GB1064011A - A process for producing 13-substituted gonapolyan-17-ß-ols - Google Patents

A process for producing 13-substituted gonapolyan-17-ß-ols

Info

Publication number
GB1064011A
GB1064011A GB4003463A GB4003463A GB1064011A GB 1064011 A GB1064011 A GB 1064011A GB 4003463 A GB4003463 A GB 4003463A GB 4003463 A GB4003463 A GB 4003463A GB 1064011 A GB1064011 A GB 1064011A
Authority
GB
United Kingdom
Prior art keywords
radical
substituted
compound
carbon atoms
alkali metal
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
GB4003463A
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
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
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of GB1064011A publication Critical patent/GB1064011A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63F—CARD, BOARD, OR ROULETTE GAMES; INDOOR GAMES USING SMALL MOVING PLAYING BODIES; VIDEO GAMES; GAMES NOT OTHERWISE PROVIDED FOR
    • A63F9/00—Games not otherwise provided for
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Multimedia (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,064,011. Steroids. TAKEDA CHEMICAL INDUSTRIES Ltd. Oct. 10, 1963 [Oct. 11, 1962 (2); Nov. 2, 1962; Nov. 24, 1962; Dec. 8, 1962; March 22, 1963], No. 40034/63. Headings C2C and C2U. The invention comprises compounds of the general formulµ wherein R<SP>1</SP> is a hydrogen atom, an alkoxy radical having up to 4 carbon atoms or a phenoxy radical and R<SP>2</SP> is an alkyl radical having up to four carbon atoms or a phenyl or benzyl radical and a process which comprises reducing a 13-substituted-1,3,5(10),8,14-pentaene-17-one with an alkali metal borohydride, alkali metal aluminium hydride, diethyl aluminium hydride or aluminium isopropoxide to form the corresponding 17#-ol, and if desired hydrogenating the latter to form a 13-substituted-gona-1,3,5(10),8-tetraen-17#-ol. The 13 - substituted -1,3,5(10),8,14 -pentaene - 17 - one may be obtained by reacting a compound of the general formula (in which R<SP>1</SP> is a hydrogen atom or an alkoxy radical having up to 4 carbon atoms) with a compound of the formula (in which R<SP>2</SP> is an alkyl radical having up to 4 carbon atoms or a phenyl or benzyl radical) in the presence of a basic catalyst to produce a compound of the general Formula III and dehydrating this compound in the presence of an acid catalyst. The tetraene products may be reduced with an alkali metal in liquid ammonia to obtain the corresponding 1,3,5(10)- trienes. The racemic products obtained may be resolved by acylation of a 17#-hydroxy group with an optically active acid.
GB4003463A 1962-10-11 1963-10-10 A process for producing 13-substituted gonapolyan-17-ß-ols Expired GB1064011A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP4514262 1962-10-11
JP4514362 1962-10-11
JP4945362 1962-11-02
JP5299662 1962-11-24
JP5569162 1962-12-08
JP1514763 1963-03-22
DET0024862 1963-10-10

Publications (1)

Publication Number Publication Date
GB1064011A true GB1064011A (en) 1967-04-05

Family

ID=31950954

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4003463A Expired GB1064011A (en) 1962-10-11 1963-10-10 A process for producing 13-substituted gonapolyan-17-ß-ols

Country Status (2)

Country Link
DE (2) DE1793619A1 (en)
GB (1) GB1064011A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5157004A (en) * 1986-12-27 1992-10-20 Takeda Chemical Industries, Ltd. Polypeptides and production thereof

Also Published As

Publication number Publication date
DE1468740A1 (en) 1969-08-07
DE1793619A1 (en) 1972-08-03

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