2,2,1-bicyclo Patents (Class 560/120)
  • Patent number: 4867750
    Abstract: The invention relates to a polymer having the structure ##STR1## and mixtures thereof wherein R is a perhalogenated aromatic or cyclo aliphatic radical containing from 6 to 7 carbon atoms in the cyclic structure; R.sup.1 is hydroxy or C.sub.1 to C.sub.10 alkoxy; R.sup.2 is hydrogen or C.sub.1 to C.sub.10 alkyl; EO represents the radical --CH.sub.2 CH.sub.2 O--; PO represents the radical ##STR2## m is an integer having a value of from 6 to 20; and x, y, z, x', y' and z' each represent an integer having a value of from 0 to 50 with the proviso that the sums of x+y+z and of x'+y'+z' are greater than 5.The application is also directed to the preparation and use of the above polymer.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: September 19, 1989
    Assignee: GAF Corporation
    Inventors: Anthony J. O'Lenick, Jr., Randy L. Rayborn
  • Patent number: 4861913
    Abstract: Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms an may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: August 29, 1989
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
  • Patent number: 4847335
    Abstract: Compounds of the formula I ##STR1## in which a is 1, 2 or 3, m is an integer from 2 to 20, R.sup.1, R.sup.2 and R.sup.3 independently of one another are hydrogen or methyl and R.sup.4 is an m-valent radical of a polyol after removal of m hydroxyl groups, can be thermally reacted to give crosslinked polymers having outstanding physical properties.The polymers are suitable especially as casting resins, matrix resins, adhesives, encapsulating resins, insulating materials for electronics and electrical engineering and in surface protection.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: July 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Andreas Kramer
  • Patent number: 4843061
    Abstract: Perfume compositions containing at least one compound having the formula 1 ##STR1## wherein said compounds have the substituents as defined in claim 1. Perfumed compositions and perfumed products containing them are characterized by flowery, fruity, green and spicy odors, sometimes accompanied by a slight minty nuance with animal and/or wood notes in the after-odor.
    Type: Grant
    Filed: June 9, 1987
    Date of Patent: June 27, 1989
    Assignee: Naarden International N.V.
    Inventors: Nicolaas L. J. M. Broekhof, Jan G. Witteveen, Antonius J. A. van der Weerdt
  • Patent number: 4837234
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: June 6, 1989
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4824606
    Abstract: The invention relates to a polymer having the structure ##STR1## and mixtures thereof wherein R is a perhalogenated aromatic or cyclo aliphatic radical containing from 6 to 7 carbon atoms in the cyclic structure; R.sup.1 is hydroxy or C.sub.1 to C.sub.10 alkoxy; R.sup.2 is hydrogen or C.sub.1 to C.sub.10 alkyl; EO represents the radical --CH.sub.2 CH.sub.2 O--; PO represents the radical ##STR2## m is an integer having a value of from 6 to 20; and x, y, z, x', y' and z' each represent an integer having a value of from 0 to 50 with the proviso that the sums of x+y+z and of x'+y'+x' are greater than 5.The application is also directed to the preparation and use of the above polymer.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: April 25, 1989
    Assignee: GAF Corporation
    Inventors: Anthony J. O'Lenick, Jr., Randy L. Rayborn
  • Patent number: 4814490
    Abstract: A prostaglandin precursor is made by reacting a bicyclic olefin with an alkyl (acetoxymercurio) carboxylate, a palladium salt, and an 1-alken-3-one to provide a keto ester bicycloheptane.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: March 21, 1989
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard L. Larock
  • Patent number: 4812543
    Abstract: A novel metathesis catalyst polymerizable composition is provided which comprises at least one ring-opening metathesis catalyst polymerizable norbornene-type monomer and at least one ring-opening metathesis catalyst polymerizable amine antioxidant comonomer.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: March 14, 1989
    Assignee: Hercules Incorporated
    Inventors: Albert S. Matlack, Martin J. Paisner
  • Patent number: 4766246
    Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: August 23, 1988
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4734424
    Abstract: Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula ##STR1## wherein m is 0 to 4; A is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; n is 1 to 5; Q is --CH.dbd.CH--, --CH.sub.2 --, ##STR2## or a single bond; R is CO.sub.2 H, CO.sub.2 alkyl, CO.sub.2 alkali metal, CO.sub.2 polyhydroxyamine salt, --CH.sub.2 OH, ##STR3## wherein R.sup.4 and R.sup.5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R.sup.4 and R.sup.5 being other than hydroxy and lower alkoxy; p is 1 to 4; R.sup.1 is H or lower alkyl; q is 1 to 12; R.sup.2 is H or lower alkyl; and R.sup.3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, ##STR4## (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl.
    Type: Grant
    Filed: September 24, 1986
    Date of Patent: March 29, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Steven E. Hall, Joyce Reid
  • Patent number: 4728747
    Abstract: Novel disubstituted bicyclo[2.2.1]heptanes of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.3 -alkyl, R.sup.2 is C.sub.1 -C.sub.8 -alkyl or-alkenyl, R.sup.3 and R.sup.4 together are .dbd.O, .dbd.CH--CN, .dbd.CH--CO--OCH.sub.3 or .dbd.CH--CO--OC.sub.2 H.sup.5, or R.sup.3 is hydrogen, --CH.sub.3, --CH.dbd.CH.sub.2 or --C.tbd.CH when R.sup.4 is --OH or --O--CO--CH.sub.3, or R.sup.3 is H when R.sup.4 is --CH.sub.2 --CO--OCH.sub.3, --CH.sub.2 --CO--OC.sub.2 H.sub.5 or --CH.sub.2 --C.tbd.N and one or both of the dashed lines may be a further bond, are obtained by subjecting cyclopentadiene to a Diels-Alder reaction with an unsaturated ketone, this reaction being catalyzed by a Lewis acid, and then subjecting the compound of the formula Ia ##STR2## initially formed to a reduction, a Grignard reaction or a reaction with diethylphosphonoacetonitrile or ethyl phosphonoacetate and NaH.They can be used as scents and/or aromas or as intermediates for scents.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: March 1, 1988
    Assignee: Basf Aktiengesellschaft
    Inventors: Werner Hoffmann, Lothar Janitschke
  • Patent number: 4717494
    Abstract: A liquid thermal accumulator composition comprising a dicarboxylic acid anhydride, an alcohol and a monoester of the dicarboxylic acid and the alcohol. A process for accumulation of thermal energy utilizing said composition is also disclosed.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: January 5, 1988
    Assignee: UBE Industries, Ltd.
    Inventors: Hiroshi Itatani, Mikito Kashima, Masami Aikawa
  • Patent number: 4683078
    Abstract: A novel liquid crystal compound suitable to use as a component of liquid crystal dielectrics and a liquid crystal composition containing the same are provided, which compound is a dihalogeno-aromatic compound expressed by the formula ##STR1## wherein R represents an alkyl group or an alkoxy group, each of 1 to 12 carbon atoms, or an alkoxymethyl group of 2 to 12 carbon atoms.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: July 28, 1987
    Assignee: Chisso Corporation
    Inventors: Shigeru Sugimori, Yasuyuki Goto, Tetsuya Ogawa
  • Patent number: 4661285
    Abstract: Balsamic fragrance compositions having fruity, fir needle notes with the character of fir balsam absolute are produced by reacting camphene, and ethylhaloacetate and di-t-butyl peroxide; reacting the mixture obtained therefrom with zinc and water; vacuum distilling the resulting product; and collecting a specified fraction.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: April 28, 1987
    Assignee: National Distillers and Chemical Corporation
    Inventors: Eugene G. Harris, Jane C. Mueninghoff
  • Patent number: 4649214
    Abstract: Norbornane-2-carboxylic acid esters are disclosed, in particular the 5(6)-formyl and the 5(6)-hydroxymethylnorbornane-2-carboxylic acid esters. The 5(6)-hydroxymethyl-norbornane-2-carboxylic acid esters may be reacted with polyols to provide a di- or polyfunctional polyol ester suitable for further reaction with polyisocyanates to prepare polyurethanes.
    Type: Grant
    Filed: November 30, 1984
    Date of Patent: March 10, 1987
    Assignee: Henkel Corporation
    Inventors: Elizabeth J. Gladfelter, Edgar R. Rogier
  • Patent number: 4647585
    Abstract: Bicycloheptane substituted ether prostaglandin analogs are provided having the structural formula ##STR1## wherein X is O or ##STR2## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
    Type: Grant
    Filed: November 8, 1984
    Date of Patent: March 3, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Melanie J. Loots, Steven E. Hall, Peter W. Sprague
  • Patent number: 4640801
    Abstract: Graft polyols comprising the liquid reaction product of a vegetable oil or unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one double bond, a cyclopentadienyl compound and a terminally unsaturated monomer having at least one hydroxyl group. These liquid low viscosity polyols when cured with a polyisocyanate, melamine, or formaldehyde compound yield high solids or solventless polyurenthane compositions useful as coatings, adhesives, potting or molding compounds.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: February 3, 1987
    Assignee: CasChem, Inc.
    Inventors: Dominic Simone, Melvin Brauer
  • Patent number: 4638071
    Abstract: The following dipeptides possess a high order of sweetness: ##STR1## wherein X=O or S;R is alkyl containing 1-3 carbon atoms;R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl-substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl, tricycloalkyl, cyclic ether, cyclic thioether, cyclic sulfoxides, cyclic sulfones, aryl, benzyl, alkylaryl, aromatic heterocyclic or alkyl substituted aromatic heterocyclic containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are each H or lower alkyl;R.sub.5 is H, lower alkyl or cycloalkyl containing 3-5 ring carbons;each n=0, 1 or 2;m=0 or 1;Z is an alkylene chain containing 0-2 carbon atoms in the principal chain and up to a total of 6 carbon atoms;and food-acceptable salts.
    Type: Grant
    Filed: December 27, 1984
    Date of Patent: January 20, 1987
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4633008
    Abstract: A phenol derivative represented by the formula ##STR1## wherein R.sup.1 is a secondary or tertiary hydrocarbon residue of having 3 to 8 carbon atoms, R.sup.2 is a hydrocarbon residue having 1 to 12 carbon atoms, X is ##STR2## wherein R.sup.3, R.sup.4 and R.sup.5 each is an alkylene group having 1 to 4 carbon atoms, Z is an n-valent group and n is an integer of 1 to 8.This compound is effective to prevent the oxidation of organic materials.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: December 30, 1986
    Assignee: Mitsubishi Yuka Fine Chemicals Co., Ltd.
    Inventors: Akiyoshi Oonishi, Kenji Tanaka, Makoto Tadeka, Kazuhiko Konno, Masaki Saito
  • Patent number: 4633006
    Abstract: Novel 3-hydroxy-4-alkyloxyphenyl aliphatic carboxylate compounds particularly well suited as sweeteners in foodstuff.
    Type: Grant
    Filed: August 14, 1985
    Date of Patent: December 30, 1986
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Jed A. Riemer, Paul R. Zanno
  • Patent number: 4627933
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4628061
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: August 23, 1983
    Date of Patent: December 9, 1986
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4622339
    Abstract: Norbornane- and norbornene-carboxylic acid amides of the formula ##STR1## in which ##STR2## represents the part structure ##STR3## A represents a ##STR4## or --CH.sub.2 --CH.sub.2 -- group, R.sup.1 and R.sup.2 each independently is hydrogen or an alkyl radical with 1-6 carbon atoms,R.sup.3 is alkyl or alkenyl which has 1-8 carbon atoms and is optionally substituted by halogen or alkyl with 1 or 2 carbon atoms, cycloalkyl or cycloalkeny wtih 3 to 7 carbon atoms, an aromatic radical which has 6 or 10 carbon atoms and and is optionally substituted by halogen, by alkyl with 1 or 2 carbon atoms or by halogenoalkyl with 1 or 2 carbon atoms, or is a five-membered or six-membered heteroaromatic radical,R.sup.4 is hydrogen or a hydroxyl group,R.sup.5 and R.sup.6 each independently is hydrogen or alkyl with 1 to 4 carbon atoms, andn is a number from 2 to 6,and, if R.sup.1 is hydrogen, also physiologically acceptable salts thereof, perform as thromboxan antagonists.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: November 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Folker Lieb, Hermann Oediger, Hans-Joachim Kabbe, Ulrich Niewohner, Elisabeth Perzborn, Friedel Seuter
  • Patent number: 4622417
    Abstract: Dipeptides of certain .alpha.-amino dicarboxylic acids and etherified hydroxy .alpha.-amino-mono-carboxylic acid esters possess a high order of sweetness. These dipeptides have the following formula: ##STR1## wherein R is alkyl containing 1-3 carbon atoms;R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl or tricycloalkyl containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 and R.sub.4 are each H or alkyl containing 1-3 carbon atoms;R.sub.3 is H, alkyl containing 1-6 carbon atoms or cycloalkyl containing 3-5 ring carbons;n=0, 1 or 2; andm=0 or 1;and food acceptable salts thereof.
    Type: Grant
    Filed: December 27, 1984
    Date of Patent: November 11, 1986
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4622418
    Abstract: Amides of .alpha.-aminodicarboxylic acids and .beta.-aminoethers are low calorie sweetners.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: November 11, 1986
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4596823
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo[2,2,1]hept-2Z-ene, bicyclo[2,2,1]heptane, 7-oxabicyclo[2,2,1]hept-2Z-ene, 7-oxabicyclo[2,2,1]heptane, bicyclo[2,2,2]oct-2Z-ene or bicyclo[2,2,2]octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR, a 6,6-dimethyl-bicyclo[3,1,1]heptane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR or at the 5-position by the group C(R.sup.2).dbd.NR and at the 6-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group C(R.sup.2).dbd.NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group C(R.sup.2).dbd.NR, R.sup.1 is a 6-caboxyhex-2-enyl group or a modification thereof as defined herein, R.sup.
    Type: Grant
    Filed: February 12, 1982
    Date of Patent: June 24, 1986
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4564697
    Abstract: Haze-free reactive flame retardant halo polyols are made by reacting (a) a halogen containing cyclic acid anhydride (e.g. tetrabromophthalic anhydride), (b) an aliphatic polyol, e.g. diethylene glycol, and (c) an epoxide, e.g. propylene oxide, and including potassium salt of fatty acids (e.g. potassium acetate) in the reaction mixture in an amount at least sufficient to neutralize residual sulfuric acid that is usually present in the halogen containing cyclic acid anhydride.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: January 14, 1986
    Assignee: Ethyl Corporation
    Inventor: Burton J. Sutker
  • Patent number: 4546155
    Abstract: A latent curing agent for epoxy resin, characterized in that the latent curing agent is an adduct obtained by reacting (a) a polyfunctional epoxy compound, (b) a compound having at least one OH, NH.sub.2, NH or SH group together with a tertiary amino group in the molecule and (c) a carboxylic acid anhydride is a good curing agent for epoxy resins. The present curing agent is useful in formulating storable, one-package, heat-curable epoxy resin-based compositions.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: October 8, 1985
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takeshi Hirose, Nobuo Ito, Kiyomiki Hirai, Koji Takeuchi
  • Patent number: 4535179
    Abstract: Bicyclic oxa prostaglandin endoperoxide analogs, and tricyclic oxa prostaglandin analogs are prepared by reacting norbornadiene palladium dichloride with tertiary butyl-6-hydroxyhexanoate in an oxypalladation reaction to provide an oxypalladium intermediate which can subsequently be elaborated into bicyclic and/or tricyclic 7-oxa prostaglandin endoperoxides. If the intermediate is carbonylated in the presence of an organic amine, preferably diisopropylethylamine, the compound is bicyclic; if the amine is eliminated, the compound is tricyclic. The analogs are novel compounds.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: August 13, 1985
    Assignee: Iowa State University Research Foundation Inc.
    Inventor: Richard C. Larock
  • Patent number: 4531010
    Abstract: A curing agent for fluorocarbon polymer coating compositions having the formula ##STR1## where R is R.sup.1 NH, R.sup.1 is an aliphatic or cycloaliphatic hydrocarbon radical, R.sup.2 is C or an aliphatic hydrocarbon group, R.sup.3 is H or CH.sub.3, where x is 3 when R.sup.2 is a hydrocarbon group and x is 4 when R.sup.2 is C; the curing agents form ambient curing fluorocarbon polymer coating compositions;These compositions are used to provide corrosion and abrasion resistant coatings for large structures in chemical plants, oil refineries, oil drilling platforms, and the interior of smoke stacks of large utility companies.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: July 23, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph A. Vasta
  • Patent number: 4473491
    Abstract: Alkanolamine salts of amide acids having the formula: ##STR1## in which the circle represents a single nucleous aromatic ring or a monocyclic or bicyclic aliphatic ring system in each case with 5 or 6 carbon atoms per ring in which R.sup.1 represents an isoalkyl radical with the longest chain of 6 to 8 carbon atoms and a total of 8 to 12 carbon atoms; R.sup.2 represents a radical alkylene-X wherein the alkylene chain is a branched or straight chain and contains 1 to 4 carbon atoms; X represents OR.sup.3, O(C.sub.2 H.sub.4 O).sub.n -R.sup.3, O(C.sub.3 H.sub.6 O).sub.n -R.sup.3, NR.sup.3 R.sup.3, CN, CONH.sub.2, and COOR.sup.3 ; R.sup.3 represents hydrogen or C.sub.1 to C.sub.4 alkyl; n is an integer of 1 to 4; and wherein the carboxyl and carbonamide groups in said formula are bonded to non-olefinic carbon atoms and arranged in adjacent positions. The use of these salts as corrosion inhibitors in aqueous systems is also disclosed.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: September 25, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Trautmann, Elmar Getto
  • Patent number: 4458091
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: July 3, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4438136
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by a grouping --C(R).dbd.N--NHCO--(NH).sub.a --R' in which R is hydrogen, an aliphatic hydrocarbon residue, an aromatic residue or an aliphatic hydrocarbon residue substituted by an aromatic residue, a is 0 or 1 and R' is an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: March 20, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4436934
    Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: March 13, 1984
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4430345
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 7, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4424376
    Abstract: A method is provided for preparing intermediates for use in prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate ##STR1## and subjecting same to a Witting reaction to form the difluoro dihydroxy prostacyclin intermediate ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: January 3, 1984
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger
  • Patent number: 4368332
    Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.
    Type: Grant
    Filed: September 3, 1980
    Date of Patent: January 11, 1983
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4352939
    Abstract: The invention relates to diacids resulting from tetrahydrophthalic acid (chlorendic acid).The diacids correspond to the formula ##STR1## in which R represents the radical ##STR2## or the radical ##STR3## They are prepared using an excess of chlorendic acid. They can be used as fireproofing additives for polymeric materials or as prepolymers for polycondensation reactions.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: October 5, 1982
    Assignee: Solvay & Cie. (Societe Anonyme)
    Inventor: Andre Paucot
  • Patent number: 4351949
    Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: September 28, 1982
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4350823
    Abstract: Described are compounds defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; and one of R.sub.1 and R.sub.2 is methyl and the other of R.sub.1 and R.sub.2 is hydrogen. In addition, organoleptic uses of such compounds are disclosed for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, chewing tobaccos, medicinal products, toothpastes, perfumes, perfumed articles (such as liquid or solid, anionic, cationic, nonionic or zwitterionic detergents), fabric softeners and dryer-added fabric softener articles.
    Type: Grant
    Filed: July 16, 1981
    Date of Patent: September 21, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Joaquin F. Vinals, Frederick L. Schmitt, Edward J. Granda
  • Patent number: 4336400
    Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-alpha-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: June 22, 1982
    Assignee: Sterling Drug Inc.
    Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway
  • Patent number: 4319036
    Abstract: Described are compounds having the generic structure: ##STR1## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond and each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents hydrogen or methyl with the proviso that one of R.sub.2 and R.sub.1 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen and R.sub.3 and R.sub.4 are not both methyl; and wherein R.sub.5 represents C.sub.1 -C.sub.4 alkyl are disclosed. In addition organoleptic uses of such compounds are disclosed for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, chewing tobaccos, medicinal products, toothpastes, perfumes, perfumed articles (such as liquid or solid anionic, cationic, nonionic or zwitterionic detergents) fabric softeners, dryer added fabric softener articles, and smoking tobaccos. Also disclosed is a process for preparing such compounds according to the reaction scheme: ##STR2## wherein R' represents C.sub.1 -C.sub.
    Type: Grant
    Filed: March 25, 1980
    Date of Patent: March 9, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Frederick L. Schmitt, Edward J. Granda
  • Patent number: 4312888
    Abstract: Described is a process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum comprising the step of adding to a foodstuff or chewing gum an aroma augmenting or enhancing quantity of a product comprising a major proportion of compounds defined according to the structure: ##STR1## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond and each of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 represents hydrogen or methyl with the proviso that one of R.sub.1, R.sub.2, R.sub.6 and R.sub.7 is methyl and each of the other of R.sub.1, R.sub.2, R.sub.6 and R.sub.7 is hydrogen and R.sub.3 and R.sub.4 are not both methyl; wherein R.sub.5 represents C.sub.1 -C.sub.
    Type: Grant
    Filed: November 13, 1980
    Date of Patent: January 26, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Joaquin F. Vinals, Frederick L. Schmitt, Edward J. Granda
  • Patent number: 4311644
    Abstract: A method is provided for preparing intermediates for use in 10,10-difluoro prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate ##STR1## and subjecting same to a Wittig reaction to form the difluoro dihydroxy prostacyclin intermediate ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: January 19, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jerome L. Moniot, Rita T. Fox, Peter W. Sprague, Martin F. Haslanger
  • Patent number: 4310681
    Abstract: Described are compounds having the generic structure: ##STR1## wherein each of the lines ++++ and the wavy line represent single or carbon-carbon double bonds; wherein each of R.sub.2, R.sub.3 and R.sub.4 represents hydrogen or methyl and R.sub.1 ' represents hydrogen, methyl or methylene; wherein R.sub.5 represents C.sub.1 -C.sub.4 alkyl; with the proviso that when R.sub.2 is CH.sub.3, R.sub.1 ' is hydrogen and ++++ represents a single bond and the wavy line represents a carbon-carbon single bond or a carbon-carbon double bond; and with the further proviso that when R.sub.2 is hydrogen, R.sub.1 ' is methyl and ++++ represents a carbon-carbon single bond and the wavy line represents a carbon-carbon double bond or a carbon-carbon single bond or R.sub.1 ' is methylene (CH.sub.2) and ++++ is a carbon-carbon double bond and the wavy line is a carbon-carbon single bond are disclosed.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: January 12, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, James M. Sanders, Manfred H. Vock, Joaquin F. Vinals, Frederick L. Schmitt, Edward J. Granda
  • Patent number: 4267111
    Abstract: This invention concerns processes for preparing .beta.-santalol, .beta.-santalene, dihydro-.beta.-santalol, tetrahydro-.beta.-santalol and related compounds from camphene. The invention further concerns novel compounds useful as intermediates in these processes and as fragrance adjuncts.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: May 12, 1981
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Philip A. Christenson, Derek H. R. Barton
  • Patent number: 4266075
    Abstract: Bicyclic aldehyde derivatives of formula ##STR1## containing a single or a double bond in the position indicated by the dotted lines and wherein symbol R.sup.1 represents a hydrogen atom or a methyl radical and R.sup.2 defines a linear or branched alkyl radical containing 1 to 6 carbon atoms.Compounds (I) find specific utility as perfuming and flavoring agents.Process for the preparation of said compounds (I) starting from cyclopentadiene or a methyl substituted cyclopentadiene and an alkyl 4-oxo-butenoate.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: May 5, 1981
    Assignee: Firmenich, S.A.
    Inventors: Ferdinand Naf, Rene Decorzant
  • Patent number: 4245109
    Abstract: The compound 5[4(acyloxy or protected hydroxy-3-oxo-2,6,6-trimethyl-cyclohex-1-en-1-yl)-3-methyl-penta-1,4-dien- 3-ol], an intermediate for the coloring agent astaxanthin, its conversion to astaxanthin and its preparation from 4-oxo-.beta.-ionone including intermediates in this synthesis.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: January 13, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans J. Mayer, Robert K. Muller
  • Patent number: 4224253
    Abstract: Novel 2-methylene-3-methyl-3-(1',3'-pentadien-1'-yl)-bicyclo-[2,2,1]-heptanes substituted in the 4'-position by methyl, alkoxycarbonyl, formyl, hydroxymethyl or cyano are obtained by reacting the novel aldehyde 2-methylene-3-methyl-3-formyl-bicyclo-[2,2,1]-heptane with 3-methyl-, 3-alkoxycarbonyl- or acetalized 3-formyl-2-butene-1-triarylphosphorylidene under the conditions of a Wittig reaction, with or without hydrolytic cleavage of the acetal group, or hydrolytic cleavage of the acetal group followed by reduction of the formyl group to the hydroxymethyl group, or hydrolytic cleavage of the acetal group, reaction of the aldehyde with a hydroxylammonium salt, and dehydration of the resulting oxime.The novel compounds are distinguished by interesting scent characteristics.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: September 23, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Baumann, Werner Hoffmann
  • Patent number: 4218347
    Abstract: Bicyclic aldehyde derivatives of formula ##STR1## containing a single or a double bond in the position indicated by the dotted lines and wherein symbol R.sup.1 represents a hydrogen atom or a methyl radical and R.sup.2 defines a linear or branched alkyl radical containing 1 to 6 carbon atoms.Compounds (I) find specific utility as perfuming and flavoring agents.Process for the preparation of said compounds (I) starting from cyclopentadiene or a methyl substituted cyclopentadiene and an alkyl 4-oxo-butenoate.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: August 19, 1980
    Assignee: Firmenich SA
    Inventors: Ferdinand Naf, Rene Decorzant