Ortho Fused Patents (Class 560/119)
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Patent number: 4533749Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: August 6, 1985Assignee: The Upjohn CompanyInventors: Paul A. Aristoff, John C. Sih
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Patent number: 4531010Abstract: 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: GrantFiled: December 30, 1983Date of Patent: July 23, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph A. Vasta
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Patent number: 4525586Abstract: 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: GrantFiled: September 19, 1983Date of Patent: June 25, 1985Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4517202Abstract: 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: GrantFiled: May 26, 1983Date of Patent: May 14, 1985Assignee: May & Baker LimitedInventors: Clive W. Bird, Helene I. Butler, Michael P. L. Caton, Edward C. J. Coffee, Geoffrey Darnbrough, Terance W. Hart
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Patent number: 4505905Abstract: 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: GrantFiled: April 15, 1982Date of Patent: March 19, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: George A. Boswell, Jr., Anthony J. Cocuzza
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Patent number: 4503072Abstract: 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: GrantFiled: June 18, 1984Date of Patent: March 5, 1985Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Ta-Jyh Lee, Robert L. Smith, Alvin K. Willard
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Patent number: 4499307Abstract: 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: GrantFiled: February 23, 1984Date of Patent: February 12, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4496745Abstract: 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: GrantFiled: October 25, 1983Date of Patent: January 29, 1985Assignee: Sankyo Company, LimitedInventors: Shigeo Amemiya, Koichi Kojima
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Patent number: 4493846Abstract: 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: GrantFiled: March 13, 1981Date of Patent: January 15, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
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Patent number: 4490555Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 19, 1982Date of Patent: December 25, 1984Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4487960Abstract: Novel compounds of the following formula: ##STR1##Type: GrantFiled: April 19, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Chiu-Hong Lin
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Patent number: 4487961Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4479966Abstract: 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: GrantFiled: January 21, 1980Date of Patent: October 30, 1984Assignee: Ono Pharmaceutical Company, Ltd.Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
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Patent number: 4466980Abstract: 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: GrantFiled: October 30, 1981Date of Patent: August 21, 1984Assignee: Teijin LimitedInventors: Toshio Tanaka, Takeshi Toru, Takeo Oba, Noriaki Okamura, Kenzo Watanabe, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi, Fukuyoshi Kamimoto, Akira Ohtsu
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Patent number: 4450171Abstract: 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: GrantFiled: June 14, 1982Date of Patent: May 22, 1984Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Robert L. Smith, Alvin K. Willard
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Patent number: 4447626Abstract: 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: GrantFiled: July 7, 1982Date of Patent: May 8, 1984Assignee: Sankyo Company LimitedInventors: Akira Terahara, Minoru Tanaka
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Patent number: 4444784Abstract: 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: GrantFiled: December 18, 1980Date of Patent: April 24, 1984Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Robert L. Smith, Alvin K. Willard
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Patent number: 4439614Abstract: 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: GrantFiled: September 22, 1982Date of Patent: March 27, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
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Patent number: 4438268Abstract: 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: GrantFiled: September 14, 1981Date of Patent: March 20, 1984Inventors: Horst Zaschke, Wolfgang Schafer, Hans-Joachim Deutscher, Dietrich Demus, Gerhard Pelzl
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Patent number: 4438277Abstract: 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: GrantFiled: April 15, 1982Date of Patent: March 20, 1984Assignee: Sankyo Company, LimitedInventors: Akira Terahara, Kiyoshi Hamano, Yoshio Tsujita, Minoru Tanaka
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Patent number: 4436934Abstract: 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: GrantFiled: December 28, 1981Date of Patent: March 13, 1984Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4435593Abstract: 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: GrantFiled: September 30, 1982Date of Patent: March 6, 1984Assignee: Standard Oil Company (Indiana)Inventors: Fields: Ellis K., Tayseer S. Nimry
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Patent number: 4432996Abstract: 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: GrantFiled: May 17, 1982Date of Patent: February 21, 1984Assignee: Merck & Co., Inc.Inventors: Vincent P. Gullo, Tony Y. K. Lam, Richard L. Monaghan
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Patent number: 4423068Abstract: 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: GrantFiled: July 14, 1982Date of Patent: December 27, 1983Assignee: Syntex (U.S.A.) Inc.Inventors: Tsung-tee Li, Michael Marx
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Patent number: 4423067Abstract: 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: GrantFiled: December 21, 1981Date of Patent: December 27, 1983Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4420491Abstract: 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: GrantFiled: May 28, 1981Date of Patent: December 13, 1983Assignee: Merck & Co., Inc.Inventors: George Albers-Schonberg, Henry Joshua, Maria B. Lopez
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Patent number: 4420632Abstract: 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: GrantFiled: December 22, 1980Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4391731Abstract: 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: GrantFiled: August 3, 1981Date of Patent: July 5, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger
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Patent number: 4387242Abstract: 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: GrantFiled: August 21, 1981Date of Patent: June 7, 1983Assignee: Merck & Co., Inc.Inventor: Tony Y. K. Lam
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Patent number: 4376863Abstract: 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: GrantFiled: August 21, 1981Date of Patent: March 15, 1983Assignee: Merck & Co., Inc.Inventor: Tony Y. K. Lam
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Patent number: 4375433Abstract: 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: GrantFiled: September 12, 1980Date of Patent: March 1, 1983Assignee: Merck & Co., Inc.Inventors: David G. Melillo, Kenneth M. Ryan
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Patent number: 4371701Abstract: 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: GrantFiled: December 14, 1981Date of Patent: February 1, 1983Assignee: Standard Oil Company (Indiana)Inventors: Ellis K. Fields, Tayseer S. Nimry
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Patent number: 4361515Abstract: 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: GrantFiled: April 21, 1981Date of Patent: November 30, 1982Assignee: Sankyo Company, LimitedInventors: Akira Terahara, Kiyoshi Hamano, Yoshio Tsujita, Minoru Tanaka
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Patent number: 4359581Abstract: 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: GrantFiled: June 5, 1981Date of Patent: November 16, 1982Assignee: Schering AGInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen
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Patent number: 4358605Abstract: 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: GrantFiled: May 8, 1980Date of Patent: November 9, 1982Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
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Patent number: 4346227Abstract: 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: GrantFiled: June 5, 1981Date of Patent: August 24, 1982Assignee: Sankyo Company, LimitedInventors: Akira Terahara, Minoru Tanaka
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Patent number: 4342767Abstract: 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: GrantFiled: June 16, 1980Date of Patent: August 3, 1982Assignee: Merck & Co., Inc.Inventors: George Albers-Schonberg, Richard L. Monaghan, Alfred W. Alberts, Carl H. Hoffman
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Patent number: 4340498Abstract: 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: GrantFiled: January 23, 1981Date of Patent: July 20, 1982Assignee: Chisso CorporationInventor: Shigeru Sugimori
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Patent number: 4338457Abstract: 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: GrantFiled: February 28, 1980Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4322435Abstract: 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: GrantFiled: May 27, 1980Date of Patent: March 30, 1982Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Kiyoshi Sakai, Shinsaku Kobayashi
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Patent number: 4319039Abstract: 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: GrantFiled: August 11, 1980Date of Patent: March 9, 1982Assignee: Merck & Co., Inc.Inventor: George Albers-Schonberg
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Patent number: 4307112Abstract: 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: GrantFiled: February 26, 1980Date of Patent: December 22, 1981Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Carlo Passarotti, William Fava, Angelo Fumagalli, Franco Faustini, Roberto Ceserani
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Patent number: 4297504Abstract: 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: GrantFiled: March 3, 1980Date of Patent: October 27, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4259512Abstract: 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: GrantFiled: October 15, 1976Date of Patent: March 31, 1981Assignee: State Board of Higher Education for and on Behalf of the University of OregonInventor: Lloyd J. Dolby
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Patent number: 4256905Abstract: 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: GrantFiled: March 3, 1980Date of Patent: March 17, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4238414Abstract: 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: GrantFiled: September 27, 1979Date of Patent: December 9, 1980Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4236019Abstract: 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: GrantFiled: June 14, 1979Date of Patent: November 25, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4223167Abstract: 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: GrantFiled: February 14, 1978Date of Patent: September 16, 1980Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Philip A. Christenson, Derek H. R. Barton
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Patent number: 4216172Abstract: 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: GrantFiled: March 13, 1978Date of Patent: August 5, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4192891Abstract: 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: GrantFiled: April 25, 1979Date of Patent: March 11, 1980Assignee: E. R. Squibb & Sons, Inc.Inventor: Martin F. Haslanger