Acyclic -c(=x)-, Wherein X Is Chalcogen, Attached Directly Or Indirectly To The Lactone Ring By Nonionic Bonding Patents (Class 549/318)
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Patent number: 5565430Abstract: Disclosed are compounds, compositions and methods for inhibiting interleukinprotease activity. The compounds, .alpha.-substituted acetamides a ##STR1## wherein: R.sub.2 =H or alkyl;R.sup.3 =halo, O(CO).sub.0-1 aryl, OPOR.sup.4 R.sup.5 ; ##STR2## where R.sup.4 and R.sup.5 =aryl;R.sup.6 =H, aryl or aralkyl;R.sup.7 =independently selected from R.sup.6, CF.sub.3 and CF.sub.2 CF.sub.3 ;R.sup.1 =R.sup.6 -CO, heteroaryl-CO, heteroaralkyl-CO and amino acid.Type: GrantFiled: August 2, 1994Date of Patent: October 15, 1996Assignee: Sterling Winthrop Inc.Inventors: Roland E. Dolle, Todd L. Graybill
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Patent number: 5508302Abstract: There are disclosed compounds of the formula: ##STR1## wherein R.sup.1 is ##STR2## X is O, or S; Y is O or NOR.sup.2 ;R.sup.2 is alkyl, alkenyl, phenyl, --CH.sub.2 CO.sub.2 R.sup.3, --CH.sub.2 Ph, --CH.sub.2 C.sub.6 F.sub.5, or ##STR3## R.sup.3 is hydrogen, alkyl, phenyl, or phenylalkyl; R.sup.4, R.sup.5, and R.sup.6 are each, independently, hydrogen, alkyl, --OH, alkoxy, --CO.sub.2 R.sup.3, halogen, --NH.sub.2, alkylamino, dialkylamino, or --NO.sub.2 ;m=0-20; andn=0-10or a pharmacologically acceptable salt thereof which are useful as anti-inflammatory agents.Type: GrantFiled: September 28, 1994Date of Patent: April 16, 1996Assignee: American Home Products CorporationInventor: Dominic Mobilio
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Patent number: 5468774Abstract: There are disclosed compounds of the formula: ##STR1## wherein X is O;R.sup.1 and R.sup.2 are each, independently, hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.20 cycloalkyl, phenylloweralkyl, or substituted phenylloweralkyl substituted by halo, lower alkyl, lower alkoxy, halo lower alkyl, amino, monoloweralkylamino, diloweralkylamino or sulfonamido;A is O, S, NR, or a chemical bond;R, if present, is hydrogen or loweralkyl;m is 0-15;n is 3-12;p is 0-15,where m+p=2-15;and the pharmacologically acceptable salts thereof. Also disclosed is a method for treating immunoimmflammatory conditions in mammals which comprises administering to a mammal so afflicted an effective amount of a compound having the formula above wherein X, R.sup.1, R.sup.2, A, R, if present, m and p are as listed above and n=3-12 and m+p=2-15.Type: GrantFiled: March 14, 1995Date of Patent: November 21, 1995Assignee: American Home Products CorporationInventors: Guy A. Schiehser, Craig E. Caufield, Nancie A. Senko, Gregory F. VonBurg
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Patent number: 5462939Abstract: Disclosed are compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is (CR.sub.5 R.sub.6).sub.n, (CR.sub.5 R.sub.6).sub.n -aryl, (CR.sub.5 R.sub.6).sub.n -heteroaryl, X-(CR.sub.5 R.sub.6).sub.n, X-(CR.sub.5 R.sub.6).sub.n -aryl or X-(CR.sub.5 R.sub.6).sub.n -heteroaryl wherein aryl and heteroaryl may be optionally substituted;X is O or NR.sub.5 ;R.sub.5 and R.sub.6 are independently H or lower alkyl;R.sub.2 is H, halo, lower alkyl or (CR.sub.5 R.sub.6).sub.n -aryl;R.sub.3 and R.sub.4 are independently H or alkyl;A is a D or L isomer of an amino acid selected from the group consisting of alanine, valine, leucine, isoleucine, proline, phenylalanine, glycine, tyrosine, methionine, asparagine, glutamine, aspattic acid, glutamic acid, lysine, arginine, histidine and .beta.-thienylalanine;Z is CH.sub.2 or O; andn is 0-4;pharmaceutical compositions containing the compounds; and a method for inhibiting interleukin-1.beta.Type: GrantFiled: May 7, 1993Date of Patent: October 31, 1995Assignee: Sterling Winthrop Inc.Inventors: Roland E. Dolle, Todd L. Graybill, Gary J. Speier, Catherine P. Prouty, Stanley J. Schmidt
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Patent number: 5428058Abstract: There are disclosed compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, arylalkyl, --(CH.sub.2).sub.r CH.dbd.CH.sub.2, --(CH.sub.2).sub.s OY, --(CH.sub.2).sub.t CH(OZ)CH.sub.3, or Ar;X is O, S, or NR.sup.2 ;Y and Z are each, independently, hydrogen, alkyl, or --COR.sup.3 ;R.sup.2 and R.sup.3 are each, independently, hydrogen, alkyl, or arylalkyl;Ar is an aryl radical that may be optionally substituted;m=1-5;n=0-1;p=1-9;r=0-6;s=2-6; andt=0-6or a pharmaceutically acceptable salt thereof which are useful as antiinflammatory agents.Type: GrantFiled: September 28, 1994Date of Patent: June 27, 1995Assignee: American Home Products CorporationInventor: Dominic R. Mobilio
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Patent number: 5366993Abstract: There are disclosed compounds of the formula: ##STR1## wherein X is O, S or NR;R is hydrogen or lower alkyl;R.sup.1 and R.sup.2 are each, independently, hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.20 cycloalkyl, phenylloweralkyl, or substituted phenylloweralkyl substituted by halo, lower alkyl, lower alkoxy, halo lower alkyl, amino, monoloweralkylamino, diloweralkylamino or sulfonamido;A is O, S, NR, or a chemical bond;m is 0-15;n is 0-20;p is 0-15,where m+p.ltoreq.15;and the pharmacologically acceptable salts thereof, which by virtue of their ability to inhibit PLA.sub.2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals, as well as in the modulation of PAF-mediated biological processes, such as embryonic implantation, thus making the compounds useful as antifertility agents.Type: GrantFiled: June 3, 1993Date of Patent: November 22, 1994Assignee: American Home Products CorporationInventors: Guy A. Schiehser, Craig E. Caufield, Nancie A. Senko, Gregory F. VonBurg
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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: 5328916Abstract: New heterocyclic compounds of the formulaX--W--CR.sup.1 R.sup.2 --CO--Y--NR.sup.3 --CHR.sup.4 --CR.sup.5 --CH.sub.2 --(CR.sup.6 R.sup.7).sub.r --Z--Het Iin which R.sup.1 to R.sup.7, W, X, Y, Z, r and Het have the meanings defined herein, and the salts thereof, inhibit the activity of human plasma renin.Type: GrantFiled: May 2, 1991Date of Patent: July 12, 1994Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Peter Raddatz, Claus J. Schmitges, Klaus-Otto Minck
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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: 5258400Abstract: 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: April 23, 1992Date of Patent: November 2, 1993Assignee: Allergan, Inc.Inventors: Michael E. Garst, Elizabeth T. Syage
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Patent number: 5256689Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents and as inhibitors of squalene synthase.Type: GrantFiled: October 26, 1992Date of Patent: October 26, 1993Assignee: Merck & Co., Inc.Inventor: Yuan-Ching P. Chiang
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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: 5202350Abstract: New compounds (3-alkyl-5-hydroxy-3,4-dihydrofuran-2-ones) of the following general structure: ##STR1## wherein R is an alkyl group or a phenylalkyl group with the alkyl moiety containing at least 6 carbon atoms, are disclosed as useful in inhibiting phospholipase A.sub.2.Type: GrantFiled: August 29, 1991Date of Patent: April 13, 1993Assignee: Bristol-Myers Squibb Co.Inventors: F. Christopher Zusi, Suresh Marathe, William Somerville, Kenneth M. Tramposch
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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: 5171864Abstract: Compounds of the formula ##STR1## in which R.sub.1 independently 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; A is (CH.sub.2).sub.n where n ranges between 5 to 30, or A is a a divalent branch chained alkyl radical, or cycloalkyl radical, having a total of 5 to 30 carbons, and X is O or NH, have anti-inflammatory activity.Type: GrantFiled: August 30, 1991Date of Patent: December 15, 1992Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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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: 5169963Abstract: Compounds of the formula ##STR1## in which R.sub.1 independently is H or alkyl of 1 to 29 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; A is (CH.sub.2).sub.n where n ranges between 0 to 30, or A is a a divalent branch chained alkyl radical, or cycloalkyl radical, having a total of 3 to 30 carbons; R.sub.3 independently is an alkyl group having 4 to 20 carbons, and X is O or NH, have anti-inflammatory activity.Type: GrantFiled: August 30, 1991Date of Patent: December 8, 1992Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5164518Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.Type: GrantFiled: July 12, 1991Date of Patent: November 17, 1992Assignee: Iowa State University Research Fondation Inc.Inventor: Richard C. Larock
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Patent number: 5162368Abstract: Butalactin, a compound of the formula I ##STR1## can be produced by cultivation of Streptomyces species Y-86,36923. Butalactin has an antibiotic activity.Type: GrantFiled: August 6, 1990Date of Patent: November 10, 1992Assignee: Hoechst AktiengesellschaftInventors: Christopher M. M. Franco, Erra K. Vijayakumar, Sugata Chatterjee, Bimal N. Ganguli, Jurgen Blumbach
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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: 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: 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: 5099034Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are --COOR.sup.4, --COOR.sup.5, and --COOR.sup.6, respectively; R.sup.4, R.sup.5, and R.sup.6 each is hydrogen, lower alkyl, or alkali metal; W is hydroxyl; X, Y, and Z each is hydrogen or hydroxyl; a dotted line indicates the presence or absence of a single bond; or where W/R.sup.3, X/R.sup.1, and/or Z/R.sup.3 may be combined together, a lactone is formed, which compound is useful as a phospholipase A.sub.2 inhibitor. Process for the production of the compound (I) and a cell culture of a microorganism Circinotrichum falcatisporum RF-641 producing the same are also provided.Type: GrantFiled: June 27, 1990Date of Patent: March 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadashi Yoshida, Hiroshi Itazaki, Hitoshi Arita, Yoshimi Kawamura, Koichi Matsumoto
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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: 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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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: 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: 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: 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: 5045458Abstract: A compound of the formula (I): ##STR1## wherein R is: (CH.sub.2).sub.8 CH.sub.3,(CH.sub.2).sub.3 CH.sup.(cis) CH(CH.sub.2).sub.5 CH.sub.3,(CH.sub.2).sub.10 CH.sub.3, or(CH.sub.2).sub.4 CH.sup.(cis) CH(CH.sub.2).sub.6 CH.sub.3.or salt thereof, and a microorganism producing the compound are provided.Type: GrantFiled: October 19, 1989Date of Patent: September 3, 1991Assignee: Shionogi & Co., Ltd.Inventors: Tadashi Yoshida, Teruo Hattori, Koichi Matsumoto, Yoshihiro Terui, Junichi Shoji
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Patent number: 5037811Abstract: Compounds of the formula ##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; X is O, S, SO--, SO.sub.2, NH--, or NR.sub.2 where R.sub.2 is phenyl, substituted phenyl or alkyl of 1 to 20 carbons, and Y is alkyl having at least 6 carbon atoms, arylalkyl, aryl, substituted aryl, substituted arylalkyl, alkenyl containing one or more olephinic bonds and at least 6 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, substituted aryl, substituted arylalkyl, alkyl, alkenyl containing one or more olephinic bonds, further Y is (CH.sub.2).sub.n --O--R.sub.4, or (CH.sub.2).sub.n --O--(CH.sub.2).sub.m --O--R.sub.4, where n, and m, are integers and are independently 1 to 25 and R.sub.Type: GrantFiled: April 17, 1990Date of Patent: August 6, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5013850Abstract: Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbon, CO--R.sub.1 * CO--O--R.sub.1 * CO--NH--R.sub.1 * or PO(OR.sub.1 *).sub.2 or PO(OR.sub.1 *)R.sub.1 * where R.sub.1 * independently is alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; X is long chain alkyl having at least 5 carbon atoms, long chain alkyl of at least 5 carbons substituted with an aryl group, or long chain alkyl of at least 5 carbons substituted with a substituted aryl group; Y is COOH, COOR.sub.2, CONH.sub.2, CONHR.sub.2, CON(R.sub.2).sub.2, CHO, COR.sub.2 ; COCF.sub.3, COCHF.sub.2, CH.dbd.NR.sub.2, CR.sub.2 .dbd.N--R.sub.2, CH.dbd.N--NHR.sub.2, CH.dbd.N--N(R.sub.2).sub.2, CH.dbd.NOH, CR.sub.2 .dbd.N--OH, CH.dbd.NOR.sub.2, CR.sub.2 .dbd.NOR.sub.2, CH.sub.2 OH, CHR.sub.2 OH, C(R.sub.2).sub.2 OH, CH.sub.2 OR.sub.2 * CHR.sub.2 OR.sub.2 * C(R.sub.2).sub.2 OR.sub.2 * SO.sub.2 R.sub.2, PO(OR.sub.3).sub.2, and PS(OR.sub.3).sub.2, where R.sub.Type: GrantFiled: March 30, 1990Date of Patent: May 7, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 4965283Abstract: Novel esters of amino acids are proposed of which the alcoholic components are formed from threo-4-alkoxy-5-arylhydroxymethyl-2(5H)-furanones. These esters may be present in the form of racemates, pure diastereomers or enantiomers or in the form of diastereomer or enantiomer mixtures. The compounds are anticonvulsive and antiepileptic and due to their good water solubility are easier to administer and more readily absorbable than known anti-convulsives and antiepileptics. A novel process is also disclosed which leads stereoselectively to the diastereomers or the enantiomers or mixtures thereof. The invention further relates to the use of the novel amino acid esters as pharmaceutical preparations and in the production of pharmaceutical preparations.Type: GrantFiled: June 28, 1989Date of Patent: October 23, 1990Assignee: Dr. Willmar Schwabe GmbH & Co.Inventors: Klaus Klessing, Shyam S. Chatterjee
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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: 4935530Abstract: A process for preparing 5-substituted-3-furaldehydes which comprises reacting 3-furaldehyde with lithium morpholide, followed by sec-butyl lithium, followed by an electrophile.Type: GrantFiled: October 18, 1988Date of Patent: June 19, 1990Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 4882434Abstract: A compound represented by formula (I): ##STR1## wherein R.sup.1 is an organic residue through a carbon atom,R.sup.2 is a carboxyl group which may be esterified or amidated, andX is an oxygen atom, or a sulfur atom which may be oxidized,or a salt thereof, which is useful as antibacterial agent or intermediate for synthesizing the same, and a process for preparing the same.Type: GrantFiled: October 21, 1987Date of Patent: November 21, 1989Assignee: Takeda Chemical Industries, Ltd.Inventor: Kouichi Yoshioka
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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: 4837344Abstract: A compound having the formula: ##STR1## wherein R is a hydroxyl-protecting group, X is a hydrogen atom, CO.sub.2 R' (wherein R' is a hydrogen atom or an alkyl group having from 1 to 7 carbon atoms, or CO.sub.2 R' is a salt of CO.sub.2 H), or a group of the formula: ##STR2## and when X is a hydrogen atom, Y is CO.sub.2 R' (wherein R' is as defined above) or a group of the formula: ##STR3## and when X is CO.sub.2 R' or the group of the formula (i), Y is a hydrogen atom.Type: GrantFiled: June 17, 1987Date of Patent: June 6, 1989Assignee: Nissan Chemical Industries Ltd.Inventors: Katsuaki Miyaji, Kazutaka Arai, Yoshio Ohara, Yasuhiro Takahashi
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Patent number: 4833259Abstract: The novel sunscreen agents which are esters, namely esters of p-methoxy-cinnamic acid with d,1-.alpha.-tocopherol, pantolactone or panthenol.Type: GrantFiled: August 24, 1987Date of Patent: May 23, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Gustav Erlemann, Christian Fizet, Horst Pauling
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Patent number: 4824972Abstract: Compounds of the general formula ##STR1## wherein R represents an ether protecting group and R.sup.1 is a group of (a)-(d) useful as intermediates.Type: GrantFiled: January 19, 1988Date of Patent: April 25, 1989Assignee: Hoffmann-LaRoche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4789749Abstract: 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: February 19, 1986Date of Patent: December 6, 1988Assignee: The Regents of the University of CaliforniaInventors: Robert S. Jacobs, D. John Faulkner
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Patent number: 4766148Abstract: Biphenylylpropionic acid derivatives of the formula: ##STR1## wherein R is an alkylcarbonyloxyalkyl group or an alkenylcarbonyloxyalkyl group having the formula: ##STR2## wherein R.sup.1 is a lower alkyl group having 1 to 5 carbon atoms and R.sup.2 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, or a lactone having the formula: ##STR3## wherein R.sup.3 and R.sup.4 are hydrogen atom or a lower alkyl group having 1 to 2 carbon atoms, and n is an integer of 1 or 2. The compounds have excellent anti-inflammatory, analgesic and antipyretic activities. Moreover, the compounds have no irritation, rapid and long-acting, and high safety margin.Type: GrantFiled: June 7, 1985Date of Patent: August 23, 1988Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Katsuhiro Uchida, Shozo Masumoto, Masao Tohno, Mitsuo Mimura, Makoto Okumura
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Patent number: 4743696Abstract: Compounds of the general formula ##STR1## wherein R represents an ether protecting group and R.sup.3 is a group of (f)-(i) useful as intermediates.Type: GrantFiled: March 5, 1987Date of Patent: May 10, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4616089Abstract: Synthetic analogs of the marine natural product manoalide include 3,7-Bis(hydroxymethyl)-4-hydroxy-11-methyl-13-(2',6',6'-trimethylcyclohexe nyl)-2,6,10-tridecatrienoic acid .gamma.-lactone, manoalide .delta.-lactone, manoalide .delta.-lactone acetate and dehydro-seco-manoalide.The method of treating mammals including humans in need of a drug having analgesic and/or anti-inflammatory activity comprising the administration of a therapeutically effective amount of a synthetic analog of manoalide.Type: GrantFiled: June 18, 1984Date of Patent: October 7, 1986Assignee: University of CaliforniaInventors: Robert S. Jacobs, D. John Faulkner
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Patent number: 4585789Abstract: Described are compounds of the formula: ##STR1## Wherein A is a lower alkylene group;R.sup.1 is a carboxy, hydroxy, lower alkoxycarbonyl, lower alkoxycarbonylamino, phenyl(lower)alkyloxy, benzoyloxy or lower alkanoyloxy group;R.sup.2 is a hydrogen or halogen atom or a halo(lower)alkyl group;R.sup.3 is a hydrogen or halogen atom;R.sup.4 is hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyloxy group; andR.sup.5 is a hydrogen or halogen atom;Q is the number of double bonds which is equal to 0 or 1;n is an integer of 0 or 1, provided that when Q is 0, n is 1 and when Q is 1, n is 0.Type: GrantFiled: June 29, 1983Date of Patent: April 29, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masanori Okamoto, Itsuo Uchida, Kazuyoshi Umehara, Masanobu Kohsaka, Hiroshi Imanaka
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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: 4443471Abstract: Novel ether, ester, urethane, thiourethane and carbonate derivatives of the ruminant growth promoters, M.139,603, M.139,603-adlehyde and oxime etc. derivatives thereof, all of which are effective in reducing the proportion of methane produced by ruminal fermentation, and increasing the proportion of propionic acid at the expense of acetic acid in the rumen contents; together with processes for their manufacture, compositions containing them, and their use in increasing growth and/or feed efficiency in ruminant animals.Type: GrantFiled: June 21, 1982Date of Patent: April 17, 1984Assignee: Imperial Chemical Industries PLCInventors: David H. Davies, Michael J. Smithers
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Patent number: 4423236Abstract: Novel condensation products between enediol ketolactones such as 5,6-0-isopropylidene ascorbic acid and 2-chloroethyl isocyanates are shown to have potent antitumor activity probably without the release of alkylating agents in vivo. While the structures of the products are not readily elucidated, activity is found to exceed that of BCNU (bis-(2-chloroethyl)-N-nitrosourea) and parallel that of the toxic and highly effective nitrosourea, MeCCNU (1-(4-trans-methylcyclohexyl)-3-(2-chloroethyl)-3-nitrosourea). Preferred compounds are condensation products of ##STR1## wherein R.sub.2 and R.sub.3 are a lower alkyl group containing 1 to 3 carbon atoms or H andhal--CH.sub.2 --CH.sub.2 --N.dbd.C.dbd.O (B)wherein hal is I, Br or Cl.Type: GrantFiled: October 23, 1981Date of Patent: December 27, 1983Assignee: National Foundation for Cancer Research, Inc.Inventor: Andrew J. Welebir