Carbocyclic Ring Having Silicon As Part Of One Substituent And The -coo- As Part Of Another Substituent Patents (Class 556/441)
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Patent number: 4703127Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4701282Abstract: This invention provides smoking compositions which contain a .beta.-hydroxy-.gamma.-ketoester compound as a flavorant-release additive.In one of its embodiments, this invention provides tobacco compositions which contain a flavorant-release additive such as dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate: ##STR1## Under cigarette smoking conditions the above illustrated .beta.-hydroxy-.gamma.-keto ester pyrolyzes into 2,3-butanedione and other products which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.Type: GrantFiled: August 30, 1985Date of Patent: October 20, 1987Assignee: Philip Morris IncorporatedInventors: W. Geoffrey Chan, Yoram Houminer
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Patent number: 4699989Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.Type: GrantFiled: February 11, 1985Date of Patent: October 13, 1987Assignee: Asahi Glass Company Ltd.Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
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Patent number: 4689426Abstract: Novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenone and process for production thereof. The novel 5-alkylidene-2-halo-4-substituted-2-cyclopentenones are represented by the following formula (I): ##STR1## wherein R.sub.a represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or a substituted or unsubstituted phenyl group, R.sub.b represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms, and X represents a halogen atom. The novel cyclopentenones possess excellent pharmaceutical activities including anti-tumor activity, antiviral activity and antimicrobial activity.Type: GrantFiled: July 5, 1984Date of Patent: August 25, 1987Assignee: Teijin LimitedInventors: Satoshi Sugiura, Toshio Tanaka, Seizi Kurozumi
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Patent number: 4681962Abstract: 7-fluoro-16-substituted 15-hydroxy PGI.sub.2 compounds which have saturated bond of the 13 position and which are useful as blood platelet anti-aggregating agents.Type: GrantFiled: September 8, 1986Date of Patent: July 21, 1987Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Hans Maag, Perry Rosen
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Patent number: 4680288Abstract: Sulfur-containing 6-ketoprostaglandins of the formula I ##STR1## in which D is a bond, alkylene having 1-3 C atoms, cis-alkenylene having 2-5 C atoms or alkinylene having 2-5 C atoms,R.sup.1 is H, alkyl having 1-4 C atoms, aryl having 6-12 C atoms or --C.sub.6 H.sub.4 NHCOC.sub.6 H.sub.5,R.sup.2 is alkyl having 1-7 C atoms, alkyl having 1-7 C atoms which is substituted by halogen, cycloalkyl having 5-6 C atoms, cycloalkyl having 5-6 C atoms which is substituted by alkyl having 1-4 C atoms, phenyl, phenyl which is substituted by F, Cl, Br, alkyl having 1-4 C atoms, OH, OCH.sub.3 or CF.sub.3, pyridyl, naphthyl, thienyl or, if D is alkylene having 1-3 C atoms, also is alkoxy having 1-4 C atoms, alkylthio having 1-4 C atoms, phenoxy or phenoxy which is substituted by F, Cl, Br, alkyl having 1-4 C atoms, OH, OCH.sub.3 or CF.sub.3,R.sup.3 and R.sup.Type: GrantFiled: January 18, 1985Date of Patent: July 14, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Klaus Irmscher, Hans-Eckart Radunz, Ernst Schulze, Bernhard Riefling
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Patent number: 4658044Abstract: Compounds of formula (C) ##STR1## where either R.sup.D represents a hydroxymethyl group and R.sup.E represents a hydroxyl group or R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.E represents a hydroxyl group and R.sup.D represents an ethenyl group and R.sup.F represents a hydroxyl or protected hydroxyl group or a leaving group with the proviso that either R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.F represents a protected hydroxyl group, which compounds are of use as intermediates in the preparation of compounds having antiviral activity.Type: GrantFiled: October 24, 1985Date of Patent: April 14, 1987Assignee: Glaxo Group LimitedInventor: Paul Ravenscroft
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Patent number: 4636573Abstract: Compounds of the formulae I and II ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 12 carbon atoms,R.sup.6 and R.sup.7 are independently alkyl having 1 to 30 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 12 carbon atoms;A is a direct bond, a methylene or an ethylene radical,B is an alkanediyl radical of 2 to 10 carbon atoms, the radical of formula --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 -- or of the formula III--CH.sub.2 CH.sub.2 --(O--CH.sub.2 CH.sub.2).sub.Type: GrantFiled: September 9, 1985Date of Patent: January 13, 1987Inventors: Stephen D. Pastor, John D. Spivack
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Patent number: 4618690Abstract: Optically pure (1S, 4R)-4-hydroxy-2-cyclopentyl ester of the formula ##STR1## in which Ac is an aliphatic acyl radical having 1 to 18 carbon atoms,is produced by contacting a meso such as porcine liver esterase. The products are useful in synthesizing cyclopentanoid products such as brefeldin A, sesquiterpenes and prostaglandins.Type: GrantFiled: May 15, 1985Date of Patent: October 21, 1986Assignee: Bayer AktiengesellschaftInventors: Manfred Schneider, Kurt Laumen
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Patent number: 4600785Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is a .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.Type: GrantFiled: December 22, 1983Date of Patent: July 15, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
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Patent number: 4588823Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: September 27, 1984Date of Patent: May 13, 1986Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4588715Abstract: Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are alkyl or aryl groups, A, B, C and D are non-reactive substituents or two are joined to form an additional ring, and Z is either of the formula Z': ##STR2## wherein R.sup.4 is H, lower alkyl or a cation; or a -6-oxotetrahydropyran-2-yl ring of the formula Z": ##STR3## e.g. 4-hydroxy-6-{2-[2-(methyldiphenylsilyl)phenyl]ethenyl]ethyenyl}-tetrahydro -2H-pyran-2-one, (trans, trans). The compounds inhibit cholesterol biosynthesis and are useful as anti-atherosclerotic agents.Type: GrantFiled: June 4, 1984Date of Patent: May 13, 1986Assignee: Sandoz, Inc.Inventor: Robert E. Damon, II
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Patent number: 4585886Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: September 27, 1984Date of Patent: April 29, 1986Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4539420Abstract: A manufacturing method is described for the preparation of optically active 1-aromatic-group-substituted-1-alkanones characterized in that an optically active alkane acid halide is allowed to react with an aromatic compound in the presence of a Lewis acid. The optically active 1-aromatic-group-substituted-1-alkanones are useful intermediates in the preparation of optically active alpha-arylalkanoic acids, which are useful as pharmaceutical, e.g. anti-inflammatory, analgesic and anti-pyretic, agents and as insecticidal agents.Type: GrantFiled: June 11, 1982Date of Patent: September 3, 1985Assignee: Syntex Pharmaceuticals International LimitedInventors: Gen-Ichi Tsuchihashi, Shuichi Mitamura, Koji Kitajima
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Patent number: 4489092Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C-- or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CH or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: September 1, 1982Date of Patent: December 18, 1984Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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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: 4479945Abstract: New inter-m-phenylene-PGI.sub.2 derivatives are prepared of the general formula I ##STR1## wherein R.sup.1 stands for hydrogen, alkyl containing 1 to 4 carbon atoms or a pharmaceutically acceptable primary, secondary, tertiary or quaternary ammonium cation or a metal cation,R.sup.2 and R.sup.3 stand independently on each other for hydrogen, alkanoly, aroyl or an acetal type or alkyl silyl type protecting group,R.sup.4 represents hydrogen or an alkyl group containing 1 to 4 carbon atoms,X stands for oxygen, or a--CH.sub.2 --group,Y stands for--C.tbd.C-- or a trans--CH.dbd.CW group, wherein W stands for chlorine, bromine or fluorine,Z represents an alkyl group having 6 to 9 carbon atoms, optionally substituted by one or more alkyl groups containing 1 to 4 carbon atoms or fluorine or it stands for an optionally substituted arylmethyl or aryloxy methyl group.The new compounds are active ingredients of pharmaceutical compositions having antiaggregatory activity.Type: GrantFiled: November 29, 1982Date of Patent: October 30, 1984Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.Inventors: Istv/a/ n Sz/e/ kely, S/a ndor Bot/a r, Marianna G. Lov/a/ sz, Krisztina K. Dolgos, G/a/ bor Kov/a/ cs, S/a/ ndor Vir/a/ g, Tam/a/ s Sz/u/ ts, Istv/a n R/a/ k/o/ czi, K/a/ roly Tihanyi, P/e/ ter K/o/ rm/o/ czy, P/a/ l Hadh/a/ zy, Istv/a n Stadler, Gy/o/ rgy Blask/o/, B/e/ la K/o/ szegi
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Patent number: 4474979Abstract: A conjugate addition reaction and novel intermediate compounds are disclosed, whereby the reaction of ##STR1## with a lithio-cuprate reagent ##STR2## produces compounds of the class: ##STR3## A new process is disclosed for preparing 1-(methyl)-16,16-(dimethyl)-11-alpha-15-alpha-dihydroxy-9-oxo-2,13,trans,t rans-prostadienoate, and congeners thereof, including racemic mixtures.Type: GrantFiled: September 27, 1982Date of Patent: October 2, 1984Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4439365Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives useful as bronchodilators, anti-ulcer agents, or as intermediates.Type: GrantFiled: July 18, 1979Date of Patent: March 27, 1984Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, John F. Poletto, Robert E. Schaub, Karel F. Bernady
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Patent number: 4414407Abstract: 16-Fluoro-13,14-dehydro-PG.sub.2 series have been prepared, and their pharmaceutical use.Type: GrantFiled: December 7, 1981Date of Patent: November 8, 1983Assignee: Farmitalia Carlo ErbaInventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4367340Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sub.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight-or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y is R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: March 4, 1981Date of Patent: January 4, 1983Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4360688Abstract: Novel compounds are disclosed of the classes: ##STR1## wherein the subscript n is an integer from 3-5, inclusive, R.sub.1 is hydrogen or R.sub.2 ; R.sub.2 and R.sub.3 consist essentially of C.sub.1 -C.sub.6 alkyl and R.sub.2 may be the same as or different from R.sub.3, and wherein Aryl consists essentially of phenyl and phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, and trifluoromethyl;(b) derivatives of furan having the formula ##STR2## wherein R.sub.4 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, and W is either carbonyl or carbinol; and(c) cyclopentenonyl compounds having the formulas ##STR3## wherein R.sub.5 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, P.sub.1 is hydrogen or a protective group, Y is either ##STR4## A new process is disclosed for preparing 1-(methyl)-16,16-(dimethyl)-11-alpha-15-alpha-dihydroxy-9-oxo-2,13,trans, trans-prostadienoate, and congeners thereof, including racemic mixtures.Type: GrantFiled: May 21, 1981Date of Patent: November 23, 1982Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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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: 4359467Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans- ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: April 22, 1981Date of Patent: November 16, 1982Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4351846Abstract: Prostaglandin analogues of the formula: ##STR1## [wherein R.sup.1 represents hydrogen or alkyl of 1 to 12 carbon atoms, R.sup.2 represents a single bond or alkylene of from 1 to 5 carbon atoms, R.sup.3 represents hydrogen, alkyl or alkoxy of 1 to 8 carbon atoms, cycloalkyl or cycloalkyloxy of 4 to 7 carbon atoms unsubstituted or substituted by alkyl of 1 to 8 carbon atoms, or phenyl or phenoxy unsubstituted or substituted by halogen, trifluoromethyl or alkyl of 1 to 4 carbon atoms, one of R.sup.4 and R.sup.5 represents hydrogen and the other represents hydroxy or R.sup.4 and R.sup.5 together represent oxo, R.sup.6 represents hydrogen or a hydroxy-protecting group which may be removed under acidic conditions, the double bond between the carbon atoms in positions 13 and 14 is trans, the wavy line attached to the carbon atom in position 15 represents .alpha.- or .beta.- configuration or a mixture thereof and, when one of R.sup.4 and R.sup.Type: GrantFiled: May 8, 1981Date of Patent: September 28, 1982Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga
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Patent number: 4315032Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.Type: GrantFiled: May 14, 1980Date of Patent: February 9, 1982Assignee: Teitin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
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Patent number: 4310465Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4306050Abstract: A method for the manufacture of organopolysiloxanes for use in abhesive coating materials wherein organopolysiloxanes having the formula ##STR1## in which R.sup.1 is an alkyl group with 1 to 4 carbon atoms, a vinyl group and/or a phenyl group, with the proviso that at least 90 mole percent of the R.sup.1 groups are methyl groups,a has a value 1.8 to 2.2, andb has a value of 0.004 to 0.5,are reacted with at least equimolar amounts of pentaerythritol triacrylate or pentaerythritol trimethacrylate and separating the product from the solid components suspended therein. The organopolysiloxanes can be rapidly cured and simultaneously fixed on the carrier.Type: GrantFiled: January 30, 1980Date of Patent: December 15, 1981Assignee: Th. Goldschmidt AGInventors: Gotz Koerner, Vaclav Kropac, Christian Weitemeyer
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Patent number: 4291168Abstract: Indanyloxy compounds having 2-alkynyl substituents which exhibit diuretic, saluretic, and uricosuric activity are described. The compounds are obtained according to a process involving selective etherification of a 5-hydroxyindanone followed by alkynylation with a silylated alkynyl bromide to provide novel silylated intermediates which are hydrolyzed to indanyloxy compounds such as (6,7-dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid.Type: GrantFiled: September 24, 1980Date of Patent: September 22, 1981Assignee: Mead Johnson & CompanyInventors: Porter C. Johnson, William L. Matier
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Patent number: 4284646Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C--or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: August 24, 1979Date of Patent: August 18, 1981Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4283505Abstract: The invention relates to a method for cross-linking radically cross-linkable polymers and for stabilizing such polymers against oxidative and/or thermal decomposition. The method is developed so that rapid and economical cross-linking of radically cross-linkable polymers is obtained in the presence of oxidation inhibitors without adverse effects on the cross-linking process due to the oxidation inhibitor. For this purpose, the invention provides that the cross-linking is carried out in the presence of oxidation inhibitors, wherein the inhibition-active --OH and/or --NH functions are at least partially substituted by protective silyl- and/or silylene groups, the inhibitor molecule containing at least one Si-alkenyl group. The method according to the invention is suitable for use with radical as well as radiation-cross-linkable polymer.Type: GrantFiled: May 18, 1979Date of Patent: August 11, 1981Assignee: Siemens AktiengesellschaftInventors: Wolfgang Kleeberg, Wolfgang Rogler, Wolfgang V. Gentzkow, Roland Rubner
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Patent number: 4263436Abstract: Novel organosilicon compounds and processes for their preparation are disclosed. The compounds are di- and trisilanes of the formula:(R--Si (R.sub.1).sub.2 --G--Y--.sub.n Qin which R represents a radical containing one double ethylene bond, R.sub.1 represents a hydrocarbon radical, G represents a carbocyclic aromatic or heterocyclic radical, Y represents CONH or COO, Q represents an organic radical and n is an integer equal to 2 or 3. The compounds are useful in preparing thermoplastic elastomers.Type: GrantFiled: September 18, 1978Date of Patent: April 21, 1981Assignee: Rhone-Poulenc IndustriesInventors: Michel Bargain, Marcel Lefort
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Patent number: 4246426Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.Type: GrantFiled: April 2, 1979Date of Patent: January 20, 1981Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4245121Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.Type: GrantFiled: February 4, 1980Date of Patent: January 13, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4226985Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.Type: GrantFiled: April 2, 1979Date of Patent: October 7, 1980Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4227019Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.Type: GrantFiled: April 2, 1979Date of Patent: October 7, 1980Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4218565Abstract: This disclosure describes 11-deoxy-11-substituted members of the E.sub.2, F.sub.2, E.sub.1, F.sub.1, dihydro E.sub.1 and dihydro F.sub.1 prostaglandin series which are useful as hypotensive agents and as anti-ulcer agents.Type: GrantFiled: March 10, 1977Date of Patent: August 19, 1980Assignee: American Cyanamid CompanyInventors: Charles V. Grudzinskas, Martin J. Weiss
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Patent number: 4214914Abstract: According to the invention, the method for producing mineral polymer fillers containing graft hydroperoxide groups consists in treating mineral fillers at a temperature of 50.degree. to 150.degree. C. and a pressure of 1.33.10.sup.2 to 4.10.sup.5 Pa (1 mm Hg to 4 atm) with organosilicon compounds of the general formula:R.sub.4-y SiX.sub.yorR'R.sub.3-z SiX.sub.z,whereR is vinyl, allyl or norbornyl,X is chlorine, alkoxy or acyloxy,y=1-3,z=1-2,R' is methyl, ethyl or propyl,whereupon the mineral filler containing graft unsaturated groups is separated from the reaction mixture, dried and ozonized with an ozone-oxygen mixture containing 4 to 6 percent by volume of ozone at a temperature of -20.degree. C. to +20.degree. C. in an aliphatic saturated monohydric alcohol or aliphatic saturated monohydric acid.The method for producing mineral polymer fillers containing graft hydroperoxide groups is quite simple and makes it possible to carry out the filling and grafting of polymers at a reduced temperature of 50.degree.Type: GrantFiled: November 20, 1978Date of Patent: July 29, 1980Inventors: Sergei S. Ivanchev, Nikolai S. Enikolopov, Boris V. Polozov, Anatoly A. Syrov, Oleg N. Primachenko, Zorislav N. Polyakov
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Patent number: 4208342Abstract: Novel organosilicon compounds and processes for their preparation are disclosed. The compounds are di- and trisilanes of the formula(R--Si (R.sub.1).sub.2 --G--Y--.sub.n Qin which R represents a radical containing one double ethylene bond, R.sub.1 represents a hydrocarbon radical, G represents a carbocyclic aromatic or heterocyclic radical, Y represents CONH or COO, Q represents an organic radical and n is an integer equal to 2 or 3. The compounds are useful in preparing thermoplastic elastomers.Type: GrantFiled: July 20, 1977Date of Patent: June 17, 1980Assignee: Rhone-Poulenc IndustriesInventors: Michel Bargain, Marcel Lefort
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Patent number: 4206151Abstract: This disclosure describes novel 15-deoxy-16 hydroxy-16-substituted prostanoic acid analogs in which the C-1 carboxyl is replaced by a primary alcohol and carboxylic acid esters, carbonates and carbomates thereof. The prostanoic carbinols and carboxylic acid esters thereof described herein have utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: December 21, 1978Date of Patent: June 3, 1980Assignee: American Cyanamid CompanyInventor: Charles V. Grudzinskas
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Patent number: 4202988Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.Type: GrantFiled: March 30, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4197407Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.Type: GrantFiled: March 30, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4197245Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: T103403Abstract: This disclosure describes esters having prostaglandin-like activity of 15-deoxy-16-hydroxy-16-substituted-prostanoic acids formed by replacing the hydroxy group of the C.sub.1 -carboxylic acid substituent with para-acetamidophenoxy, methylsulfonylamido, para-acetylphenoxy, para-phenylphenoxy, C.sub.3 -C.sub.10 cycloalkoxy, arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms, phenoxy or phenoxy substituted with 1-3 chlorine atoms or C.sub.1 -C.sub.3 alkyl, phenacyloxy or phenacyloxy ring-substituted with from 1-3 bromine atoms, a nitro moiety, C.sub.1-C.sub.8 arylalkyl, or arylalkoxy wherein the alkoxy group has from 7-12 carbon atoms; substituted arylamino (C.sub.1 -C.sub.12), substituted-naphthoxy, fluorenoxy, carboxyalkoxy (C.sub.5 -C.sub.Type: GrantFiled: May 3, 1982Date of Patent: September 6, 1983Inventors: Martin J. Weiss, Charles V. Grudzinskas, Middleton B. Floyd, Jr., Sow-Mei L. Chen