DOCSLIB.ORG

United States Patent Office Patented June 2, 1964

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent Office Patented June 2, 1964 3,135,743 United States Patent Office Patented June 2, 1964 2 The 18, 19-bisnorsteroid, 18,19-norsteroid and normal 3,135,743 Steroid moieties in the compounds of the invention con STERGIDOI2,3-dSOXAZOLES AND PREPARATION tain, respectively, seventeen, eighteen and nineteen car THEREOF bon atoms plus any carbon content which may be pro Raynorad O. Clinton, East Greenbisia, and Andrew John vided by one or more nuclearly substituted carbon con Maason, North Greenbush, N.Y., assignors to Sterling taining radicals, up to and including a total of about Drug Inc., New York, N.Y., a corporation of Delaware twenty-three carbon atoms, exclusive of ester radicals. No Drawing. Filed June 29, 1960, Ser. No. 39,458 When acyloxy radicals are present in the steroid moiety, 32 Claims. (C. 260-239.55) the acyl radicals are preferably derived from carboxylic This invention relates to heterocyclic substituted ste O acids having from one to about ten carbon atoms, con roids, and in particular it is concerned with steroido (2.3- ventionally employed in the steroid art, and having a disoxazoles and the preparation thereof. molecular weight less than about 200. Representative of It has been found that new and useful compounds are the acyl radicals which can be present are lower-alkanoyl produced when an isoxazole ring is fused through its 4 radicals, e.g., formyl, acetyl, propionyl, butyryl, isobutyr and 5-positions to the 2- and 3-positions, respectively, of 5 yl, caproyl, heptanoyl, octanoyl, trimethylacetyl, and the a steroid nucleus, said steroid having from seventeen to like; carboxy-lower-alkanoyl radicals, e.g., succinyl (B- about twenty-three carbon atoms exclusive of ester radi carboxypropionyl); cycloalkyl-lower-alkanoyl radicals, cals. e.g., g-cyclopentylpropionyl, 3-cyclohexylpropionyl, and The ring structure of the compounds of the invention is the like; monocarbocyclic aroyl radicals, e.g., benzoyl, p represented by the following structure: 20 toluyl, p-nitrobenzoyl, 3,4,5-trimethoxybenzoyl, and the like; monocarbocyclic aryl-lower-alkanoyl or -alkenoyl radicals, such as phenylacetyl, 3-phenylpropionyl, cin namoyl, and the like; and monocarbocyclic aryloxy lower-alkanoyl radicals, such as p-chlorophenoxyacetyl, 25 and the like. Esters of inorganic acids such as phosphoric acid are also contemplated. The compounds of the invention are prepared by react ing a 2-(1-hydroxyalkylidene)-3-oxo-steroid with hy droxylamine or an acid-addition salt thereof according to 30 the following equation: The exact nature of the steroid moiety is not critical, and it can be derived from any steroid of the general type R known to exhibit hormonal or other pharmacological or endocrinological properties. Such steroid moieties have 35 HNOH -- Hot-6Q --> N 4.YQ. -- 2:O from seventeen to about twenty-three carbon atoms, not -3 N counting carbon content which may be provided by esteri O fied hydroxy groups. Esterified hydroxy-steroids are in () (II) cluded within the scope of the invention, but the carbon content contributed by the acid moiety of the ester is not 40 In the above general Formulas I and II, Q represents considered part of the essential carbon content of the the remaining portion of the steroid moiety described steroid. above. In the above Formulas I and II, R represents a The steroid moiety can be any member of the estrane, hydrogen atom or a lower-alkyl radical, the latter hav 18-norestrane, androstane, etiocholane, pregnane or allo ing preferably from one to about four carbon atoms, thus pregnane series. The foregoing can contain varying de 45 including such groups as methyl, ethyl, propyl, isopropyl, grees of unsaturation and a variety of substituents in the butyl, and the like. form of hydrocarbon radicals or functional groups con The condensation of the hydroxylamine with a 2-hy ventionally employed in the steroid art. Representative droxyalkylidene-3-oxo-steroid is carried out by heating of the steroid moieties which make up the compounds Said steroid with at least one molar equivalent of hy of the invention are those having at position 17 a hy 50 droxylamine or acid-addition salt thereof in an inert sol droxy, acyloxy, oxo, or both a hydroxy and a lower-alkyl vent at a temperature between about 50° C. and 150° C. radical, characteristic of the androgenic and anabolic The inert solvent is preferably a lower-alkanol, e.g., meth steroids; or a lower-alkenyl, lower-alkynyl, acetyl, hy anol, or ethanol, or a lower-alkanoic acid, e.g., acetic droxyacetyl, 1,2-dihydroxyethyl, 1-hydroxyethyl, and the acid or propionic acid, or a mixture of an alcohol and like radicals, characteristic of the progestational and 55 an acid. The reaction is catalyzed by the presence of a adrenal cortical steroids. The steroid moiety can also weak or moderate acid such as acetic acid, although if a have one or more substituents at other positions of the strong acid is present it may cause dehydration of a hy nucleus, for example, hydroxy, acyloxy, or oxo radicals droxy group in the 17-position, followed by deep-seated at positions 6, 7, 11, 12, 14 or 16; halogen atoms, prefer rearrangement of the steroid nucleus. In the event an ably fluorine, chlorine or bromine, for example, at the 60 acid-addition salt of hydroxylamine, such as the hydro 4-, 6-, 7-, 9-, 12-, 16-, 17- or 21-positions; and lower-alkyl chloride, is used, an approximately equivalent amount of groups, for example, at the 4-, 5-, 6-, 7-, 11- or 16-posi a Salt of a strong base and a weak acid, e.g., sodium tions. The steroid moiety can also have one or more acetate, is added to convert the strong acid of addition double bonds, especially at the 4,5- and/or 1,2- and/or to a weak acid in order to prevent dehydration and re 6,7-positions. The steroid moiety usually possesses angu 65 arrangement. 17-hydroxy groups can also be protected lar methyl groups at C1 and C13, although 18- and 19 by esterification prior to isoxazole formation, norsteroids and 18, 19-bisphorsteroids, lacking one or both If the steroid moiety has a double bond already pres of the angular methyl groups at C13 and C10, respectively, ent in the 1,2-position, the essential steroid intermediate are also representative steroids. is a 2-formyl-A-steroid (III; R is H) or a 2-lower-alka 3,135,743 4. noyl-Al-steroid (III; R is lower-alkyl). The reaction is In the above general Formulas V, VI and VII, R', when represented by the following equation: it represents a lower-alkyl, lower-alkenyl, or lower-alkynyl R radical, has from one to about four carbon atoms and may be straight or branched, and thus includes such groups R d 5 as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary O=C- % - ? ? butyl, vinyl, 1-propenyl, 2-propenyl, ethynyl, propargyl, HNOH + . Q. --> N Q. --2HO and the like. O= The compounds of Formulas V, VI and VII are pre O N pared by reacting the appropriate 2-(1-hydroxyalkyli (III) (IV) 0 dene)-3-oxo-steroid, viz.: The intermediate 2-acyl-Al-steroid (III) can be pre pared by bromination or chlorination of a 2-acyl steroid R (I) in the 2-position, followed by dehydrohalogenation Y Z. with collidine or with lithium chloride in dimethylform amide solution. R Y Compounds having an aromatic ring A characteristic of r estrogens (estratriene compounds), viz.: Ho-3- f O - C 20 (VIII) or the corresponding compounds where double bonds are ... present in the 4,5- or the 4,5- and 6,7-positions, with hy KCCN/ N droxylamine or an acid-addition salt thereof; R, R, X, Z, can be prepared by dehydrogenation of the correspond 25 Y and Y have the same meanings given above. When ing A-19-norsteroido-isoxazole by conventional proce the steroid moiety contains, oxo groups in addition to the dures, as by heating with palladium-on-carbon catalyst. one at position 3, they can be protected as a ketal derival A particularly preferred group of compounds, derived tive to prevent side reactions with the hydroxylamine from readily available starting materials, comprises those (oxime formation). For example, when compounds in having the structural formula which R' represents acetyl or hydroxyacetyl are desired, 30 these radicals can be ketalized by known methods, e.g., R - with ethylene glycol, prior to introduction of the hydroxy Vrz alkylidene radical at the 2-position and reaction with hy - X droxylamine. It has been found, however, that 3,20 d;f Y r 35 dioxo-steroids bearing hydroxy groups at the 17- and 21 N positions can be selectively formylated in the 2-position without protecting the 20-oxo group by ketalization. The 20-monoketals of 3,20-dioxo-steroids are prepared from the 3,20-diketals by selective hydrolysis by known methods, e.g., by allowing the diketal to stand at room tem (V) perature in acetone solution containing a trace of p-tolu wherein R represents hydrogen or a lower-alkyl radical; enesulfonic acid. The ketal groups are readily cleaved by R’ represents hydrogen or a lower-alkyl, lower-alkenyl, dilute acid after the condensation with hydroxylamine. lower-alkynyl, the acetyl, the hydroxyacetyl, the 1,2-dihy An oxo group at the 11-position is relatively unreactive droxyethyl or the 1-hydroxyethyl radical; X is selected and need not be protected before reaction with hydroxyl from the group consisting of H2. (H) (OH) and O; Y amine. - and Y represent hydrogen or the methyl radical; and Z In addition to the other uses set forth below, the com represents hydrogen or the hydroxy radical, Z being re pounds of the invention are useful as intermediates in the stricted to hydroxy when R represents hydrogen, or a preparation of different species within the scope of the lower-alkyl, lower-alkenyl or lower-alkynyl radical.
Load more

Recommended publications
  • Seco-Steroids C07C)
    CPC - C07J - 2021.08 C07J STEROIDS (seco-steroids C07C) Definition statement This place covers: Compounds containing a cyclopenta[a]hydrophenanthrene skeleton (see below) or a ring structure derived therefrom: • by contraction or expansion of one ring by one or two atoms; • by contraction or expansion of two rings each by one atom; • by contraction of one ring by one atom and expansion of one ring by one atom; • by substitution of one or two carbon atoms of the cyclopenta[a]hydrophenanthrene skeleton, which are not shared by rings, by hetero atoms, in combination with the above defined contraction or expansion or not, or; • by condensation with carbocyclic or heterocyclic rings in combination with one or more of the foregoing alterations or not. Preparation of steroids including purification, separation, stabilisation or use of additives unless provided for elsewhere, as specified below. Treatment and modification of steroids provided that • the treatment is not provided for elsewhere and • the resultant product is a compound under the subclass definition. Relationships with other classification places In class C07, in the absence of an indication to the contrary, a compound is classified in the last appropriate place, i.e. in the last appropriate subclass. For example cyclopenta [a] hydrophenantrenes are classified in subclass C07J as steroids and not in subclasses C07C or C07D as carbocyclic or heterocyclic compounds. Subclass C07J is a function-oriented entry for the compounds themselves and does not cover the application or use of the compounds under the subclass definition. For classifying such information other entries in the IPC exist, for example: Subclass A01N: Preservation of bodies of humans or animals or plants or parts thereof; biocides, e.g.
    [Show full text]
  • Research Collection
    Research Collection Doctoral Thesis Some reactions in the D-ring of the steroids Author(s): Boyce, Sam Framroze Publication Date: 1958 Permanent Link: https://doi.org/10.3929/ethz-a-000089222 Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library Prom. Nr. 2111 SOME REACTIONS IN THE D-RING 0! THE STEROIDS Thesis presented to The Swiss Federal Institute of Technology Zurich for the Degree of Doctor of Technical Science by SAM FRAMROZE BOYCE Indian Citizen Accepted on the recommendation of Prof. Dr. L. Ruzicka Priv. Doz. Dr. H. Heusser The Commercial Printing Press Private Ltd., Bombay 1958 TO THE MEMORY OF MY DEAR PARENTS ACKNOWLEDGEMENTS For giving me the opportunity to carry out this work, for his encouragement and keen interest during its progress, I here express my deep gratitude to Prof. L. Ruzicka. I am also indebted to Prof. L. Ruzicka and Prof. PI. A. Plattner for guidance of this work. My sincere thanks are also due to P. D. Dr. H. Heussor for his continued co-operation and helpful suggestions during the course of this work. To Prof. V. Prelog, I am obliged for the valuable discussions and critical comments. Finally, I am indebted to Prof. M. Giinthard for the infra-red spectra and to Mr. W. Manser for the micro-analysis. m CONTENTS GENERAL INTRODUCTION 1 Pabt I REARRANGEMENT OF a-HALOGENO-20-KETOSTEROIDS Theoretical Part 3 Experimental Part 10 Pabt Ha BASE CATALYSED REACTIONS WITH A16-3 jS-ACETOXY- 14,15 0-EPOXY-5-ALLOETIOCHOLENIC ACID METHYL ESTER Theoretical Part 18 Experimental Part 27 Pabt lib BASE AND ACID CATALYSED REACTIONS WITH A16-3j3- ACETOXY-14,15/3-EPOXY-20-KETO-5-ALLOPREGNENE Theoretical Part ..
    [Show full text]
  • UNITED STATES PATENT OFFICE 2,636,042 WATER-SOLUBLE HORMONE COMPOUNDS Ralph Salkin, Jackson Heights, N.Y., Assignor to S
    Patented Apr. 21, 1953 2,636,042 UNITED STATES PATENT OFFICE 2,636,042 WATER-SOLUBLE HORMONE COMPOUNDS Ralph Salkin, Jackson Heights, N.Y., assignor to S. B. Penick and Company, New York, N. Y., a corporation of Delaware No Drawing. Application July 8, 1949 Serial No. 103,759 5 Claims. (C. 260-39.4) 1. 2 My invention relates to an improvement in the ether, and the sulfate is then Salted out of the manufacture of water-soluble compounds of the aqueous solution by the addition of a, caustic estrane series, and in particular it is concerned solution under cooling. The liberated hormone With an improvement in the synthesis of alkali sulfate is extracted into a suitable Solvent, for and alkaline-earth metal salts of the sulfates of 5 instance butanol, pyridine being preferred how the estranes. ever. The hormone sulfate solution is exhaus The estranes to which my invention applies are tively extracted with ether to remove the solvent. steroids having a free hydroxyl group in the The resultant semicrystalline product is recrys 3-position and a hydroxy or keto group in the tallized from a dilute monohydric alcohol. Or 17-position of the molecule, such as estrone, O Water to give the pure sterol.ester. equilin, equilenin, estradiol and similar com In order to get pure ester Salts, I have found pounds. it essential that the tertiary amine-sulfur trioxide These products which are commonly known as adduct be absolutely pure when being reacted With conjugated estrogens can be obtained from nat the hormones. Improved yields and more readily ural sources such as the urine of pregnant mares purifiable light colored granular products result, or of stallions.
    [Show full text]
  • Labeling and Synthesis of Estrogens and Their Metabolites
    Labeling and Synthesis of Estrogens and Their Metabolites Paula Kiuru University of Helsinki Faculty of Science Department of Chemistry Laboratory of Organic Chemistry P.O. Box 55, 00014 University of Helsinki, Finland ACADEMIC DISSERTATION To be presented with the permission of the Faculty of Science of the University of Helsinki, for public criticism in Auditorium A110 of the Department of Chemistry, A. I. Virtasen Aukio 1, Helsinki, on June 18th, 2005 at 12 o'clock noon Helsinki 2005 ISBN 952-91-8812-9 (paperback) ISBN 952-10-2507-7 (PDF) Helsinki 2005 Valopaino Oy. 1 ABSTRACT 3 ACKNOWLEDGMENTS 4 LIST OF ORIGINAL PUBLICATIONS 5 LIST OF ABBREVIATIONS 6 1. INTRODUCTION 7 1.1 Nomenclature of estrogens 8 1.2 Estrogen biosynthesis 10 1.3 Estrogen metabolism and cancer 10 1.3.1 Estrogen metabolism 11 1.3.2 Ratio of 2-hydroxylation and 16α-hydroxylation 12 1.3.3 4-Hydroxyestrogens and cancer 12 1.3.4 2-Methoxyestradiol 13 1.4 Structural and quantitative analysis of estrogens 13 1.4.1 Structural elucidation 13 1.4.2 Analytical techniques 15 1.4.2.1 GC/MS 16 1.4.2.2 LC/MS 17 1.4.2.3 Immunoassays 18 1.4.3 Deuterium labeled internal standards for GC/MS and LC/MS 19 1.4.4 Isotopic purity 20 1.5 Labeling of estrogens with isotopes of hydrogen 20 1.5.1 Deuterium-labeling 21 1.5.1.1 Mineral acid catalysts 21 1.5.1.2 CF3COOD as deuterating reagent 22 1.5.1.3 Base-catalyzed deuterations 24 1.5.1.4 Transition metal-catalyzed deuterations 25 1.5.1.5 Deuteration without catalyst 27 1.5.1.6 Halogen-deuterium exchange 27 1.5.1.7 Multistep labelings 28 1.5.1.8 Summary of deuterations 30 1.5.2 Enhancement of deuteration 30 1.5.2.1 Microwave irradiation 30 1.5.2.2 Ultrasound 31 1.5.3 Tritium labeling 32 1.6 Deuteration estrogen fatty acid esters 34 1.7 Synthesis of 2-methoxyestradiol 35 1.7.1 Halogenation 35 1.7.2 Nitration of estrogens 37 1.7.3 Formylation 38 1.7.4 Fries rearrangement 39 1.7.5 Other syntheses of 2-methoxyestradiol 39 1.7.6 Synthesis of 4-methoxyestrone 40 1.8 Synthesis of 2- and 4-hydroxyestrogens 41 2.
    [Show full text]
  • REVIEW Steroid Sulfatase Inhibitors for Estrogen
    99 REVIEW Steroid sulfatase inhibitors for estrogen- and androgen-dependent cancers Atul Purohit and Paul A Foster1 Oncology Drug Discovery Group, Section of Investigative Medicine, Imperial College London, Hammersmith Hospital, London W12 0NN, UK 1School of Clinical and Experimental Medicine, Centre for Endocrinology, Diabetes and Metabolism, University of Birmingham, Birmingham B15 2TT, UK (Correspondence should be addressed to P A Foster; Email: [email protected]) Abstract Estrogens and androgens are instrumental in the maturation of in vivo and where we currently stand in regards to clinical trials many hormone-dependent cancers. Consequently,the enzymes for these drugs. STS inhibitors are likely to play an important involved in their synthesis are cancer therapy targets. One such future role in the treatment of hormone-dependent cancers. enzyme, steroid sulfatase (STS), hydrolyses estrone sulfate, Novel in vivo models have been developed that allow pre-clinical and dehydroepiandrosterone sulfate to estrone and dehydroe- testing of inhibitors and the identification of lead clinical piandrosterone respectively. These are the precursors to the candidates. Phase I/II clinical trials in postmenopausal women formation of biologically active estradiol and androstenediol. with breast cancer have been completed and other trials in This review focuses on three aspects of STS inhibitors: patients with hormone-dependent prostate and endometrial 1) chemical development, 2) biological activity, and 3) clinical cancer are currently active. Potent STS inhibitors should trials. The aim is to discuss the importance of estrogens and become therapeutically valuable in hormone-dependent androgens in many cancers, the developmental history of STS cancers and other non-oncological conditions.
    [Show full text]
  • University Microfilms, Inc., Ann Arbor, Michigan ADRENOCORTICAL STEROID PROFILE IN
    This dissertation has been Mic 61-2820 microfilmed exactly as received BESCH, Paige Keith. ADRENOCORTICAL STEROID PROFILE IN THE HYPERTENSIVE DOG. The Ohio State University, Ph.D., 1961 Chemistry, biological University Microfilms, Inc., Ann Arbor, Michigan ADRENOCORTICAL STEROID PROFILE IN THE HYPERTENSIVE DOG DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of the Ohio State University By Paige Keith Besch, B. S., M. S. The Ohio State University 1961 Approved by Katharine A. Brownell Department of Physiology DEDICATION This work is dedicated to my wife, Dr. Norma F. Besch. After having completed her graduate training, she was once again subjected to almost social isolation by the number of hours I spent away from home. It is with sincerest appreciation for her continual encouragement that I dedi­ cate this to her. ACKNOWLEDGMENTS I wish to acknowledge the assistance and encourage­ ment of my Professor, Doctor Katharine A. Brownell. Equally important to the development of this project are the experience and information obtained through the association with Doctor Frank A. Hartman, who over the years has, along with Doctor Brownell, devoted his life to the development of many of the techniques used in this study. It is also with extreme sincerity that I wish to ac­ knowledge the assistance of Mr. David J. Watson. He has never complained when asked to work long hours at night or weekends. Our association has been a fruitful one. I also wish to acknowledge the encouragement of my former Professor, employer and good friend, Doctor Joseph W.
    [Show full text]
  • The Metabolism of Desmosterol in Human Subjects During Triparanol Administration
    THE METABOLISM OF DESMOSTEROL IN HUMAN SUBJECTS DURING TRIPARANOL ADMINISTRATION DeWitt S. Goodman, … , Joel Avigan, Hildegard Wilson J Clin Invest. 1962;41(5):962-971. https://doi.org/10.1172/JCI104575. Research Article Find the latest version: https://jci.me/104575/pdf Journal of Clinical Investigation Vol. 41, No. 5, 1962 THE METABOLISM OF DESMOSTEROL IN HUMAN SUBJECTS DURING TRIPARANOL ADMINISTRATION * BY DEWITT S. GOODMAN, JOEL AVIGAN AND HILDEGARD WILSON (From the Section on Metabolism, National Heart Institute, and the National Institute of Arthritis and Metabolic Diseases, Bethesda, Md.) (Submitted for publication October 25, 1961; accepted January 25, 1962) Recent studies with triparanol (1-[p-,3-diethyl- Patient G.B. was a 55 year old man with known arterio- aminoethoxyphenyl ]-1- (p-tolyl) -2- (p-chloro- sclerotic heart disease and mild hypercholesterolemia; phenyl)ethanol) have demonstrated that this com- since 1957 he had maintained a satisfactory and stable cardiac status. At the time of the present study he had pound inhibits cholesterol biosynthesis by blocking been taking 250 mg triparanol daily for 4 weeks, and had the reduction of 24-dehydrocholesterol (desmos- a total serum sterol level in the high normal range. terol) to cholesterol (2-4). Administration of Patient F.A. was a 40 year old man with a 4- to 5-year triparanol to laboratory animals and to man re- history of gout and essential hyperlipemia. At the time sults in of of this study he had been on an isocaloric low purine diet the accumulation desmosterol in the for several weeks, and both the gout and hyperlipemia plasma and tissues, usually with some concom- were in remission.
    [Show full text]
  • US2940991.Pdf
    2,940,991 Paterated Jj Line 4, 1960 United States Patent Office 2 provide easy access to other biologically active steroid compounds. 2,940,991 These and other objects of this invention will become apparent on reading the following description in con METHOD OF EPIMERIZING 11-BROMO junction with the drawings in which: STERODS Figure 1 is a schematic representation of the process Percy L. Juliana, Oak Park, and Arthur Magnani, Wi in accordance with this invention. w X mette, Ill., assignors to The Julian Laboratories, ne, With respect to the following description, it is desired Frankin Park, I., a corporation of Illinois to point out that reduction providing an OH group in the O 12-position results in a mixture of compounds, some Filed Mar. 1, 1957, Ser. No. 643,353 having the OH bonded by a bond in the or position and 7 Claims. (C. 260-397.45) some by a bond in the 6 position. In the starting mate rial triols either the 12c ol or 126 ol compounds or a Rixture thereof may be employed. The structural formu This invention relates to novel steroid compounds and 15 las herein and in the claims are intended to cover both to processes for their preparation. The compounds of the 12c, ols and 12p ols where discussed and/or claimed. this invention are particularly useful as intermediates in It is also desired to point out that the steroid com the preparation of cortical hormones which have useful pounds discussed and claimed exist in either the 3ox,56 therapeutic activity.
    [Show full text]
  • Nomenclature of Steroids
    Pure&App/. Chern.,Vol. 61, No. 10, pp. 1783-1822,1989. Printed in Great Britain. @ 1989 IUPAC INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY and INTERNATIONAL UNION OF BIOCHEMISTRY JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE* NOMENCLATURE OF STEROIDS (Recommendations 1989) Prepared for publication by G. P. MOSS Queen Mary College, Mile End Road, London El 4NS, UK *Membership of the Commission (JCBN) during 1987-89 is as follows: Chairman: J. F. G. Vliegenthart (Netherlands); Secretary: A. Cornish-Bowden (UK); Members: J. R. Bull (RSA); M. A. Chester (Sweden); C. LiCbecq (Belgium, representing the IUB Committee of Editors of Biochemical Journals); J. Reedijk (Netherlands); P. Venetianer (Hungary); Associate Members: G. P. Moss (UK); J. C. Rigg (Netherlands). Additional contributors to the formulation of these recommendations: Nomenclature Committee of ZUB(NC-ZUB) (those additional to JCBN): H. Bielka (GDR); C. R. Cantor (USA); H. B. F. Dixon (UK); P. Karlson (FRG); K. L. Loening (USA); W. Saenger (FRG); N. Sharon (Israel); E. J. van Lenten (USA); S. F. Velick (USA); E. C. Webb (Australia). Membership of Expert Panel: P. Karlson (FRG, Convener); J. R. Bull (RSA); K. Engel (FRG); J. Fried (USA); H. W. Kircher (USA); K. L. Loening (USA); G. P. Moss (UK); G. Popjiik (USA); M. R. Uskokovic (USA). Correspondence on these recommendations should be addressed to Dr. G. P. Moss at the above address or to any member of the Commission. Republication of this report is permitted without the need for formal IUPAC permission on condition that an acknowledgement, with full reference together with IUPAC copyright symbol (01989 IUPAC), is printed.
    [Show full text]
  • United States Patent (19) 11 Patent Number: 4,585,591 Nitta Et Al
    United States Patent (19) 11 Patent Number: 4,585,591 Nitta et al. (45) Date of Patent: Apr. 29, 1986 (54) 17B-ETHYNYLSTEROIDs AND PROCESS 56) References Cited FOR PREPARNG SAME U.S. PATENT DOCUMENTS 75) Inventors: Issei Nitta, Machida; Shinichiro 3,023,206 2/1962 Burnet al. ..................... 260/239.55 Fujimori, Yokohama; Toshio Haruyama, Sagamihara; Shinya FOREIGN PATENT DOCUMENTS Inoue, Yamato, all of Japan 845441 8/1960 United Kingdom ............. 260/397.4 73 Assignee: Mitsubishi Chemical Industries, Ltd., OTHER PUBLICATIONS Tokyo, Japan L. A. van Dijck et al., "Synthesis and Reactions of 3-Methoxy-17-Hydroxy-17-Ethynyl-1,3,5(10)-Estra 21 Appl. No.: 325,026 triene', Recueil Journal of the Royal Netherlands Chemical Society, 96,7-8, Jul.-Aug., pp. 200-205 22 Filed: Nov. 25, 1981 (1977). Primary Examiner-Elbert L. Roberts 30 Foreign Application Priority Data Attorney, Agent, or Firm-Oblon, Fisher, Spivak, Dec. 10, 1980 JP Japan ................................ 55-174065 McClelland & Maier Dec. 10, 1980 JP Japan ... ... 55-174.066 Feb. 23, 1981 JP Japan .................................. 56-25307 (57) ABSTRACT Jul. 28, 1981 (JP) Japan ................................ 56-18343 This is disclosed novel intermediates, i.e. 1743-ethynyl steroids, which are useful for the preparation of corti 51) Int. Cl. .................................................. CO7J 1/00 coids such as hydrocortisone and prednisolone, and a 52 U.S. C. ............................ 260/3974; 260/397.45; process for preparing the same. 260/239.55 C, 260/397.5; 260/397.47 58) Field of Search ......................... 260/397.4, 397.45 4 Claims, No Drawings 4,585,591 1 2 17(3-ETHYNYLSTEROIDS AND PROCESS FOR -continued PREPARING SAME CECH BACKGROUND OF THE INVENTION This invention relates to a novel intermediate for use in the preparation of corticoids (adrenocortical hor mones) such as hydrocortisone, prednisolone and the MeO like.
    [Show full text]
  • The Use of Altrenogest to Control Reproductive Function in Beef Cattle" (2004)
    Louisiana State University LSU Digital Commons LSU Doctoral Dissertations Graduate School 2004 The seu of altrenogest to control reproductive function in beef cattle Clarence Edward Ferguson Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_dissertations Part of the Animal Sciences Commons Recommended Citation Ferguson, Clarence Edward, "The use of altrenogest to control reproductive function in beef cattle" (2004). LSU Doctoral Dissertations. 3957. https://digitalcommons.lsu.edu/gradschool_dissertations/3957 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Doctoral Dissertations by an authorized graduate school editor of LSU Digital Commons. For more information, please [email protected]. THE USE OF ALTRENOGEST TO CONTROL REPRODUCTIVE FUNCTION IN BEEF CATTLE A Dissertation Submitted to the Graduate Faculty of Louisiana State University and Agricultural and Mechanical College In partial fulfillment of the Requirements for the degree of Doctor of Philosophy in The Interdepartmental Program in Animal and Dairy Sciences by Clarence Edward Ferguson B.S., McNeese State University, 1996 M.S. Stephen F. Austin State University, 1999 M.N.A.S., Southwest Missouri State University, 2000 December 2004 ACKNOWLEDGEMENTS The author would like to convey his sincere gratitude to his major professor, Dr. Robert A. Godke for his direction, patience, and commitment to train him as a research scientist. The author believes that the training he received in Dr. Godke’s Program has been and will continue to be an invaluable experience that will aid him in overcoming obstacles later in life.
    [Show full text]
  • ラッ ト肝 の Steroid 5Β-Reductase 活性 に 対す る酢酸第 二水銀
    〔614〕 ラ ッ ト肝 の steroid 5β-reductase 活 性 に 対 す る酢 酸 第 二 水 銀 の 影 響 The Effect of Mercuric Acetate on the Activity of Steroid 5β-reductase in the Rat Liver 北海道大学医学部衛生学教室 富 田 勤 ・佐 藤 敏 雄 ・高 桑 栄 松 北海道大学大学院環境科学研究科環境医学教室 斎 藤 和 雄 Tsutomu Tomita, Toshio Sato and Eimatsu Takakuwa Department of Hygiene and Preventive Medicine, Hokkaido University School of Medicine, Sapporo Kazuo Saito Department of Environmental Medicine, Graduate School of Environmental Science, Hokkaido University, Sapporo The increase of urinary δ-aminolevulinic acid in man and animals exposed to high concentration of mercury is studied, but the mechanism of the increase has not been clearly explained. In this paper, the content of 5β type steroid, inducing δ-aminolevulinic acid synthetase, was studied by noticing the activities of steroid 5β-reductase, which is the rate limiting enzyme in metabolism of steroid hormones, 3α- and 3β-hydroxysteroid dehydrogenase. For measurement of these activities, 105,000×g supernatant of rat liver was used. The testosterone and ⊿4-androstene-3, 17-dione 5β-reductase activities decreased on either the fourth or eleventh day after either intraperitoneal or subcutaneous administration of mercuric acetate, respe- ctively, and the adrenosterone 5β-reductase activity increased on the eleventh day after the subcutaneous administration of mercuric acetate. These changes mentioned above, however, were not significant. The progesterone and 17α-hydroxy progesterone 5β-reductase activities decreased on either the fourth or eleventh day after either intraperitioneal or subcutaneous administration of mercuric acetate, but there were no significant changes.
    [Show full text]