Polycyclo Ring System Patents (Class 568/808)
  • Patent number: 5112869
    Abstract: This invention concerns compounds having the structure: ##STR1## wherein each of R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.2', R.sup.3', R.sup.4', and R.sup.5', is independently hydrogen (--H), or a hydroxyl (--OH), methoxy (--OMe), methyl (--Me), carboxaldehyde (--CHO) or phenylformazen (Ph--N.dbd.CH--) group.This invention also provides a novel process of synthesizing the compounds of the subject invention, including intermediate compounds useful in the process.The present invention also provides pharmaceutical compositions comprising a pharmaceutically effective amount of a compound according to the subject invention and a pharmaceutically acceptable carrier. Finally, the invention provides spermicidal methods and methods of killing or of retarding the proliferation of, cancer cells.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: May 12, 1992
    Assignee: Sloan-Kettering Institute For Cancer Research
    Inventors: Kyoichi A. Watanabe, Tsann-Long Su, Jai-Tung Huang
  • Patent number: 5101059
    Abstract: This invention relates to compounds of the formula a compound of the formula ##STR1## wherein X is O, CR.sub.7 R.sub.8, S or NR.sub.9 wherein R.sub.7 and R.sub.8 are independently hydrogen, or lower alkyl, and R.sub.9 is lower alkyl;n is 0 or 1;R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, aryl, or nitro;R.sub.3 is hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, 9-fluorenylalkyl, cycloalkyl, aryl or aralkyl;R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, or aryl or one of R.sub.4 and R.sub.5 is 9-fluorenyl;R.sub.6 is H or COZ wherein Z is an amino acid, a peptide residue or a leaving group; andwith the provisos that when n is 0 and R.sub.3 is hydrogen, R.sub.1 and R.sub.2 are not hydrogen, halogen or nitro; that when n is 0 and R.sub.3 is lower alkyl, R.sub.1 and R.sub.2 are not hydrogen; and that when X is O or CR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are H, that R.sub.1, R.sub.2, R.sub.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: March 31, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, An-Chuu Wu
  • Patent number: 5084575
    Abstract: There are disclosed compounds of the formula ##STR1## wherein a is alkyl 3-19 carbon atoms, diloweralkyl allyl, diahaloallyl, diphenylallyl, lower alkynyl, ##STR2## W is --CR.sub.2 O--, --CH.dbd.CH-- or --CH.dbd.CHCH.sub.2 O-- X is N or CR;Z is ##STR3## R is hydrogen or lower alkyl; Y is ##STR4## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring, optionally substituted by halo;R.sup.3 is --OR, ##STR5## -- NHSO.sub.2 R.sup.4 ; R.sup.4 is phenyl or loweralkyl substituted phenyl;R.sup.5 is halo;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as alelrgic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: January 28, 1992
    Assignee: American Home Products Corporation
    Inventors: Anthony F. Kreft, III., John H. Musser, James J. Bicksler, John W. Giberson, Dennis M. Kubrak, Annette L. Banker
  • Patent number: 5079245
    Abstract: The compounds 2-trifluoromethyl-7-substituted-6,7,8,9-tetrahydro-[5H]-benzocycloheptenes are disclosed and disclosed to be useful in the treatment of metabolic illnesses such as diabetes, obesity, and their complications. A perferred compound is 2-trifluoromethyl-7-amino-6,7,8,9-tetrahydro-[5H-benzocycloheptane.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: January 7, 1992
    Assignee: Adir et Compagnie
    Inventors: Michel Wierzbicki, Pierre Hugon, Jacques Duhault, Francoise Lacour
  • Patent number: 5041620
    Abstract: A method for producing an optically active 2-cyclopenten-4-one-1-ol ester useful as an intermediate for medicines, agricultural chemicals and represented by the general formula (I), ##STR1## wherein R represents a saturated or unsaturated aliphatic hydrocarbon residue which may or may not be substituted with a halogen atom, and a mark * represents an asymmetric carbon,which comprises bringing a 2-cyclopenten-4-one-1-ol ester represented by the general formula ##STR2## wherein R represents a saturated or unsaturated aliphatic hydrocarbon residue which may or may not be substituted with a halogen atom, into contact with an optically active 1,6-diphenyl-2,4-hexadiyne-1,6-diol derivative represented by the general formula (II), ##STR3## wherein R' represents a halogenated phenyl, lower alkylphenyl, naphthyl or tertiary lower alkyl group, and a mark * represents an asymmetric carbon,in an organic solvent to obtain an optically active cyclopentenone ester complex which is a bound product of the optically active 2-c
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: August 20, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumio Toda, Masayoshi Minai
  • Patent number: 5030764
    Abstract: Novel styryl-tetrahydronaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 5030765
    Abstract: The present invention is concerned with novel tetrahydronaphthalene and indane derivatives of the formula ##STR1## useful as for combatting dermatoses as well as neoplasmas.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4990703
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 5, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4990691
    Abstract: The novel compound provided by the invention is a higher carboxylic acid triester of adamantane triol such as adamantane-1,3,5-triol tricaprylate not known in the prior art. The compound has a high kinematic viscosity at elevated temperatures despite the low pour point and has high thermal stability in an oxidizing atmosphere so that it is useful as an ingredient of a high-performance lubricating oil.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: February 5, 1991
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Kosaku Honna, Hiromichi Seiki
  • Patent number: 4990650
    Abstract: 1. An aromatic derivative having the formula (I) or the salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, hydroxyl, a halogen atom, or OR.sup.3 wherein R.sup.3 is C.sub.1 -C.sub.10 alkyl; A-B represents a hydrocarbon moiety having 1 to 10 carbon atoms and containing at least one double bond or a sulfur- or oxygen-containing hydrocarbon moiety having 1 to 10 carbon atoms; n is an integer of 2 to 4; X represents a group ##STR2## and Y represents a hydrogen atom; alkyl having 1 to 5 carbon atoms which may be substituted with aryl; alkenyl having 2 to 5 carbon atoms which may be substituted with aryl or aryl substituted with at least one C.sub.1 -C.sub.5 alkoxy; aryl which may be substituted with at least one carboxy or C.sub.1 -C.sub.5 alkoxycarbonyl or C.sub.1 -C.sub.5 alkoxy; provided that, when R.sup.1 and R.sup.2 are both hydrogen, the moiety --A--B--(CH.sub.2).sub.n --X--Y does not represent ##STR3## wherein n=2 to 4 and R.sup.4 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: February 5, 1991
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4983627
    Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
  • Patent number: 4968667
    Abstract: A novel 1,1-dimethyl-3-hydroxymethylindane represented by formula (I) is disclosed. ##STR1## A perfumery composition comprising the same is also disclosed.The compound represented by formula (I) of the present invention possesses a lasting floral, fruity, herbal, and woody odor based on a rosy tone. The perfumery compositions comprising Compound (I) can widely be used as a perfurmery material for perfumes, soaps, shampoos, room flavors, detergents, and the like.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: November 6, 1990
    Assignee: Kao Corporation
    Inventors: Hiroaki Ohnuma, Yoshiaki Fujikura, Manabu Fujita, Nao Toi
  • Patent number: 4958033
    Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
  • Patent number: 4956502
    Abstract: A process for preparing a compound of the formula ##STR1## in which both Rs and H or OH; comprising the steps a. of treating the ethyl ester of caffeic acid with trialkylsilyl chloride at ambient conditions in equimolar proportions in the presence of a base;b. the reduction of the ester to the corresponding allylic alcohol with aluminum hydride reagent;c. of oxidizing the resulting product with manganese dioxide at ambient temperature and in excess molar proportion to yield the corresponding allylic aldehyde;d. of coupling the latter with the silyl ether of the relative phenyl acetylide; ande. of hydrolysis of this coupled product with alkylammonium fluoride at ambient conditions in equimolar proportions.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: September 11, 1990
    Assignee: Rooperol (N.A.) NV
    Inventors: George L. Wenteler, Karl H. Regel, Siegfried Drews, Hans Kundig
  • Patent number: 4954659
    Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: September 4, 1990
    Assignee: Chemex Pharmaceuticals, Inc.
    Inventors: Robert M. Parkhurst, Ronald S. Pardini
  • Patent number: 4950796
    Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wolf, Hans Theobald, Norbert Goetz
  • Patent number: 4940822
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halo, halo-substituted alkyl, alkyl, cycloalkyl, aralkyl, aryl, heterocyclic, alkoxy, alkaryl, aryloxy, thioalkoxy, nitro, or N,N-dialkylamino are prepared by reacting 1-bromo-4-(trifluoromethyl)benzene with n-butyl lithium; reacting the product with a benzaldehyde of the formula: ##STR2## to produce a novel intermediate such as lithium 4-(trifluoromethyl)-.alpha.-]4-(trifluoromethyl)phenyl]benzenemethanol, and then reacting the lithium product with an acid or acid salt.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: July 10, 1990
    Assignee: Warner-Lambert Company
    Inventors: James G. Davidson, III, Brian S. Swierenga
  • Patent number: 4940696
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: July 10, 1990
    Assignee: Centre International de Recherches Dermatologioues (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4935560
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: June 19, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4886919
    Abstract: A process for the gas phase hydrogenation of unsaturated trisubstituted monoesters to the saturated trisubstituted alcohols using a Zn.sub.a Cu.sub.b X.sub.c Ni.sub.d O.sub.e reduced catalyst.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: December 12, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Ernesto Vera-Castaneda, John E. Logsdon
  • Patent number: 4882439
    Abstract: Total synthesis of steroids with substitution in the 2,3, 6, 11 or 17 positions comprising the step of cyclization of a compound having the formula ##STR1## or analogues thereof, where X represents .dbd.O, ##STR2## or .beta.-substituted ##STR3## Y represents .dbd.O, .beta.-oriented ##STR4## or .beta.-orientated OH, R' and R.sup.2 may be the same or different and R' represents alkyl or aryl and R.sup.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: November 21, 1989
    Assignee: The University of Sheffield
    Inventor: David N. Jones
  • Patent number: 4866181
    Abstract: A process for preparing optically active alcohols by reducing ketones using mono- or diisopinocampheylhaloboranes as reducing agents.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 12, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4840971
    Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4837307
    Abstract: A 2,2'-bridged[1,1'-biphenyl]-3-ylmethyl compound of the following formula is an intermediate to insecticidal esters. ##STR1## wherein n is 1-4 and Y is a leaving group readily displaced by carboxylate anions.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: June 6, 1989
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4820879
    Abstract: The present invention provides a process for making hydrocarbyloxy magnesium halides by reacting in an inert atmosphere under anhydrous conditions activated magnesium metal with an oxygen containing compound of 1 to 20 carbon atoms and an anhydrous hydrogen halide to produce a hydrocarbyloxy magnesium halide.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: April 11, 1989
    Assignee: Lithium Corporation of America
    Inventor: Vijay C. Mehta
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4735966
    Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --;X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);is an integer of 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: April 5, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Helen Y. Wu, Walter Kurz
  • Patent number: 4727200
    Abstract: A process for the homologation of an alkanol by reaction with synthesis gas in contact with a system containing rhodium atom, ruthenium atom, iodine atom and a bis(diorganophosphino) alkane to selectivity produce the next higher homologue.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventors: Richard W. Wegman, Kenneth G. Moloy
  • Patent number: 4719236
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid additon salts thereof; wherein Ar is a perylene or substituted perylene ring system; R.sup.1 contains not more than eight carbon carbon atoms and is a group ##STR1## wherein m is 0 or 1;R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: January 12, 1988
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4709088
    Abstract: A process for producing 2,6-naphthalenedicarboxylic acid which comprises oxidizing 2,6-diisopropylnaphthalene or its oxidation product as a starting material with molecular oxygen in a reaction medium containing at least 50% by weight of an aliphatic monocarboxylic acid having not more than 3 carbon atoms in the presence of an oxidation catalyst comprising (A) at least one heavy metal element selected from the group consisting of cobalt and manganese, and (B) bromine element, the 2,6-diisopropylnaphthalene and/or its oxidation product being used in a proportion of 0.1 to 5 moles per gram-atom of the heavy metal element of the oxidation catalyst.
    Type: Grant
    Filed: July 15, 1986
    Date of Patent: November 24, 1987
    Assignee: Teijin Petrochemical Industries, Ltd.
    Inventors: Isao Hirose, Tamio Amemiya, Tokuji Sakai
  • Patent number: 4683330
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4668814
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 26, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4658033
    Abstract: New interphenylene prostaglandin (PGH) analogs are prepared by a method which involves reacting a bicyclic olefin, an acetylene compound and a benzylic halide together, in the presence of a palladium(O) catalyst in a single-step synthesis. By this technique a large number of new interphenylene PGH analogs can be prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: April 14, 1987
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4598085
    Abstract: Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.
    Type: Grant
    Filed: January 21, 1982
    Date of Patent: July 1, 1986
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Heeres, Leo J. J. Backx, Joseph A. Mostmans
  • Patent number: 4581380
    Abstract: New 2,6-disubstituted derivatives of naphthalene have the formula ##STR1## wherein n is 1 or 2,R.sub.1 to R.sub.4 are hydrogen or CH.sub.3,R.sub.5 is ##STR2## (iv) 2-oxazolinyl, wherein m is 0 or 1, R.sub.6 is hydrogen, alkyl, OR.sub.9 wherein R.sub.9 is H, alkyl or ##STR3## wherein R.sub.10 is alkyl or aryl, or R.sub.6 is ##STR4## when m=1, r' and r" representing H, alkyl, mono- or poly-hydroxyalkyl, aryl or a heterocycle when taken together, R.sub.7 is H or alkyl, R.sub.8 is H, alkyl and the acetal of said compounds, and the salts of the compounds of formula I. These compounds are usefully employed in the pharmaceutical and cosmetic fields.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: April 8, 1986
    Assignee: Groupement Economique dite: Centre National de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
  • Patent number: 4581377
    Abstract: Compounds of formula I below are useful as anti-inflammatory, analgesic and/or anti-pyretic agents: ##STR1## in which R.sup.1 is hydrogen, nitro, amino, hydroxyl, alkoxy of one to four carbon atoms, alkyl of one to four carbon atoms or halogen; R.sup.2 is hydrogen or alkyl of one to four carbon atoms; is a saturated or unsaturated bond; A is CO, CHOH, C(R.sup.5)OH or CHOCOR.sup.6, where R.sup.5 and R.sup.6 are alkyl of one to four carbon atoms; B is alkyl of one to twelve carbon atoms; and X is H.sub.2 or O.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: April 8, 1986
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Yoshihisa Shibata, Yoshihiko Yoshimoto
  • Patent number: 4528408
    Abstract: Disclosed are novel compounds of the formula ##STR1## in which R.sup.1 is hydrogen or methyl; R.sup.2 is phenyl or phenylmethyl either of which is optionally ring substituted with lower alkyl or halogen; R is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substitutedphenyl)-2-methylpropylcarbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substitutedvinylcyclopropanecarbonyl group; and, with respect to the indanyl substituents, the 1,3-trans isomer is present in an isomeric excess over the corresponding 1,3-cis isomer. The compounds wherein R is other than hydrogen are insecticides, and the compounds wherein R is hydrogen are insecticide intermediates.
    Type: Grant
    Filed: October 16, 1984
    Date of Patent: July 9, 1985
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4520007
    Abstract: Compounds having blood-anticoagulant properties of the general molecular formula: ##STR1## in which Z represents a halogen atom, preferably a chlorine atom, and n is 0, 1 or 2 and R.sup.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: May 28, 1985
    Assignee: Shell Oil Company
    Inventors: Ian D. Entwistle, Peter Boehm
  • Patent number: 4515990
    Abstract: An indane, tetralin or phenyl alcohol is made by a heterogeneous, fast, exothermic Friedel Craft reaction and the reaction mixture is cooled to a temperature at which substantial by-product formation is avoided by continuously utilizing the heat of reaction to boil solvent from the reaction mixture. The reaction mixture is generally maintained below atmospheric pressure, typically 20 to 100 mm Hg. The process is of particular value for the production of aryl alcohols by reacting an indane or tetralin with ethylene oxide or propylene oxide.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: May 7, 1985
    Assignee: Bush Boake Allen Limited
    Inventors: John G. Ferber, Peter J. Goddard, Robert S. Holden
  • Patent number: 4504663
    Abstract: The present invention concerns novel heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: March 12, 1985
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4497960
    Abstract: The invention declares new chiral, optically active compounds of the general formula ##STR1## wherein a 5 or 6 membered lactol ring (E), with X and Y meaning (CR.sup.1 R.sup.2).sub.n, with n=0 to 2 and R.sup.1, R.sup.2 =H, lower alkyl or aryl in any combination which does not impair the anomeric selectivity of I in forming acetals, is fused in a stereospecific manner to a bicyclo[2.2.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: February 5, 1985
    Inventor: Christian Noe
  • Patent number: 4486598
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 4, 1984
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4477668
    Abstract: (+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine, and its pharmaceutically acceptable salts is useful as an anxiolytic, antidepressant, anticonvulsant, muscle relaxant and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease. The racemate of the compound is produced by a four-step synthetic process in about 65% yield from 5H-dibenzo[a,d]cyclohepten-5-one.
    Type: Grant
    Filed: September 3, 1982
    Date of Patent: October 16, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Dean R. Bender, Sandor Karady, Theresa Rothauser
  • Patent number: 4461899
    Abstract: A series of ester and salt derivatives of fluorene-9-carboxylic acid and fluorene-1-carboxylic acid exhibit significant plant growth regulating properties, useful in controlling the size, shape, dormancy time, flowering time and/or fruit setting of plants, depending upon the concentrations used. They may also be used to control the growth rate, texture and color of turf grass. Presently preferred compounds include the cis-2,5-dimethylpyrrolidine salt of 1-fluorenecarboxylic acid, 9-cis-2,5-dimethyl-1-pyrrolidinyl-2-chlorofluorene-9-carboxylic acid, methyl ester, the 2,6-dimethylpiperidine salt of 1-fluorenecarboxylic acid, and the cis-2,5-dimethylpyrrolidine salt of 9-hydroxyfluorene-9-carboxylic acid.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: July 24, 1984
    Assignee: Diamond Shamrock Chemicals Company
    Inventors: William J. Pyne, Han S. Ku, Robert E. Holm
  • Patent number: 4433182
    Abstract: 2,2'-Bridged[1,1'-biphenyl]-3-ylmethyl cyclopropanecarboxylates and insecticidal compositions containing these esters are useful for the control of a broad range of insects and acarids.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: February 21, 1984
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4431851
    Abstract: The present invention concerns compounds of the formula ##STR1## wherein n=1, 2 or 3; and R' represents phenyl or orthofluorophenyl. Said compounds are used as intermediates in the preparation of heterocyclic aminoalkyl derivatives which are useful as analgesics and antidepressants.
    Type: Grant
    Filed: March 8, 1983
    Date of Patent: February 14, 1984
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4423255
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: December 27, 1983
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4421739
    Abstract: The invention provides compounds which are particularly valuable for use as the active ingredient in sun tan lotions and creams and the like. These compounds have the general formula: ##STR1## in which Y denotes hydrogen or the radical SO.sub.3 H or a salt thereof with an organic or inorganic base, and Z denotes the radical --CH.sub.2 Br or --CHBrBr or a radical Z' which denotes the radical --CH.sub.2 I, --CH.sub.2 R, --CHR'R', --CHO or --COOR", in which R denotes --NR.sub.1 R.sub.2, --N.sup.+ R.sub.1 R.sub.2 R.sub.3, --OR.sub.4, --OCOR.sub.5, --SR.sub.6, --CN, -COOR" or --SSO.sub.3 Na, in which R.sub.1 and R.sub.2 independently denote hydrogen, C.sub.1-18 alkyl or hydroxyalkyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, denote a heterocyclic ring, R.sub.3 denotes C.sub.1-4 alkyl or hydroxyalkyl or sulphonatopropyl, R.sub.4 denotes hydrogen, alkyl, polyoxyethylene, aryl which is optionally substituted, menthyl or dialkylaminoalkyl, R.sub.
    Type: Grant
    Filed: March 14, 1978
    Date of Patent: December 20, 1983
    Assignee: L'Oreal
    Inventors: Claude Bouillon, Charles Vayssie
  • Patent number: 4417078
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: November 22, 1983
    Assignee: FMC Corporation
    Inventor: John F. Engel