Tricyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/458)
  • Patent number: 5244917
    Abstract: 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: Grant
    Filed: June 2, 1992
    Date of Patent: September 14, 1993
    Assignee: The DuPont Merck Pharmaceutical Company
    Inventors: Joseph J. Petraitis, Donald J. P. Pinto
  • Patent number: 5233059
    Abstract: 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: Grant
    Filed: July 25, 1991
    Date of Patent: August 3, 1993
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Richard C. Larock, Nam H. Lee
  • Patent number: 5219835
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: June 15, 1993
    Assignee: International Flavors & Fragrance Inc.
    Inventors: Wilhelmus J. Wiegers, Marie R. Hanna
  • Patent number: 5202447
    Abstract: 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: Grant
    Filed: January 2, 1991
    Date of Patent: April 13, 1993
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Hiroshi Nagase, Yutaka Hosono, Hisanori Wakita, Koji Kawai, Hideo Yoshiwara
  • Patent number: 5189187
    Abstract: 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: Grant
    Filed: June 24, 1992
    Date of Patent: February 23, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hirofumi Nakano, Shozo Kawada, Yoichi Uosaki, Yutaka Saito, Katsushige Gomi, Toshiaki Iwazaki
  • Patent number: 5169959
    Abstract: 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: Grant
    Filed: September 23, 1991
    Date of Patent: December 8, 1992
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Richard C. Larock, Nam H. Lee
  • Patent number: 5136099
    Abstract: 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: Grant
    Filed: August 1, 1990
    Date of Patent: August 4, 1992
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Golfo Skokotas, Kyriacos C. Nicolaou
  • Patent number: 5086071
    Abstract: 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: Grant
    Filed: March 13, 1990
    Date of Patent: February 4, 1992
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Atsushi Ohtake, Takashi Endoh, Shigeki Itou, Kazuhiro Hoshi
  • Patent number: 5084581
    Abstract: 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: Grant
    Filed: December 18, 1990
    Date of Patent: January 28, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David Kronenthal, John K. Thottathil
  • Patent number: 5077417
    Abstract: 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: Grant
    Filed: June 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Roger L. Snowden, Claudio Tarchini, Beatrice Baer, Christian Vial
  • Patent number: 5061398
    Abstract: 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: Grant
    Filed: April 27, 1990
    Date of Patent: October 29, 1991
    Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical Research, Sagami Chemical Research Center
    Inventors: Sadao Takehara, Takeshi Kuriyama, Kayoko Nakamura, Tadao Shoji, Toru Fujisawa, Masashi Osawa, Tamejiro Hiyama, Tetsuo Kusumoto, Akiko Nakayama, Kiyoharu Nishide
  • Patent number: 5011950
    Abstract: 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: Grant
    Filed: February 2, 1988
    Date of Patent: April 30, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 5008286
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 16, 1991
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4978761
    Abstract: 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: Grant
    Filed: June 9, 1989
    Date of Patent: December 18, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
  • Patent number: 4975457
    Abstract: 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: Grant
    Filed: September 25, 1989
    Date of Patent: December 4, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Kathleen M. Rupprecht, Joshua S. Boger
  • Patent number: 4975451
    Abstract: 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: Grant
    Filed: March 2, 1989
    Date of Patent: December 4, 1990
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
  • Patent number: 4966973
    Abstract: 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: Grant
    Filed: June 9, 1989
    Date of Patent: October 30, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Shigenori Ohkawa, Naohisa Fukuda
  • Patent number: 4943589
    Abstract: 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: Grant
    Filed: October 27, 1988
    Date of Patent: July 24, 1990
    Assignees: Syntex (U.S.A.) Inc., The Regents of the Univ. of California
    Inventors: Phillip Crews, Thomas R. Matthews, Paul Horton
  • 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
  • Patent number: 4918205
    Abstract: 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: Grant
    Filed: September 28, 1988
    Date of Patent: April 17, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Eckhard Hickmann, Rainer Becker, Gerald Lauterbach
  • Patent number: 4885373
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: December 5, 1989
    Assignee: ADIR Et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4880939
    Abstract: 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: Grant
    Filed: December 4, 1987
    Date of Patent: November 14, 1989
    Assignee: Toray Industries
    Inventors: Kiyotaka Ohno, Toshiya Takahashi, Shintaro Nishio
  • Patent number: 4866073
    Abstract: 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: Grant
    Filed: October 22, 1987
    Date of Patent: September 12, 1989
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4866070
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.
    Type: Grant
    Filed: December 11, 1987
    Date of Patent: September 12, 1989
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4863951
    Abstract: 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: Grant
    Filed: March 25, 1988
    Date of Patent: September 5, 1989
    Assignee: ADIR Et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4857516
    Abstract: 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: Grant
    Filed: December 22, 1987
    Date of Patent: August 15, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Yoshitaka Maki
  • Patent number: 4851429
    Abstract: 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: Grant
    Filed: March 25, 1988
    Date of Patent: July 25, 1989
    Assignee: Adir et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4838924
    Abstract: 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: Grant
    Filed: April 1, 1987
    Date of Patent: June 13, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Takematsu, Daisuke Fukuoka, Katsuya Takahashi, Isao Hashimoto
  • Patent number: 4837226
    Abstract: A method for the treatment of cerebrovascular disorders by administering a fluorenamine, dibenzofuranamine, or dibenzothiophenamine derivative.
    Type: Grant
    Filed: April 27, 1988
    Date of Patent: June 6, 1989
    Assignee: Warner-Lambert Company
    Inventors: Linda L. Coughenour, Graham Johnson
  • Patent number: 4822804
    Abstract: 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: Grant
    Filed: September 29, 1987
    Date of Patent: April 18, 1989
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
  • Patent number: 4822803
    Abstract: 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: Grant
    Filed: February 4, 1988
    Date of Patent: April 18, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
  • Patent number: 4814469
    Abstract: 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: Grant
    Filed: November 3, 1987
    Date of Patent: March 21, 1989
    Assignee: Firmenich, SA
    Inventors: George M. Whitesides, Rene Decorzant, Ferdinand Naef
  • Patent number: 4788302
    Abstract: 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: Grant
    Filed: January 31, 1986
    Date of Patent: November 29, 1988
    Assignee: Duke University
    Inventors: John D. Costlow, Irving R. Hooper, Daniel Rittschof
  • Patent number: 4788305
    Abstract: 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: Grant
    Filed: July 17, 1987
    Date of Patent: November 29, 1988
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4775692
    Abstract: 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: Grant
    Filed: January 23, 1987
    Date of Patent: October 4, 1988
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Atsushi Ohtake, Hiroshi Nagase, Shintaro Nishio, Toshiya Takahashi, Hisanori Wakita
  • Patent number: 4755529
    Abstract: 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: Grant
    Filed: June 26, 1986
    Date of Patent: July 5, 1988
    Assignee: Harbor Branch Oceanographic Institution Inc.
    Inventors: Tatsuo Higa, Shinichi Sakemi
  • Patent number: 4745127
    Abstract: 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: Grant
    Filed: January 7, 1987
    Date of Patent: May 17, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
  • Patent number: 4701543
    Abstract: 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: Grant
    Filed: July 18, 1986
    Date of Patent: October 20, 1987
    Assignee: Firmenich S.A.
    Inventors: Ferdinand Naef, Christian Vial
  • Patent number: 4654362
    Abstract: Derivatives of 2,2'-iminobisethanol having useful properties in the treatment and/or the prevention of disorders of the coronary-vascular system.
    Type: Grant
    Filed: October 12, 1984
    Date of Patent: March 31, 1987
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Guy R. E. Van Lommen, Marcel F. L. De Bruyn, Marc F. J. Schroven
  • Patent number: 4633011
    Abstract: 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: Grant
    Filed: March 10, 1986
    Date of Patent: December 30, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4613710
    Abstract: 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: Grant
    Filed: August 8, 1984
    Date of Patent: September 23, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4585760
    Abstract: 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: Grant
    Filed: July 16, 1981
    Date of Patent: April 29, 1986
    Assignee: American Cyanamid Company
    Inventor: Ving J. Lee
  • Patent number: 4585737
    Abstract: 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: Grant
    Filed: October 29, 1984
    Date of Patent: April 29, 1986
    Assignee: British-American Tobacco Company Limited
    Inventors: Adrian G. Barnes, Peter C. Bevan
  • Patent number: 4564620
    Abstract: 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: Grant
    Filed: January 3, 1984
    Date of Patent: January 14, 1986
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
  • Patent number: 4539414
    Abstract: 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: Grant
    Filed: October 14, 1983
    Date of Patent: September 3, 1985
    Inventors: Ming L. King, Chin-Chih Chiang, Han-Chin Ling, Masahito Ochiai, Eiichi Fujita, Andrew T. McPhail
  • Patent number: 4503240
    Abstract: 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: Grant
    Filed: July 28, 1983
    Date of Patent: March 5, 1985
    Assignee: Consortium F/u/ r Elektrochemische Industrie GmbH
    Inventors: Gerhard Staiger, Antonio Macri
  • Patent number: 4487778
    Abstract: 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: Grant
    Filed: January 27, 1983
    Date of Patent: December 11, 1984
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4485112
    Abstract: 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: Grant
    Filed: February 22, 1983
    Date of Patent: November 27, 1984
    Assignee: A. Menarini S.A.S.
    Inventors: Vittorio Pestellini, Mario Ghelardoni, Carlo Alberto Maggi, Gabrio Roncucci, Alberto Meli
  • Patent number: 4474802
    Abstract: 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: Grant
    Filed: January 19, 1983
    Date of Patent: October 2, 1984
    Assignee: Toray Industries, Inc.
    Inventors: Kiyotaka Ohno, Hiroshi Nagase, Kazuhisa Matsumoto, Shintaro Nishio
  • Patent number: RE32196
    Abstract: 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: Grant
    Filed: May 19, 1982
    Date of Patent: July 1, 1986
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, William J. Ross