Cyclopentanohydrophenanthrene Ring System Patents (Class 536/5)
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Patent number: 5795870Abstract: The present invention relates to methods and compositions for the transformation of cells. In particular, compositions and methods are disclosed which include combinations of the nucleic acid of interest and polyhydroxylated or polyglycosylated steroid molecules. Most preferably, exogenous or endogenous nucleic acid is contacted with the cell in the presence of a bile acid (e.g., cholic acid) derivatized with an amine-containing side chain.Type: GrantFiled: November 7, 1994Date of Patent: August 18, 1998Assignee: Trustees of Princeton UniversityInventor: Suzanne Walker Kahne
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Patent number: 5780444Abstract: The present invention relates to methods and compositions for the transformation of cells. In particular, compositions and methods are disclosed which include combinations of the nucleic acid of interest and polyhydroxylated or polyglycosylated steroid molecules. Most preferably, exogenous or endogenous nucleic acid is contacted with the cell in the presence of a bile acid (e.g., cholic acid) derivatized with an amine-containing side chain.Type: GrantFiled: April 20, 1995Date of Patent: July 14, 1998Assignee: Trustees of Princeton UniversityInventor: Suzanne Walker Kahne
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Patent number: 5770578Abstract: The use of triterpensaponins, like notoginsenoside R1 (NR1) and/or astragaloside (ASIV) for the production of medicaments for stimulating the fibrinolytic activity and blocking the endotoxin effect, especially for the treatment of patients and animals which suffer from endotoxin shock or to limit the endotoxin shock. Corresponding medicaments are also suitable prophylactive and therapeutic treatment of patients of coronary heart disease, peripheral arterial disease for patients who suffer from angina pectoris and for the prevention of such diseases in healthy persons.Type: GrantFiled: January 4, 1996Date of Patent: June 23, 1998Assignee: Bergi GmbHInventors: Bernd Binder, Weijian Zhang, Johann Wojta
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Patent number: 5770701Abstract: This disclosure describes a method for constructing targeting agent drug conjugates from the family of methyltrithio antibacterial and antitumor agents.Type: GrantFiled: October 26, 1994Date of Patent: June 23, 1998Assignee: American Cyanamid CompanyInventors: William James McGahren, Martin Leon Sassiver, George A. Ellestad, Philip R. Hamann, Lois M. Hinman, Janis Upeslacis
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Patent number: 5762943Abstract: Methods and compositions for treating type I immunoglobin E (IgE)-dependent hypersensitivity by the administration of monophosphoryl lipid A (MLA) or 3-deacylated monophosphoryl lipid A (3D-MLA) are disclosed. MLA or 3D-MLA administered alone or in combination with an allergen to a patient suffering from type I hypersensitivity reduces levels of total or allergen specific IgE and increases levels of IgG antibody in that patient. MLA and 3D-MLA can be administered as part of a desensitization regimen or as a component of a prophylactic vaccine to prevent a type I hypersensitivity reaction.Type: GrantFiled: May 14, 1996Date of Patent: June 9, 1998Assignee: Ribi ImmunoChem Research, Inc.Inventors: Jerry Dolovich, J. Terry Ulrich, Jean S. Marshall
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Patent number: 5763582Abstract: Triterpenoid acid derivatives are described that exhibit dual pharmacophobic activities, specifically selectin ligand and leukotriene biosynthetic inhibitory activities, and that thus have significant applications for the treatment or prevention of certain diseases including cancer and diseases associated with the inflammatory process as well as applications for the diagnosis of disease.Type: GrantFiled: June 6, 1995Date of Patent: June 9, 1998Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Mark Brian Anderson, John Henry Musser
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Patent number: 5744453Abstract: The present invention relates to methods of preventing or treating an infection or disease caused by an infectious agent. The present invention also relates to the augmentation of the efficacy of existing anti-infective agents by the co-administration of the compounds described herein.Type: GrantFiled: January 5, 1996Date of Patent: April 28, 1998Inventors: Clifford S. Mintz, Natan A. Kogan, Ramesh Kakarla, Helena R. Axelrod, Michael J. Sofia
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Patent number: 5739302Abstract: There are described novel glycosides of catechol estrogen, a method of preparing the same, and a medicament comprising one of the glycosides as an active ingredient. The glycosides are shown by the formula of ##STR1## wherein X is carbonyl group or ##STR2## R.sub.10 is hydroxyl group or glycosyloxy group, and R.sub.2 is a hydrogen atom or ethynyl group; R.sub.11 is a hydrogen atom, hydroxyl group, or glycosyloxy group; R.sub.12 is hydroxyl group or glycosyloxy group; and R.sub.13 is hydroxyl group or glycosyloxy group, in which glycosyloxy group is selected from the group consisting of glycosyloxy, galactosyloxy, mannosyloxy, arabinosyloxy, ribosyloxy, xylosyloxy, fructosyloxy, rhamnosyloxy, fucosyloxy, maltosyloxy, cellobiosyloxy, lactosyloxy, sucrosyloxy, maltotriosyloxy, maltotetraosyloxy, maltopentaosyloxy, maltohexaosyloxy, maltoheptaosyloxy, and sialosyloxy, and in this case, at least one of R.sub.10, R.sub.11, R.sub.12, and R.sub.13 is glycosyloxy group as defined above.Type: GrantFiled: October 5, 1994Date of Patent: April 14, 1998Assignee: Institute of Applied BiochemistryInventors: Takehiko Suzuki, Sadaaki Komura, Naoko Ishida, Nobuko Ohishi, Kunio Yagi
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Patent number: 5721217Abstract: Disclosed are 14-aminosteroid compounds, including pharmaceutically acceptable acid salts and esters thereof, useful in treating individuals afflicted with congestive heart failure, which compounds have the general formula: ##STR1## wherein R.sub.3 is a deoxy or oxygen-substituted monosaccharide sugar residue and R.sub.1, R.sub.2 and R.sub.4 are various other substituents as defined herein.Type: GrantFiled: June 2, 1995Date of Patent: February 24, 1998Assignee: The Procter & Gamble CompanyInventors: Song Liu, David Edward Portlock, Gilles Yves Genain, Jean-Jacques Koenig, Jacques de Rostolan
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Patent number: 5716937Abstract: A method of treating cardiac malfunction by administering a positive inotropic effect-producing amount of Hypothalamic Inhibitory factor (HIF).Type: GrantFiled: November 10, 1994Date of Patent: February 10, 1998Assignee: The General Hospital CorporationInventor: Garner Haupert, Jr.
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Patent number: 5710259Abstract: The present invention relates to oligosaccharide-containing 14-aminosteroid compounds and the pharmaceutically-acceptable acid salts or esters thereof of the general formula: ##STR1## wherein a) R.sub.1 is(i) COOR.sub.5, whereR.sub.5 is hydrogen, a 1-6 carbon lower alkyl; a 1-6 carbon lower alkyl substituted by an amino group; an arylalkyl or heteroarylalkyl or a carbocyclic ring, or(ii) CHR.sub.6 OH, whereR.sub.6 is a hydrogen atom or 1-6 carbon lower alkyl group, or(iii) COR'", where R'" is hydrogen; 1-6 carbon lower alkyl; 1-6 carbon lower alkyl substituted amino; amino or dialkylamino; andb) R.sub.2 is --NR.sub.7 R.sub.8, whereR.sub.7 and R.sub.8, which may be the same or different, are hydrogen atoms or a 1-6 carbon lower alkyl; andc) R.sub.3 is an oligosaccharide sugar residue; andd) R.sub.4 is(i) OH, or(ii) H, or(iii) OR.sub.13, whereR.sub.13 is a monosaccharide sugar residue; acetoxy; benzoxy; arylalkyl or heteroarylalkyl; ande) Z is(i) --CH--, wherea and b are single bonds, or(ii) .dbd.Type: GrantFiled: June 2, 1995Date of Patent: January 20, 1998Assignee: The Procter & Gamble CompanyInventors: Paul Michael Dybas, Roland Norman Johnson, Randy Stuart Muth, Song Liu
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Patent number: 5703052Abstract: Certain steroidal glycosides are useful as hypochoelsterolemic agents and antiatherosclerosis agents.Type: GrantFiled: June 6, 1995Date of Patent: December 30, 1997Assignee: Pfizer Inc.Inventors: Michael Paul Deninno, Peter Andrew McCarthy
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Patent number: 5698527Abstract: Ergostanone derivatives substituted with dissaccharides are cholesterol absorption inhibitors useful in the treatment of hypercholesterolemia and related disorders. These cholesterol absorption inhibitors may be employed alone or in combination with other cholesterol lowering agents.Type: GrantFiled: July 30, 1996Date of Patent: December 16, 1997Assignee: Merck & Co., Inc.Inventor: Dooseop Kim
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Patent number: 5695738Abstract: Compositions of sterodial glycosides are described wherein the glycoside is linked directly, or indirectly to a desired steroidal compound via a carbon, or similar stable linkage, and methods of using the compositions to treat patients by binding to and/or blocking cellular receptors for a variety of diseases including cancer, inflammation, and autoimmune diseases.Type: GrantFiled: June 15, 1995Date of Patent: December 9, 1997Assignee: Glycomed IncorporatedInventors: Mark Anderson, John Henry Musser
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Patent number: 5693769Abstract: Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes, either in admixture or as conjugates, are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is provided. Methods for the permeabilization of membranes and the enhancement of the activity of predetermined compounds are also provided.Type: GrantFiled: April 20, 1994Date of Patent: December 2, 1997Assignees: Transcell Technologies, Inc., Trustees Of Princeton UniversityInventors: Daniel Evan Kahne, Suzanne Walker Kahne
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Patent number: 5693770Abstract: The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Novel intermediates and related compounds are also disclosed. In particular, the present invention permits the conversion of cholic acid esters to the 3-amino-7,12-bis(glucosyl)cholic acid esters via an azide intermediate. Conditions for the purification and isolation of the desired product is also disclosed to provide an overall manufacturing process suitable for large-scale production.Type: GrantFiled: June 23, 1995Date of Patent: December 2, 1997Assignee: Transcell Technologies, Inc.Inventors: Anna K. Chen, Ramesh Kakarla, Dashan Liu, Michael J. Sofia, Thomas C. Zebovitz
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Patent number: 5691307Abstract: Novel O.sup.6 -substituted guanine compounds and pharmaceutical compositions thereof are useful for effectively reducing O.sup.6 -alkylguanine-DNA alkyltransferase (AGT). The novel compounds are useful for treating tumors and when used with anti-neoplastic alkylating agents enhance the chemotherapeutic treatment of tumor cells in a host.Type: GrantFiled: June 7, 1994Date of Patent: November 25, 1997Assignees: The United States of America as represented by the Department of Health and Human Services, The Penn State Research Foundation, Arch Development CorporationInventors: Robert C. Moschel, M. Eileen Dolan, Anthony E. Pegg, Mark G. McDougall, Mi-Young Chae
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Patent number: 5679644Abstract: Triterpenoid acid derivatives are described that exhibit dual pharmacophobic activities, specifically selectin ligand and leukotriene biosynthetic inhibitory activities, and that thus have significant applications for the treatment or prevention of certain diseases including cancer and diseases associated with the inflammatory process as well as applications for the diagnosis of disease.Type: GrantFiled: June 6, 1995Date of Patent: October 21, 1997Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Mark Brian Anderson, John Henry Musser
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Patent number: 5652346Abstract: What is disclosed is a dicarboxylic acid oxidation product of a immunologically reactive mono- or a polysaccharide having vicinal diols.Type: GrantFiled: March 6, 1996Date of Patent: July 29, 1997Assignee: Johnson & Johnson Clinical Diagnostics, Inc.Inventors: Michael Ray Detty, Susan Jean Danielson
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Patent number: 5650398Abstract: Disclosed herein are modified saponins or fractions thereof obtainable by modification of a crude Quillaja saponaria extract or by modification of purified saponins obtainable from a crude Quillaja saponaria extract useful in pharmaceutical compositions for enhancing the transport of pharmacologically active substances across mucous membranes of an animal. Also disclosed are modified saponins having reduced irritability wherein the aldehyde group is reduced and the fatty acid moiety may be removed by hydrolysis. Also disclosed are pharmaceutical compositions comprising the modified saponins of the invention.Type: GrantFiled: June 2, 1995Date of Patent: July 22, 1997Assignee: Cambridge Biotech CorporationInventors: Charlotte A. Kensil, Sean Soltysik, Dante J. Marciani, Joanne Recchia
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Patent number: 5643889Abstract: A cholesterol-cordycepin conjugate having the formula ##STR1## wherein: n is an integer from 1 to 8; R.sub.1 is selected from the group of consisting of T, T' and Y; T is ##STR2## T' is ##STR3## where x is an integer from 1 to 18; Y is ##STR4## where m is zero, 1, 2, or 3; each R.sub.2 is independently selected from the group consisting of oxygen and sulfur; each R.sub.3 is independently selected from the group consisting of hydrogen and hydroxyl; R.sub.4 is selected from the group consisting of hydrogen, hydroxyl and T or T'; R.sub.5 is selected from the group consisting of hydrogen, hydroxyl and T or T'; provided that all R.sub.1, R.sub.4 and R.sub.5 may not be T or T'; at least one R.sub.3 is hydrogen or R.sub.4 is hydrogen; and at least one of R.sub.1, R.sub.4 and R.sub.5 must be T or T'; or a water soluble salt thereof. The compounds possess increased antiviral activity and/or metabolic stability.Type: GrantFiled: September 14, 1994Date of Patent: July 1, 1997Assignee: Temple University-of the Commonwealth System of PennsylvaniaInventors: Robert J. Suhadolnik, Wolfgang Pfleiderer
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Patent number: 5643884Abstract: This invention relates generally to the field of medicinal chemistry, and more specifically to derivatives of a subclass of triterpenoid acids that have multi-medicament properties, that is derivatives of the lupane, betulinic acid, formulations containing such, and their use to prevent or treat certain diseases, and preferably to derivatives or analogues of betulinic acid, that have the following structural formula (1): ##STR1## wherein: Y is OR.sup.1, NR.sup.1.sub.2, O.sup.- M.sup.1 ;R.sup.1 is H, LOWER ALKYL,M.sup.1 is Na.sup.+, K.sup.+, Mg.sup.++, Ca.sup.++ ions;each R.sup.2 is independently CH.sub.2 OR.sub.1 or CH.sub.3 ;each R.sup.3 is independently H, CH.sub.3, lower alkyl, COY, CH.sub.2 OH, CH.sub.2 OCH.sub.2 CH=CH.sub.2, CH.sub.2 OSO.sub.3.sup.- M.sup.1 ;each Z is independently NHR.sup.1.sub.2, NR.sup.1 Ac, NR.sup.1 Bz, H, OCH.sub.3, lower alkyl, OH, OSO.sub.3.sup.- M.sup.1, OCH.sub.2 CH=CH.sub.2, OCH.sub.2 CO.sub.2 H or O-glucoside;each X is independently O, S, NR.sup.1 or NR.sub.2.sup.Type: GrantFiled: August 9, 1993Date of Patent: July 1, 1997Assignee: Glycomed IncorporatedInventors: Mark Brian Anderson, John Henry Musser
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Patent number: 5629295Abstract: The application discloses steroidal glycoside compounds, especially spirostanyl glycosides, which have a glycosyl group O-linked to the C-3 hydroxy radical of the steroid and where the moieties at the C-10 and C-11 positions of the steroid are the same or different and are selected from the group consisiting of methylene, hydroxy and carbonyl. These steroid glycosides are useful as hypocholesterolemic agents and anti-atherosclerosis agents.Type: GrantFiled: December 20, 1994Date of Patent: May 13, 1997Assignee: Pfizer Inc.Inventors: Michael P. Deninno, Peter A. McCarthy
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Patent number: 5627270Abstract: Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes, either in admixture or as conjugates, are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is provided. Methods for the permeabilization of membranes and the enhancement of the activity of predetermined compounds are also provided.Type: GrantFiled: June 23, 1994Date of Patent: May 6, 1997Assignees: Trustees of Princeton University, Transcell Technologies, Inc.Inventors: Daniel E. Kahne, Suzanne W. Kahne, Michael J. Sofia, Nicole T. Hatzenbuhler
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Patent number: 5620690Abstract: The invention relates to immunogenic complexes such as two-dimensional lamellae having a honeycomb structure and in particular three-dimensional iscoms, which immunogenic complexes are composed of at least one sterol, one saponin and, in the case of iscoms, also a phospholipid and also, optionally, at least one antigen generating an immune reaction. The saponin used is at least one of the fractions which are derived from Quil A by means of hydrophobic interaction chromatography and have the designations QA 1 to QA 23, as is shown in the figure by the numerals 1 to 23. Preferably, the saponin used is one or more of the fractions derived from Quil A having the designations QA 3, QA 17 and QA 23.Type: GrantFiled: April 19, 1993Date of Patent: April 15, 1997Assignee: De Stat Der Nederlanden Vertegenwoordigd Door De Minister Van Welzijn Volksgezondheid En CultuurInventors: Gideon F. A. Kersten, Arjan Spiekstra, Gerrit Van Der Werken, Eduard C. Beuvery
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Patent number: 5612317Abstract: The present invention relates to methods for the treatment or prevention of osteoporosis and the alleviation of the symptoms of menopause by the administration of an estrogen glycoside or estrogen orthoester glycoside.Type: GrantFiled: August 4, 1994Date of Patent: March 18, 1997Inventor: Michael F. Holick
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Patent number: 5610151Abstract: Monomeric bile acid derivatives, processes for their preparation and the use of these compounds as medicamentsMonomeric bile acid derivatives of the formula IZ--X--GS I,in which GS, X and Z have the meanings given, and processes for their preparation are described. The compounds have useful pharmacological properties and can therefore be used as medicaments.Type: GrantFiled: May 5, 1994Date of Patent: March 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Heiner Glombik, Alfons Enhsen, Werner Kramer, G unther Wess
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Patent number: 5606041Abstract: Processes for the synthesis of tigogenin beta-O-cellobioside heptaalkanoate which is an intermediate for the known hypo-cholesterolemic agent tigogenin beta-cellobioside. The process comprises reacting .alpha.-cellobiosyl bromide heptaalkanoate and .beta.-tigogenin in the presence of zinc fluoride or zinc cyanide under conditions capable of forming said tigogenyl .beta.-O-cellobioside heptaalkanoate. The analogous preparations of hecogenin .beta.-O-cellobioside heptaalkanoate 11-ketotigogenin .beta.-O-cellobioside heptaalkanoate, and diosgenin .beta.-O-cellobioside heptaalkanoate are also disclosed. The process provides both high .beta.-anomeric selectivity and high yields.Type: GrantFiled: December 20, 1994Date of Patent: February 25, 1997Assignee: Pfizer Inc.Inventors: Frank R. Busch, Kathleen D. Goggin, John F. Lambert, Russell J. Shine, Stanley W. Walinsky
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Patent number: 5597806Abstract: There are disclosed novel compounds having the formula ##STR1## which exhibit antifungal activity.Type: GrantFiled: May 9, 1995Date of Patent: January 28, 1997Assignee: Merck & Co., Inc.Inventors: Wendy H. Clapp, Guy H. Harris, Gerald F. Bills, James E. Curotto, Anne W. Dombrowski, Sarah J. Driekorn, Myra B. Kurtz, Maria S. Meinz, Janet C. Onishi, Jon D. Polishook, Stanley L. Streicher, John R. Thompson, Marie Williams, Deborah L. Zink
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Patent number: 5591836Abstract: Disclosed are novel saponins containing 5-C-hydroxymethylhexose and a sterol or triterpene. These materials, when consumed by humans and animals, lower the cholesterol level in the blood. These compounds can be administered as pharmaceutical preparation to the diet, or incorporated into food compositions.Type: GrantFiled: October 7, 1993Date of Patent: January 7, 1997Assignee: The Procter & Gamble CompanyInventors: Adam W. Mazur, Stanislaw Pikul, Bruce P. Daggy
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Patent number: 5585470Abstract: The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Novel intermediates and related compounds are also disclosed.Type: GrantFiled: June 23, 1994Date of Patent: December 17, 1996Assignee: Transcell Technologies, Inc.Inventors: Anna K. Chen, Ramesh Kakarla, Dashan Liu, Michael J. Sofia, Thomas C. Zebovitz
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Patent number: 5583112Abstract: Saponin/antigen conjugates and the use thereof for enhancing immune responses in individuals are disclosed. The saponins may be substantially pure or mixtures of saponins.Type: GrantFiled: July 2, 1992Date of Patent: December 10, 1996Assignee: Cambridge Biotech CorporationInventors: Charlotte A. Kensil, Sean Soltysik, Dante J. Marciani
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Patent number: 5571795Abstract: Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes, either in admixture or as conjugates, are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is also provided.Type: GrantFiled: December 14, 1992Date of Patent: November 5, 1996Assignee: The Trustees of Princeton UniversityInventors: Daniel E. Kahne, Suzanne Walker Kahne
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Patent number: 5545623Abstract: The present invention discloses a method of inhibiting secretion of inflammatory cytokines in a host which includes administering one or more digitalis compounds in an amount effective for inhibiting secretion of an inflammatory cytokine to the host in need of inhibition of secretion of the inflammatory cytokine. The invention also discloses a method of treating diseases caused by abnormal formation or abnormal secretion of inflammatory cytokines. The invention is useful in the treatment of various diseases ascribed to abnormal secretion/formation of IL=6, IL-8, MCAF, G-CSF and/or GM-CSF.Type: GrantFiled: June 7, 1995Date of Patent: August 13, 1996Assignees: Akira Matsumori, Otsuka Pharmaceutical Co., Ltd.Inventor: Akira Matsumori
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Patent number: 5529835Abstract: Graphic laminar sheet material in which a barrier layer separates a base layer and an eradicable layer of color contrasting with the base layer.Type: GrantFiled: July 22, 1993Date of Patent: June 25, 1996Assignee: Cooley, IncorporatedInventors: Philip R. Siener, Jr., Peter H. Scott
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Patent number: 5527890Abstract: Triterpenoid acid derivatives are described that exhibit dual pharmacophobic activities, specifically selectin ligand and leukotriene biosynthetic inhibitory activities, and that thus have significant applications for the treatment or prevention of certain diseases including cancer and diseases associated with the inflammatory process as well as applications for the diagnosis of disease.Type: GrantFiled: April 16, 1993Date of Patent: June 18, 1996Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Mark B. Anderson, John H. Musser
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Patent number: 5527783Abstract: Solid compositions based on plants, capable of being converted to a dry and porous galenic form (lyophilized or equivalent form) which is undivided or powdered. Said dry and porous galenic form comprises a solid composition II consisting ofa solid composition I composed of:(A) one or more of the plants' active principles included in a homogeneous suspension of fresh or dry plants obtained by (a) cleaning and/or drying of the plant or part of the plant, (b) cryocomminution at a temperature below 0.degree. C. until a particle size of less than about 100 .mu.Type: GrantFiled: April 21, 1994Date of Patent: June 18, 1996Assignee: Laboratoires ArdevalInventors: Guy Derrieu, Bernard Raynier
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Patent number: 5521169Abstract: Ascosteroside, obtainable by cultivation of a strain of Ascotricha amphitricha A.T.C.C. No. 74237, analogs thereof and salts and prodrugs of these compounds. The compounds have antifungal activity for use in a method for treating and preventing a fungal infection. Further, the compounds are useful in a method for inhibiting fungal growth.Type: GrantFiled: January 14, 1994Date of Patent: May 28, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Jessica A. Gorman, Joseph O'Sullivan, John E. Leet, Stephen W. Mamber
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Patent number: 5519008Abstract: Triterpenoid acid derivatives have been found to have structures similar to natural ligands to the extent that these derivatives bind to natural selectin receptors including endothelial leukocyte adhesion molecule-1 (ELAM-1) and leukocyte/endothelial cell adhesion molecule-1 (LECAM-1). The molecules can be administered to the patients by themselves or in pharmaceutical formulations; in order to alleviate inflammation and/or treat other abnormalities associated with the excessive binding of leukocytes to endothelial receptors.Type: GrantFiled: September 10, 1992Date of Patent: May 21, 1996Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Mark B. Anderson, John J. Naleway, John H. Musser
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Patent number: 5502038Abstract: Glycosides having neotigogenin aglycone moieties, administered orally to mammals are shown to inhibit the absorption of cholesterol. These compounds are useful in the treatment of hypercholesterolemia. Particular compounds are derived from tomato seeds and include neotigogenin trisaccharide.Type: GrantFiled: June 21, 1993Date of Patent: March 26, 1996Assignee: Medical Research Foundation of OregonInventor: M. Rene Malinow
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Patent number: 5496806Abstract: Novel glycosides 7-ketosteryl di-O-acyl-pyranoside and 7-.beta.-hydroxycholesteryl 2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside. The glycosides possess valuable pharmacological properties as a medicament. In particular, the cholesterol glycoside in vivo exhibits a selective cell-destructive activity on malignant cells which activity is substantially free of side effects on normal cells. The glycosides possess useful properties, especially pharmacological properties which are the same as the respective unglycosylated aglycon.Type: GrantFiled: May 6, 1994Date of Patent: March 5, 1996Assignee: R. Erich KlemkeInventor: R. Erich Klemke
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Patent number: 5486506Abstract: The invention describes a method for normalizing a cardiac inotropic irregularity, via administering an effective amount of 12(R)HETE. Also described are therapeutic compositions which combine a cardiac glycoside and 12(R)HETE.Type: GrantFiled: July 28, 1994Date of Patent: January 23, 1996Assignee: Meditech, Ltd.Inventor: Michael Dunn
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Patent number: 5455335Abstract: Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is also provided.Type: GrantFiled: April 8, 1994Date of Patent: October 3, 1995Assignee: The Trustees of Princeton UniversityInventors: Daniel E. Kahne, Suzanne W. Kahne
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Patent number: 5438125Abstract: Sialic acid compounds of formula ##STR1## wherein X is hydrogen, a lower alkyl group or benzyl, Y is hydrogen or acetyl, Ac is acetyl, and the wavy line represents that the compound of the formula (I) includes both a .alpha.-anomer and .beta.-anomer, have excellent chemical and enzymatical stability and are useful in the treatment of central or peripheral nervous diseases.Type: GrantFiled: March 4, 1992Date of Patent: August 1, 1995Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kaoru Okamoto, Shinji Morita
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Patent number: 5426179Abstract: Steroid compounds active on the cardiovascular system of formula ##STR1## wherein X, n, R, R.sub.1 and R.sub.2 have the meanings mentioned in the description are described.Type: GrantFiled: February 12, 1992Date of Patent: June 20, 1995Assignee: Zambon Group S.p.A.Inventors: Giorgio Bertolini, Cesare Casagrande, Stefania Montanari, Gabriele Norcini, Francesco Santangelo
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Patent number: 5424304Abstract: Cardioactive steroidal compounds of the formula I ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 have the meanings shown in the description, and pharmaceutical compositions containing them.Type: GrantFiled: January 15, 1993Date of Patent: June 13, 1995Inventors: Giorgio Bertolini, Cesare Casagrande, Gabriele Norcini, Francesco Santangelo
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Patent number: 5416203Abstract: An oligonucleotide conjugated to a steroid the oligonucleotide comprising: ##STR1## wherein A is selected from the group consisting of an aliphatic alkyl, branched aliphatic alkyl and an alkyl (branched) chain of 2 to 18 carbon atoms, R is selected from the group consisting of H and lower alkyl up to 12 carbon atoms; B is a naturally occurring base, the steroid is bound to the oligonucleotide utilizing the naturally occurring bases through an (-oxycarbonyl-amino)-decylamine-moiety, and NUC is an oligonucleotide.Type: GrantFiled: July 26, 1993Date of Patent: May 16, 1995Assignee: Northwestern UniversityInventor: Robert L. Letsinger
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Patent number: 5413996Abstract: The invention provides compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein [D] is the residue of a drug having a reactive functional group, said functional group being attached, directly or through a bridging group, via an oxygen-phosphorus bond to the phosphorus atom of the ##STR2## moiety; R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.12 aralkyl; R.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.4 -C.sub.9 heteroaryl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloheteroalkyl or C.sub.7 -C.sub.12 aralkyl; and R.sub.3 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.8 alkenyl having one or two double bonds; (C.sub.3 -C.sub.7 cycloalkyl)--C.sub.r H.sub.2r -- wherein r is zero, one, two or three, the cycloalkyl portion being unsubstituted or bearing 1 or 2 C.sub.1 -C.sub.4 alkyl substituents on the ring portion; (C.sub.6 -C.sub.10 aryloxy)C.sub.1 -C.sub.Type: GrantFiled: October 16, 1992Date of Patent: May 9, 1995Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5405944Abstract: There are described novel glycosides of catechol estrogen, a method of preparing the same, and a medicament comprising one of the glycosides as an active ingredient. The glycosides are shown by the formula of ##STR1## wherein X is carbonyl group or ##STR2## R.sub.10 is hydroxyl group or glycosyloxy group, and R.sub.2 is a hydrogen atom or ethynyl group; R.sub.11 is a hydrogen atom, hydroxyl group, or glycosyloxy group; R.sub.12 is hydroxyl group or glycosyloxy group; and R.sub.13 is hydroxyl group or glycosyloxy group,in which glycosyloxy group is selected from the group consisting of glucosyloxy, galactosyloxy, mannosyloxy, arabinosyloxy, ribosyloxy, xylosyloxy, fructosyloxy, rhamnosyloxy, fucosyloxy, maltosyloxy, cellobiosyloxy, lactosyloxy, sucrosyloxy, maltotriosyloxy, maltotetraosyloxy, maltopentaosyloxy, maltohexaosyloxy, maltoheptaosyloxy, and sialosyloxy, and in this case, at least one of R.sub.10, R.sub.11, R.sub.12, and R.sub.13 is glycosyloxy group as defined above.Type: GrantFiled: September 25, 1992Date of Patent: April 11, 1995Assignee: Institute of Applied BiochemistryInventors: Takehiko Suzuki, Sadaaki Komura, Naoko Ishida, Nobuko Ohishi, Kunio Yagi
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Patent number: 5376641Abstract: A complex of branched beta cyclodextrin and steroid is formed by mixing a steroid and a branched beta cyclodextrin together in water for a period of about 4 to 24 hours under ambient conditions. The solubility of the steroid is increased about 95 times by employing the complex.Type: GrantFiled: July 16, 1993Date of Patent: December 27, 1994Assignee: American Maize Technology, Inc.Inventor: Robert N. Ammeraal