Additional Chalcogen Bonded Directly To The Lactone Ring Patents (Class 549/313)
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Patent number: 5457245Abstract: A process for synthesizing (23S,25R)-calcitriol lactone and related Vitamin D analogs comprises reacting protected enantiomerically pure glycidol or 2-alkylglycidol with protected De-A,B-8.beta.-hydroxy-24-nor-cholan-23-al, removing the protective groups from the epimeric product mixture and separating the epimers, to give a hydrindane tetrol product, followed by oxidation and protection of the hydrindane tetrol product, reacting the tetrol product with the lithium salt of (3S)-(3.alpha.,5.beta.,Z)-2-(2-methylene-3,5-bis-((1,1-dimethylethyl)dimet hylsilyloxy)cyclohexylidene)ethyl diphenyl phosphine oxide and removing the final protective groups. Certain intermediate compounds also show biological activity as angiostatic agents.Type: GrantFiled: July 11, 1994Date of Patent: October 10, 1995Assignee: Alcon Laboratories, Inc.Inventor: Raymond E. Conrow
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Patent number: 5453516Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.Type: GrantFiled: December 13, 1993Date of Patent: September 26, 1995Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos
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Patent number: 5447954Abstract: Compounds of the formula ##STR1## where the substituents are defined in the specification useful in the treatment of hyperlipidemia.Type: GrantFiled: November 4, 1994Date of Patent: September 5, 1995Assignee: SmithKline Beecham p.l.c.Inventors: Andrew D. Gribble, Pieter H. E. Groot, Antony N. Shaw, Roland E. Dolle
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Patent number: 5441974Abstract: This invention relates to compounds having the following formula ##STR1## wherein Z is a lactone or a lactone which is fused to a benzene ring which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidines derivatives.Type: GrantFiled: May 25, 1994Date of Patent: August 15, 1995Assignee: G. D. Searle & Co.Inventors: Philippe R. Bovy, Thomas E. Rogers, Masateru Miyano, Joseph G. Rico
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Patent number: 5412111Abstract: Providing a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide conveniently and selectively from a widely available raw material in a high yield. A carbonyl group of the 2-position of levoglucosenone is reduced to obtain a hydroxyl group of a .beta.-configuration. Then, an iodo-group of an .alpha.-configuration and an acyloxy ion of a .beta.-configuration are introduced regioselectively and stereoselectively to the double bond at the 4-position and the 3-position of the above-mentioned levoglucosenone, respectively, keeping a trans stereochemical relationship. An alkoxide is then formed, by hydrolysis and an oxirane ring of a .beta.-configuration is formed by removing an iodo-group by intramolecular nucleophilic displacement reaction of the alkoxide.Type: GrantFiled: July 23, 1993Date of Patent: May 2, 1995Assignee: Japan Tobacco IncorporatedInventors: Katsuya Matsumoto, Takashi Ebata, Koshi Koseki, Koji Okano, Hiroshi Kawakami, Hajime Matsushita
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Patent number: 5391769Abstract: The present invention discloses a method of preparing 3-DPA-lactone, which is difficult to obtain in a large amount from nature. According to the method of the present invention, the target compound can be synthesized at a high yield in fewer steps and more easily than by the conventional synthesizing technique, and selectively from a widely available material. In the method of the present invention, the hydroxyl groups at the 2- and 5 -positions of .gamma.-ribonolactone are protected, and then the hydroxyl group at the 3-position is eliminated so as to form a double bond between the 2- and 3-positions. After that, the protecting groups for the hydroxyl groups are eliminated.Type: GrantFiled: March 10, 1993Date of Patent: February 21, 1995Assignee: Japan Tobacco IncorporatedInventors: Katsuya Matsumoto, Takashi Ebata, Hiroshi Kawakami, Koshi Koseki, Hajime Matsushita
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Patent number: 5354872Abstract: A process for synthesizing (23S,25R)-calcitriol lactone and related Vitamin D analogs comprises reacting protected enantiomerically pure glycidol or 2-alkylglycidol with protected De-A,B-8.beta.-hydroxy-24-nor-cholan-23-al, removing the protective groups from the epimeric product mixture and separating the epimers, to give a hydrindane tetrol product, followed by oxidation and protection of the hydrindane tetrol product, reacting the tetrol product with the lithium salt of (3S)-(3.alpha.,5.beta.,Z)-2-(2-methylene-3,5-bis-((1,1-dimethylethyl)dimet hylsilyloxy)cyclohexy lidene)ethyl diphenyl phosphine oxide and removing the final protective groups. Certain intermediate compounds also show biological activity as angiostatic agents.Type: GrantFiled: May 28, 1993Date of Patent: October 11, 1994Assignee: Alcon Laboratories, Inc.Inventor: Raymond E. Conrow
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Patent number: 5322955Abstract: In the method of the present invention for manufacturing 3-DPA-lactone, a protective group is introduced in the first step into the hydroxyl group at 4-position of .gamma.-ribonolactone by an ordinary method. Then, an acid anhydride or an acid chloride is added in the presence of a tertiary amine compound so as to conduct a .beta.-elimination of the hydroxyl group at the 3-position. As a result, a double bond is formed between the 2- and 3-positions and, at the same time, the hydroxyl group at the 2-position is acylated. The double bond between the 2- and 3-positions is reduced in the next step by means of a catalytic hydrogenation. Finally, the protective group of the hydroxyl group is eliminated by an ordinary method. The particular method permits using readily available raw materials, decreasing the number of manufacturing steps, and easily and selectively synthesizing the desired 3-DPA-lactone, which is hardly obtained from nature in a large amount, in high yield, compared with the conventional method.Type: GrantFiled: October 22, 1992Date of Patent: June 21, 1994Assignee: Japan Tobacco, Inc.Inventors: Katsuya Matsumoto, Takashi Ebata, Hiroshi Kawakami, Koshi Koseki, Hajime Matsushita
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Patent number: 5319110Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-linked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.Type: GrantFiled: October 26, 1992Date of Patent: June 7, 1994Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 5310947Abstract: A new process for the production of tetronic acid alkyl esters of the general formula: ##STR1## starting from 4-haloacetoacetic acid alkyl esters of the general formula: ##STR2## The 4-haloacetoacetic acid alkyl esters of general formula II are converted in a first step with a dialkylsulfite of the general formula:(RO).sub.2 S.dbd.O IIIin the presence of a strong acid into a 4-halo-3-alkoxy-but-2E-enoic acid alkyl ester of the general formula: ##STR3## The latter is cyclized in a second step with a formate and a strong acid to the end product according to formula I.Type: GrantFiled: June 8, 1993Date of Patent: May 10, 1994Assignee: Lonza Ltd.Inventor: Joachim Lenzner
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Intermediates and processes for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents
Patent number: 5298633Abstract: Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formulas: ##STR1##Type: GrantFiled: October 28, 1992Date of Patent: March 29, 1994Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst -
Patent number: 5278322Abstract: A process for the preparation of a compound of the formula ##STR1## comprising reacting 1R, cis 2,2-dimethyl 3-(2-oxopropyl)-cyclopropane-1-carboxylic acid with an alkali metal, alkaline-earth metal or magnesium hypohalite, and oxidizing the 1R, cis 2,2-dimethyl 3-(hydroxy-carboxy-methyl)-cyclopropane-1-carboxylic acid or its salt or lactonic form thereof thus obtained with an oxidizing agent to obtain the compound of formula I and novel intermediates.Type: GrantFiled: October 29, 1992Date of Patent: January 11, 1994Assignee: Roussel UclafInventors: Francis Brion, Colette Colladant, Jacques Lagouardat, Jacques Scholl
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Patent number: 5276167Abstract: A process for preparation of a compound of the formula ##STR1##Type: GrantFiled: October 21, 1992Date of Patent: January 4, 1994Assignee: Roussel UclafInventors: Neerja Bhatnagar, Francois Brion, Colette Colladant
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Patent number: 5254697Abstract: The invention provides a novel process for the manufacture of enantiomerically-pure halolactones of the formula I which are useful for the production of certain 5-amino-4-hydroxyvaleric acid derivatives, themselves valuable intermediates in the production of compounds which are renin inhibitors. The process involves a diastereoselective alkylation of an oxazolidinone of the formula III, followed by a highly stereoselective and novel halolactonisation of an oxazolidinone of the formula II. Certain of the oxazolidinones of the formula II are novel and are provided as a further feature of the invention. The invention also provides a novel process for the production of the pharmaceutically-useful 5-amino-4-hydroxyvaleric acid derivatives of formula VI.Type: GrantFiled: June 4, 1990Date of Patent: October 19, 1993Assignee: Imperial Chemical Industries PLCInventor: David Waterson
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Patent number: 5242945Abstract: There are disclosed compounds of the formula: ##STR1## wherein X is --CH.sub.2 R;R is ##STR2## and further when Y=S, R may also be --(CH.sub.2).sub.e CH.sub.3 ; Y is --O--or --S--;R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl;R.sup.3 is indolyl, furyl, phenyl or phenyl optionally mono- or disubstituted independently by alkyl of 1-7 carbon atoms, --C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3, haloloweralkyl, perfluoroalkyl, lower alkoxy, aryl alkoxy, halo or nitro;R.sup.4 and R.sup.5 are, independently, --COCH.sub.2 R.sup.7, --CO.sub.2 R.sup.7, --CONHR.sup.7, geranyl or CH.sub.2 R.sup.3 ;R.sup.6 is hydrogen or lower alkyl;R.sup.7 is geranyl and any moiety selected from R other than ##STR3## A and B are, independently, --O--, --S-- or --NR.sup.6 --; and a is 0-8;b is 1-10 when Y=S, and 2-10 when Y=O;c is 1-3;d is 0-9; ande is 3-18;which by virtue of their ability to inhibit PLA.sub.Type: GrantFiled: April 12, 1991Date of Patent: September 7, 1993Assignee: American Home Products CorporationInventors: Craig E. Caufield, James M. Rinker
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Patent number: 5225571Abstract: Compounds of the formula ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.2, CO--O--R.sub.2, CO--NH--R.sub.2, or PO(OR.sub.2).sub.2 or PO(OR.sub.2)R.sub.2, where R.sub.2 independently is H, alkyl of 1 to 20 carbons, phenyl, or lower alkyl substituted phenyl or halogen substituted phenyl; n is an integer between 8 to 14; Y is H, alkyl having 1-20 carbon atoms, aryl[lower alkyl], aryl, lower alkyl[aryl], alkenyl containing one or more olephinic bonds and 1-20 carbon atoms, CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3 where R.sub.3 is aryl[lower alkyl], aryl, lower alkyl[aryl], alkenyl containing one or more olephinic bonds and 1-20 carbon atoms, further Y is PO(OH).sub.2, PO(OH)OR.sub.4, PO(OH)R.sub.4 PO(OR.sub.4).sub.2, where R.sub.4 is independently alkyl of 1-20 carbons or phenyl, have anti-inflammatory activity.Type: GrantFiled: April 30, 1991Date of Patent: July 6, 1993Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5219884Abstract: The present invention relates to an immunosuppressive agent which comprises at least one compound selected from the compounds of formula ##STR1## wherein R represents a hydrogen atom or an acyl, Y represents carbonyl or hydroxymethylene and represents a single bond or a double bond and their lactones, in an effective amount and a pharmaceutically acceptable carrier; a method of prophylaxis and therapy for suppressing rejection or autoimmune diseases which comprises administering the above-mentioned compound or its lactone in an effective amount; and a novel compound of formula ##STR2## or its lactone.Type: GrantFiled: March 1, 1990Date of Patent: June 15, 1993Assignees: Taito Co., Ltd., Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Tetsuro Fujita, Takeshi Ikumoto, Shigeo Sasaki, Takeki Okumoto, Kenji Chiba
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Patent number: 5200531Abstract: Threo-4-alkoxy-5-(arylhydroxymethyl)-2(5H)-furanones are obtained by condensation of 4-alkoxy-2(5H)-furanones with benzaldehydes in the presence of lithium hydroxide without contamination by the corresponding erythro stereoisomers. The condensation is preferably performed in aqueous acetonitrile and the product is precipitated from the alkaline reaction mixture by the addition of water. The products that can be produced according to the process of the invention are known pharmaceutical active ingredients with anticonvulsive or antiepileptic action.Type: GrantFiled: December 17, 1991Date of Patent: April 6, 1993Assignee: Lonza Ltd.Inventor: David Laffan
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Patent number: 5183906Abstract: Novel anti-inflammatory furanone compounds have the following formula ##STR1## where R.sub.1 independently is H, phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl of 1 to 6 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached either to the 3 or to the 5 position of the 2-furanone, when n is 2 then R.sub.1 is attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H; Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olephinic bonds, PO(OH).sub.2, PO(OH)OR.sub.2, PO(OH)R.sub.2, PO(OR.sub.2).sub.2, where R.sub.2 is independently alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, further Y.sub.1 is CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3, (CH.sub.2).sub.p --O--R.sub.3, or (CH.sub.2).sub.p --O--(CH.sub.2).sub.m --O--R.Type: GrantFiled: April 30, 1991Date of Patent: February 2, 1993Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst, George Sachs
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Patent number: 5171863Abstract: Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formulas: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons; X is H, OH, NH.sub.2, I or Br; R.sub.4 is H, alkyl of 1-20 carbons, phenyl[C.sub.1 -C.sub.20 alkyl], naphthyl[C.sub.1 -C.sub.20 alkyl], CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, CH.sub.2 --COOH or CH.sub.2 --COOR.sub.5, and R.sub.5 is alkyl of 1 to 6 carbons, with the proviso that when X is hydrogen then R.sub.4 is selected from the group consisting of CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, or CH.sub.2 --COOR.sub.5 ; ##STR2## in which R.sub.1, R.sub.2 R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.sub.5 is alkyl of 1 to 6 carbons; ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.sub.Type: GrantFiled: November 15, 1991Date of Patent: December 15, 1992Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst
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Patent number: 5153218Abstract: The compound of the formula: ##STR1## in which X, Y and Z are, independently, hydrogen, halogen, hydroxy, nitro, cyano, carboxyl, trifluoromethyl, phenyl, amino, alkylamino, dialkylamino, alkyl or alkoxy; R.sub.1 is alkyl, hydroxyalkyl, alkenyl, cycloalkyl, phenyl, benzyl, phenylethyl or substituted phenyl, benzyl or phenylethyl, alkoxy, halogen, cyano, trifluoromethyl, amino, alkylamino, dialkylamino, nitro, phenyl, benzyl or phenethyl or R.sub.1 is thienyl, imidazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl or benzamidazolyl; R.sub.2 is hydrogen, alkyl, cycloalkyl, phenyl, benzyl or substituted phenyl or benzyl, alkoxy, hologen, cyano, trifluoromethyl amino, nitro, alkylamino or dialkylamino; or a pharmaceutically acceptable salt thereof, are useful as ACAT inhibitors.Type: GrantFiled: October 28, 1991Date of Patent: October 6, 1992Assignee: American Home Products CorporationInventor: William F. Fobare
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Patent number: 5142063Abstract: The present invention describes novel chiral rhodium-diphosphine complexes having the formula[Rh(X) (Y) (Lp)]owherein X represents a residue of the formula X--COO.sup.- in which Z signifies a group ##STR1## aryl or substituted aryl, wherein R.sup.1, R.sup.2, R.sup.3 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro-C.sub.1-20 -alkyl, aryl, substituted aryl, the group --OR.sup.7, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n, with the proviso that at least one of R.sup.1, R.sup.2, and R.sup.3 represents --OR.sup.7, aryl or substituted aryl,R.sup.4, R.sup.5, R.sup.6 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro--C.sub.1-20 -alkyl, aryl, substituted aryl, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n,R.sup.7 =hydrogen, lower alkyl, partially or completely halogenated lower alkyl, aryl, substituted aryl or aryl-lower alkyl,A=The residue --OR or NR'.sub.Type: GrantFiled: November 20, 1990Date of Patent: August 25, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Emil A. Broger, Yvo Crameri
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Patent number: 5134128Abstract: New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.Type: GrantFiled: May 13, 1991Date of Patent: July 28, 1992Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst, John N. Bonfiglio, Elizabeth T. Syage
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Patent number: 5128370Abstract: New furans and lactones from streptomycetes, a process for the preparation thereof, and the use thereof.It is possible with the aid of various streptomycetes species to prepared new compounds having a furan or lactone structure. These compounds have a pharmacological, especially antibiotic, action.Type: GrantFiled: March 20, 1989Date of Patent: July 7, 1992Assignee: Hoechst AktiengesellschaftInventors: Susanne Grabley, Joachim Wink, Klaus Kuhlein, Gerhard Seibert, Klaus Hutter, Hermann Uhr, Axel Zeeck
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Patent number: 5118820Abstract: A 2,2-difluoro-2-desoxycarbohydrate is used to prepare antiviral nucleosides.Type: GrantFiled: February 7, 1991Date of Patent: June 2, 1992Assignee: Eli Lilly and CompanyInventor: Larry W. Hertel
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Patent number: 5116954Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.Type: GrantFiled: August 2, 1989Date of Patent: May 26, 1992Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
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Patent number: 5112853Abstract: New furanone compounds have anti-inflammatory, immunosuppresive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-[3,6-dihydro-6-hydroxy-5-(3-phenylpropyl)-2H-pyran-2-yl]-5-hydroxy-2-(5H )-furanone.Type: GrantFiled: June 3, 1991Date of Patent: May 12, 1992Assignee: Allergan, Inc.Inventors: Michael E. Garst, Elizabeth T. Syage
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Patent number: 5106407Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.Type: GrantFiled: December 4, 1989Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
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Patent number: 5094681Abstract: Herbicidal 5H-furan-2-one derivatives of the formula ##STR1## in which X represents the radical OR.sup.1 or the radical ##STR2## q represents the number 0 or 1,R.sup.2 is optionally substituted aryl, andR.sup.3 and R.sup.6 are hydrogen or various organic radicals, with certain provisos and exceptions.Type: GrantFiled: August 30, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Gerd Kleefeld, Jurgen Bachmann, Peter Babczinski, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5089485Abstract: New furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-(1-thioacetoxytridecyl-5-hydroxy-2(5H)-furanone.Type: GrantFiled: October 25, 1989Date of Patent: February 18, 1992Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5084464Abstract: The present invention provides conjugated .gamma.-hydroxybutenolide compounds represented by the general formula: ##STR1## wherein R represents, when n is 1, furyl groups, thienyl groups or naphthyl groups, unsubstituted or substituted with alkyl group or alkoxy group; phenyl groups substituted with dialkylamino group, acyl group or pyridinyl group; or ##STR2## when n is 2 or 3, phenyl groups unsubstituted or substituted with alkyl group or alkoxy group; and antiulcer agents comprising an aforementioned conjugated .gamma.-hydroxybutenolide compound as an active ingredient.Type: GrantFiled: September 13, 1990Date of Patent: January 28, 1992Assignee: Kuraray Company Ltd.Inventors: Yoshin Tamai, Masahiro Torihara, Yoichi Kido, Johji Yamahara
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Patent number: 5084392Abstract: The invention provides a method for producing an optically active hydroxy lactone which comprises reacting under substantially anhydrous conditions and in the presence of an enzyme an ester and a racemic compound represented by the general formula (I): ##STR1## wherein n is 0 or 1, any one of R.sup.1 and R.sup.2 is a hydroxy group, and R.sup.2 =R.sup.3 =H or R.sup.2 =R.sup.3 =CH.sub.3 when R.sup.1 is the hydroxy group, and R.sup.1 =R.sup.3 =H when R.sup.2 is the hydroxy group, to effect a transesterification reaction, and resolving to an optically active alcohol which has R- or S-configuration and the ester of the symmetric alcohol.Type: GrantFiled: December 12, 1990Date of Patent: January 28, 1992Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida
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Patent number: 5082859Abstract: Derivatives of benzocycloalkenyldihydroxyalkanoic acids, inhibitors of HMG CoA reductase, antagonists of thromoboxane A.sub.2 receptors and antifungals, denoted by the formula I ##STR1## in which X=CH.sub.2, O or S; R.sub.1 and R.sub.2, identical or different, =H, C.sub.1-3 alkyl or together from a --(CH.sub.2).sub.n -- chain (n=4,5) optionally substituted symmetrically by one or two C.sub.1-3 alkyl radicals.R.sub.3 and R.sub.4, identical or different, =H, CF.sub.3, halogen (Cl, F, Br), C.sub.1-5 N,N-dialkylamino, C.sub.1-4 alkyl, C.sub.1-5 -alkoxy, C.sub.1-3 alkylthio, or phenyl optionally substituted by at most two substitutents which may be identical or different and may denote C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals or halogens (F, Cl), it being understood that when one of R.sub.3 and R.sub.4 denotes the radicals: CF.sub.3, N,N-dialkylamino, C.sub.6 H.sub.5 or substituted phenyl, it is present at the vertices 3', 4'or 5' according to formula 1 and the other denotes a hydrogen atom.R.sub.5 and R.sub.Type: GrantFiled: January 24, 1990Date of Patent: January 21, 1992Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Didier Festal, Jean-Yves Nioche, Denis Descours, Robert Bellemin, Jacques Decerprit
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Intermediates and processes for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents
Patent number: 5082954Abstract: Anti-inflammatory 4-substituted 2-furanones are made from intermediates having the formulas: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons; X is H, OH, NH.sub.2, I or Br; R.sub.4 is H, alkyl of 1-20 carbons, phenyl[C.sub.1 -C.sub.20 alkyl], naphthyl[C.sub.1 -C.sub.20 alkyl], CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, CH.sub.2 --COOH or CH.sub.2 --COOR.sub.5, and R.sub.5 is alkyl of 1 to 6 carbons, with the proviso that when X is hydrogen then R.sub.4 is selected from the group consisting of CH.sub.2 OH, CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 OH, CH.sub.2 --CHO, or CH.sub.2 --COOR.sub.5 ; ##STR2## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl or 1 to 6 carbons, and R.sub.5 is alkyl or 1 to 6 carbons; ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 independently are n-alkyl of 1 to 6 carbons, or branched chain alkyl of 1 to 6 carbons, and R.Type: GrantFiled: April 24, 1991Date of Patent: January 21, 1992Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst -
Patent number: 5081147Abstract: Compounds of the formula ##STR1## where R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1 *, CO--O--R.sub.1 *, CO--NH--R.sub.1 *, or PO(OR.sub.1 *).sub.2, PO(OR.sub.1 *)R.sub.1 * where R.sub.1 * independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl;R.sub.2 is H or alkyl of 1 to 20 carbons;X is H, R.sub.3, CO--R.sub.3, CO--O--R.sub.3, CO--NH--R.sub.3, CO--N--(R.sub.3).sub.2, PO(OR.sub.3).sub.2, PO(OR.sub.3)R.sub.3, and R.sub.3 independently is H, phenyl, substituted phenyl, alkyl of 1 to 20 carbons or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy or with a COR.sub.3 * group where R.sub.3 * is H, lower alkyl, OH, OR.sub.3 **, NH.sub.2, NHR.sub.3 ** or N(R.sub.3 **).sub.2 group wherein R.sub.3 ** independently is H or lower alkyl, with the proviso that when X is CO--O--R.sub.3 or is CO--NH--R.sub.3 then R.sub.3 is not hydrogen;Y is H, R.sub.4, CO--R.sub.4, CO--O--R.sub.Type: GrantFiled: March 15, 1990Date of Patent: January 14, 1992Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5081261Abstract: Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.* or PO(OR.sub.1.sup.*).sub.2 or PO(OR.sub.1.sup.*)R.sub.1.sup.* where R.sub.1.sup.* independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; R.sub.2 is H, alkyl of 1 to 20 carbons, or R.sub.2 and Y jointly represent a heterocycle which incorporates the sulfonamide nitrogen in the ring as a heteroatom; R.sub.3 is H or alkyl of 1 to 20 carbons; X is H, R.sub.4, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, CO--N--(R.sub.4).sub.2, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, and R.sub.4 independently is H, phenyl, substituted phenyl, alkyl of 1 to 20 carbons or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy, with a O--COR.sub.4.sup.* group or with a COR.sub.4.sup.* group where R.sub.4.sup.* is H, lower alkyl, OH, OR.sub.4.sup.**, NH.sub.2, NHR.sub.4.sup.** or N(R.sub.4.sup.**).sub.Type: GrantFiled: March 23, 1990Date of Patent: January 14, 1992Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5071871Abstract: New benz[b]pyranes and pyranopyridines of formula I, ##STR1## wherein the significances of substituents V, T, W, R.sub.3 to R.sub.5, R.sub.9, R.sub.10, m, X, Y and Z are given in claim 1 and their N-oxides and their salts and their use in the treatment of raised blood pressure in the treatment of vascular disorders and other disorders in which a reduction in tension of the smooth muscles is therapeutically useful, as well as in the treatment of hair loss and baldness. Further the compounds are useful in the treatment of asthma and obstructive disorders of the respiratory system as well as in the prophylactic treatment of obstructive or inflammatory airways disease, for example asthma, as well as novel pharmaceutical compositions comprising said K.sup.+ channel activators suitable for such use.Type: GrantFiled: July 10, 1990Date of Patent: December 10, 1991Assignee: Sandoz Ltd.Inventors: Stefan Blarer, John Morley, Ian D. Chapman
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Patent number: 5072005Abstract: Methyl 4-oxobutyrate and its methanol addition products, methyl 4,4-dimethoxybutyrate and gamma-methoxy-gamma-butyrolactone, which are useful as intermediates in the preparation of such industrially important compounds as gamma-butyrolactone, 1,4-butanediol and glutamic acid, are produced from the reaction of acrolein, carbon monoxide and methanol in the presence of a catalyst system which consists of (a) a Group VIII metal component selected from palladium metal or a palladium-containing composition which generates palladium metal under reaction conditions, (b) a hydrogen halide and (c) an arylarsine catalyst copromoter.Type: GrantFiled: July 9, 1987Date of Patent: December 10, 1991Assignee: National Distillers and Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5059611Abstract: New 5-hydroxy-2-furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.Type: GrantFiled: October 25, 1989Date of Patent: October 22, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5026725Abstract: This invention relates to 4-substituted-5-hydroxy-2(5H)-furanones, to the process for their preparation, to pharmaceutical compositions containing said 4-substituted-5-hydroxy-2(5H)-furanones and to the use of said 4-substituted-5-hydroxy-2(5H)-furanones for modifying the balance between bone production and bone resorption in a host animal, including man.Type: GrantFiled: February 23, 1990Date of Patent: June 25, 1991Assignee: American Home Products CorporationInventors: Marshall A. Hayward, Joseph P. Sabatucci, Ivo L. Jirkovsky, Yvon Lefebvre
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Patent number: 5015743Abstract: A 2,2-difluoro-2-desoxycarbohydrate is used to prepare antiviral nucleosides.Type: GrantFiled: December 15, 1989Date of Patent: May 14, 1991Assignee: Eli Lilly and CompanyInventor: Larry W. Hertel
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Patent number: 4968817Abstract: A process for preparing a substituted or unsubstituted gamma-crotonolactone is provided which comprises reacting a substituted or unsubstituted glycidol of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: July 10, 1989Date of Patent: November 6, 1990Assignee: National Distillers and Chemical CorporationInventor: Thomas S. Brima
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Patent number: 4965374Abstract: The present invention provides a process for preparing lactone intermediates to 2',2'-difluoronucleosides whereby reversion back to the lactone's open chain precursor is minimized and the desired erythro enantiomer can be selectively isolated from an enantiomeric mixture of erythro and threo lactones in crystalline form. Also provided is a process for producing 2'-deoxy-2',2'-difluoronucleosides in about a 1:1 .alpha./.beta. anomeric ratio, and processes for selectively isolating .beta.-2'-deoxy-2',2'-difluorocytidine, or an organic or inorganic acid addition salt thereof, from the 1:1 .alpha./.beta. mixture.Type: GrantFiled: December 4, 1989Date of Patent: October 23, 1990Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Perry C. Heath, Lawrence E. Patterson
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Patent number: 4957917Abstract: New furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-[1-acetoxy-2-N-(dodecyl) amidoethyl]-5-hydroxy-2(5H)-furanone.Type: GrantFiled: October 25, 1989Date of Patent: September 18, 1990Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 4952605Abstract: Analogs of the marine natural product manoalide are useful in treating mammals, including humans, in need of a drug having analgesic/anti-inflammatory, immunosuppressive, and/or antiproliferative activity.Type: GrantFiled: November 18, 1988Date of Patent: August 28, 1990Assignee: The Regents of the University of CaliforniaInventors: Robert S. Jacobs, D. John Faulkner
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Patent number: 4950818Abstract: A novel and useful method for treating and/or preventing ulcer in human beings is provided which comprises administering an effective amount of a pharmaceutical composition comprising at least one of the conjugated .gamma.-oxybutenolide compounds represented by the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different and represent hydrogen atoms, alkyl groups, hydroxyl groups, alkoxy groups, nitro groups, cyano groups or halogen atoms; and optionally at least one pharmaceutically acceptable carrier.Type: GrantFiled: June 21, 1989Date of Patent: August 21, 1990Assignee: Kuraray Company, Ltd.Inventors: Yoshin Tamai, Masahiro Torihara, Yoichi Kido, Johji Yamahara, Masayoshi Ito
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Patent number: 4923982Abstract: The 4-acyloxyazetidin-2-ones, which are intermediates in the production of carbapenems and penems, are produced from 4-furanylazetidin-2-ones by a sequential oxidation-reduction-oxidation reaction scheme.Type: GrantFiled: June 21, 1989Date of Patent: May 8, 1990Assignee: Merck & Co., Inc.Inventors: Joseph E. Lynch, William L. Laswell, Ralph P. Volante, Ichiro Shinkai
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Patent number: 4916241Abstract: This invention relates to 4-substituted-5-hydroxy-2(5H)-furanones, to the process for their preparation, to pharmaceutical compositions containing said 4-substituted-5-hydroxy-2(5H)-furanones and to the use of said 4-substituted-5-hydroxy-2(5H)-furanones for modifying the balance between bone production and bone resorption in a host animal, including man.Type: GrantFiled: June 6, 1988Date of Patent: April 10, 1990Assignee: American Home Products CorporationInventors: Marshall A. Hayward, Joseph P. Sabatucci, Ivo L. Jirkovsky, Yvon Lefebvre
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Patent number: 4891435Abstract: 4,4-Dimethyltetrahydrofuran-2,3-dione is prepared by reacting a dimethylpyruvate (II) with formaldehyde or a formaldehyde donor at 80.degree.-150.degree. C.Type: GrantFiled: April 3, 1985Date of Patent: January 2, 1990Assignee: BASF AktiengesellschaftInventors: Klaus Halbritter, Manfred Eggersdorfer