.sub.2 independently are H, lower alkyl or fluoroalkyl; R.sub.3 is hydrogen, lower alkyl, Cl or Br; R.sub.4 is lower alkyl, fluoroalkyl or halogen; R.sub.5 is H or lower alkyl, and B is hydrogen, 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: May 31, 1996
    Date of Patent: September 2, 1997
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
  • Patent number: 5659049
    Abstract: Water or lipid soluble, pharmacologically active, antioxidant, anti-phospholipase compounds that are chemically defined. The compounds protect mammalian cells by inhibiting PLA.sub.2 and preventing oxidation. In particular, each compound has at least two fatty moieties and no active hydroxy group. The compound may also have at least one ionizable group, which may a carboxyl group, and each of the fatty moieties has from sixteen to twenty carbon atoms and at least one cis-unsaturated double bond.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 19, 1997
    Assignee: Virginia Commonwealth University
    Inventors: Richard C. Franson, Raphael M. Ottenbrite
  • Patent number: 5648486
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: July 15, 1997
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5635537
    Abstract: A compound of the formula ##STR1## Z is hydrogen or halogen, Q is COR.sup.1 or 5-or 6-membered aryl which may contain 1 or 2 heteroatoms selected from N, 0 or S and may be substituted or fused wherein R is hydrogen or C.sub.1 -methyl (cis-configuration), R.sup.1 is C.sub.1 -C.sub.6 alkyl or an aromatic ring which may contain heteroatoms selected from O and S and may be substituted or fused to an optionally substituted benzene ring, R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sup.3 may be different groups defined in claim 1, and enantiomers/salts thereof, processes for preparation of said compounds, pharmaceutical preparations containing said compounds, use of and method of treatment of disorders in CNS by using said compounds.
    Type: Grant
    Filed: March 18, 1993
    Date of Patent: June 3, 1997
    Assignee: Astra Aktiebolag
    Inventors: Nils-Erik Anden, Berit C. E. Backlund Hook, Anna L. Bjork, Uli A. Hacksell, Sven-Erik Hillver, Ye Liu, Eva C. Mellin, Eva M. Persson, Karl J. Vallg.ang.rda, Hong Yu
  • Patent number: 5591869
    Abstract: Methylene compounds are preferably prepared by reducing an aluminum halide complex of the formula ##STR1## in which R.sup.1 represents a C.sub.6 -C.sub.10 -aryl radical which is optionally substituted by 1 to 4 C.sub.1 -C.sub.4 -alkyl radicals, 1 to 4 fluorine, chlorine and/or bromine atoms, one C.sub.1 -C.sub.8 -alkoxy group and/or one acetoxy group, or represents a heteroaryl radical which is optionally substituted by one C.sub.1 -C.sub.4 -alkyl radical and/or one fluorine, chlorine or bromine atom and contains 5 to 10 C atoms and one O or S atom andR.sup.2 represents a C.sub.1 -C.sub.12 -alkyl radical which is optionally substituted by 1 to 5 fluorine, chlorine and/or bromine atoms, independently of R.sup.1 represents a radical as defined for R.sup.1 and, in the case where R.sup.1 =a C.sub.6 -C.sub.
    Type: Grant
    Filed: December 6, 1995
    Date of Patent: January 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Fiege, Ferdinand Hagedorn
  • Patent number: 5550258
    Abstract: The present invention provides an ester compound represented by a formula I: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group, or a C.sub.1 -C.sub.1 6 alkyl group which may be substituted with at least one halogen atom; and R.sub.3 represents an acid residue of pyrethroids.The invention also relates to an active agent for controlling noxious insect pests containing the ester compound as an active ingredient, an intermediate for production of the ester compound and a process for producing the intermediate. The ester compound represented by the formula I has good activities for controlling noxious insect pests.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: August 27, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
  • Patent number: 5543534
    Abstract: Compounds of Formula 1 ##STR1## wherein X is S or O; R.sub.1 -R.sub.5, m, o, X, Y, A, B are as defined in the specification.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: August 6, 1996
    Assignee: Allergan
    Inventors: Vidyasagar Vuligonda, Min Teng, Richard L. Beard, Alan T. Johnson, Yuan Lin, Roshantha A. Chandraratna
  • Patent number: 5534636
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: July 9, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5534639
    Abstract: There are disclosed novel hydroquinone derivatives of the formulas: ##STR1## The derivatives of the formula (I) have various pharmacological activities such as antioxidation in living bodies and are useful as medicaments, and the derivatives of the formula (II) are intermediates for the production thereof.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: July 9, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirotomo Masuya, Masayoshi Yamaoka
  • Patent number: 5534640
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: July 9, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5455265
    Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 3, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5446069
    Abstract: Disclosed are compounds of formula ##STR1## wherein F represents: ##STR2## or a pharmaceutically acceptable salt. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflamation.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: August 29, 1995
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5444084
    Abstract: Substituted heterocyclic derivatives represented by the formula (I) ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, Q.sup.1, Q.sup.2, Q.sup.3, Q.sup.4, X and Y are as defined, including, specifically, the compound (E)-3-[3-[3-(2-methoxymethyl-8,8-dimethyl-4-nonen-6-ynyl)phenoxymethyl]phe nyl]thiophene, exhibit squalene epoxidase inhibiting activity and are useful in the treatment or prophylaxis of hypercholesterolemia, hyperlipidemia and arteriosclerosis.
    Type: Grant
    Filed: February 11, 1994
    Date of Patent: August 22, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshimi Tsuchiya, Takashi Nomoto, Morihiro Mitsuya, Katsumasa Nonoshita, Masahiro Hayashi, Toshihiko Satoh, Yoshio Sawasaki, Toshio Kamei
  • Patent number: 5434151
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: July 18, 1995
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5389656
    Abstract: Acetylene derivatives of the Formula IR.sup.1 --C.tbd.C--R.sup.2 Iwhere R.sup.1 is an unsubstituted or substituted five-membered heteroaromatic structure and R.sup.2 is an unsubstituted or substituted mononuclear to trinuclear aromatic ring system, their preparation, insecticides and acaricides containing them and methods for their use.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Uwe Kardorff, Christoph Kuenast, Hans Theobald, Thomas Kuekenhoehner
  • Patent number: 5385942
    Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where X and Y may be the same or different from each other and are each a hydroxyl group, a group represented by the formula --(--OCH.sub.2 --).sub.n --OR.sup.6, wherein n is 0 or 1 and R.sup.6 is a lower alkyl group, or an acyl group.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: January 31, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
  • Patent number: 5371240
    Abstract: 3-substituted thiophene compounds contaminating the analogous 2-substituted thiophene compounds, e.g. 3-acetylthiophene contaminating 2-acetyl thiophene, are removed by a selective electrophilic substitution process, e.g. bromination, followed by fractional distillation. It has been found that electrophilic substitution as exemplified by bromination is highly selective towards the 3-substituted thiophenes, yielding compounds of significantly higher molecular weights for separation purposes, to give high purity 2-substituted thiophene compounds.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: December 6, 1994
    Assignee: Torcan Chemical Ltd.
    Inventor: Clarke Slemon
  • Patent number: 5358938
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl terahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiphenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: October 25, 1994
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Saijat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5304658
    Abstract: Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.tbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturate fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: April 19, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Yoshitaka Maki
  • Patent number: 5286750
    Abstract: Unsaturated phenylacetic acid derivatives of the general formula ##STR1## where U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3 or .dbd.CH--S--CH.sub.3 andZ.sup.1 and Z.sup.2 are hydrogen, halogen, trifluoromethyl, cyanide, NO.sub.2 or unsubstituted or substituted alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, COR.sup.4 or NR.sup.5 R.sup.6, and Z.sup.1 and Z.sup.2 may also form a ring,A is meta or para and is (CH.sub.2).sub.n, CH.dbd.CH, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, CH.sub.2 --O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: February 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Mueller, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz, Franz Roehl
  • Patent number: 5246962
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: September 21, 1993
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5237116
    Abstract: A process and catalyst are disclosed for the catalyzed reaction of an organometallic reagent with a reactive halide in the presence of a diphosphine complex of a nickel carboxylate or sulfonate. The process can be employed in the synthesis of aromatic compounds such as bisbenzocyclobutenes.
    Type: Grant
    Filed: April 3, 1991
    Date of Patent: August 17, 1993
    Assignee: Shell Oil Company
    Inventor: Larry S. Corley
  • Patent number: 5225436
    Abstract: Certain aryl substituted naphthalene, benzoxepine, benzazepine and henzocycloheptene derivatives are disclosed. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflammation.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5210219
    Abstract: Novel conjugated stilbenylene polymers are disclosed having non-linear optical properties, and which can be converted to electrically conductive polymers. Such polymers are produced by reacting a novel bis-cycloalkylene sulfonium salt of 2,5-dimethyl stilbene, e.g. 2,5-(4'-methoxy)-stilbene dimethylene bis-(tetramethylene sulfonium bromide), with alkali metal hydroxide to form a cycloalkylene sulfonium salt precursor polymer, and then heating the precursor polymer under conditions to produce the stilbenylene vinylene polymer, e.q. poly(2,5-(4'-methoxy) stilbenylene vinylene).
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: May 11, 1993
    Inventor: John Stenger-Smith
  • Patent number: 5202347
    Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p -- or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p -- (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: April 13, 1993
    Inventor: Nicholas S. Bodor
  • Patent number: 5194619
    Abstract: The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical,R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 andR.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: March 16, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
  • Patent number: 5180838
    Abstract: A method is provided herein for controlling insects which are harmful to agriculture and forestry and which are also harmful both to humans and to domestic animals. The method involves the steps of applying to a locus infested with such insects, a composition comprising a carrier and a biocidal-amount of a specifically-recited phototoxic, naturally-occurring thiophene, acetylene, or a synthetic, structurally-related derivative, analogue or acetylenic compound. Then, that composition, while at that locus, is subjected to UV radiation in the range about 300 nm to about 400 nm, for a sufficient time to impart, to such phototoxic naturally-occurring thiophene, acetylene, or synthetic, structurally-related derivative, analogue or acetylenic compound the desired insect control activity. Certain of these phototoxic naturally-occurring thiophenes, or acetylenes or synthetic, structurally-related compounds are also novel and provide novel insect control compositions.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: January 19, 1993
    Assignee: Her Majesty the Queen as represented by the Minister of National Defense of Her Majesty's Canadian Government
    Inventors: Peter Morand, John T. Arnason, Bernard J. R. Philogene, Anita M. MacEachern, Leonard C. Leitch, Jerzy Kaminski
  • Patent number: 5164518
    Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: November 17, 1992
    Assignee: Iowa State University Research Fondation Inc.
    Inventor: Richard C. Larock
  • Patent number: 5159088
    Abstract: Novel sulfonium salts suitable for use as photoinitiators for cationic polymerization and for photoresists have the general formula (I) ##STR1## where X is 1, 2 or 3,R is a hydrocarbon radicalR.sup.1 is hydrogen, alkyl, alkoxy, halogen or nitro,R.sup.2 is a monovalent radical containing more than 6 carbon atoms,Y is a single bond or a bridge member andA.sup..crclbar. is a non-nucleophilic counterion.
    Type: Grant
    Filed: July 12, 1990
    Date of Patent: October 27, 1992
    Assignee: BASF Aktiengesellschaft
    Inventor: Reinhold Schwalm
  • Patent number: 5149705
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: September 22, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5101053
    Abstract: Radiation sensitive sulfonium salts which contain (1) a sulfonium initiator portion, (2) a spacer portion, and (3) a reactive group portion. The spacer portion has the formula "-o-w- x-z-" wherein "w" is a single bond or one of --C(O)--, --C(O)O--, --C(O)S--, --C(O)NH-- --C(O)N(alkyl)--, --C(S)--, --C(S)S--,--S(O)--, --S(O)(O)--, or --S(O)(O)O--; "X" is an unsubstituted or substituted alkylene radical; and "Z" is --O--, --NH--, --N(C,--C.sub.6 -alkyl)--, or --N(phenyl)--. The reactive group portion is --CH.dbd.CH.sub.2 or --C(O)--C(Y).dbd.CH.sub.2 wherein "Y" is H, C.sub.1 -.sub.6 -alkyl, or phenyl. The sulfonium salts find use in curing monomers which can be subjected to cationic polymerization.
    Type: Grant
    Filed: January 9, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventor: Andreas Boettcher
  • Patent number: 5045563
    Abstract: A method is provided herein for controlling insects which are harmful to agriculture and forestry and which are also harmful both to humans and to domestic animals. The method involves the steps of applying to a locus infested with such insects, a composition comprising a carrier and a biocidal-amount of a specifically-recited phototoxic, naturally-occurring thiophene, acetylene, or a synthetic, structurally-related derivative, analogue or acetylenic compound. Then, that composition, while at that locus, is subjected to UV radiation in the range of about 300 nm to about 400 nm, for a sufficient time to impart, to such phototoxic naturally-occurring thiophene, acetylene, or synthetic structurally-related derivative, analogue or acetylenic compound the desired insect control activity. Certain of these phototoxic naturally-occurring thiophenes, or acetylenes or synthetic, structurally-related compounds are also novel and provide novel insect control compositions.
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: September 3, 1991
    Assignee: Her Majesty the Queen in right of Canada, as represented by Minister of National Defence of Her Majesty's Canadian Government
    Inventors: Peter Morand, John T. Arnason, Bernard J. R. Philogene, Anita M. MacEachern, Leonard C. Leitch, Jerzy Kaminski
  • Patent number: 5001294
    Abstract: Aromatic alkenes, especially diarylbutadienes are produced in a simple economic process by reaction of an anil with an organic compound having a non-aromatic unsaturated system conjugated with an aromatic system, and a terminal methyl group pendent from the non-aromatic unsaturated system; in particular the organic compound is a propenyl-substituted aromatic compound.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: March 19, 1991
    Inventor: Allan S. Hay
  • Patent number: 4980484
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: March 13, 1990
    Date of Patent: December 25, 1990
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4927947
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: May 22, 1990
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4826829
    Abstract: Thiophene derivatives of the following formula are effective as acaricdies: ##STR1## wherein A is selected from -phenylthienyl and -phenyl optionally carrying one or more substitutents selected from -lower alkyl, -lower alkoxy, -phenoxy, -hydroxy, -halogen, -lower haloalkyl, -phenylcarbonyl, -lower alkyl carbonyloxy, -lower alkyl sulfonyl, -lower alkyl sulfonyloxy, -amino, -lowr alkyl carboxamido, and -lower haloalkyl carboxamido;R.sub.4 is selected from -hydrogen and -lower alkyl; andR.sub.5 is selected from -thienyl optionally carrying one or more substituents selected from -lower alkyl, -phenylethynyl, -lower alkylthio, -lower haloalkyl carbonyl, and lower alkyl sulfoxy; or -phenyl optionally carrying one or more substituents selected from -lower alkyl and -lower alkoxy.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: May 2, 1989
    Assignee: FMC Corporation
    Inventors: Susan E. Eurkart, Richard B. Phillips, David M. Roush
  • Patent number: 4820827
    Abstract: A small group of 2,3-diaryl-5-bromothiophene compounds such as 5-bromo-2-(4-methylthiophenyl)-3-(4-fluorophenyl)thiophene have been found to possess significant and unexpected antiinflammatory activity, and inhibition of prostaglandin synthetase useful for the treatment of arthritis and dysmenorrhea.
    Type: Grant
    Filed: February 10, 1984
    Date of Patent: April 11, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stephen B. Haber
  • Patent number: 4814472
    Abstract: There are disclosed diethynylated diphenyl hexafluoropropane compounds, which are suitable for forming copolymers and carbon-carbon composites. These compounds are prepared in high yields by first providing a dihalogenated diphenyl hexafluoropropane compound, coupling the dihalogenated compound with ethynyltrimethylsilane in the presence of an organometallic catalyst to form a silylated ethynyl terminated diphenyl substituted compound and subsequently desilylating the compound to form the desired diethynylated diphenyl hexafluoropropane compound.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: March 21, 1989
    Assignee: Hughes Aircraft Company
    Inventor: Kreisler S. Y. Lau
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel