The Two Cyclos Share At Least Three Ring Members (i.e., Bridged) Patents (Class 549/463)
  • Publication number: 20030187282
    Abstract: The present invention provides a method of industrially advantageously producing 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives under mild conditions in a high yield. The present invention relates to a production method of a 7-oxabicyclo[2.2.
    Type: Application
    Filed: March 14, 2003
    Publication date: October 2, 2003
    Inventors: Tomoya Kuwayama, Katsuji Ujita, Kazuya Shimizu, Shiro Terashima
  • Patent number: 6605632
    Abstract: The invention concerns compounds of formula (I): R—A—R′ wherein: A is as defined in the description; R represents a group (V), (VI), (VII) or (VIII), where E, Q, R1, R2, R3, v and R4 are as defined in the description; R′ represents a —(CH2)t—R5 group wherein t and R5 are as defined in the description
    Type: Grant
    Filed: November 10, 2000
    Date of Patent: August 12, 2003
    Assignee: Les Laboratoires Servier
    Inventors: Daniel Lesieur, Frédérique Klupsch, Gérald Guillaumet, Marie-Claude Viaud, Michel Langlois, Caroline Bennejean, Pierre Renard, Philippe Delagrange
  • Publication number: 20030105125
    Abstract: New tropane analogs that bind to monoamine transporters are described, particularly, 8-aza, 8carbo and 8-oxo tropanes having 6- or 7-hydroxyl or ketone substituents. The compounds of the present invention can be racemic, pure R-enantiomers, or pure S-enantiomers. Certain preferred compounds of the present invention have a high selectivity for the DAT versus the SERT. Also described are pharmaceutical therapeutic compositions comprising the compounds formulated in a pharmaceutically acceptable carrier and a method for inhibiting 5-hydroxy-tryptamine reuptake of a monoamine transporter by contacting the monoamine transporter with a 5-hydroxytryptamine reuptake inhibiting amount of a compound of the present invention. Preferred monoamine transporters for the practice of the present invention include the dopamine transporter, the serotonin transporter and the norepinephrine transporter.
    Type: Application
    Filed: December 27, 2001
    Publication date: June 5, 2003
    Inventors: Peter C. Meltzer, Bertha K. Madras, Paul Blundell
  • Patent number: 6462077
    Abstract: A method of treating ocular hypotension, hypertension, hemorrhage, myocardial ischemia, angina pectoris, coronary contraction, cerebrovascular contraction after subarachnoidal hemorrhage, cerebral hemorrhage and asthma which comprises administering to a mammal suffering therefrom a therapeutically effective amount of a thromboxane ligand which is a compound formula I, wherein Y is (CH2)x; Z is selected from the group consisting of O, OCH2, and (CR2)x, x is an integer of 1 or 2; n is 0 or 1; R2 is hydrogen or an alkyl radical of from 1 to 4 carbons; A is an alkylene or alkenylene radical having from two to seven carbon atoms, which radical may be substituted with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups or said alkylene or alkenylene may have one or more enchained oxa or imino radicals; B is a methyl radical or a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical, selected from the group consisting of hydrocarbyl aryl and heteroar
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: October 8, 2002
    Assignee: Allergan, Inc.
    Inventors: Robert M. Burk, Achim H-P Krauss, David F. Woodward
  • Patent number: 6403824
    Abstract: The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula wherein R1, R2, R3 and R4 are defined in the specification, starting from furan. 4,5-Diamino shikimic acid derivatives are potent inhibitors of viral neuraminidase.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: June 11, 2002
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Stefan Abrecht, Martin Karpf, René Trussardi, Beat Wirz
  • Patent number: 6359153
    Abstract: The present invention relates to monomers for preparing photoresist polymer resins which can be used in a photolithography process employing a deep ultraviolet light source, and the preparation of the same. Preferred monomers are represented by following Chemical Formula 1: <Chemical Formula 1> wherein, X represents CH2, CH2CH2, or oxygen; R1 represents hydrogen, C1-C5 alkyl, or R′OH; R2 represents hydrogen; —OH, C1-C5 alkoxy, or —OR′—OH; R′ represents:  and, m is an integer from 1-5, n is 1 or 2 and p is 0 or 1.
    Type: Grant
    Filed: October 27, 1999
    Date of Patent: March 19, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Chang Il Choi, Hyeong Soo Kim, Jin Soo Kim, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6271252
    Abstract: Cyclic amino acid derivatives of Formula I are antagonists of VLA-4 and/or &agr;4&bgr;7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of asthma, allergies, inflammation, multiple sclerosis, and other inflammatory and autoimmune disorders.
    Type: Grant
    Filed: May 23, 2000
    Date of Patent: August 7, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Linda Chang, William K. Hagmann, Malcolm MacCoss
  • Patent number: 6245828
    Abstract: The present invention is directed to polymerizable dental compositions containing a) 3 to 80 wt. % of cycloaliphatic epoxides; b) 0 to 80 wt. % of an epoxide or a mixture of epoxides which are different from a); c) 3 to 85 wt. % of a filer material; d) 0.01 to 25 wt. % of initiators, inhibitors and/or accelerators; e) 0 to 25 wt. % of auxiliary agents, the individual percentages of which are in relation to the total weight. The new polymerizable agents are particularly suited as dental material.
    Type: Grant
    Filed: September 21, 1998
    Date of Patent: June 12, 2001
    Assignee: ESPE Dental AG
    Inventors: Wolfgang Weinmann, Oswald Gasser, Rainer Guggenberger, Gunther Lechner, Wolfgang Soglowek, Joachim Zech
  • Patent number: 6200731
    Abstract: The present invention discloses a cross-linking monomer for a photoresist polymer represented by following Chemical Formula 1: <Chemical Formula 1> wherein, V represents CH2, CH2CH2, oxygen or sulfur; Y is selected from the group consisting of straight or branched C1-10 alkyl, oxygen, and straight or branched C1-10 ether; R′ and R″ individually represent H or CH3; i is a number of 1 to 5; and n is a number of 0 to 3; and a process for preparing a photoresist copolymer comprising the same.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: March 13, 2001
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Cha Won Koh, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6090845
    Abstract: A method of treating ocular hypotension, hypertension, hemorrhage, myocardial ischemia, angina pectoris, coronary contraction, cerebrovascular contraction after subarachnoidal hemorrhage, and asthma which comprises administering to a mammal suffering therefrom a therapeutically effective amount of a thromboxane ligand which is a compound formula I, ##STR1## wherein Y is (CH.sub.2).sub.x ; Z is selected from the group consisting of O, OCH.sub.2, ##STR2## and (CR.sub.2).sub.x, x is an integer of 1 or 2; R.sub.
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: July 18, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Robert M. Burk, Achim H. Krauss, David F. Woodward
  • Patent number: 6077864
    Abstract: A compound of the formula ##STR1## wherein n, X, Y and Ar are as defined herein, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, macular degeneration, restenosis, periodontal disease, epidermolysis bullosa, scleritis, and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID'S) and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: June 20, 2000
    Assignee: Pfizer Inc.
    Inventors: Laurence Edward Burgess, James Patrick Rizzi
  • Patent number: 6057460
    Abstract: Polymerizable hybrid monomers with norbornenyl or norbornadienyl groups are described which can be radically cured at room temperature and are suitable in particular for use in the dental field.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: May 2, 2000
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Volker Rheinberger, Frank Zeuner
  • Patent number: 6017953
    Abstract: A method of treating ocular hypotension, hypertension, hemorrhage, myocardial ischemia, angina pectoris, coronary contraction, cerebrovascular contraction after subarachnoidal hemorrhage, and asthma which comprises administering to a mammal suffering therefrom a therapeutically effective amount of a thromboxane ligand which is a compound formula I, ##STR1## wherein Y is (CH.sub.2).sub.x ; Z is selected from the group consisting of O, OCH.sub.2, ##STR2## and (CR.sub.2).sub.x, x is an integer of 1 or 2; R.sub.
    Type: Grant
    Filed: September 9, 1997
    Date of Patent: January 25, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Robert M. Burk, Achim H. Krauss, David F. Woodward
  • Patent number: 5965718
    Abstract: Sarcodictyin A and B, eleutherobin, and bioactive analogs thereof synthesized using solid phase and solution phase chemistries. The synthetic method employs an attachment of common precursors, e.g., compounds 1880 or 200, on a solid support for generating conjugates 230 and 240, followed by standard chemical manipulations. A combinatorial library of sarcodictyins and eletherobin analogs was constructed with modified C-8 ester, C-15 ester and C-4 ketal functionalities and was screened for activity with respect to tubulin polymerization and cytotoxic activity against tumor cells, including Taxol-resistant lines. Compounds 600, 610, 630, 660-700, 730, 760, 850, and 920 were identified to be of equal or superior biological activities as compared to their corresponding natural product.
    Type: Grant
    Filed: September 1, 1998
    Date of Patent: October 12, 1999
    Assignee: The Scripps Research Institute
    Inventors: Kyriacos C. Nicolaou, Floris VanDelft, Seijiro Hosokawa, Sanghee Kim, Tianhu Li, Takashi Ohshima, Jeff Pfefferkorn, Dionisios Vourloumis, Jin-You Xu, Nicolas Winssinger
  • Patent number: 5852090
    Abstract: The antioxidants of the formulae I and II ##STR1## in which R.sub.1 is methyl or H,R.sub.2 is H or methyl,R.sub.3 is H or C.sub.1 -C.sub.4 alkyl,R.sub.4 is C.sub.1 -C.sub.5 alkyl,R.sub.5 is C.sub.1 -C.sub.5 alkyl, and the group Z is CH.sub.2 or O,are particularly suitable for stabilizing styrene (co)polymers.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: December 22, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hans Rudolf Meier, Andreas Muhlebach
  • Patent number: 5744010
    Abstract: The invention relates to a process for the preparation of acesulfam salts by reaction of salts of amidosulfonic acid with diketene to give a salt of acetoacetamidosulfonic acid (I), ring closure by the action of at least about an equivalent amount of SO.sub.3, at least this ring closure reaction being carried out in the presence of a halogenated, aliphatic hydrocarbon as an inert solvent, treatment of the cyclization product with water and conversion of the resulting acesulfam-H (II) into the form of a non-toxic salt, which comprises, in the work-up by distillation of the resulting crude solvent, after removal of water and low-boilers and recovery of solvent sufficiently pure for reuse in the preparation of compounds (I) and/or (II), directly returning :he remaining, solvent-containing distillation residue, without further purification, into the system downstream of the reaction vessel for carrying out the ring closure reaction.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Roscher, Heinz Litterer, Axel Engelmann, Wolf-Dietmar Kaufmann, Bernd Laugwitz, Hans-Dietmar Schnabel
  • Patent number: 5616780
    Abstract: The novel compounds of the formula I ##STR1## in which A is a group of the formula IIa or IIb, ##STR2## Y is oxygen, methylene, ethylidene or a >C.dbd.C(CH.sub.3).sub.2 group, Z is nitrogen, ##STR3## R.sub.1 and R.sub.2 are, for example C.sub.1 -C.sub.5 alkyl, R.sub.3 and R.sub.4 are, for example, hydrogen or methyl, and R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13 and R.sub.14 are, for example, hydrogen, are suitable for stabilizing organic material against oxidative, thermal or light-induced degradation.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: April 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Bernard Gilg
  • Patent number: 5539130
    Abstract: A method is provided for preparing carboxylic acid intermediates of the structure ##STR1##
    Type: Grant
    Filed: September 14, 1995
    Date of Patent: July 23, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: Michael A. Poss, Paul D. Pansegrau, Shaopeng Wang, John K. Thottahil, Janak Singh, Richard H. Mueller
  • Patent number: 5491152
    Abstract: The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: February 13, 1996
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
  • Patent number: 5405830
    Abstract: This invention relates to certain herbicidal ethers, agriculturally suitable compositions thereof, and a method for their use as broad spectrum preemergent or postemergent herbicides.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: April 11, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alan R. Rendina, Wendy S. Taylor
  • Patent number: 5347007
    Abstract: A method is provided for preparing 7-oxabicycloheptyl substituted heterocyclic aide prostaglandin analogs which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonists/thromboxane synthetase inhibitors useful, for example, in the treatment of thrombotic and/or vasospastic disease, wherein a vinyl bromide of the formula, for example, ##STR1## wherein m, n, R.sup.1 and R.sup.2 are as defined herein is treated with a cyclizing agent to forth the corresponding oxazole.
    Type: Grant
    Filed: October 4, 1993
    Date of Patent: September 13, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jagabandhu Das, David Kronenthal
  • Patent number: 5266710
    Abstract: Disclosed herein is a process for preparing a novel monoester of the formula ##STR1## in which the associated novel diester ##STR2## is hydrolyzed in the presence of one or more water-soluble enzymes or microorganisms capable of selectively hydrolyzing the --O--C(O)--R.sup.1 group, wherein the treatment is carried out in a biphasic solvent system comprising an aqueous phase having the enzymes or microorganisms and an organic phase immiscible in water having the diester. Also disclosed is a process for preparing [1S-[1.alpha., 2.alpha.(Z),3.alpha.,4.alpha.]]-7-[3[[[[(1-oxoheptyl)amino]acetyl]amino]me thyl-7-oxabicyclo-[2.2.1]hept-2-yl]-5-heptenoic acid using this enzymatic/microbial process.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: November 30, 1993
    Inventors: Ramesh N. Patel, Laszlo J. Szarka, John K. Thottathil, David Kronenthal
  • Patent number: 5260448
    Abstract: A method is provided for preparing 7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonists/thromboxane synthetase inhibitors useful, for example, in the treatment of thrombotic and/or vasospastic disease, wherein a vinyl bromide of the formula, for example, ##STR1## wherein m, n, R.sup.1 and R.sup.2 are as defined herein is treated with a cyclizing agent to form the corresponding oxazole.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: November 9, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jagabandhu Das, David Kronenthal
  • Patent number: 5245055
    Abstract: A compound having the structure ##STR1## is reacted with Ph.sub.3 P.dbd.CH(CH.sub.2).sub.3 Y wherein Y is --CO.sub.2 .sup..crclbar. M.sup..sym. or --C.tbd.N to form ##STR2## which is aminated and esterified to form ##STR3## which may be used to form [1S-[1.alpha.,2.alpha.(Z),3.alpha., 4.alpha.[[-7-[3-[[[[1-oxoheptyl) -amino]acetyl]amino]methyl]-7-oxabicyclo-[2.2.1]-hept-2-yl]-5-heptenoic acid.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: September 14, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David Kronenthal, Robert Waltermire
  • Patent number: 5241104
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: August 31, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5240907
    Abstract: Described are substituted cyclopentyl oxabicyclooctanes, cyclopentyl vinyl pyrans, cyclopentylformylcyclohexenes and cyclopentylhydroxymethyl cyclohexenes having the generic structures: ##STR1## wherein R.sub.1, R.sub.2, R', R", R.sub.1 ', R.sub.2 ', R.sub.1 " and R.sub.2 " represent hydrogen or methyl with the provisos that:(i) R.sub.1 and R.sub.2 are not both methyl;(ii) R' and R" are not both methyl;(iii) when R.sub.1 ' is methyl, R.sub.2 ' is hydrogen; and(iv) when R.sub.2 " is methyl, then R.sub.1 " is hydrogen,processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: August 31, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Franc T. Schiet, Charles E. J. Beck, Charles J. Vinals, Marie R. Hanna
  • Patent number: 5235072
    Abstract: The invention relates to 2-oxabicyclo[2.2.1]heptane derivatives of formula I ##STR1## as well as their enantiomers, in which, e.g., A means --(CH.sub.2).sub.n --, (E)-- or (Z)--CH.dbd.CH--, --C.tbd.C, --O-- or --S--,B means hydrogen, C.sub.1 -C.sub.10 alkyl, --OR.sup.2, halogen, --C.tbd.N, --N.sub.3, --COOR.sup.3,R.sup.1 means oxygen or a --CH.sub.2 group, ##STR2## Z means --(CH.sub.2).sub.p --, (E)--CH.dbd.CH--, --C.tbd.C--, W means a direct bond, a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## in which the OH group can be respectively in alpha- or beta-position, D means a direct bond, a saturated alkylene group with 1-5 C atoms, a branched saturated or a straight-chain of branched unsaturated alkylene group with 2-5 C atoms,E means a direct bond, --C.tbd.C-- or --CH.dbd.CR.sup.7,R.sup.8 means hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, optionally substituted C.sub.6 -C.sub.12 aryl or a 5- or 6-member heterocyclic radical, andif R.sup.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: August 10, 1993
    Assignee: Schering Aktiengsellschaft
    Inventors: Ulrich Klar, Helmut Vorbruggen, Hartmut Rehwinkel, Karl H. Thierauch, Claus S. Sturzebecher
  • Patent number: 5234900
    Abstract: The present invention relates to novel oxabicyclo ether derivative compounds, compositions containing these ether derivative compounds, and methods of using these compounds or compositions to control the growth of undesired vegetation. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals or broadleaf crops.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: August 10, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Jr., Wendy S. Taylor
  • Patent number: 5200533
    Abstract: A process suitable for industrially preparing 2,3-trans-1,4-bridged cyclohexane sulfonamide derivatives, especially useful as an intermediate for the synthesis of a trans bicyclo[2,2,1] heptane carboxylic acid derivative, a clinically important thromboxane A.sub.2 antagonist, comprising: allowing to react corresponding a cis/trans mixture of sulfonamide derivatives with an anionoid or water-soluble carbonyl reagent at pH 3-7 so that the trans isomer may form a water-soluble adduct with the anionoid or carbonyl reagent, separating the resulting adduct dissolved in an aqueous layer, and recovering the trans isomer by treating the adduct with a base or an acid. Also provided is an alkali metal hydrogen sulfite adduct of 2,3-trans 1,4-bridged cyclohexane sulfonamide derivative.
    Type: Grant
    Filed: March 12, 1992
    Date of Patent: April 6, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
  • Patent number: 5183909
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: February 2, 1993
    Assignee: Shionogi & Company, Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5158967
    Abstract: 7-Oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs are provided which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonist/thromboxane synthetase inhibitors and have the structural formula ##STR1## wherein R is SO.sub.3 H, P(O)OR.sup.3 OH or P(O)R.sup.4 OH, X is O or NH, and Z, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: October 27, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Steven E. Hall
  • Patent number: 5157134
    Abstract: Dihydroxyheptonic acids containing an oxabicycloheptane nucleus are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## and X, R.sub.1, R.sub.2 and R.sub.3 are as defined herein.
    Type: Grant
    Filed: March 12, 1992
    Date of Patent: October 20, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5137914
    Abstract: Sulfonylamino substituted bicyclyl hydroxamic acid derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen or lower alkyl; R.sup.3 is hydrogen, lower alkyl, lower alkoxy, hydroxy or halogen; X is alkylene or alkenylene: Y is methylene or oxygen; and n is 0, 1, or 2, or the pharmaceutically acceptable salt thereof. These compounds have an advanced antagonistic activity to thromboxane A.sub.2 (TXA.sub.2)-receptor and are useful for the treatment of thrombosis, vasoconstriction, or bronchoconstriction, and the like disease which are induced by TXA.sub.2.
    Type: Grant
    Filed: March 15, 1991
    Date of Patent: August 11, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura, Kazuhiro Shirahase
  • Patent number: 5128317
    Abstract: Described are camphonyl spirocyclooxaoctane-containing compositions having the generic structures: ##STR1## and mixtures of same with substituted cyclopentenyl-oxabicyclooctanes defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " each represents hydrogen or methyl and R.sub.4 ' represents hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: July 7, 1992
    Assignee: International Flavors and Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton Van Ouwerkerk, Olivier Gillotin
  • Patent number: 5125954
    Abstract: The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: June 30, 1992
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Richard B. Phillips
  • Patent number: 5126370
    Abstract: Prostaglandin analogs useful in treating thrombotic and vasospastic disease having the structural formula ##STR1## wherein: m is 1, 2 or 3:n is 1, 2 or 3, except that n is O when Y is vinylene;p is 1, 2 or 3;R is CO.sub.2 R', CH.sub.2 OH, CONHSO.sub.2 R.sup.3, CONHR.sup.4, or --CH.sub.2 -5-tetrazolyl;R' is hydrogen, alkyl, or alkali metal;Y is --O--, a single bond or vinylene, except that Y cannot be --O-- when n is 0;and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: June 30, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Raj N. Misra
  • Patent number: 5124462
    Abstract: A process for preparing a compound of Formula (I): ##STR1## wherein R' is optionally protected --CH.sub.2 OH or --COOH; R.sup.2 is phenyl or substituted phenyl; and Y is oxygen, methylene, or substituted methylene, which comprises treating a norbornyl acid amide of formula (II): ##STR2## wherein R is optionally protected --CH.sub.2 OH or --COOR.sup.1 ; R.sup.1 is hydrogen or ester-forming group; and Y is oxygen, methylene, or substituted methylene under the reaction conditions for the Hofmann Rearrangement, and then with a substituted sulfonyl halide of formula (III):R.sup.2 SO.sub.2 X (III)wherein R.sup.2 is phenyl or substituted phenyl; and X is halogen atom.
    Type: Grant
    Filed: June 18, 1991
    Date of Patent: June 23, 1992
    Assignee: Shiongi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura, Yoshinori Hamada, Shoji Shinomoto
  • Patent number: 5120865
    Abstract: A process suitable for industrially preparing 2,3-trans-1,4-bridged cyclohexane sulfonamide derivatives, especially useful as an intermediate for the synthesis of a trans bicyclo[2,2,1] heptane carboxylic acid derivative, a clinically important thromboxane A.sub.2 antagonist, comprising: allowing to react corresponding a cis/trans mixture of sulfonamide derivatives with an anionoid or water-soluble carbonyl reagent at pH3-7 so that the trans isomer may form a water-soluble adduct with the anionoid or carbonyl reagent, separating the resulting adduct dissolved in an aqueous layer, and recovering the trans isomer by treating the adduct with a base or an acid. Also provided is an alkali metal hydrogen sulfite adduct of 2,3-trans 1,4-bridged cyclohexane sulfonamide derivative.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: June 9, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
  • Patent number: 5097047
    Abstract: Fungicidal and plant growth-regulating azolylmethylcyclopropyl derivatives of the formula ##STR1## in which R represents halogen, alkyl or optionally substituted phenyl, or represents the groupings --Y--R.sup.2,whereinY represents oxygen, sulphur, SO or SO.sub.2 andR.sup.2 represents optionally substituted phenyl,R.sup.1 represents hydrogen, alkyl or acyl,X represents nitrogen or a CH group,Z represents halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 halogen atoms or phenyl which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen, or represents phenoxy which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen andm represents the number 0, 1, 2 or 3, and addition products thereof with acids and metal salts.
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
  • Patent number: 5084387
    Abstract: Disclosed herein is a process for preparing a novel monoester of the formula ##STR1## in which the associated novel diester ##STR2## is hydrolyzed in the presence of one or more water-soluble enzymes or microorganisms capable of selectively hydrolyzing the --O--C(O)--R.sup.1 group, wherein the treatment is carried out in a biphasic solvent system comprising an aqueous phase having the enzymes or microorganisms and an organic phase immiscible in water having the diester. Also disclosed is a process for preparing [1S-[1.alpha., 2.alpha.(Z),3.alpha.,4.alpha.]]-7-[3[[[[(1-oxoheptyl)amino]acetyl]-amino]m ethyl-7-oxabicyclo-[2.2.1]hept-2-yl]-5-heptenoic acid using this enzymatic/microbial process.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: January 28, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ramesh N. Patel, Laszlo J. Szarka, John K. Thottathil, David Kronenthal
  • Patent number: 5081266
    Abstract: A new process for preparing [1S-[1.alpha.,2.alpha.(Z),-3.alpha.,4.alpha.]]-7-[3-[[[[(1-oxoheptyl)-amin o]acetyl]amino]methyl]-7-oxabicyclo [2.2.1]-hept-2-yl]-5-heptenoic acid. New intermediates are also described. [1S-(1.alpha.,2.alpha.(9Z),3.alpha.,4.alpha.]]-7-[3-[[[[(1-oxoheptyl)-amin o]acetyl]amino]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid is useful in the treatment of thrombotic disease.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: January 14, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: David Kronenthal
  • Patent number: 5077309
    Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5047574
    Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: September 10, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Takaharu Matsuura
  • Patent number: 5008409
    Abstract: A process for preparing a compound of Formula (I): ##STR1## wherein R is phenyl or phenyl substituted with hydroxy, lower alkoxy, halogen or lower alkyl; Y is unsubstituted or substituted methylene, ethylene, vinylene or oxygen; m is 0 or 1; n is 0, 1 or 2; and q is 1, 2, 3 or 4; with the limitation that when m is 0, n is not 0, and when m is 1, n is not 2, which process comprises:(a) reacting an aldehyde of Formula (II); ##STR2## wherein R, Y, m and n are as defined above, under reaction conditions for the Wittig Reaction with a ylide of Formula (III):(R.sup.1).sub.3 P.dbd.CH(CH.sub.2).sub.q COOM (III)wherein R.sup.1 is C.sub.1 -C.sub.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: April 16, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
  • Patent number: 5006539
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1]heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: April 9, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4978762
    Abstract: A new process for preparing [1S-[1.alpha.,2.alpha.(Z),-3.alpha.,4.alpha.]]-7-[3-[[[ (1-oxoheptyl)amino]acetyl]amino]-methyl]-7-oxabicyclo[2,2,1]hept-2-yl]-5-h eptenoic acid. New intermediates are also described. [1S-(1.alpha.,2.alpha.(Z),3.alpha.,4.alpha.]]-7-[3-[[[[(1-oxoheptyl)-amino ]acetyl]amino]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid is useful in the treatment of thrombotic disease.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: December 18, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: David Kronenthal
  • Patent number: 4960909
    Abstract: Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or hetelocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms and may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: October 2, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
  • Patent number: 4958036
    Abstract: A process is provided for preparing a 7-oxabicycloheptane amino alcohol intermediate of the general structure ##STR1## (wherein the above structures represents (D) or (L) isomers)which is useful in preparing thromboxane A.sub.2 receptor antagonists. This intermediate is prepared by reacting mesanhydride with an aryl amine ##STR2## wherein R is alkyl, CH.sub.2 OH, CO.sub.2 H or CO.sub.2 alkyl, to form the acid ##STR3## which is reduced by treatment with lithium aluminum hydride or diisobutylaluminum hydride or Red-Al to form the alcohol ##STR4## wherein R.sup.1 is CH.sub.2 OH when R is CO.sub.2 H, CO.sub.2 alkyl or CH.sub.2 OH, and R.sup.1 is alkyl when R is alkyl; where in the above alcohol R.sup.1 is CH.sub.2 OH, such alcohol compound is treated with an alkyl chloroformate in the presence of base such as an alkali metal alkoxide to form the alcohol ##STR5## which undergoes cleavage by treatment with alkali metal, ammonia and acid to form the amino alcohol intermediate.Where in the above alcohol R.sup.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: September 18, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John K. Thottathil
  • Patent number: 4945106
    Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 31, 1990
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4935532
    Abstract: All possible isomeric forms of a compound of the formula ##STR1## wherein A has a structure selected from the group consisting of ##STR2## wherein Y.sub.1 and Y.sub.2 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine and alkyl of 1 to 6 carbon atoms, or Y.sub.1 and Y.sub.2 together with the carbon to which they are attached form a carbon homocycle of 3 to 7 carbon atoms and Z is selected from the group consisting of hydrogen, chlorine, bromine and iodine, Y is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms unsubstituted or substituted with at least one halogen, the .beta., .alpha. bond together with Y can be part of A and and R is selected from the group consisting of non-heterocyclic primary, secondary or teritiary alcohol moiety having at least one asymetric carbon or the remainder of a substituted alcohol with a chirality due to the dissymetric spatial configuration of the entire molecule.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: June 19, 1990
    Assignee: Roussel Uclaf
    Inventors: Jean Tessler, Jean-Pierre Demoute