Ortho Fused Patents (Class 560/119)
  • Patent number: 4533749
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: August 6, 1985
    Assignee: The Upjohn Company
    Inventors: Paul A. Aristoff, John C. Sih
  • 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: 4525586
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: June 25, 1985
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4517202
    Abstract: Prostaglandin analogues of the general formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group, Y.sup.1 represents a carbonyl or hydroxymethylene group, represents a single or double bond, A.sup.1 represents an alkylene linkage containing 2 or 3 carbon atoms and optionally bearing a methyl or ethyl substituent, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen atom or else R.sup.2 and R.sup.3 form an alkylene linkage containing 2 or 3 carbon atoms, optionally bearing a methyl or ethyl substituent, such that the symbols A.sup.1, R.sup.2 and R.sup.3, together with the carbon atoms through which they are connected, form a cycloalkyl ring of 6, 7 or 8 carbon atoms, optionally bearing one or two methyl or ethyl substituents, X.sup.1 represents an ethylene or trans-vinylene group, Y.sup.2 represents a carbonyl or hydroxymethylene group, and either (i) A.sup.
    Type: Grant
    Filed: May 26, 1983
    Date of Patent: May 14, 1985
    Assignee: May & Baker Limited
    Inventors: Clive W. Bird, Helene I. Butler, Michael P. L. Caton, Edward C. J. Coffee, Geoffrey Darnbrough, Terance W. Hart
  • Patent number: 4505905
    Abstract: Certain 7-oxobicyclo[3.2.0] hept-2-en-2-carboxylic acids, esters, and salts thereof useful as antibacterial agents or as intermediates for antibacterial agents, and methods for making and using them.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: March 19, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: George A. Boswell, Jr., Anthony J. Cocuzza
  • Patent number: 4503072
    Abstract: Compounds of general structural formula: ##STR1## wherein Q is: ##STR2## or pharmaceutically acceptable salts, C.sub.1-3 alkyl esters or .alpha.-monoglyceride when Q is a dihydroxy acid are useful as antihypercholesterolemic agents for the treatment of atherosclerosis, familial hypercholesterolemia, hyperlipemia and like diseases. They also have useful antifungal activity.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: March 5, 1985
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta-Jyh Lee, Robert L. Smith, Alvin K. Willard
  • Patent number: 4499307
    Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: February 12, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
  • Patent number: 4496745
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or a hydroxy-protecting group:R.sup.3 represents an alkyl group having from 1 to 12 carbon atoms which is optionally substituted, an alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms or a cycloalkyl group which is optionally substituted; andX represents an ethylene group, a trans-vinylene group or an ethynylene group) and salts and esters thereof are useful intermediates in the conversion of 5Z-carbacyclin derivatives to their 5E-isomers and in the preparation of certain other carbacyclin compounds.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: January 29, 1985
    Assignee: Sankyo Company, Limited
    Inventors: Shigeo Amemiya, Koichi Kojima
  • Patent number: 4493846
    Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R.sup.a and R.sup.b are each as defined above), Y is an ethylene group or a vinylene group, R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sub.1 and R.sub.2, when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: January 15, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
  • Patent number: 4490555
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: December 25, 1984
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4487960
    Abstract: Novel compounds of the following formula: ##STR1##
    Type: Grant
    Filed: April 19, 1982
    Date of Patent: December 11, 1984
    Assignee: The Upjohn Company
    Inventor: Chiu-Hong Lin
  • Patent number: 4487961
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: December 11, 1984
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4479966
    Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein the symbol between the carbon atoms in positions 5 and 6 represents a single or double bond, Y represents ethylene or trans-vinylene, R.sup.1 represents hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 12 carbon atoms, cycloalkyl of 4 to 7 carbon atoms optionally substituted by alkyl of 1 to 4 carbon atoms, phenyl optionally substituted by chlorine, trifluoromethyl, alkyl of 1 to 4 carbon atoms or phenyl, a --C.sub.m H.sub.2m COOR.sup.7 group (wherein m represents an integer of from 1 to 12 and R.sup.7 represents alkyl of 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.8 group (wherein n represents an integer of from 2 to 12 and R.sup.8 represents hydrogen or alkyl of 1 to 4 carbon atoms) or a ##STR2## group (wherein R.sup.9 and R.sup.10 each represent alkyl of 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents hydrogen or a hydroxy-protecting group, R.sup.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: October 30, 1984
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
  • Patent number: 4466980
    Abstract: A novel compound selected from the group consisting of 7-(or 6- or 4-)thiaprostaglandin E.sub.1 derivatives of the formula (I). ##STR1## wherein A represents --CH.sub.2 -- or ##STR2## in which n is 0, 1 or 2, provided that only one A cut of three is ##STR3## R.sup.1 -R.sup.7 and G are as defined in the specification, the 15-epimers of said thiaprostaglandin E.sub.1 derivatives, the enatiomers of said thiaprostaglandin E.sub.1 derivatives or their 15-epimers, and mixtures of these compounds.A 7-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by subjecting an .alpha.,.beta.-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: August 21, 1984
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Takeshi Toru, Takeo Oba, Noriaki Okamura, Kenzo Watanabe, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi, Fukuyoshi Kamimoto, Akira Ohtsu
  • Patent number: 4450171
    Abstract: 6(R)-[2-(8'-acyloxy-2'-methyl-6'-methyl (or hydrogen)-polyhydronaphthyl-1')-ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H- pyran-2-ones are prepared by acylation of the corresponding 8'-hydroxy compounds. The products are strong inhibitors of the biosynthesis of cholesterol.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: May 22, 1984
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Robert L. Smith, Alvin K. Willard
  • Patent number: 4447626
    Abstract: A compound of formula (I): ##STR1## (called 6-methoxy-IsoML-236B lactone) and its corresponding free hydroxy-carboxylic acid and salts and esters of said acid may be prepared by the enzymatic alkoxylation of an ML-236B compound, preferably using a microorganism of the genus Syncephalastrum, Absidia or Cunninghamella, e.g. Absidia coerulea, or a cell-free enzyme-containing extract from said microorganism. If desired, the lactone or carboxylic acid may be converted by conventional salification or esterification techniques to the desired salt or ester. These compounds have the ability to inhibit the biosynthesis of cholesterol and are thus of value in the treatment of hypercholesteraemia, for which purpose they may be formulated as compositions in admixture with conventional pharmaceutical carriers or diluents.
    Type: Grant
    Filed: July 7, 1982
    Date of Patent: May 8, 1984
    Assignee: Sankyo Company Limited
    Inventors: Akira Terahara, Minoru Tanaka
  • Patent number: 4444784
    Abstract: 6(R)-[2-(8'-acyloxy-2'-methyl-6'-methyl (or hydrogen)-polyhydronaphthyl-1')-ethyl]-4 (R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones are prepared by acylation of the corresponding 8'-hydroxy compounds. The products are strong inhibitors of the biosynthesis of cholesterol.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: April 24, 1984
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Robert L. Smith, Alvin K. Willard
  • Patent number: 4439614
    Abstract: 5,6-Methano-5,6-dihydroretinoids such as ethyl (E)-5,6-methano-5,6-dihydroretinoate and (E)-1-(4-carbethoxyphenyl)-2-methyl-4-(2,2,6-trimethylbicyclo[4.1.0]hept-1 -yl)-1,3-butadiene are disclosed. These componds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: March 27, 1984
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
  • Patent number: 4438268
    Abstract: This invention relates to new nematic liquid crystal substances for electro-optical components.The object of this invention is to create substances for electro-optical components combining chemical and thermal stability with low melting and high clear points at low operational voltage, as well as to processes for their production.It has been found that new liquid-crystal trans-6-n-alkyl-decalin-2-carbonic acid ester of the general formula ##STR1## can be introduced into electro-optical components. These substances are produced by the catalytic high-pressure hydrogenation of 6-n-alkylnaphthalene-2-carbonic acids, separation of the trans-isomers by distillation, and esterification with the corresponding hydroxy compounds of the acyl chlorides obtained through reaction with thionyl chloride.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: March 20, 1984
    Inventors: Horst Zaschke, Wolfgang Schafer, Hans-Joachim Deutscher, Dietrich Demus, Gerhard Pelzl
  • Patent number: 4438277
    Abstract: Compounds of formula (I): ##STR1## (in which: Z represents a group of formula ##STR2## A represents a group of formula ##STR3## B represents a group of formula ##STR4## R.sup.1 represents a hydrogen atom or a methyl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are the same or different and each represents a hydrogen atom or an acyl group;R.sup.5 represents a carboxy group;R.sup.7 represents a hydrogen atom, an alkyl group or an acyl group;X represents a halogen atom; andthe bond represents a double bond)and salts and esters of the carboxy group represented by R.sup.5 have useful anti-hypercholesteraemic activity and may be prepared from certain natural products obtainable by cultivation of microorganisms of the genera Penicillium or Monascus.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: March 20, 1984
    Assignee: Sankyo Company, Limited
    Inventors: Akira Terahara, Kiyoshi Hamano, Yoshio Tsujita, Minoru Tanaka
  • 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: 4435593
    Abstract: Disclosed are adducts of 1-cyclohexene-1,2-dicarboxylic anhydride with olefins and preparation thereof by reacting an olefinically unsaturated compound and 1-cyclohexene-1,2-dicarboxylic anhydride using actinic radiation as an energy source at a temperature of from -30.degree. C. to 150.degree. C., preferably at from about 25.degree. C. to 100.degree. C. Derivatives of these compounds are useful as rust inhibitors in gasoline.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: March 6, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: Fields: Ellis K., Tayseer S. Nimry
  • Patent number: 4432996
    Abstract: Substances isolated after cultivation of a micoorganism belonging to the genus Penicillium in a culture medium comprises compounds which have strucures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesterolemic and hypolipemic medicaments.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: February 21, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Vincent P. Gullo, Tony Y. K. Lam, Richard L. Monaghan
  • Patent number: 4423068
    Abstract: Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) ##STR1## as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein:n is an integer from one to four;R.sub.1 is hydroxy;R.sub.2 is hydrogen; orR.sub.1 and R.sub.2 together are an oxo group;R.sub.3 is ##STR2## wherein A is --CH.sub.2 --CH.sub.2 --; trans-CH.dbd.CH--; --C.tbd.C--; andR.sub.4 is linear or branched alkyl of one to twelve carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or optionally substituted phenylalkyl.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: December 27, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Tsung-tee Li, Michael Marx
  • Patent number: 4423067
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: December 27, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4420491
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise compounds which have structures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.
    Type: Grant
    Filed: May 28, 1981
    Date of Patent: December 13, 1983
    Assignee: Merck & Co., Inc.
    Inventors: George Albers-Schonberg, Henry Joshua, Maria B. Lopez
  • Patent number: 4420632
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 13, 1983
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4391731
    Abstract: Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: July 5, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger
  • Patent number: 4387242
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium include a compound with structural formula: ##STR1## Together with the corresponding free acid of the above ester, its salts and lactone, compound I is a member of a class of hypocholesterolemic and hypolipemic medicaments.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: June 7, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Tony Y. K. Lam
  • Patent number: 4376863
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium include a compound with structural formula: ##STR1## compound I is a member of a class of hypocholesterolemic and hypolipemic medicaments.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: March 15, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Tony Y. K. Lam
  • Patent number: 4375433
    Abstract: Disclosed is a process for preparing the antibiotic 6-hydroxymethyl-2-(.beta.-aminoethylthio)-1-carbadethiapen-2-em-3-carboxyl ic acid (I) ##STR1## and its pharmaceutically acceptable salt and ester derivatives. An intermediate for the production of these compounds are compounds of the formula ##STR2## wherein R.sup.5 and R are readily removable protecting groups.
    Type: Grant
    Filed: September 12, 1980
    Date of Patent: March 1, 1983
    Assignee: Merck & Co., Inc.
    Inventors: David G. Melillo, Kenneth M. Ryan
  • Patent number: 4371701
    Abstract: Disclosed are adducts of 1-cyclohexene-1,2-dicarboxylic anhydride with olefins and preparation thereof by reacting an olefinically unsaturated compound and 1-cyclohexene-1,2-dicarboxylic anhydride using actinic radiation as an energy source at a temperature of from -30.degree. C. to 150.degree. C., preferably at from about 25.degree. C. to 100.degree. C. Derivatives of these compounds are useful as rust inhibitors in gasoline.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: February 1, 1983
    Assignee: Standard Oil Company (Indiana)
    Inventors: Ellis K. Fields, Tayseer S. Nimry
  • Patent number: 4361515
    Abstract: Compounds of formula (I): ##STR1## (in which: Z represents a group of formula ##STR2## A represents a group of formula ##STR3## B represents a group of formula ##STR4## R.sup.1 represents a hydrogen atom or a methyl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are the same or different and each represents a hydrogen atom or an acyl group;R.sup.5 represents a carboxy group;R.sup.7 represents a hydrogen atom, an alkyl group or an acyl group;X represents a halogen atom; andthe bond represents a double bond)and salts and esters of the carboxy group represented byR.sup.5 and compounds of formula (II): ##STR5## (in which R.sup.1, is as defined above and R.sup.2 represents an .alpha.-methylbutyryl group; and R.sup.4 represents a hydrogen atom) have useful anti-hypercholesteraemic activity and may be prepared from certain natural products obtainable by cultivation of microorganisms of the genera Penicillium or Monascus.
    Type: Grant
    Filed: April 21, 1981
    Date of Patent: November 30, 1982
    Assignee: Sankyo Company, Limited
    Inventors: Akira Terahara, Kiyoshi Hamano, Yoshio Tsujita, Minoru Tanaka
  • Patent number: 4359581
    Abstract: A process for preparing a 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester of the formula ##STR1## wherein R.sub.1 is alkyl of 1-6 carbon atoms or phenalkyl of 7-10 carbon atoms andR.sub.2 is hydrogen, alkyl or 1-6 carbon atoms, phenalkyl of 7-10 carbon atoms, tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, tri-C.sub.1-4 -alkylsilyl, wherein the alkyl moieties can optionally be substituted by phenyl, or ##STR2## wherein R.sub.3 is alkyl of 1-6 carbon atoms or aryl of 6-12 carbon atoms, comprises oxidizing the corresponding 7-hydroxy-2-oxabicyclo [3,3,0]octan-3-ylideneacetic acid ester of the formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, to form the corresponding ketone, reacting the latter with a base which opens the ether oxygen containing ring, and then reducing the resultant product to prepare the 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: November 16, 1982
    Assignee: Schering AG
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen
  • Patent number: 4358605
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16- substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion, and particularly, alkyl esters, such as the methyl ester, of such acids.
    Type: Grant
    Filed: May 8, 1980
    Date of Patent: November 9, 1982
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • Patent number: 4346227
    Abstract: Compounds of formula (I): ##STR1## (wherein R represents a group of formula ##STR2## and the corresponding ring-closed lactones, salts (especially alkali metal salts) and esters (especially C.sub.1 -C.sub.5 alkyl esters) thereof may be prepared by subjecting ML-236B, or ML-236B carboxylic acid or a salt or ester thereof to enzymatic hydroxylation, which may be effected by means of microorganisms of the genera Mucor, Rhizopus, Zygorynchus, Circinella, Actinomucor, Gongronella, Phycomyces, Martierella, Pycnoporus, Rhizoctonia, Absidia, Cunninghamella, Syncephalastrum and Streptomyces, or cell-free, enzyme-containing extracts from said microorganisms. The compounds are capable of inhibiting biosynthesis of cholesterol and are thus useful in the treatment of hypercholesteraemia.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: August 24, 1982
    Assignee: Sankyo Company, Limited
    Inventors: Akira Terahara, Minoru Tanaka
  • Patent number: 4342767
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise compounds which have structures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: August 3, 1982
    Assignee: Merck & Co., Inc.
    Inventors: George Albers-Schonberg, Richard L. Monaghan, Alfred W. Alberts, Carl H. Hoffman
  • Patent number: 4340498
    Abstract: New halogenated ester derivatives and liquid crystal compositions containing the same are provided. The derivatives are expressed by the general formula ##STR1## wherein X is ##STR2## R is 1-15C alkyl group or alkoxy group; and Y is carboxyl group. The derivatives are useful as component(s) of liquid crystal compositions which have higher mesomorphic temperature ranges, nevertheless have lower viscosities; and also have lower absolute values of dielectric anisotropy, nevertheless can be driven at lower voltages.
    Type: Grant
    Filed: January 23, 1981
    Date of Patent: July 20, 1982
    Assignee: Chisso Corporation
    Inventor: Shigeru Sugimori
  • Patent number: 4338457
    Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: July 6, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4322435
    Abstract: Prostacyclin derivatives of formula (I): ##STR1## (wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an alkenyl group having from 8 to 12 carbon atoms; and n represents an integer of from 1 to 8, inclusive) and pharmaceutically acceptable salts thereof, are valuable pharmaceuticals, showing excellent thrombocyte agglutination inhibitory, coronary blood vessel dilatory and bronchodilatory effects, and may be prepared by introducing the .dbd.CH(CH.sub.2).sub.n COOR.sup.1 side chain onto an appropriate compound by means of a Wittig reaction.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: March 30, 1982
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Kiyoshi Sakai, Shinsaku Kobayashi
  • Patent number: 4319039
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise compounds which have structures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.
    Type: Grant
    Filed: August 11, 1980
    Date of Patent: March 9, 1982
    Assignee: Merck & Co., Inc.
    Inventor: George Albers-Schonberg
  • Patent number: 4307112
    Abstract: 9-deoxy-9A-methylene-isosteres of PGI.sub.2, including processes for their preparation and pharmaceutical and veterinary compositions containing same, are disclosed. The compounds are useful as therapeutic agents, for example as anti-aggregating agents, disaggregating agents, and as vasodilators.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: December 22, 1981
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Carlo Passarotti, William Fava, Angelo Fumagalli, Franco Faustini, Roberto Ceserani
  • Patent number: 4297504
    Abstract: The present invention provides novel 19-hydroxy-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.CROSS REFERENCE TO RELATED APPLICATIONThe present invention is a divisional application of U.S. Ser. No. 054,811, filed July 5, 1979, now U.S. Pat. No. 4,225,508.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: October 27, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259512
    Abstract: Preparation of 5,5-Dimethyl-8-carboalkoxybicyclo [4.3.0]non-1-(6)-ene-2,7-dione by condensing dimethylpyruvic acid and 5-ono-6-heptenoic acid to produce a dibasic acid. Esterification of the acid produces a diester which is cyclized to produce the compound.
    Type: Grant
    Filed: October 15, 1976
    Date of Patent: March 31, 1981
    Assignee: State Board of Higher Education for and on Behalf of the University of Oregon
    Inventor: Lloyd J. Dolby
  • Patent number: 4256905
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-6a-carba-PGI.sub.1 compounds which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: March 17, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4238414
    Abstract: The present invention relates to novel 2-decarboxy-2-aminomethyl-6a-carba-PGI.sub.2 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.
    Type: Grant
    Filed: September 27, 1979
    Date of Patent: December 9, 1980
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4236019
    Abstract: Acyl-substituted phenyl esters of prostacyclin-type compounds, for example the 4-acetylphenyl ester of prostacyclin (PGI.sub.2) illustrated by the formula ##STR1## and including esters of the isomeric 6-hydroxy-PGI.sub.1 and 6-keto-PGF.sub.1.alpha. compounds, said esters having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: June 14, 1979
    Date of Patent: November 25, 1980
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4223167
    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: February 14, 1978
    Date of Patent: September 16, 1980
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Philip A. Christenson, Derek H. R. Barton
  • Patent number: 4216172
    Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: August 5, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • Patent number: 4192891
    Abstract: Prostacyclin analogs are provided having the structure ##STR1## wherein X represents .dbd.O or OH, R.sub.1 and R.sub.2 are OH or H, provided at least one of R.sub.1 and R.sub.2 is other than hydroxyl, R.sub.3 is H or alkyl of 1 to 4 carbons, m is an integer of from 2 to 5, and n is an integer of from 2 to 10, or pharmaceutically acceptable salts thereof. These compounds have been found to be potent inhibitors of arachidonic acid-induced platelet aggregation and bronchoconstriction.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: March 11, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Martin F. Haslanger