Plural Double Bonds Between Ring Members Of The Hetero Ring Patents (Class 549/471)
-
Patent number: 4623737Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and analogues thereof, which have demonstrated antiatherosclerotic activity.Type: GrantFiled: December 7, 1984Date of Patent: November 18, 1986Assignee: The Upjohn CompanyInventor: Ayako Yamashita
-
Patent number: 4609739Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and other furochromone analogues, which have demonstrated antiatherosclerotic activity. These novel intermediates and processes can also be used for the preparation of benzofurans and benzothiophenes which inhibit the synthesis of leukotriene and/or lipoxygenase.Type: GrantFiled: November 6, 1984Date of Patent: September 2, 1986Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4581457Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## W is ##STR3## Y is ##STR4## n is 0-8; R.sup.1 is hydrogen, loweralkyl, loweralkoxy, lower alkanoyl, halo, trifluoromethyl, cyano or nitro;R.sup.2 is hydrogen or loweralkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and in antithrombotic therapy.Type: GrantFiled: September 21, 1984Date of Patent: April 8, 1986Assignee: American Home Products CorporationInventors: John H. Musser, Dennis M. Kubrak
-
Patent number: 4558143Abstract: A 4-oxo-4,5,6,7-tetrahydrobenzofuran derivative is prepared by reacting a 1,3-cyclohexanedione derivative with chloroacetaldehyde in the presence of a base while maintaining the reaction mixture at a pH of from 4 to 10, and treating the reaction mixture with an acid. The 4-oxo-4,5,6,7-tetrahydrobenzofuran derivatives are useful as an intermediate for synthesis of various kinds of drugs.Type: GrantFiled: August 4, 1983Date of Patent: December 10, 1985Assignee: Sagami Chemical Research CenterInventors: Masakatsu Matsumoto, Nobuko Watanabe
-
Patent number: 4546177Abstract: The present invention provides novel 1-(6-hydroxy-4- or 7-methoxy or 4,7-dimethoxy-5-benzofuranyl)-4-substituted-1,3-butanediones which are useful as intermediates in the synthesis of khellin and related anti-atherosclerotic furochromones.Type: GrantFiled: April 24, 1984Date of Patent: October 8, 1985Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4537903Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: October 12, 1983Date of Patent: August 27, 1985Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
-
Patent number: 4535086Abstract: Heterocyclic compounds of the formula ##STR1## wherein X is --CH.dbd.CH--, --O-- or --S--; R.sup.1 is a group Ar--R.sup.2 or --CH.dbd.CH--C(CH.sub.3).dbd.CH--R.sup.21 ; Ar is phenyl, pyridyl, furyl or thienyl; R.sup.2 is a group --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3, lower-alkylsulphonyl or formyl; R.sup.21 is a group--CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3 or formyl; R.sup.3 is hydrogen or lower-alkyl and R.sup.4 is hydrogen, hydroxy, amino, lower alkylamino, di-(lower alkyl)amino or lower-alkyl; at least one ring of the molecule being heterocyclic, salts thereof, processes for their preparation, rodenticidal compositions containing these compounds as the active ingredient and methods of use of the rodenticidal compositions are disclosed.Type: GrantFiled: June 27, 1983Date of Patent: August 13, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Harald Weiser
-
Patent number: 4532340Abstract: The present invention provides novel intermediates used for preparation of anti-atherosclerotic furochromones.Type: GrantFiled: October 27, 1983Date of Patent: July 30, 1985Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4529721Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.Type: GrantFiled: September 21, 1983Date of Patent: July 16, 1985Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
-
Patent number: 4463185Abstract: The present invention provides novel 1-(6-hydroxy-4- or 7-methoxy or 4,7-dimethoxy-5-benzofuranyl)-4-substituted-1,3-butanediones which are useful as intermediates in the synthesis of khellin and related anti-atherosclerotic furochromones.Type: GrantFiled: July 30, 1982Date of Patent: July 31, 1984Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4459420Abstract: The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.Type: GrantFiled: May 17, 1982Date of Patent: July 10, 1984Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4434296Abstract: The present specification provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof. 3-Furoic acid is treated with succinic anhydride and diesterified to 3-carboxy-.delta.-oxo-2-furanbutanoic acid bis (alkyl ester). Following amination, cyclization and bis methylation, 6-formyl-4,7-dimethoxy-5-benzofurancarboxcyclic acid alkyl ester is prepared. This compound is then converted to known intermediates in the synthesis of khellin and analogs. Further, the present invention provides numerous novel anti-atherosclerotic 4,9-di-(C.sub.2 -C.sub.4)-alkoxyfurochromones.Type: GrantFiled: May 17, 1982Date of Patent: February 28, 1984Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4431650Abstract: This invention relates to novel esters of benzofuranyl acids, novel intermediates therefor, synthesis thereof, and the control of pests.Type: GrantFiled: December 22, 1980Date of Patent: February 14, 1984Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
-
Patent number: 4424231Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.Type: GrantFiled: March 19, 1982Date of Patent: January 3, 1984Assignee: Fisons LimitedInventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
-
Patent number: 4412071Abstract: The present invention provides novel antiatherosclerotic furobenzoxazinones, e.g., 4,9-dimethoxy-4H-furo[3,2-g][1,3]benzoxazin-4-ones. These compounds are structurally and pharmacologically related to khellin and are useful antiatherosclerotic agents.Type: GrantFiled: May 17, 1982Date of Patent: October 25, 1983Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
-
Patent number: 4402968Abstract: Imidazole compounds of the formula ##STR1## wherein A is a group of the formula ##STR2## and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or a halogen atom,pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions containing these compounds are described. The compounds of formula I are useful as antifungal agents. Processes for preparing the novel compounds are also disclosed.Type: GrantFiled: May 29, 1981Date of Patent: September 6, 1983Assignee: Hoffmann-La Roche Inc.Inventor: Joseph A. Martin
-
Patent number: 4372970Abstract: There are provided benzofuran-substituted acetic acid esters and compositions thereof having arthropocidal activity.Type: GrantFiled: July 9, 1981Date of Patent: February 8, 1983Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Malcolm R. Hadler, David R. Woodward, Andrew A. Godfrey
-
Patent number: 4355168Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.Type: GrantFiled: December 2, 1980Date of Patent: October 19, 1982Assignee: Montedison S.p.A.Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
-
Patent number: 4341792Abstract: Heterobicyclic glyoxylic acids, L- and DL-heterobicyclic glycines and their derivatives of the formulae ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein R is OR.sup.2 or NHR.sup.3 ;R.sup.2 is hydrogen or alkyl having from one to four carbon atoms;R.sup.3 is hydrogen, alkyl having from one to four carbon atoms, alkoxyalkyl having from one to four carbon atoms in each of the alkyl groups or R.sup.4 R.sup.5 C.sub.6 H.sub.3 CH.sub.2 -- where R.sup.4 and R.sup.5 are H, OH, F, Cl, Br, I, or alkyl or alkoxy having from one to four carbon atomsR.sup.1 is hydrogen, alkyl having from one to four carbon atoms or R.sup.4 R.sup.5 C.sub.6 H.sub.3 --; X is oxygen or sulfur; n is 0 or 1 and the broken line represents an optionally present double bond; useful in treatment of diseases and conditions which are characterized by reduced blood flow, reduced oxygen availability or reduced carbohydrate metabolism in the cardiovascular system.Type: GrantFiled: July 6, 1981Date of Patent: July 27, 1982Assignee: Pfizer Inc.Inventors: Ian T. Barnish, Peter E. Cross
-
Patent number: 4328169Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of an alkylene oxide derivative and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.Type: GrantFiled: October 27, 1980Date of Patent: May 4, 1982Assignee: Emery Industries, Inc.Inventor: Allen L. Hall
-
Patent number: 4328168Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of a cyclic polyether compound and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.Type: GrantFiled: October 27, 1980Date of Patent: May 4, 1982Assignee: Emery Industries, Inc.Inventor: Richard G. Fayter, Jr.