Tricyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/458)
-
Patent number: 5244917Abstract: This invention relates to substituted naphthofurans as anti-inflammatory and anti-allergic agents, pharmaceutical compositions containing them, processes for their preparation, and their use as anti-inflammatory and anti-allergic agents. The naphthofurans are of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 is CN or COOR.sup.9 ;R.sup.2 and R.sup.8 independently are H, C.sub.1 -C.sub.4 alkyl, COR.sup.9 or COR.sup.10 ;R.sup.3, R.sup.4, R.sup.6 and R.sup.7 are independently H, C.sub.1 -C.sub.4 alkyl, halogen, phenyl, CF.sub.3 or OR.sup.9 ;R.sup.5 is H, C.sub.1 -C.sub.4 alkyl, or COR.sup.9 ; andR.sup.9 and R.sup.10 are independently C.sub.1 -C.sub.4 alkyl, halogen or aryl.Type: GrantFiled: June 2, 1992Date of Patent: September 14, 1993Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Joseph J. Petraitis, Donald J. P. Pinto
-
Patent number: 5233059Abstract: A method is provided for preparing benzoprostacyclins by the palladium-catalyzed tandem alkene insertion into a 1,4-bisoxy-substituted cyclopent-2-ene intermediate.Type: GrantFiled: July 25, 1991Date of Patent: August 3, 1993Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larock, Nam H. Lee
-
Patent number: 5219835Abstract: Described are polyhydrodimethylnaphthalene spirofuran derivatives defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond a process for preparing same and uses thereof in augmenting, enhancing or imparting an aroma in or to perfume compositions, colognes and perfumed articles including but not limited to solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations.Type: GrantFiled: October 23, 1992Date of Patent: June 15, 1993Assignee: International Flavors & Fragrance Inc.Inventors: Wilhelmus J. Wiegers, Marie R. Hanna
-
Patent number: 5202447Abstract: The present invention provides a process for preparing 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivative [VII] using 3a,8b-cis-dihydro-3H-5,7-dibromocyclopenta[b]benzofuran (1) as a starting material, as well as compounds of the formulae (8) and (11) which are intermediates for the preparation of the compound of the formula (1).Type: GrantFiled: January 2, 1991Date of Patent: April 13, 1993Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Yutaka Hosono, Hisanori Wakita, Koji Kawai, Hideo Yoshiwara
-
Patent number: 5189187Abstract: A clerodane-type diterpene derivative, which has antibacterial and antitumor activities, as well as chemically equivalent tautomers thereof and a process for producing said derivative using a microorganism belonging to the genus Streptomyces.Type: GrantFiled: June 24, 1992Date of Patent: February 23, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hirofumi Nakano, Shozo Kawada, Yoichi Uosaki, Yutaka Saito, Katsushige Gomi, Toshiaki Iwazaki
-
Patent number: 5169959Abstract: A method is provided for preparing benzoprostacyclins by the free-radical-catalyzed tandem alkene insertion into a 1,4-bisoxy-substituted cyclopent-2-ene intermediate.Type: GrantFiled: September 23, 1991Date of Patent: December 8, 1992Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larock, Nam H. Lee
-
Patent number: 5136099Abstract: 5-Hydroxy-benzo-(1',2')-cyclodeca-2,7-diyne-1-one and derivatives thereof and related fused ring diyneone macrocyclic compounds are disclosed. The compounds possess DNA-cleaving, antibiotic and tumor growth-inhibiting properties. Methods of making and using the same are also disclosed.Type: GrantFiled: August 1, 1990Date of Patent: August 4, 1992Assignee: Scripps Clinic and Research FoundationInventors: Golfo Skokotas, Kyriacos C. Nicolaou
-
Patent number: 5086071Abstract: Pharmaceutically useful compounds are 2,5,6,7-tetranor-4,8-inter-m-phenylene PGI.sub.2 derivatives which are excellently stable and potent in vivo.Type: GrantFiled: March 13, 1990Date of Patent: February 4, 1992Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Atsushi Ohtake, Takashi Endoh, Shigeki Itou, Kazuhiro Hoshi
-
Patent number: 5084581Abstract: Disclosed herein is a novel process in which novel aldehydes ##STR1## and the trans isomer thereof are hydrolyzed by treatment with an alkali metal carbonate, bicarbonate or hydroxide and water to form the cis enantiomer ##STR2## Also disclosed is a 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-heptenoic acid using the above process.Type: GrantFiled: December 18, 1990Date of Patent: January 28, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: David Kronenthal, John K. Thottathil
-
Patent number: 5077417Abstract: Process for the preparation of polycyclic ethers of formula ##STR1## wherein X represents --(CH.sub.2).sub.n --, index n stands for integer 0 or 1, symbol R.sup.4 designates a hydrogen atom or a methyl radical, symbols R.sup.1 and R.sup.2, identical or different, represent each a hydrogen atom or a lower alkyl radical from C.sub.1 to C.sub.3 and R designates either a C.sub.1 to C.sub.6 linear or branched alkyl radical, or a substituted or unsubstituted alkylene radical having 2 or 3 carbon atoms in the main chain, said alkylene radical forming a ring such as indicated by the dotted line, which process comprises the cyclization by means of an acidic agent of an unsaturated compound:a) of formula ##STR2## having a double bond in one of the positions indicated by the dotted lines, and wherein index m defines an integer number equal to 1 or 2, symbol R.sup.Type: GrantFiled: June 15, 1990Date of Patent: December 31, 1991Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Roger L. Snowden, Claudio Tarchini, Beatrice Baer, Christian Vial
-
Patent number: 5061398Abstract: An optically active lactone derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 represents a straight-chain or branched alkyl, alkoxyl, alkanoyloxy, alkoxycarbonyl, alkoxyalkyl, alkoxyalkanoyloxy, or alkoxyalkoxyl group having 1 to 20 carbon atoms or an optically active group of each of the above kinds, R.sup.2 represents a straight-chain or branched alkyl group having 1 to 20 carbon atoms, ##STR2## or trans-1,4-cyclohexylene group of the formula and the asymmetric carbon atoms at the 2- and 4-positions in the lactone ring each independently is of the (S) or (R) configuration, an intermediate therefor, a process for producing the intermediate, a liquid-crystal composition, and a liquid-crystal display device.Type: GrantFiled: April 27, 1990Date of Patent: October 29, 1991Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical Research, Sagami Chemical Research CenterInventors: Sadao Takehara, Takeshi Kuriyama, Kayoko Nakamura, Tadao Shoji, Toru Fujisawa, Masashi Osawa, Tamejiro Hiyama, Tetsuo Kusumoto, Akiko Nakayama, Kiyoharu Nishide
-
Patent number: 5011950Abstract: Novel aromatic amine derivatives of specific structure are useful intermediates for herbicides. The aromatic amine compounds have the structure shown by formula [I]: ##STR1## wherein Ar and A are as defined herein.Type: GrantFiled: February 2, 1988Date of Patent: April 30, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
-
Patent number: 5008286Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.Type: GrantFiled: August 28, 1989Date of Patent: April 16, 1991Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
-
Patent number: 4978761Abstract: The present invention relates to a compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or a lower alkyl; R.sup.2 is methyl which is substituted by a carboxy, alkoxycarbonyl, cyano, halogen, aryl or heterocyclic group of C.sub.2-15 chain hydrocarbon residue having no lower alkyl at the .alpha.-position which may be substituted by a carboxy, alkoxycarbonyl, cyano, halogen, aryl or heterocyclic group; R.sup.3 is a lower alkyl; R.sup.4 is hydrogen or acyl; and R.sup.5 and R.sup.6 each is a lower alkyl or lower alkoxy, or R.sup.5 and R.sup.6 combinedly are butadienylene or a salt thereof.The compound (I) of the present invention has a strong 5- and 12-lipoxygenase inhibiting action, is of high safety and is useful as, among others, an agent for ameliorating dysfunction circulatory system, an anti-allergic agent and a pharmaceutical agent for central nervous system.Type: GrantFiled: June 9, 1989Date of Patent: December 18, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
-
Patent number: 4975457Abstract: Certain trans-2,3-disubstituted-2,3-dihydro-5-hydroxybenzofurans are described. The synthesis involves an intramolecular Michael addition to yield the thermodynamic trans isomer. The compounds were found to be inhibitors of 5-lipoxygenase, an enzyme crucial to the biosynthesis of leukotrienes and useful for the treatment of various inflammatory diseases.Type: GrantFiled: September 25, 1989Date of Patent: December 4, 1990Assignee: Merck & Co., Inc.Inventors: Kathleen M. Rupprecht, Joshua S. Boger
-
Patent number: 4975451Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; and Ar.sup.1 is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 2-methyl[1-1'-biphenyl]-3-yl, or 6-phenoxy-2-pyridyl, exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively nontoxic to fish.Type: GrantFiled: March 2, 1989Date of Patent: December 4, 1990Assignee: FMC CorporationInventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
-
Patent number: 4966973Abstract: The present invention relates to a compound of the formula ##STR1## wherein R.sup.1 stands for hydrogen or a lower alkyl; n denotes an integer of 1 to 6; X stands for an optionally oxidized sulphur atom, oxygen atom or an optionally substituted imino; R.sup.2 stands for methyl or an organic residual group bonded through methylene, methine a quaternary carbon; R.sup.3 stands for a lower alkyl; R.sup.4 stands for hydrogen or acyl; R.sup.5 and R.sup.6 each stand for a lower alkoxy or a lower alkyl, or R.sup.5 and R.sup.6 combinedly stand for butadienylene, and salts thereof.The compound (I) of the present invention has a strong 5-lipoxygenase inhibiting action, is of high safety and is useful as, among others, an agent for ameliorating dysfunction of circulatory system, an anti-allergic agent and a pharmaceutical agent for central nervous system.Type: GrantFiled: June 9, 1989Date of Patent: October 30, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
-
Patent number: 4943589Abstract: This invention is directed to a method for treating helminthiasis which comprises administering to an animal in need thereof an anthelmintically effective amount of a compound of Formula (I): ##STR1## where R.sup.1 is hydrogen or --SR.sup.2,whereinR.sup.2 is hydrogen, --C(O)--CH.sub.3, or ##STR2## or a pharmaceutically acceptable salt thereof. This invention is also directed to a composition for treating helminthiasis in an animal which comprises a pharmaceutically acceptable excipient and an anthelmintically effective amount of a compound of Formula (I). This invention is also directed to novel compounds of Formula (I) wherein R.sup.Type: GrantFiled: October 27, 1988Date of Patent: July 24, 1990Assignees: Syntex (U.S.A.) Inc., The Regents of the Univ. of CaliforniaInventors: Phillip Crews, Thomas R. Matthews, Paul Horton
-
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
-
Patent number: 4918205Abstract: Alkylated dodecahydronaphtho[2,1-b]furans of the general formula I ##STR1## where R.sup.1 and R.sup.2 are identical and each is hydrogen or methyl are prepared by reacting alkylated 2-hydroxydecahydronaphthalene-1-ethanol of the formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, with a sulfonyl chloride in the presence of basic catalysts by performing the cyclization in the presence of concentrated aqueous alkali metal hydroxides and a phase transfer catalyst, preferably a tetra-substituted ammonium or phosphonium salt, the sulfonyl chloride used preferably comprising a sulfonyl chloride of the general formula IIIR.sub.3 -SO.sub.2 Clwhere R.sup.3 is C.sub.1 -C.sub.3 -alkyl or phenyl which may be substituted in the para position by methyl, chlorine, bromine or nitro.Type: GrantFiled: September 28, 1988Date of Patent: April 17, 1990Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Eckhard Hickmann, Rainer Becker, Gerald Lauterbach
-
Patent number: 4885373Abstract: Compounds of general formula I, ##STR1## in which: R.sub.1 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 7-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 6-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.3 and R.sub.Type: GrantFiled: January 27, 1989Date of Patent: December 5, 1989Assignee: ADIR Et CieInventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
-
Patent number: 4880939Abstract: Disclosed herein are novel prostaglandin I.sub.2 (PGI.sub.2) derivatives exhibiting excellent physiological activities, said derivatives being represented by the general formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein.Type: GrantFiled: December 4, 1987Date of Patent: November 14, 1989Assignee: Toray IndustriesInventors: Kiyotaka Ohno, Toshiya Takahashi, Shintaro Nishio
-
Patent number: 4866073Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 29 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a C.sub.8-13 fused heterotricyclic ring system containing at least two aromatic rings and no more than 3 heteroatoms (in separate rings), or a C.sub.10-17 fused heterotetracyclic ring system containing at least two aromatic rings and no more than 4 heteroatoms (in separate rings) or a C.sub.Type: GrantFiled: October 22, 1987Date of Patent: September 12, 1989Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
-
Patent number: 4866070Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.Type: GrantFiled: December 11, 1987Date of Patent: September 12, 1989Assignee: Burroughs Wellcome Co.Inventor: Kenneth W. Bair
-
Patent number: 4863951Abstract: Compounds of general formula I, ##STR1## in which: R.sub.1 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 7-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 6-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.3 and R.sub.Type: GrantFiled: March 25, 1988Date of Patent: September 5, 1989Assignee: ADIR Et CieInventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
-
Patent number: 4857516Abstract: A compound of the formula ##STR1## wherein R is a lower alkyl group, R.sup.0 is hydrogen or an acyl group, R.sup.1 and R.sup.2 are lower alkyl groups which may optionally be substituted or wherein R.sup.1 and R.sup.2 are combined to form a butadienylene group which may optionally be substituted, R.sup.3 and R.sup.4 are hydrogen or alkyl groups which may optionally be substituted or wherein R.sup.3 and R.sup.4 are combined to form a polymethylene group, and R.sup.5 is a lower alkyl, aromatic or heterocyclic group which may optionally be substituted or a pharmaceutically acceptable salt thereof, exerts cardiovascular system improving action and antiallergic action and can be used as pharmaceutics, e.g. antithromotics, antiallergic agents etc.Type: GrantFiled: December 22, 1987Date of Patent: August 15, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Yoshitaka Maki
-
Patent number: 4851429Abstract: Compound of general formula I ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, each denote a hydrogen atom, a benzyl radical, a cyclohexylmethyl radical or a linear or branched alkyl radical containing from 1 to 10 carbon atoms, optionally substituted with a hydroxy radical, with a carboxy radical or with an alkoxy radical having 1 to 5 carbon atoms, with an alkoxycarbonyl radical having 2 to 6 carbon atoms, with an alkylphenyl radical having 7 to 16 carbon atoms or with a 2-alkylthienyl radical having 5 to 14 carbon atoms,R.sub.3 denotes a hydrogen atom or a linear or branched alkyl radical containing from 1 to 4 carbon atoms,A denotes a single bond or a methylene radical, or a radical of formula ##STR2## in which R.sub.4 is a linear or branched alkyl radical containing from 1 to 4 carbon atoms.Type: GrantFiled: March 25, 1988Date of Patent: July 25, 1989Assignee: Adir et CieInventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
-
Patent number: 4838924Abstract: This invention relates to novel compounds of formula [I], a process for their production, and their use as a herbicide. ##STR1## wherein A represents the bond ##STR2## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group;B represents a hydrogen atom, a methyl group or a methoxy group; andAr represents one member selected from the group consisting of ##STR3## in which R.sup.1 to R.sup.38, are as defined hereinafter.Type: GrantFiled: April 1, 1987Date of Patent: June 13, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Tetsuo Takematsu, Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
-
Patent number: 4837226Abstract: A method for the treatment of cerebrovascular disorders by administering a fluorenamine, dibenzofuranamine, or dibenzothiophenamine derivative.Type: GrantFiled: April 27, 1988Date of Patent: June 6, 1989Assignee: Warner-Lambert CompanyInventors: Linda L. Coughenour, Graham Johnson
-
Patent number: 4822804Abstract: Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-16,16-dimethyl-.omega.-homo PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(S)-methyl-.omega.-homo PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2-nor-17(R)-methyl-.omega.-homo PGI.sub.2,5,6, 7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16-p ropoxy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-et ho xy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,18,19,20-tetranor-16,16-dimethyl-17-pr op oxy PGI.sub.2,5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16-phenoxy PGI.sub.2 and methyl esters thereof.5,6,7-trinor-4,8-inter-m-phenylene-2,17,18,19,20-pentanor-16,16-dimethyl-16 -phenoxy PGI.sub.Type: GrantFiled: September 29, 1987Date of Patent: April 18, 1989Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
-
Patent number: 4822803Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: February 4, 1988Date of Patent: April 18, 1989Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
-
Patent number: 4814469Abstract: Novel hydroperoxide of formula ##STR1## and use of same as intermediate for the preparation of 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan, also known as AMBROX (registered tradename of FIRMENICH SA, Geneva/Switzerland).Process for its preparation via an oxidation of sclareol by means of hydrogen peroxide in the presence of an acidic agent.Type: GrantFiled: November 3, 1987Date of Patent: March 21, 1989Assignee: Firmenich, SAInventors: George M. Whitesides, Rene Decorzant, Ferdinand Naef
-
Patent number: 4788302Abstract: A tissue extract containing a low molecular weight, non-proteinaceous compound selected from the group consisting of (A) methanol-soluble compounds obtainable from Leptogorgia virgulata with R.sub.f values in reverse-phase, thin layer, silica gel chromatography of (1) 0.42, 0.54, and 0.62; (2) 0.35, 0.50, and 0.58; (3) 0.37, 0.47, and 0.58; or (4) 0.31, 0.43, and 0.54, respectively, in 1:1:1 methanol:ethyl acetate:water, 2:1:1 methanol:ethyl acetate:water, and 1:2:1 methanol:ethyl acetate:water, or (B) methanol-soluble compounds obtainable from Renilla reinformis with R.sub.f values in thin layer, silica gel chromatography of (1) 0:44, 0.37, and 0.53; (2) 0.52, 0.42, and 0.60; (3) 0.56, 0.43, and 0.63; or (4) 0.32, 0.26, and 0.37, respectively, in 9:1 chloroform:acetonitrile, 9:1 methylene chloride:acetonitrile, and 4:1 methylene chloride:acetonitrile and compositions containing the same, which is useful as antifouling compositions, is disclosed.Type: GrantFiled: January 31, 1986Date of Patent: November 29, 1988Assignee: Duke UniversityInventors: John D. Costlow, Irving R. Hooper, Daniel Rittschof
-
Patent number: 4788305Abstract: Compounds of the formula ##STR1## wherein A is a hydrocarbon chain containing 1 to 16 groups, the said chain containing at least one heteroatom, at least one unsaturation, the assembly of the group constituting the chain may be a mono- or polycyclic system including a spiro or endosystem and the assembly of chain A and the carbon atoms attached thereto can contain at least one chiral atom or the hemiacetal moiety thereto which can present a chirality due to the dissymetric spatial configuration of the molecule and Y is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms optionally substituted, --CY.sub.3 ' and the .beta.,.gamma. bond together with Y can be part of A and Y' is bromine or chlorine.Type: GrantFiled: July 17, 1987Date of Patent: November 29, 1988Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute
-
Patent number: 4775692Abstract: Disclosed herein are novel prostaglandin I.sub.2 (PGI.sub.2) derivatives exhibiting excellent in vivo duration and activities, said derivatives being represented by the general formula: ##STR1## wherein R.sub.1, X, R.sub.2 and R.sub.3 are as defined herein.Type: GrantFiled: January 23, 1987Date of Patent: October 4, 1988Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Atsushi Ohtake, Hiroshi Nagase, Shintaro Nishio, Toshiya Takahashi, Hisanori Wakita
-
Patent number: 4755529Abstract: This invention relates to novel guaiazulene compositions which are useful as antitumor, immunomodulatory and antifungal compositions and a process of producing guaiazulene compositions and a method for immunomodulation and inhibiting tumors and fungi utilizing guaiazulene compositions. More particularly, the compositions are derived from marine gorgorian Acalycigorgia, sp.Type: GrantFiled: June 26, 1986Date of Patent: July 5, 1988Assignee: Harbor Branch Oceanographic Institution Inc.Inventors: Tatsuo Higa, Shinichi Sakemi
-
Patent number: 4745127Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: January 7, 1987Date of Patent: May 17, 1988Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
-
Patent number: 4701543Abstract: Oxygenated decaline derivatives of formula ##STR1## wherein X represents a COOH or a CHO group are obtained according to a process which consists in the oxidation of a ketone of formula ##STR2## by means of oxygen in a basic medium constituted by potassium tert-butoxide in 1,2-dimethoxyethane.Compounds (I) are useful starting materials for the preparation of AMBROX.RTM. (registered tradename of Firmenich SA, Geneva, Switzerland) which is an ingredient in perfumes.Type: GrantFiled: July 18, 1986Date of Patent: October 20, 1987Assignee: Firmenich S.A.Inventors: Ferdinand Naef, Christian Vial
-
Patent number: 4654362Abstract: Derivatives of 2,2'-iminobisethanol having useful properties in the treatment and/or the prevention of disorders of the coronary-vascular system.Type: GrantFiled: October 12, 1984Date of Patent: March 31, 1987Assignee: Janssen Pharmaceutica, N.V.Inventors: Guy R. E. Van Lommen, Marcel F. L. De Bruyn, Marc F. J. Schroven
-
Patent number: 4633011Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.Type: GrantFiled: March 10, 1986Date of Patent: December 30, 1986Assignee: Firmenich SAInventors: George H. Buchi, Hans Wuest
-
Patent number: 4613710Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.Type: GrantFiled: August 8, 1984Date of Patent: September 23, 1986Assignee: Firmenich SAInventors: George H. Buchi, Hans Wuest
-
Patent number: 4585760Abstract: Dimethyfurano analogs of daunomycin are described, including (.+-.)-8.alpha.-acetyl-6,7,8,9-tetrahydro-5,6.beta.,8.beta.,10-tetrahydrox y-1,3-dimethyl-anthra[2,3-c]-furan-4,11-dione-6-(3-amino-2,3-6-trideoxy-.al pha.-L-lyxo-hexopyranoside), which are useful in the treatment of cancer in mammals, such as melanoma, squamous cell, myeloma and pranceatic.Type: GrantFiled: July 16, 1981Date of Patent: April 29, 1986Assignee: American Cyanamid CompanyInventor: Ving J. Lee
-
Patent number: 4585737Abstract: In a method for the production of an agent for modifying a smoke-flavor, ambroxide is contacted with a microbial culture to effect a transformation of at least a proportion of the ambroxide to a product comprising at least one oxygenated derivative of ambroxide. The said product may comprise at least one of the compounds A, B and C, each as defined in the specification. The respective Compound, (particularly Compound A), may be extracted from said product for incorporation with a smoking material. Thus a smoke-flavor modifying agent produced by the aforesaid method for incorporation with, or included in, a smoking material or smoking article may comprise at least one compound of the aforesaid group.The loading level of the said agent may be within a range of 0.1 to 100 parts per million or, suitably, of 0.5 to 10 parts per million, of the said smoking material.Type: GrantFiled: October 29, 1984Date of Patent: April 29, 1986Assignee: British-American Tobacco Company LimitedInventors: Adrian G. Barnes, Peter C. Bevan
-
Patent number: 4564620Abstract: Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as 5,6,7-trinor-4,8-inter-m-phenylene-13,14-didehydro PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-16,16-dimethyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17-.alpha.-methyl-20-homo PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17,18,19,20-tetranor-16-phenoxy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-20-isopropylidene PGI.sub.2, 5,6,7-trinor-4,8-inter-(5-methyl-1,3-phenylene) PGI.sub.2, and 5,6,7-trinor-4,8-inter-m-phenylene-2,3-didehydro-16,17,18,19,20-pentanor-1 5-phenyl PGI.sub.2. They are useful in treatment of ulcers, thrombii and hypertension for example.Type: GrantFiled: January 3, 1984Date of Patent: January 14, 1986Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
-
Patent number: 4539414Abstract: Substantially pure compounds having the general formula ##STR1## wherein (1) ##STR2## R.sup.2 is .beta.-hydroxy and R.sup.3 and R.sup.4 together form an oxygen bridge, or (2) ##STR3## R.sup.2 and R.sup.3 together form an additional carbon-carbon bond, and R.sup.4 is hydroxy, are disclosed. These compounds exhibit antileukemic activity against P388 lymphocytic leukemia in CDF.sub.1 mice and inhibitory activity in vitro against cells derived from human epidermoid carcinoma of the nasopharynx(KB) cells.Type: GrantFiled: October 14, 1983Date of Patent: September 3, 1985Inventors: Ming L. King, Chin-Chih Chiang, Han-Chin Ling, Masahito Ochiai, Eiichi Fujita, Andrew T. McPhail
-
Patent number: 4503240Abstract: Process for the preparation of 8,12-epoxy-13,14,15,16-tetranorlabdane by way of converting farnesyl bromide to farnesyl cyanide, followed by the saponification of the farnesyl cyanide to homofarnesic acid which is then cyclized to norambreinolide in the presence of titanium tetrachloride, converting the norambreinolide with LiAlH.sub.4 to 8-hydroxy-13,14,15,16-tetranorlabdane-12-ol, and cyclization of the diol in the presence of POCl.sub.3 to 8,12-epoxy-13,14,15,16-tetranorlabdane. The resulting product exhibits an amber scent, used in perfumery.Type: GrantFiled: July 28, 1983Date of Patent: March 5, 1985Assignee: Consortium F/u/ r Elektrochemische Industrie GmbHInventors: Gerhard Staiger, Antonio Macri
-
Patent number: 4487778Abstract: Certain benzocycloalkaneheteroaromaticmethyl, e.g., benzocycloalkanethiophenemethyl, esters and insecticidal compositions containing these esters are useful for the control of a broad range of insects and acarids.Type: GrantFiled: January 27, 1983Date of Patent: December 11, 1984Assignee: FMC CorporationInventor: Ernest L. Plummer
-
Patent number: 4485112Abstract: A 2-substituted benzofuran derivative of general formula I or II ##STR1## in which R.sub.1 and R.sub.2, can be the same or different, and are a hydrogen atom, a halogen atom, an alkyl group containing 1 to 4 carbon atoms, an arylalkyl group, an aryl group, a hydroxyl group, an alkoxy group, or an NH.sub.2, NH-alkyl, N(alkyl).sub.2, NH(CO-alkyl), NH(CO-aryl) or NO.sub.2 group, or R.sub.1 and R.sub.2 can together form a ring of 5-8 carbon atoms; R.sub.3 is a hydrogen atom, an alkyl group containing 1 to 4 carbon atoms or an aryl group; R.sub.4 is a hydrogen atom, an alkyl group, an aryl or an arylalkyl group, R.sub.5 is a hydroxyl group, an alkoxy group, an OCO-aryl an OCO-alkyl, OCONH-alkyl or OCONH-aryl group, ##STR2## where n is a number between 1 and 4, R.sub.7 is a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, and R.sub.8 and R.sub.Type: GrantFiled: February 22, 1983Date of Patent: November 27, 1984Assignee: A. Menarini S.A.S.Inventors: Vittorio Pestellini, Mario Ghelardoni, Carlo Alberto Maggi, Gabrio Roncucci, Alberto Meli
-
Patent number: 4474802Abstract: A compound of the formula ##STR1## wherein R.sup.1 is a pharmaceutically acceptable cation, hydrogen or n-alkyl of 1 to 12 carbon atoms; R.sup.2 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R.sup.3 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R.sup.4 is hydrogen, methyl or ethyl; R.sup.5 is n-alkyl of 1 to 5 carbon atoms; n is an integer of 0 to 4; A is --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH--; and X is --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH--. The compounds are useful in anti-ulcer, hypotensive and platelet aggregation inhibiting compositions.Type: GrantFiled: January 19, 1983Date of Patent: October 2, 1984Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Kazuhisa Matsumoto, Shintaro Nishio
-
Patent number: RE32196Abstract: Substituted aurones of formula (I): ##STR1## wherein R.sup.1, R.sup.2 R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and can each represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.3-8 cycloalkyl, optionally substituted phenyl, C.sub.1-6 haloalkyl, amido, amino, cyano, hydroxy, nitro, C.sub.2-4 alkenyl, carboxyl, tetrazol-5-yl and --CH.dbd.CHCOOH; orwherein R.sup.1 and R.sup.2 taken together can represent a group of formula --CH.dbd.CH--CH.dbd.CH-- provided that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is carboxyl, tetrazol-5-yl or --CH.dbd.CHCOOH;or a pharmaceutically-acceptable salt or ester thereof, are effective in the prophylactic chemotherapy of allergic conditions such as bronchial asthma.Type: GrantFiled: May 19, 1982Date of Patent: July 1, 1986Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William B. Jamieson, William J. Ross