GB1059548A - Steroid 2'-acylamino-2'-deoxy-glucosides and -galactosides - Google Patents

Steroid 2'-acylamino-2'-deoxy-glucosides and -galactosides

Info

Publication number
GB1059548A
GB1059548A GB652764A GB652764A GB1059548A GB 1059548 A GB1059548 A GB 1059548A GB 652764 A GB652764 A GB 652764A GB 652764 A GB652764 A GB 652764A GB 1059548 A GB1059548 A GB 1059548A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
keto
steroid
acyloxy
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB652764A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US259383A external-priority patent/US3206359A/en
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1059548A publication Critical patent/GB1059548A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C21—METALLURGY OF IRON
    • C21D—MODIFYING THE PHYSICAL STRUCTURE OF FERROUS METALS; GENERAL DEVICES FOR HEAT TREATMENT OF FERROUS OR NON-FERROUS METALS OR ALLOYS; MAKING METAL MALLEABLE, e.g. BY DECARBURISATION OR TEMPERING
    • C21D1/00—General methods or devices for heat treatment, e.g. annealing, hardening, quenching or tempering
    • C21D1/56—General methods or devices for heat treatment, e.g. annealing, hardening, quenching or tempering characterised by the quenching agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Novel compounds of the formulae <FORM:1059548/C2/1> <FORM:1059548/C2/2> and the 41-epimers thereof (in which R is C1-5 alkanoyl, Y is C1- 6 alkanoyl and Z is the residue of a 20-keto-D 4-(3-keto or [3,2-c]pyrazolo)-11 -(keto, hydroxy or acyloxy)-17a -(hydroxy or acyloxy)-21-hydroxy-steroid of the pregnane series from which the 21-hydroxy group has been removed and in which any 16-hydroxy group is in free alcohol form or is formed, together with a 17a -hydroxy group, into a 16,17-acetonide, or the residue of a 20-keto-D 4-(3-keto or [3,2-c] pyrazolo) - 11 - (keto, hydroxy or acyloxy)-17a -(hydroxy or acyloxy)-16a ,21-dihydroxy steroid of the pregnane series from which the 16a -hydroxy group has been removed, and Z1 is the same are prepared by reacting the appropriate 21-hydroxy steroid in which any 16-hydroxy group is protected or the appropriate 16a -hydroxy-21-acyloxy steroid (prepared by acylation of the 16a ,21-diol and separation from the 16a ,21-diacylate by extraction with sodium tetraborate in which the monoacylate dissolves and which is precipitated by addition of hydrochloric acid) with a 1-halo-N-(C1- 5 alkanoyl)-glucosamine tri-(C1- 6 alkanoate) or its 41-epimer and reacting the product with an alkaline hydrolysing agent. The hydrolysis removes the 21-acyl group as well as the O-acyl groups. The steroids may contain further substituents such as alkyl groups and halogen atoms and further double bonds, e.g. D 1 and D 6. 1 - Chloro - N - acetylglucosamine triacetate is prepared by acetylating glucosamine hydrochloride to give N -acetylglucosamine and then reacting this with acetyl chloride, acetic acid and hydrogen chloride. 1-Chloro-N-acetylgalactosamine triacetate is prepared similarly. The steroid 21-acylamino-21-deoxy-glucosides and -galactosides of the invention, which are stated to have anti-inflammatory activity, may be made up into pharmaceutical compositions for oral or parenteral use with suitable carriers. They may also contain flavouring agents.
GB652764A 1963-02-18 1964-02-17 Steroid 2'-acylamino-2'-deoxy-glucosides and -galactosides Expired GB1059548A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25938463A 1963-02-18 1963-02-18
US259383A US3206359A (en) 1963-02-18 1963-02-18 Galacturonides of the anti-inflammatory pregnane series

Publications (1)

Publication Number Publication Date
GB1059548A true GB1059548A (en) 1967-02-22

Family

ID=26947268

Family Applications (2)

Application Number Title Priority Date Filing Date
GB610864A Expired GB1047542A (en) 1963-02-18 1964-02-13 21-galacturonides of steroids
GB652764A Expired GB1059548A (en) 1963-02-18 1964-02-17 Steroid 2'-acylamino-2'-deoxy-glucosides and -galactosides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB610864A Expired GB1047542A (en) 1963-02-18 1964-02-13 21-galacturonides of steroids

Country Status (8)

Country Link
BE (2) BE643984A (en)
BR (2) BR6456819D0 (en)
CH (2) CH443288A (en)
DE (1) DE1468307A1 (en)
DK (1) DK111141B (en)
FR (4) FR1558253A (en)
GB (2) GB1047542A (en)
NL (2) NL6401472A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0721956A1 (en) * 1993-09-29 1996-07-17 Nissin Shokuhin Kabushiki Kaisha 21-substituted steroid compound
US6630453B1 (en) 1999-05-04 2003-10-07 Strakan Limited Androgen derivatives and uses thereof
JP4610734B2 (en) * 1998-03-19 2011-01-12 三笠製薬株式会社 21-substituted glycosyl steroid compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0721956A1 (en) * 1993-09-29 1996-07-17 Nissin Shokuhin Kabushiki Kaisha 21-substituted steroid compound
EP0721956A4 (en) * 1993-09-29 1996-11-20 Nissin Food Products Ltd 21-substituted steroid compound
US5945404A (en) * 1993-09-29 1999-08-31 Nissin Shokuhin Kabushiki Kaisha 21-Substituted steroid compound
JP4610734B2 (en) * 1998-03-19 2011-01-12 三笠製薬株式会社 21-substituted glycosyl steroid compounds
US6630453B1 (en) 1999-05-04 2003-10-07 Strakan Limited Androgen derivatives and uses thereof

Also Published As

Publication number Publication date
BE643984A (en) 1964-08-18
NL6401472A (en) 1964-08-19
FR3627M (en) 1965-10-18
FR4730M (en) 1967-01-09
FR1552765A (en) 1969-01-10
FR1558253A (en) 1969-02-28
BR6456819D0 (en) 1973-08-14
DE1468307A1 (en) 1969-10-23
GB1047542A (en) 1966-11-09
BE643983A (en) 1964-08-18
CH451130A (en) 1968-05-15
DK111141B (en) 1968-06-17
NL6401467A (en) 1964-08-19
CH443288A (en) 1967-09-15
BR6456929D0 (en) 1973-09-20

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