Chalcogen Attached Indirectly To The Lactone Ring By Acyclic Nonionic Bonding Patents (Class 549/305)
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Patent number: 5374745Abstract: The invention relates to a process for the production of prostaglandin precursors of formula I ##STR1## as well as their enantiomers in which X is A--W or W--A,A is a --C.tbd.C-- group,W is a hydroxymethylene group, in which the OH group can be functionally modified by etherification or esterification,D is a straight-chain or branched-chain alkylene group with 2-5 C atoms each or a ##STR2## group, n i s 1 to 3,E is a --C.tbd.C-- group or a --CR.sub.3 .dbd.CR.sub.4 group with R.sub.3 and R.sub.4 each meaning a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group,R.sub.1 is a hydrogen atom or a hydroxy group, which can be functionally modified as in W,R.sub.2 is a straight-chain or branched-chain alkyl group with 1-7 C atoms, characterized in that vinyl bromides of formula II ##STR3## in which Z means the group ##STR4## and R.sub.1, W, D, E and R.sub.2 have the above-indicated meanings and hydroxy groups unprotected in R.sub.1 and W or represented by an optionally substituted benzoyl radical, a C.sub.1 -C.sub.Type: GrantFiled: September 29, 1992Date of Patent: December 20, 1994Assignee: Schering AktiengesellschaftInventor: Ulrich Klar
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Patent number: 5369125Abstract: This invention relates to compounds of structural formula (I): ##STR1## which are squalene synthase inhibitors and thus useful as cholesterol lowering agents and antifungal agents. These compounds are also inhibitors of farnesyl protein transferase and farnesylation of the oncogene protein Ras and thus useful in treating cancer.Type: GrantFiled: March 19, 1993Date of Patent: November 29, 1994Assignee: Merck & Co., Inc.Inventors: Gregory D. Berger, James D. Bergstrom, Tesfaye Biftu, Robert L. Bugianesi, Robert M. Burk, Narindar N. Girotra, C. H. Kuo, William H. Parsons, Mitree M. Ponpipom, Lori L. Whiting
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Patent number: 5362752Abstract: New cholesterol lowering compounds are formed from the photochemical treatment of zaragozic acid A.Type: GrantFiled: May 17, 1993Date of Patent: November 8, 1994Assignee: Merck & Co., Inc.Inventors: Byron H. Arison, Gregory D. Berger, Leeyuan Huang, John G. MacConnell
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Patent number: 5360919Abstract: A process for the preparation of a compound of Formula (1): ##STR1## wherein: W.sup.1 is aryl;X.sup.1 and X.sup.2 are each independently selected from --H, --CN, halogen, alkyl, aryl and --COOH;Y is --H;Z is --OH; orY and Z together form a group of Formula (2): ##STR2## wherein: W.sup.2 is aryl;which comprises reacting a compound of Formula (3): ##STR3## wherein: X.sup.1, X.sup.2, Y and Z are as hereinbefore defined with a compound of Formula (4): ##STR4## wherein the substituents are as defined in the specification.Type: GrantFiled: March 8, 1993Date of Patent: November 1, 1994Assignee: Zeneca LimitedInventor: Michael C. H. Standen
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Patent number: 5359095Type: GrantFiled: February 8, 1994Date of Patent: October 25, 1994Assignee: Pharmacia ABInventor: Bahram Resul
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Patent number: 5322525Abstract: A process is disclosed for treating polyamide fiber containing materials which process comprises applying a benzofuran-2-one compound to the material in order to enhance its moulding stability. In addition, compositions containing a fluorescent whitening agent and a benzofuran-2-one, and optionally one or more dyes, are disclosed.Type: GrantFiled: October 30, 1992Date of Patent: June 21, 1994Assignee: Ciba-Geigy CorporationInventors: Manfred Rembold, Claude Eckhardt, Peter Nesvadba
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Patent number: 5312967Abstract: A single step process for converting aldaric acid salts to activated aldarates utilizing a lower alkanol as both solvent and esterifying agent is described. The activated aldarates are particularly useful as monomers for polymerizations with primary diamines in which the nitrogen atoms are bound to aliphatic carbon atoms to form poly(aldaramides).Type: GrantFiled: August 12, 1992Date of Patent: May 17, 1994Assignee: UAB Research FoundationInventors: Donald E. Kiely, Liang Chen, David W. Morton
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Patent number: 5268490Abstract: A benzofuranone of the Formula (1): ##STR1## wherein: R.sup.1 and R.sup.2 are each independently --H or optionally substituted C.sub.1-20 -alkyl;R.sup.3 and R.sup.4 are each independently --H or optionally substituted C.sub.1-6 -alkyl;R.sup.5 is selected from --H, --CN, --COOR.sup.10 and --COR.sup.10, in which R.sup.10 is --H or C.sub.1-6 -alkyl;R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently selected from --H, --NR.sup.1 R.sup.2, --NO.sub.2, halogen, optionally substituted C.sub.1-6 -alkyl and optionally substituted C.sub.1-6 -alkoxy.Type: GrantFiled: October 1, 1992Date of Patent: December 7, 1993Assignee: Imperial Chemical Industries PLCInventors: Richard A. Hann, Nigel Hall, Gary W. Morrison, Dean Thetford
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Patent number: 5252643Abstract: Compounds which are benzofuran-2-ones having two organothiomethyl substituents directly attached to the benzo ring are suitable for stabilizing organic materials against thermal, oxidative or light-induced degradation.Type: GrantFiled: June 24, 1992Date of Patent: October 12, 1993Assignee: Ciba-Geigy CorporationInventor: Peter Nesvadba
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Patent number: 5229529Abstract: The present invention provides a method of preparing .alpha.,.beta.-unsaturated ketolactones which are useful for production of prostaglandins having one or more halogen substituent(s) at the 16 or 17 portion in high yield, in which, a dimethyl (2-oxoalkyl) phosphonate having one or more halogen substituents, a starting material, is reacted with a bicyclolactone aldehyde under the presence of an alkali metal hydride and a zinc compound.Type: GrantFiled: April 1, 1992Date of Patent: July 20, 1993Assignee: R-Tech Ueno Ltd.Inventors: Ryuji Ueno, Tomio Oda
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Patent number: 5216052Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.8 cycloalkyl or C.sub.7 -C.sub.9 phenylalkyl, A.sub.1 and A.sub.4 are phenyl, ##STR2## or phenyl which is substituted by 1 to 3 radicals R.sub.3, which radicals R.sub.3 are each independently of one another selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.18 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.7 -C.sub.9 phenylalkoxy, C.sub.5 -C.sub.8 cycloalkoxy, C.sub.1 -C.sub.18 alkanoyloxy, C.sub.3 -C.sub.18 alkenoyloxy, benzoyloxy, phenoxy and hydroxy, m is 1 or 2, A.sub.2 and A.sub.3, together with the linking carbon atom, form a C.sub.5 -C.sub.7 cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups, are very suitable for stabilising organic materials against thermal, oxidative or light-induced degradation.Type: GrantFiled: June 24, 1992Date of Patent: June 1, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Nesvadba, Carla Attinger-Sorato
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Patent number: 5169976Abstract: Variously substituted 4-(biphen-2-ylmethylcarbamoyl)-3-hydroxybutyric acids and esters, also named as N-(biphen-2-yl)-3-hydroxyglutaramic acid derivatives, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: May 3, 1990Date of Patent: December 8, 1992Assignee: Pfizer Inc.Inventor: Peter A. McCarthy
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Patent number: 5164412Abstract: A Derivative of 5-hetero-6-oxo-PGE A derivative of 5-hetero-6-oxo-PGE of the formula: ##STR1## wherein R.sup.1 is (1) a group of the formula: COOR11(2) hydroxymethylcarbonyl,(3) hydroxymethyl or(4) a group of the formula:CO--AAwherein AA is an amino acid-residue,Z is oxygen, sulfur or a group of the formula: NR21 wherein R21 is hydrogen or alkyl of C1--4;R2 is a single-bond or alkylene of C1--4;R3 isi) alkyl of C1-7,ii) cycloalkyl of C4-7 or cycloalkyl of C4-7 substituted by alkyl of C1-7,iii) phenyl, phenoxy, phenyl or phenoxy substituted by one group selected from alkyl of C1-4, halogen and trihalomethyl, is single-bond or a double bond.Possess PG-like activity, especially cytoprotection, and therefore are useful for treatment for and/or prevention of cytodamage.Type: GrantFiled: April 8, 1991Date of Patent: November 17, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Yoshitaka Konishi, Masanori Kawamura
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Patent number: 5162573Abstract: 2-Propyl-2-pentanoic acid (valproic acid) esters and (E)-2-propyl-2-pentenoic acid [(E)-2-valproenoic acid] esters surprisingly proved to have valuable properties, in that they show anticonvulsive and antiepileptic activities comparable with those of valproic acid, as well as an improved bioavailability and a markedly reduced toxicity.Type: GrantFiled: June 17, 1987Date of Patent: November 10, 1992Assignee: Chiesi Farmaceutici S.p.A.Inventors: Paolo Chiesi, Vittorino Servadio, Flavio Villani
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Patent number: 5089635Abstract: 13-alkyl-11.beta.-phenyl-gonanes of general formula I ##STR1## wherein A and B together stand for an oxygen atom, a CH.sub.2 group or a second bond between carbon atoms 9 and 10,X is an oxygen atom or the hydroxyimino grouping N.about.OH,R.sub.1 is a straight-chained or branched, saturated or unsaturated alkyl radical with up to 8 carbon atoms, which contains the grouping ##STR2## with X as described above, R.sub.2 is a methyl or ethyl radical in the .alpha. or .beta. position,R.sub.9, R.sub.10, R.sub.11 and R.sub.12 each stand for a hydrogen atom, a hydroxy, alkyl, alkoxy or acyloxy group with 1 to 4 carbon atoms respectively or a halogen atom and R.sub.3 and R.sub.4 have a variety of meanings, have antigestagenic and antiglucocorticoid effects.Type: GrantFiled: February 7, 1986Date of Patent: February 18, 1992Assignee: Schering AktiengesellschaftInventors: Gunter Neef, Sybille Beier, Walter Elger, David Henderson, Eckard Otto, Ralph Rohde
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Patent number: 4927945Abstract: Diphenyl ether derivatives of formula II ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or an alkyl or haloalkyl group, R.sub.2 and R.sub.3, which may be the same or different, each independently represents a hydrogen or halogen atom, or an alkyl, haloalkyl, nitro or cyano group, R.sub.4 represents an alkyl group and X represents an oxygen or sulphur atom, useful as intermediates in the preparation of diphenyl ether herbicides, are prepared by treating a compound of formula III ##STR2## where R.sub.1, R.sub.2, R.sub.3 and X are as defined above and R.sub.6 is a hydrogen atom or an alkyl group, with an alkali under hydrolyzing conditions.Type: GrantFiled: August 9, 1988Date of Patent: May 22, 1990Assignee: Shell Internationale Research Maatschappij, B.V.Inventors: Stuart P. Briggs, Derek A. Wood
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Patent number: 4912134Abstract: Azulene derivatives of the following formula ##STR1## wherein R.sup.1 stands for an alkyl group of 1 to 3 carbon atoms, R.sup.2 stands for an alkyl group of 1 to 3 carbon atoms, and R.sup.3 is at the 5- or 6-position and stands for an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 9 carbon atoms or an aralkyl group of 7 to 10 carbon atoms; have antihyperlipidemic activity. Many of the compounds are also novel per se.Type: GrantFiled: March 10, 1988Date of Patent: March 27, 1990Assignee: Ajinomoto Company, Inc.Inventors: Masabumi Yasunami, Kahei Takase, Takashi Meguro, Katsumi Suzuki, Osamu Hiwatashi, Masaru Okutsu, Nobuo Kato, Toru Nakamura
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Patent number: 4900844Abstract: A process for the preparation of oxophthalazinyl acetic acids having benzothiazole or other heterocyclic side chains comprising reacting an oxophthalizinyl acetic acid ester with an aniline derivative is disclosed. Also disclosed are processes for the preparation of such oxopthalizinyl esters.Type: GrantFiled: May 19, 1989Date of Patent: February 13, 1990Assignee: Pfizer Inc.Inventors: Banavara L. Mylari, William J. Zembrowski
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Patent number: 4868317Abstract: A compound of the formula ##STR1## in its d, 1 or d1 form and mixtures thereof and their preparation and their use in the synthesis of pyrethrinoids.Type: GrantFiled: January 17, 1989Date of Patent: September 19, 1989Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute
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Patent number: 4868301Abstract: Oxophthalazinyl acetic acids having aldose reductase inhibitory properties of the formula ##STR1## wherein Z is hydrogen or methyl, U is S, CH.sub.2 or a covalent bond, and R.sup.1, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as herein defined, are prepared by reacting an intermediate oxophthalazinyl acetic acid ester having a cyano or alkylamido group with an aniline derivative of the formula ##STR2## Processes for the preparation of the intermediate oxophthalazinyl acetic esters are disclosed.Type: GrantFiled: March 8, 1988Date of Patent: September 19, 1989Assignee: Pfizer Inc.Inventors: Banavara L. Mylari, William J. Zembrowski
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Patent number: 4859700Abstract: The invention relates to new 2-(2,3-dihydro-2-oxo-3-benzofuranyl)acetic acid compounds of general formula I: ##STR1## in which: R.sub.1 denotes a hydrogen atom, a linear or branched alkyl radical having 1 to 4 carbon atoms or a phenyl radical optionally substituted with a halogen atom or with an alkoxy radical containing 1 to 4 carbon atoms or an alkyl radical having 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen or halogen atom, a hydroxyl radical, an alkyl radical having 1 to 4 carbon atoms or an alkoxy radical containing 1 to 4 carbon atoms,R denotes a hydroxyl radical, a linear or branched alkoxy radical having 1 to 4 carbon atoms, a benzyloxy radical or a radical of general formula A: ##STR2## in which: X and Y, which may be identical or different, each denote a linear or branched alkyl radical containing 1 to 5 carbon atoms, a radical of general formula A.sub.Type: GrantFiled: February 12, 1988Date of Patent: August 22, 1989Assignee: ADIR Et CieInventors: Gilbert Lavielle, Jean Lepagnol
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Patent number: 4855446Abstract: Racemic carboxylic acids are resolved into their enantiomers using optically active enantiomers of four lactones as resolving agents. The four lactones are 2,3-isopropylidene-ribonic acid-1,4-lactone, 1,2-isopropylidene-glucofuranurono-3,6-lactone, 2-hydroxy-3,3-dimethyl-1,4-butyrolactone and 3,4-isopropylidene-arabino-1,5-lactone. Novel diastereoisomeric esters of the acids with the lactones are disclosed.Type: GrantFiled: December 17, 1984Date of Patent: August 8, 1989Assignee: The Sherwin Williams CompanyInventors: Colin C. Duke, Robert J. Wells
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Patent number: 4847286Abstract: Cromoglycic acid derivatives of the general formula ##STR1## wherein R.sup.1 is an .alpha.-, .beta.- or .gamma.-amino acid residue (for ester bonding) whose amino group may optionally be substituted by at least one lower alkyl group, and R.sup.2 and R.sup.3 each independently is a lower alkyloxy-substituted or an unsubstituted lower alkyl group, an 1-alkanoyloxyalkyl group, an 1-alkoxycarbonyloxyalkyl group, a phthalidyl group or a 5-methyl-1,3-dioxol-2-on-4-ylmethyl group; nontoxic salts thereof; and pharmaceutical compositions containing such compounds. Since the compounds have antiallergic activity and are readily absorbable into the blood stream, they are useful as oral antiallergic agents.Type: GrantFiled: March 27, 1987Date of Patent: July 11, 1989Assignee: Kyoto Pharmaceutical Industries, Ltd.Inventors: Satoshi Tamaki, Masaru Kitagawa, Hirokazu Tsuda, Susumu Nishizawa, Nobuhara Kakeya, Kazuhiko Kitao
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Patent number: 4810805Abstract: There are disclosed a (2-chloro-3-oxo-1-alkenyl)-bicyclo[3.3.0 octene derivative represented by the formula: ##STR1## wherein R.sup.1 represents --CH.sub.2 CH.sub.2 CH.sub.2 COOR.sup.5, --CH.sub.2 CH.sub.2 --O--CH.sub.2 COOR.sup.5, --CH.dbd.CHCH.sub.2 COOR.sup.5 or --CH.sub.2 CH.sub.2 C.tbd.C--COOR.sup.5 group where R.sup.5 in the groups represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom, an acyl group having 1 to 7 carbon atoms, a tri(1 to 7 carbon atoms)-hydrocarbylsilyl group or a group forming an acetal bonding with an oxygen atom of a hydroxy group; R.sup.Type: GrantFiled: December 19, 1986Date of Patent: March 7, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Masakatsu Shibasaki, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Aoki, Yoshio Hayashi
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Patent number: 4788299Abstract: New ketolactones of the formula I ##STR1## wherein R.sup.1 is H, alkyl having 1-6 C atoms or aryl having 6-14 C atoms andR.sup.2 and R.sup.3 together are an O atom or together are a bond,and salts thereof,can be used as intermediate products in the preparation of prostaglandin derivatives.Type: GrantFiled: June 17, 1987Date of Patent: November 29, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventor: Bernhard Riefling
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Patent number: 4739078Abstract: The present invention provides a novel process for reducing 15-keto prostaglandin intermediates. This process stereospecifically reduces these 15-keto intermediates using sodium borohydride and ceriumtrichloride, yielding a predominance of the 15.alpha. epimer.Type: GrantFiled: February 17, 1984Date of Patent: April 19, 1988Assignee: The Upjohn CompanyInventor: Bruce A. Pearlman
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Patent number: 4704458Abstract: Disclosed herein is an improved process for preparing 1RS-3'RS epimer of aminated phthalideisoquinolines represented by the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen atom or a lower alkoxy group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen atom, amino group or a lower alkoxy group with at least one of R.sup.3 -R.sup.6 being amino group, and R.sup.7 is a lower alkyl group. The improvement comprises, after having reduced a mixture of epimers of corresponding nitro compounds of the general formula (I) wherein the amino group is replaced by nitro group into the amino compounds (I), treating said amino compound at a temperature in the range of 20.degree.-100.degree. C. in an aliphatic lower alcohol in the presence of an alkali to epimerize 1RS-3'SR epimer of said amino compound into said 1RS-3'RS epimer thereof.Type: GrantFiled: January 23, 1985Date of Patent: November 3, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshiyuki Takeda, Osamu Kawashima, Shiro Furukawa, Yasukazu Ogino
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Patent number: 4698435Abstract: A novel process for preparing a 3-phenacylidene phthalide of the general formula (II) ##STR1## which comprises reacting a halogenating reagent with a 2-carboxydibenzoylmethane.The 2-carboxydibenzoylmethane can be inexpensively prepared, so that the 3-phenacylidene phthalides which are useful as a growth regulant for plants and a safering agent to reduce herbicidal injury to plants can be readily obtained economically in high yield.Type: GrantFiled: September 19, 1986Date of Patent: October 6, 1987Assignee: Kao CorporationInventors: Naotake Takaishi, Kimihiko Hori
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4680418Abstract: A process for the production of (1R,Cis)-4-acetyl-6, 6-dimethyl-3-oxabicyclo-(3.1.0.)-hex-2-one of the formula: ##STR1## which involves reacting (1R,Cis)-4,7,7-trimethyl-3-oxabicyclo-(4.1.0.)-hept-4-en-2-one of the formula: ##STR2## with bromine at a temperature of from 0.degree. C. to 25.degree. C. and treating the brominated reaction mixture at ambient temperature with water, an aqueous solvent solution or an aqueous base solution.Type: GrantFiled: September 26, 1985Date of Patent: July 14, 1987Assignee: IEL LimitedInventors: Arun K. Mandal, Damodar G. Jawalkar, Satish W. Mahajan
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4650881Abstract: Arenes, such as benzoic acid and substituted benzoic acids, are readily thallated by thallium(III) compounds such as the trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, dienes, allylic halides, vinyl halides, vinyl esters, or unsaturated cyclopropanes or unsaturated cyclobutanes to give isocoumarins.Type: GrantFiled: April 1, 1985Date of Patent: March 17, 1987Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larock, Sudarsanan Varaprath
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Patent number: 4634782Abstract: 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: June 24, 1985Date of Patent: January 6, 1987Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Hans Maag, Perry Rosen
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Patent number: 4622410Abstract: The present invention relates to intermediates of the general formula: ##STR1## (wherein Y and Z, which may be the same or different, each represents a trans-vinylene group or an ethylene group, R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R.sup.4 represents an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group of 1 to 8 carbon atoms or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group of 1 to 4 carbon atoms, R.sup.5 represents a hydroxy- protecting group which can be removed in acidic conditions and W.sup.1 represents a group of the formula: --COOR.sup.1, --CON(R.sup.6).sub.2, --CH.sub.2 OR.sup.5 or --CH(OR.sup.7)CH.sub.2 OR.sup.5 (in which R.sup.1 represents a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, the groups R.sup.Type: GrantFiled: March 18, 1985Date of Patent: November 11, 1986Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Nobuyuki Hamanaka, Hideo Takada, Yoshinobu Arai
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Patent number: 4578482Abstract: A process for producing prostacyclins of the formula ##STR1## wherein the symbol G.sup.1, R.sup.1, R.sup.2, R.sup.31 and R.sup.41 are as defined in claim 1,which comprises reacting 5,6-dehydroprostaglandins F.sub.2 of the formula ##STR2## wherein the symbol G, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1,with a mercury (II) compound in an inert organic solvent in the presence of tri(C.sub.1 -C.sub.6)alkylamine, treating the reaction product with a boron hydride compound, and if necessary, subjecting the reaction product to deprotecting reaction, hydrolysis reaction, or salt-forming reaction.This process is industrially advantageous process for the preparation of prostacyclin and its derivatives.Type: GrantFiled: December 21, 1983Date of Patent: March 25, 1986Assignee: Teijin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Akira Yanagisawa, Seizi Kurozumi
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Patent number: 4558142Abstract: The prostacyclins 7-fluoro-6,9-epoxy-16-substituted-15-hydroxyprost-[4 or 5,13]-dienoic acids and esters useful as anti-secretory agents, blood pressure lowering agents, anti-ulcerogenic agents, anti-hypertensive agents, bronchodilation agents and for combating gastro-hyperacidity and as anti-blood platelet aggregating agents.Type: GrantFiled: September 7, 1982Date of Patent: December 10, 1985Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Perry Rosen, Hans Maag
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Patent number: 4554361Abstract: A novel process for the preparation of sulfonic acid esters containing a lactonic ring comprising compounds in the trans form in the 4- and 5-positions having (4SR,5RS), (4S,5R) or (4R,5S) configuration of the formula ##STR1## wherein Z is selected from the group consisting of alkyl of 1 to 4 carbon atoms and cycloalkyl and monocyclic aryl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and nitro and R is organic residue of an optionally chiral alcohol of the formula ROH and a process using the compounds of formula I to prepare compounds of (1RS, 4RS, 5SR), (1S, 4S, 5R) or (1R, 4R, 5S) configuration of the formula ##STR2## wherein X is selected from the group consisting of hydrogen and R useful for the preparation of insecticidally active esters.Type: GrantFiled: July 27, 1983Date of Patent: November 19, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4540785Abstract: Hydroquinones of the formula ##STR1## wherein X is the residue of a 5- or 6-membered ring, R.sub.1 is hydrogen, alkyl or aryl, R.sub.1,R.sub.3, R.sub.4 and R.sub.5 are hydrogen or alkyl and R.sub.6 is hydrogen or a group of the formula ##STR2## wherein X and R.sub.1 are as defined above, are of use as protected developing agents in photographic silver halide material.Type: GrantFiled: November 8, 1983Date of Patent: September 10, 1985Assignee: Ciba-Geigy AGInventor: Norman A. Smith
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Patent number: 4529737Abstract: The present invention concerns novel phthalidyl esters of arylalkanoic acids having improved pharmacological properties in respect to the corresponding arylalkanoic acids having analgesic and anti-inflammatory activity, as well as pharmaceutical compositions containing them as active ingredients. The invention further relates to a method for improving the pharmacological properties of said arylalkanoic acids having analgesic and anti-inflammatory activity, by introducing, through an ester bond, a phthalidyl group.Type: GrantFiled: November 13, 1980Date of Patent: July 16, 1985Assignee: Resfar S.r.I.Inventors: Guido Vandoni, Marino Gobetti
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Patent number: 4526987Abstract: Lactones of the formula ##STR1## wherein R is hydrogen or a CX.sub.3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.Type: GrantFiled: January 3, 1979Date of Patent: July 2, 1985Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Daiei Tunemoto
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Patent number: 4501908Abstract: Racemic carboxylic acids are resolved into their enantiomers using optically active enantiomers of four lactones as resolving agents. The four lactones are 2,3-isopropylidene-ribonic acid-1,4-lactone, 1,2-isopropylideneglucofuranurono-3,6-lactone, 2-hydroxy-3,3-dimethyl-1,4-butyrolactone and 3,4-isopropylidene-arabino-1,5-lactone. Novel diastereoisomeric esters of the acids with the lactones are disclosed.Type: GrantFiled: March 1, 1982Date of Patent: February 26, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Colin C. Duke, Robert J. Wells
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Patent number: 4472428Abstract: Novel 5- or 7-monohalogenated or 5,7-dihalogenated .sup.6 -PGI.sub.1 and 5- or 7-monohalogenated or dihalogenated PGI.sub.2 (except 5-monofluorinated PGI.sub.2). The novel halogenated prostacyclins are useful for controlling vascular actions and also in organ transplantation, extra-corporeal circulation and the like. The present invention also provides processes for preparing the novel halogenated prostacyclins.Type: GrantFiled: December 4, 1981Date of Patent: September 18, 1984Assignee: Teijin LimitedInventors: Takeshi Toru, Kiyoshi Bannai, Takeo Oba, Toshio Tanaka, Noriaki Okamura, Kenzo Wantanabe, Seizi Kurozumi, Akira Ohtsu, Tatsuyuki Naruchi
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Patent number: 4448986Abstract: (1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-2-acetoxy-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane intermediate.Type: GrantFiled: July 14, 1982Date of Patent: May 15, 1984Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4409398Abstract: (1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-4-acetoxy-6,6-dimethyl-2-oxo-3-oxabicyclo [3.1.0]hexane intermediate.Type: GrantFiled: August 13, 1981Date of Patent: October 11, 1983Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4401824Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 8, 1982Date of Patent: August 30, 1983Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4362880Abstract: An improved process for the preparation of 3-substituted thiophenes. The thiophenes are useful for the preparation of penicillins and cephalosporins.The process is for the preparation of a thiophene of formula (I): ##STR1## where R.sup.1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R.sup.2 represents a group suitable for use as an .alpha.-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating under basic conditions a compound of formula (II): ##STR2## wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur ionically bound to a polymeric support.Type: GrantFiled: March 30, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Kenneth T. Veal, Trevor J. Grinter
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Patent number: 4350813Abstract: A novel process for producing 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone, and its intermediates. 7-Alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone can be obtained by reacting substituted methylenetriphenylphosphorane with 3,5-dimethyl-4-alkoxycarbonylphthalic anhydride to obtain 6-alkoxycarbonyl-5,7-dimethyl-.DELTA..sup.3,.alpha. -substituted methylenephthalide, reacting the latter with hydrazine to obtain a phthalazone derivative, hydrolyzing the latter, halogenating the hydrolyzate to obtain 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone and then directly hydrolyzing and decarboxylating the latter or, when said 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone is 7-alkoxycarbonyl-6,8-dimethyl-1-phthalazone-4-.alpha.Type: GrantFiled: July 23, 1980Date of Patent: September 21, 1982Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yukio Takei, Masao Yoshida, Rinzo Nishizawa
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Patent number: 4349689Abstract: 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), 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: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4344884Abstract: Novel intermediates for production of insecticidal cis-3-(2,2-disubstituted-ethenyl)-2,2-dimethylcyclopropanecarboxylates, processes for preparing the intermediates, and processes for preparing the final product insecticides via a novel bicyclic lactone intermediate are described and exemplified.Type: GrantFiled: June 30, 1980Date of Patent: August 17, 1982Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
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Patent number: 4341793Abstract: Compounds of formula (III): ##STR1## and esters, amides and pharmaceutically acceptable salts thereof, wherein A.sup.1 is hydrogen or methyl;A.sup.2 is hydrogen or methyl;n is 1, 2 or 3; andR is hydrogen, chlorine, bromine, hydroxy, nitro, amino or trifluoromethyl,are useful as anti-hyperglycaemic agents and/or anti-obesity agents.Type: GrantFiled: November 7, 1980Date of Patent: July 27, 1982Assignee: Beecham Group LimitedInventor: Michael J. Ferris