Oxygen Bonded Directly At The 1-, 2-, Or 4-position Patents (Class 552/541)
  • Publication number: 20130323382
    Abstract: Recombinant DNA techniques are used to produce oleaginous recombinant cells that produce triglyceride oils having desired fatty acid profiles and regiospecific or stereospecific profiles. Genes manipulated include those encoding stearoyl-ACP desturase, delta 12 fatty acid desaturase, acyl-ACP thioesterase, ketoacyl-ACP synthase, and lysophosphatidic acid acyltransferase. The oil produced can have enhanced oxidative or thermal stability, or can be useful as a frying oil, shortening, roll-in shortening, tempering fat, cocoa butter replacement, as a lubricant, or as a feedstock for various chemical processes. The fatty acid profile can be enriched in midchain profiles or the oil can be enriched in triglycerides of the saturated-unsatturated-saturated type.
    Type: Application
    Filed: July 12, 2013
    Publication date: December 5, 2013
    Inventors: Scott Franklin, Aravind Somanchi, George Rudenko, Riyaz Bhat, Xinhua Zhao, Risha Bond, Walter Rakitsky, Alejandro Marangoni, Diza Braksmayer
  • Patent number: 8536354
    Abstract: The present invention relates to steroidal ligands for use in nuclear receptor-based inducible gene expression systems. The invention further relates to methods of modulating the expression of genes of interest with a system containing one or more nuclear receptor complexes and one or more steroidal ligands. Further aspects include ligand compositions including therapeutic compositions.
    Type: Grant
    Filed: March 16, 2009
    Date of Patent: September 17, 2013
    Assignee: Intrexon Corporation
    Inventors: Robert E. Hormann, Silvia Lapenna, Laurence Neil Dinan
  • Publication number: 20120190871
    Abstract: Disclosed are the isolation, purification and analysis of the triterpenoid compositions (including ergostane and lanostane) in the fruiting body of Antrodia cinnamomea using HPLC and NMR, as well as the stereo structures and the amounts of the triterpenoid compositions. The cytotoxicity of triterpenoids is also revealed. Based on the aforementioned techniques, the presence and amounts of ergostane and lanostane in the drugs, healthcare food or other goods are able to be detected.
    Type: Application
    Filed: January 17, 2012
    Publication date: July 26, 2012
    Applicant: KAOHSIUNG MEDICAL UNIVERSITY
    Inventors: YANG-CHANG WU, FANG-RONG CHANG, MEI-CHIN LU, YING-CHI DU, TUNG-YING WU, YU-MING HSU
  • Publication number: 20120165553
    Abstract: [Problem to be Solved] An immunostimulant highly safe and administrable for a long period of time as well as a pharmaceutical composition containing the immunostimulant as an active ingredient and drink or food products for immunostimulation are developed and provided. [Solution] An immunostimulant containing a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient is provided. R1 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R2 to R5 are independently a hydrogen atom, or a substituted or unsubstituted lower alkyl or lower acyl group, X is —(CH2)2—, —(CH2)3—, —(CH2)4—, —CO—CH2—, —CO—(CH2)2—, —CO—(CH2)3—, —CH2—CO—CH2—, —CO—O—CH2—, —CO—O—(CH2)2—, —O—CO—CH2—, —O—CO—(CH2)2—, —CH2—O—CH2—, —CH2—O—(CH2)2—, —O—CH2—, —O—(CH2)2—, —O—(CH2)3—, —NHY—CO—CH2—, —NHYCO—(CH2)2—, —CO—NHY—CH2— or —CO—NHY—(CH2)2—, Y herein is a hydrogen atom or a lower alkyl group.
    Type: Application
    Filed: December 12, 2011
    Publication date: June 28, 2012
    Applicant: RIKEN
    Inventors: Kenji Ogawa, Takeshi Nakano
  • Patent number: 8106036
    Abstract: The invention provides compositions comprising formula 1 steroids, e.g., 16?-bromo-3?-hydroxy-5?-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16?-bromo-3?-hydroxy-5?-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.
    Type: Grant
    Filed: December 9, 2009
    Date of Patent: January 31, 2012
    Assignee: Harbor Biosciences, Inc.
    Inventor: James M. Frincke
  • Patent number: 8022234
    Abstract: The invention provides compositions comprising formula 1 steroids, e.g., 16?-bromo-3?-hydroxy-5?-androstan-17-one hemihydrate and one or more excipients, including compositions that comprise a liquid formulation comprising less than about 3% v/v water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16?-bromo-3?-hydroxy-5?-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using the compounds. The invention also provides methods to make and use these immunomodulatory compositions and formulations.
    Type: Grant
    Filed: September 30, 2009
    Date of Patent: September 20, 2011
    Assignee: Harbor BioSciences, Inc.
    Inventor: James M. Frincke
  • Publication number: 20110082307
    Abstract: There is disclosed a method for isolation and purification of phytosterols from tall oil pitch comprising the steps of: a) contacting the tall oil pitch with a solvent to form a tall oil solvent mixture; b) separating the tall oil pitch solvent mixture in at least two separate streams wherein one process stream is enriched in acidic pitch components and a second stream enriched in free- and bound sterols in the form of steryl esters; c) subjecting the stream enriched in free- and steryl esters to treatment with an alcohol under transesterification conditions wherein a reaction mixture is formed and sterols comprising the steryl esters are liberated as free sterols; and d) separating the free sterols from the reaction mixture of step c) by crystallization and extraction with one or more solvents. There are disclosed free fatty acids and resin acids separated from the tall oil pitch. Moreover, there is disclosed a manufacture and separation of fatty acid alkyl esters by the method.
    Type: Application
    Filed: February 10, 2009
    Publication date: April 7, 2011
    Inventors: Lars Stigsson, Valeri Naydenov
  • Patent number: 7888000
    Abstract: Salt sensitivity is measured as a function of the urinary 25-OHD binding activity, which may be evaluated by measuring 25-hydroxyvitamin D binding activity using radiolabeled 25-hydroxyvitamin D3. High binding activity is indicative of salt sensitivity and is an important predictor for development of salt-sensitivity related hypertension.
    Type: Grant
    Filed: July 11, 2003
    Date of Patent: February 15, 2011
    Assignee: Morehouse School of Medicine
    Inventors: Myrtle Thierry-Palmer, Akins Doherty, Keri J. Griffin, Mohamed A. Bayorh
  • Publication number: 20110033561
    Abstract: For reducing the negative effects of the metabolic syndrome on mammal organisms, it is proposed to use phytoecdysones for diminishing the fat body mass in individuals, notably with a weight excess. Phytoecdysones are advantageously incorporated into a food composition. The phytoecdysones can come from food plants, such as quinoa.
    Type: Application
    Filed: November 19, 2008
    Publication date: February 10, 2011
    Applicants: INSTITUT BIOPHYTIS SAS, UNIVERSITE PIERRE ET MARIE CURIE
    Inventors: Stanislas Veillet, Rene Lafont
  • Publication number: 20100273749
    Abstract: The subject application provides an aqueous composition suitable for use as an artificial tear solution comprising one or more lipids produced by an enzyme of the diacylglycerol acyltransferase 2 (DGAT2) family and/or the acyl-CoA cholesterol acytransferase (ACAT) family. This invention also provides related methods.
    Type: Application
    Filed: December 28, 2006
    Publication date: October 28, 2010
    Inventors: Stephen L. Sturley, Aaron Turkish, Stephen Trokel
  • Publication number: 20100204460
    Abstract: The present invention relates to natural brassinosteroids of general formula (I), wherein R is CH2 or O—CH2 group, R2 is hydrogen or hydroxyl, R3 is hydroxyl, R24 is alkyl or alkenyl, which are selected from the group consisting of methyl, ethyl, propyl, isopropyl, methylen, ethylen and propylen, and R25 is alkyl selected from the group consisting of methyl and ethyl, and a pharmaceutically acceptable salt thereof, for use for treating hyperproliferation, treating proliferative diseases and reducing adverse effects of steroid dysfunction in mammals. The present invention also provides methods capable to arrest of the cell cycle by natural brassinosteroids resulting in apoptotic changes in cancer cells. More specifically, the present invention relates to use for treatment of the adverse effects of hyperproliferation on mammalian cells in vitro and in vivo, especially treatment of hyperproliferative diseases in mammals by administering compositions containing natural brassinosteroids.
    Type: Application
    Filed: August 20, 2008
    Publication date: August 12, 2010
    Inventors: Jana Oklestková, Lucie Hoffmannová, Jana Steigerová, Ladislav Kohout, Zdenêk Kolár, Miroslav Strnad
  • Publication number: 20100168451
    Abstract: A method for producing dihydrocucurbitacin F-25-0-acetate consisting of the steps as followed: percolating radix hemsleyae using acetone as solvents to obtain extract; eluting the extract in silica gel column using chloroform: methanol as eluting agent (gradient) to obtain the crude; recrystallizating the crude using methanol or ethanol to obtain di-hydrocucurbitacin F-25-O-acetate (purity:>98%). And the use of dihydrocucurbitacin F-25-O-acetate in the manufacture of medicaments for treating cancers of liver, lung, stomach, larynx, prostate and leukemia.
    Type: Application
    Filed: October 19, 2007
    Publication date: July 1, 2010
    Inventors: Xiane Fan, Renwei Zhang, Huijia Cheng
  • Publication number: 20100041633
    Abstract: The invention relates to nitrooxyderivative of corticosteroids of general formula (I) and pharmaceutically acceptable salts or stereoisomers thereof wherein R is a corticosteroid residue selected from: The compounds are useful in the treatment of respiratory diseases.
    Type: Application
    Filed: January 28, 2008
    Publication date: February 18, 2010
    Applicant: NICOX S.A.
    Inventors: Francesca Benedini, Stefano Biondi, Ennio Ongini
  • Patent number: 7235679
    Abstract: The present invention provides crystals of the compound represented by formula (I): crystals of a vitamin D derivative which are obtained by purifying a crude or preliminarily purified product of the vitamin D derivative through a reverse phase chromatography and then crystallizing the purified derivative from an organic solvent; novel compounds which are formed during the synthesis of a vitamin D derivative as by-product; and a method for purifying a vitamin D derivative or the precursor thereof. The method of the present invention makes it possible to supply a highly purified vitamin D derivative, especially ED-71, in bulk and steadily.
    Type: Grant
    Filed: June 1, 2006
    Date of Patent: June 26, 2007
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventor: Tsuyoshi Yamauchi
  • Patent number: 7067504
    Abstract: The present invention is a di-steroidal prodrug of ethinyl estradiol according to formula I:
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: June 27, 2006
    Assignee: Warner Chilcott Company, Inc.
    Inventors: John Alexander King, James Keown, James William McIlroy, William Paul Armstrong, Michael Anthony McKervey, Austin McMordie
  • Patent number: 7067505
    Abstract: The present invention is a di-steroidal prodrug of estradiol having the following formula:
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: June 27, 2006
    Assignee: Warner Chilcott Company, Inc.
    Inventors: John Alexander King, James Keown, James William McIlroy, William Paul Armstrong, Michael Anthony McKervey, Austin McMordie
  • Patent number: 6967195
    Abstract: Compounds of formula (I) in which: R1 represents a hydrogen atom or an O-protecting group; R2 represents a hydroxyl, lower alkoxy, carboxaldehyde, lower alk-1-enyl or hydroxy- or lower alkoxy-substituted lower alkyl group; R3 represents a methyl group having ?- or ?-configuration; X represents a C1-3 alkylene group or a valence bond; Y represents a carboxaldehyde group or a group of formula —C(R4)(R5)OR1 where R1 is as defined above and R4 and R5, which may be the same or different, are each selected from hydrogen atoms, alkyl, alkenyl and alkynyl groups such that the total carbon content of R4 and R5 does not exceed three atoms, with the proviso that X is a valence bond when both R4 and R5 are other than hydrogen; and the dotted line signifies that a double bond may optionally be present at the 16(17)-position exhibit potent cell modulating activity, including antiproliferative and antiangiogenic effects.
    Type: Grant
    Filed: May 11, 2001
    Date of Patent: November 22, 2005
    Assignee: Research Institute for Medicine and Chemistry, Inc.
    Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Maurice Murdoch Pechet, Michael Gile
  • Patent number: 6881730
    Abstract: Compounds of Formula (I) in which: R1 and R2, which may be the same or different, each represents a lower alkyl, alkenyl or alkynyl group; R3 represents a methyl group having ?- or ?-configuration; R4 represents a hydrogen atom or an etherifying or esterifying group; R5 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group; X represents a group OR4, wherein R4 is as defined above, or a group NR6R7 wherein R6 represents a hydrogen atom, an aliphatic or araliphatic organic group, or an acyl group comprising an aliphatic, araliphatic or aryl organic group linked to the nitrogen atom by way of a carbonyl group; and R7 is a hydrogen atom or a lower alkyl group; Y represents a lower alkylene, alkenylene or alkynylene group optionally substituted by a hydroxyl, etherified hydroxyl or esterified hydroxyl group; and the dotted lines signify that double bonds may be present at the 16(17)-position and/or either at the 6(7)- and 8(9)-positions or at the 7(8)-position exhibit potent effects on modulation of
    Type: Grant
    Filed: May 11, 2003
    Date of Patent: April 19, 2005
    Assignee: Research Institute for Medicine & Chemistry, Inc.
    Inventors: Robert Henry Hesse, Sundara Katugam Srinivasasetty Setty, Malathi Ramgopal, Sanga Kugabalnsooriar
  • Publication number: 20040053896
    Abstract: A liver-targeting active compound has the general formula (I):- wherein A is &agr;-OH or &bgr;-OH, B is &agr;-H or &bgr;-H, C is —H, &agr;-OH or &bgr;-OH, or B and C together form a double bond, D is —H, &agr;-OH or &bgr;-OH, E is —H, &agr;-OH or &bgr;-OH, —G-is a side chain moiety, —NH—J is selected from (i) a residue of an amino group-containing active compound wherein said —NH— group is provided by said amino group of the active compound, and (ii) a residue of an active compound to which an amino group has been added wherein said —NH— group is provided by said added amino group; each of X and Y independently represents a single bond, —(CH2)z— (where z is 1 to 8), —O— or —S—; n is 0 or 1; m is 0 or 1; and p is 0 or 1; provided that, when —NH—J is (i), m is 1. A method of producing such as compound is also disclosed.
    Type: Application
    Filed: September 18, 2003
    Publication date: March 18, 2004
    Inventor: Charles Oswald Mills
  • Patent number: 6555530
    Abstract: Analysis of full-blood glucose, serum insulin, serum triglycerides and total serum cholesterol were performed. Glucose levels in blood samples from the oral glucose tolerance test were used for calculation of the incremental Area Under the Curve (AUC0-120 min−baseline). All data are expressed as percentage change of vehicle treated animals (cf. FIGS. 1 and 2).
    Type: Grant
    Filed: January 31, 2000
    Date of Patent: April 29, 2003
    Assignee: Novo Nordisk A/S
    Inventor: Karsten Wassermann
  • Publication number: 20030018206
    Abstract: The present invention provides crystals of the compound represented by formula (I): 1
    Type: Application
    Filed: July 12, 2002
    Publication date: January 23, 2003
    Applicant: CHUGAI SEIYAKU KABUSHIKI KAISHA
    Inventor: Tsuyoshi Yamauchi
  • Publication number: 20020007079
    Abstract: Certain novel sterol derivatives having no hydroxy group in the 3-position can be used to regulate the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives.
    Type: Application
    Filed: July 9, 1999
    Publication date: January 17, 2002
    Inventors: ANTHONY MURRAY, PETER FAARUP
  • Patent number: 6271402
    Abstract: Compound of formula I: wherein the R groups are as defined by the specification. The compounds are useful in the inhibition of HIV integrase, the treatment of infection of HIV and treatment of AIDS.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: August 7, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Sheo Bux Singh, Deborah L. Zink, Daria Jean Hazuda, Peter J. Felock, Anne W. Dombrowski
  • Patent number: 6239073
    Abstract: Disclosed are compositions and methods for promoting plant growth. The compounds are cyclopropyl-, cyclobutyl-, and cyclopentyl-substituted brassinosteroids having high growth promoting ability. They may be used alone or in combination with other plant growth regulating agents.
    Type: Grant
    Filed: November 4, 1999
    Date of Patent: May 29, 2001
    Assignee: Exelixis Plant Sciences, Inc.
    Inventors: Thomas G. Back, Richard P. Pharis, Suanne K. Nakajima
  • Patent number: 6063731
    Abstract: Disclosed are compositions and methods for promoting plant growth. The compounds are cyclopropyl- and cyclobutyl-substituted brassinosteroids having high growth promoting ability. They may be used alone or in combination with other plant growth regulating agents.
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: May 16, 2000
    Assignee: Agritope, Inc.
    Inventors: Thomas G. Back, Richard P. Pharis, Suanne K. Nakajima
  • Patent number: 5874598
    Abstract: A process for the production of a compound of formula (II), which comprises reacting an epoxy compound of formula (I) with an alcohol, wherein the reaction is carried out under a basic condition. ##STR1## R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are as defined in the specification. The compounds are useful intermediates for the production of vitamin D.sub.3 derivatives.
    Type: Grant
    Filed: November 29, 1996
    Date of Patent: February 23, 1999
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventor: Noboru Kubodera
  • Patent number: 5834452
    Abstract: A compound of the formula ##STR1## having progestomimetic activity, wherein the substituents are as defined in the specification and compositions of a compound of formula I and an estrogen compound.
    Type: Grant
    Filed: May 22, 1997
    Date of Patent: November 10, 1998
    Assignee: Roussel Uclaf
    Inventors: Jacques Biton, Jean-Pierre Marchandeau, Robert Azerad, Isabelle Lacroix
  • Patent number: 5703067
    Abstract: The present invention is directed to steroidal or terpenoidal compounds which inhibit farnesyl-protein transferase (FPTase). The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and treatment of cancer.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: December 30, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Hiranthi Jayasuriya, Russell B. Lingham, Fernando Pelaez, Manuel Sanchez, Keith C. Silverman, Sheo Bux Singh, Deborah L. Zink
  • Patent number: 5646138
    Abstract: Steroid compounds of the contignasterol family, including stereoisomers and pharmaceutically acceptable salts, as well as compositions containing these materials and a pharmaceutically acceptable carrier, are disclosed. The steroid compounds have a 3.alpha.-hydroxyl, a 4.beta.-hydroxyl, a 6.alpha.-hydroxyl, a 7.beta.-hydroxyl, a 15-ketone, a trans A/B ring juncture and a cis or trans C/D ring juncture. The compounds and compositions may be used, for example, for the prevention of inflammatory or allergic reactions, or the treatment of cardiovascular or haemodynamic disorders.
    Type: Grant
    Filed: September 5, 1995
    Date of Patent: July 8, 1997
    Assignees: University of British Columbia, University of Alberta
    Inventors: Raymond J. Andersen, Theresa M. Allen, David L. Burgoyne
  • Patent number: 5591733
    Abstract: Method, compositions, and compounds for modulating brain excitability to alleviate stress, anxiety, insomnia and seizure activity using certain steroid derivatives that act at a newly identified site on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: January 7, 1997
    Assignee: University of Southern California
    Inventors: Michael B. Bolger, Kelvin W. Gee, Nancy C. Lan, Robert H. Purdy, Seid Mirsadeghi, Syed Hasan Tahir, Delia Belelli
  • Patent number: 5391777
    Abstract: A method is provided for isolating 5,7-diene-containing steroids, particularly 3.beta.-ols and esters of 3.beta.-ols, from a sterol mixture. The method involves (1) treating the mixture with a dienophile or with an oxidizable dienophile precursor in combination with an oxidizing agent so as to provide a Diels-Alder adduct of the 5,7-diene to be isolated, followed by (2) removal of the adduct from the mixture and (3) regeneration of the 5,7-diene with a suitable reducing agent. The invention also encompasses subsequent purification steps and intermediate modification of the Diels-Alder intermediate, e.g., wherein chemical conversion of the Diels-Alder adduct is effected prior to regeneration of the 5,7-diene. Novel compounds which are Diels-Alder adducts of 5,7-diene-containing steroids are provided as well.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: February 21, 1995
    Assignee: SRI International
    Inventors: Masato Tanabe, John G. Johansson, Dennis Yasuda
  • Patent number: 5359055
    Abstract: There are provided pregnane derivatives represented by formula ##STR1## wherein A.sup.1 represents a hydrogen atom or a hydroxyl group, A.sup.2 represents a substituent such as a hydroxyl group when A.sup.1 represents a hydrogen atom, or A.sup.2 represents a hydrogen atom when A.sup.1 represents a hydroxyl group, or A.sup.1 and A.sup.2 are combined together to form an oxo group; D.sup.1 represents a substituent such as a hydroxyl group, and D.sup.2 represents a hydrogen atom, or D.sup.1 and D.sup.2 are combined together to form an epoxy group or a single bond; D.sup.3, D.sup.5 and D.sup.7 each represents a hydrogen atom, D.sup.4 represents a hydroxyl group, and D.sup.6 represents a substituent such as a hydroxyl group, or D.sup.3 and D.sup.4 may be combined together to form an epoxy group or a single bond, or D.sup.4 and D.sup.5 may be combined together to form a single bond, or D.sup.5 and D.sup.6 may be combined together to form an epoxy group or a single bond, or D.sup.6 and D.sup.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: October 25, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Jiro Tsuji, Takashi Takahashi, Masao Tsuji, Naoshi Nakagawa, Tetsuo Takigawa
  • Patent number: 5352781
    Abstract: The process of the invention comprises reacting a C-22-halo-23,24-bisnorsteroid or C-22-halo-23,24-bisnor-9,10-secosteroid with a nickel complex of an electron withdrawing alkene of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxycarbonyl, lower alkoxycarbonyl, lower alkylcarbonyl or unsubstituted or substituted lower alkyl, and R.sub.2 is hydroxyl, lower alkoxy, or unsubstituted or substituted lower alkyl, to yield a C-25 or C-26 precursor of the formula ##STR2## which is appropriately functionalized for conversion into the corresponding steroid or secosteroid by treatment as hereinafter described.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: October 4, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George P. Yiannikouros, Percy S. Manchand
  • Patent number: 5302719
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.A, R.sub.A.sup.1, R.sub.B R.sub.B.sup.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms or R.sub.A and R.sub.A.sup.1 or R.sub.B and R.sub.B.sup.1 together with the nitrogen atom to which they are attached form a 5- to 6-member heterocycle optionally substituted with alkyl of 1 to 3 carbon atoms and Y is hydrogen or ##STR2## wherein R.sub.6 is selected from the group consisting of hydrogen, --CH.sub.3, --F and --Cl, R.sub.9 and R.sub.11 form a second bond at 9(11) or R.sub.9 is hydrogen or --F and R.sub.11 is hydrogen, --OH or .dbd.0, R.sub.16 is --CH.sub.3 or hydrogen, R.sub.17 is hydrogen, --OH or acyloxy, the dotted lines indicate the possible presence of a second bond at 1(2) and 6(7)-positions and the wavy line indicates the .alpha.- and .beta.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: April 12, 1994
    Assignee: Roussel Uclaf
    Inventors: Andre Claussner, Jacques LeClaire, Lucien Nedelec, Daniel Philibert
  • Patent number: 5244886
    Abstract: New 11.beta.-phenyl-14.beta.H-steroids of general formula (I), where Z is an oxygen atom or the hydroxyimino-grouping N.about.OH, and M and N are either jointly a second compound or L is a hydrogen atom and M is an .alpha.-permanent hydroxy group and either A and B together are a second compound and D is a hydrogen atom, where R.sup.1 is a five or six-part heteroalkyl residue or a cycloalkyl, cycloalkenyl or aryl residue or A is a hydrogen atom and B and D together are a methylene bridge, where R.sup.1 besides the aforementioned residues may be a possibly substituted hydrocarbon residue with up to 10 C atoms, a possibly substituted amino group, a hydroxy or C.sub.1-8 alkoxy, mercapto or thioalkyl group, R.sup.2 is a methyl or ethyl residue, and R.sup.3 /R.sup.4 represents the usual combination of substituents on the C17 atom in steroid chemistry, having antigestagenic and other properties.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: September 14, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Stefan Scholz, Gunter Neef, Eckhard Ottow, Walter Elger, Sybille Beier, Krzysztof Chwalisz
  • Patent number: 5194431
    Abstract: Vitamin D.sub.2 analogs in which a cyclopropane ring is introduced onto the 24-carbon of the side chain of 1.alpha.,25-dihydroxyvitamin D.sub.2 and 1.alpha.-hydroxyvitamin D.sub.2. The compounds are characterized by a marked intestinal calcium transport activity while exhibiting much lower activity than 1.alpha.,25-dihydroxy-vitamin D.sub.3 in their ability to mobilize calcium from bone. Because of their preferential calcemic activity, these compounds would be useful for the treatment of diseases where bone formation is desirbed, such as osteoporosis.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: March 16, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Naoshi Nakagawa
  • Patent number: 5182393
    Abstract: The process of the invention comprises reacting a C-22-halo-23,24-bisnorsteroid or C-22-halo-23,24-bisnor-9,10-secosteroid with a nickel complex of an electron withdrawing alkene of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxycarbonyl, lower alkoxycarbonyl, lower alkylcarbonyl or unsubstituted or substituted lower alkyl, and R.sub.2 is hydroxyl, lower alkoxy, or unsubstituted or substituted lower alkyl,to yield a C-25 or C-26 precursor of the formula ##STR2## which is appropriately functionalized for conversion into the corresponding steroid or secosteroid by treatment as hereinafter described.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: January 26, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George P. Yiannikouros, Percy S. Manchand
  • Patent number: 5117015
    Abstract: A process for producing a 1.alpha.,3.beta.,24-trihydroxy-.DELTA..sup.5 -steroid represented by the formula (II): ##STR1## wherein R.sub.1 and R.sub.2, independently, represent a hyrogen atom, or R.sub.1 and R.sub.2 together form a single bond, R.sub.3 represents an unsubstituted or halogen-substituted lower alkyl, and R.sub.4 represents a hydrogen atom, hydroxy or a protected hydroxy, comprising reducing a 1.alpha.,2.alpha.-epoxy-.DELTA..sup.4,6 -3,24-dioxosteroid represented by the formula (I) ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in formula (II), using an alkaline metal or alkaline earth metal and a proton donor in a solvent comprising ammonia or amine characterized in that at an early stage of the reaction, the 1.alpha.,2.alpha.-epoxy-.DELTA..sup.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Tatuo Yarino, Takao Fujii
  • Patent number: 5087709
    Abstract: (22E)-5,7,22-Ergostatriene-1.alpha.,3.beta.,25-triol and the 24-epimer thereof which are new intermediates for the synthesis of 1.alpha.,25-dihydroxyvitamin D.sub.2 and the 24-epimer thereof. A new process for the preparation of 1.alpha.,25-dihydroxyvitamin D.sub.2 and the 24-epimer thereof is also described which comprises irradiation of (22E)-5,7,22-ergostatriene-1.alpha.,3.beta.,25-triol or the 24-epimer thereof followed by isomerization.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: February 11, 1992
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Masahiro Tsuji, Shinji Yokoyama, Yoji Tachibana
  • Patent number: 4954446
    Abstract: Invented are substituted acrylate analogues of steroidal synthetic compounds, pharmaceutial compositions containing the compounds, and methods of using these compounds to inhibit steroid 5-.alpha.-reductase including using these compounds to reduce prostate size. Also invented are intermediates used in preparing these compounds.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: September 4, 1990
    Assignee: SmithKline Beecham Corporation
    Inventors: Dennis A. Holt, Mark A. Levy, Brian W. Metcalf
  • Patent number: RE35517
    Abstract: Method, compositions, and compounds for modulating brain excitability to alleviate stress, anxiety, and seizure activity using certain steroid derivatives that act at a newly identified site on the gamma-ammobutyric acid/benzodiazepine receptor-chloride ionpore (GBR) complex.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: May 20, 1997
    Assignee: University of Southern California
    Inventors: Kelvin W. Gee, Michael B. Bolger, Nancy C. Lan