The Two Cyclos Share At Least Three Ring Members (i.e., Bridged) Patents (Class 549/463)
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Publication number: 20030187282Abstract: 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: ApplicationFiled: March 14, 2003Publication date: October 2, 2003Inventors: Tomoya Kuwayama, Katsuji Ujita, Kazuya Shimizu, Shiro Terashima
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Patent number: 6605632Abstract: 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 descriptionType: GrantFiled: November 10, 2000Date of Patent: August 12, 2003Assignee: Les Laboratoires ServierInventors: Daniel Lesieur, Frédérique Klupsch, Gérald Guillaumet, Marie-Claude Viaud, Michel Langlois, Caroline Bennejean, Pierre Renard, Philippe Delagrange
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Publication number: 20030105125Abstract: 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: ApplicationFiled: December 27, 2001Publication date: June 5, 2003Inventors: Peter C. Meltzer, Bertha K. Madras, Paul Blundell
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Patent number: 6462077Abstract: 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 heteroarType: GrantFiled: July 5, 2001Date of Patent: October 8, 2002Assignee: Allergan, Inc.Inventors: Robert M. Burk, Achim H-P Krauss, David F. Woodward
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Patent number: 6403824Abstract: 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: GrantFiled: February 6, 2001Date of Patent: June 11, 2002Assignee: Hoffmann-La Roche Inc.Inventors: Stefan Abrecht, Martin Karpf, René Trussardi, Beat Wirz
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Patent number: 6359153Abstract: 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: GrantFiled: October 27, 1999Date of Patent: March 19, 2002Assignee: 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
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Patent number: 6271252Abstract: 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: GrantFiled: May 23, 2000Date of Patent: August 7, 2001Assignee: Merck & Co., Inc.Inventors: Linda Chang, William K. Hagmann, Malcolm MacCoss
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Patent number: 6245828Abstract: 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: GrantFiled: September 21, 1998Date of Patent: June 12, 2001Assignee: ESPE Dental AGInventors: Wolfgang Weinmann, Oswald Gasser, Rainer Guggenberger, Gunther Lechner, Wolfgang Soglowek, Joachim Zech
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Patent number: 6200731Abstract: 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: GrantFiled: December 16, 1999Date of Patent: March 13, 2001Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Geun Su Lee, Cha Won Koh, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
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Patent number: 6090845Abstract: 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: GrantFiled: September 28, 1999Date of Patent: July 18, 2000Assignee: Allergan Sales, Inc.Inventors: Robert M. Burk, Achim H. Krauss, David F. Woodward
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Patent number: 6077864Abstract: 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: GrantFiled: June 17, 1999Date of Patent: June 20, 2000Assignee: Pfizer Inc.Inventors: Laurence Edward Burgess, James Patrick Rizzi
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Patent number: 6057460Abstract: 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: GrantFiled: February 21, 1997Date of Patent: May 2, 2000Assignee: Ivoclar AGInventors: Norbert Moszner, Volker Rheinberger, Frank Zeuner
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Patent number: 6017953Abstract: 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: GrantFiled: September 9, 1997Date of Patent: January 25, 2000Assignee: Allergan Sales, Inc.Inventors: Robert M. Burk, Achim H. Krauss, David F. Woodward
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Patent number: 5965718Abstract: 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: GrantFiled: September 1, 1998Date of Patent: October 12, 1999Assignee: The Scripps Research InstituteInventors: Kyriacos C. Nicolaou, Floris VanDelft, Seijiro Hosokawa, Sanghee Kim, Tianhu Li, Takashi Ohshima, Jeff Pfefferkorn, Dionisios Vourloumis, Jin-You Xu, Nicolas Winssinger
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Patent number: 5852090Abstract: 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: GrantFiled: January 29, 1997Date of Patent: December 22, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Hans Rudolf Meier, Andreas Muhlebach
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Patent number: 5744010Abstract: 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: GrantFiled: June 19, 1995Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Heinz Litterer, Axel Engelmann, Wolf-Dietmar Kaufmann, Bernd Laugwitz, Hans-Dietmar Schnabel
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Patent number: 5616780Abstract: 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: GrantFiled: January 31, 1996Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Bernard Gilg
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Patent number: 5539130Abstract: A method is provided for preparing carboxylic acid intermediates of the structure ##STR1##Type: GrantFiled: September 14, 1995Date of Patent: July 23, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Michael A. Poss, Paul D. Pansegrau, Shaopeng Wang, John K. Thottahil, Janak Singh, Richard H. Mueller
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Patent number: 5491152Abstract: 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: GrantFiled: March 23, 1994Date of Patent: February 13, 1996Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
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Patent number: 5405830Abstract: 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: GrantFiled: July 29, 1993Date of Patent: April 11, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Alan R. Rendina, Wendy S. Taylor
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Patent number: 5347007Abstract: 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: GrantFiled: October 4, 1993Date of Patent: September 13, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Jagabandhu Das, David Kronenthal
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Patent number: 5266710Abstract: 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: GrantFiled: July 30, 1991Date of Patent: November 30, 1993Inventors: Ramesh N. Patel, Laszlo J. Szarka, John K. Thottathil, David Kronenthal
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Patent number: 5260448Abstract: 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: GrantFiled: June 18, 1992Date of Patent: November 9, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Jagabandhu Das, David Kronenthal
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Patent number: 5245055Abstract: 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: GrantFiled: December 18, 1990Date of Patent: September 14, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: David Kronenthal, Robert Waltermire
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Patent number: 5241104Abstract: 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: GrantFiled: June 23, 1992Date of Patent: August 31, 1993Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5240907Abstract: 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: GrantFiled: October 23, 1992Date of Patent: August 31, 1993Assignee: 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
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Patent number: 5235072Abstract: 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: GrantFiled: May 7, 1991Date of Patent: August 10, 1993Assignee: Schering AktiengsellschaftInventors: Ulrich Klar, Helmut Vorbruggen, Hartmut Rehwinkel, Karl H. Thierauch, Claus S. Sturzebecher
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Patent number: 5234900Abstract: 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: GrantFiled: March 11, 1992Date of Patent: August 10, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: James E. Powell, Jr., Wendy S. Taylor
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Patent number: 5200533Abstract: 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: GrantFiled: March 12, 1992Date of Patent: April 6, 1993Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
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Patent number: 5183909Abstract: 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: GrantFiled: June 20, 1991Date of Patent: February 2, 1993Assignee: Shionogi & Company, Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5158967Abstract: 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: GrantFiled: June 12, 1991Date of Patent: October 27, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: Steven E. Hall
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Patent number: 5157134Abstract: 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: GrantFiled: March 12, 1992Date of Patent: October 20, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5137914Abstract: 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: GrantFiled: March 15, 1991Date of Patent: August 11, 1992Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura, Kazuhiro Shirahase
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Patent number: 5128317Abstract: 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: GrantFiled: July 25, 1991Date of Patent: July 7, 1992Assignee: International Flavors and Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton Van Ouwerkerk, Olivier Gillotin
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Patent number: 5125954Abstract: 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: GrantFiled: November 2, 1990Date of Patent: June 30, 1992Assignee: E.I. Du Pont de Nemours and CompanyInventors: James E. Powell, Richard B. Phillips
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Patent number: 5126370Abstract: 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: GrantFiled: December 24, 1990Date of Patent: June 30, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: Raj N. Misra
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Patent number: 5124462Abstract: 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: GrantFiled: June 18, 1991Date of Patent: June 23, 1992Assignee: Shiongi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura, Yoshinori Hamada, Shoji Shinomoto
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Patent number: 5120865Abstract: 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: GrantFiled: August 30, 1991Date of Patent: June 9, 1992Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
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Patent number: 5097047Abstract: 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: GrantFiled: October 26, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
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Patent number: 5084387Abstract: 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: GrantFiled: December 18, 1990Date of Patent: January 28, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Ramesh N. Patel, Laszlo J. Szarka, John K. Thottathil, David Kronenthal
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Patent number: 5081266Abstract: 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: GrantFiled: September 26, 1990Date of Patent: January 14, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: David Kronenthal
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Patent number: 5077309Abstract: 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: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5047574Abstract: 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: GrantFiled: December 12, 1989Date of Patent: September 10, 1991Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5008409Abstract: 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: GrantFiled: December 7, 1989Date of Patent: April 16, 1991Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Kyozo Kawata
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Patent number: 5006539Abstract: 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: GrantFiled: March 6, 1989Date of Patent: April 9, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4978762Abstract: 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: GrantFiled: February 26, 1990Date of Patent: December 18, 1990Assignee: E. R. Squibb & Sons, Inc.Inventor: David Kronenthal
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Patent number: 4960909Abstract: 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: GrantFiled: March 23, 1989Date of Patent: October 2, 1990Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
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Patent number: 4958036Abstract: 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: GrantFiled: April 17, 1989Date of Patent: September 18, 1990Assignee: E. R. Squibb & Sons, Inc.Inventor: John K. Thottathil
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Patent number: 4945106Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.Type: GrantFiled: July 6, 1989Date of Patent: July 31, 1990Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4935532Abstract: 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: GrantFiled: May 25, 1988Date of Patent: June 19, 1990Assignee: Roussel UclafInventors: Jean Tessler, Jean-Pierre Demoute