GB929275A - Steroids and their production - Google Patents

Steroids and their production

Info

Publication number
GB929275A
GB929275A GB4841359A GB4841359A GB929275A GB 929275 A GB929275 A GB 929275A GB 4841359 A GB4841359 A GB 4841359A GB 4841359 A GB4841359 A GB 4841359A GB 929275 A GB929275 A GB 929275A
Authority
GB
United Kingdom
Prior art keywords
methyl
steroids
group
general formula
keto
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
GB4841359A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB929275A publication Critical patent/GB929275A/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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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
    • A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • A61K31/5685—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
    • 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
    • A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • A61K31/569—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material 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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 10a -methyl-9a -steroids of the general formula VI shown in the Figure, wherein R2 represents no double bonds or one or more double bonds at one or more positions 1, 3, 4, 5 and 6, R4 represents a keto, hydroxy, esterified hydroxy or etherified hydroxy group, QVI represents a methyl group and QVII represents an aldehyde group or a cyanhydrin or bisulphite addition product thereof, or an O-acyl <FORM:0929275/IV(a)/1> group, or QVI represents hydrogen and QVII represents a -COOR group, 'acyl' is derived from an aliphatic carboxylic acid having from 1 to 6 carbon atoms and R represents an alkyl group having from 1 to 6 carbon atoms; the preparation thereof, wherein QVI represents a methyl group and QVII represents an aldehyde group, by dehydrobrominating 10a -methyl-9a -steroids of the general formula IIIA in the Figure wherein R2 and R4 have the above significance, for example, by reacting with a basic metal oxide or hydroxide or with a primary, secondary or tertiary amine; the preparation thereof, wherein QVI represents a methyl group and QVII represents an O-acyl group, by reacting 10a -methyl-9a -steroids of the general formula V shown in the Figure with the isopropenyl ester of acetic acid or other aliphatic carboxylic acid having from 1 to 6 carbon atoms to produce 10a -methyl-9a -steroids of the general formula VA shown in the Figure, and treating these compounds with p-toluenesulphonic acid or other catalyst effective to move the double bond from the 20(21)-position to the 17(20)-position (in this process a 3-keto-D 4-grouping may be converted to a D 3,5-3-enol-acylate grouping which will necessitate iodinating the reaction product with iodosuccinimide in dioxan and then deiodinating with sodium bisulphite to reform the 3-keto-D 4-grouping); and the preparation thereof, wherein QVI represents hydrogen and QVII represents a -COOR group, R having the above significance, by reacting 10a -methyl-9a -steroids of the general formula V, wherein R2 and R4 have the above significance, with a dialkyl oxalate in the presence of an alkali metal alkoxide as condensing agent, to form 10a -methyl-9a -steroids of the general formula VB shown in the Figure, brominating these compounds and decomposing the dibrominated products with an alkali metal enolate (in this process a 3-keto-D 4-grouping may be converted to a D 3,5-3-enol-acylate grouping which will necessitate iodinating the reaction product with iodosuccinimide in dioxan and then deiodinating with sodium bisulphite to reform the 3-keto-D 4-grouping); and the preparation thereof, wherein QVI represents hydrogen and QVII represents a -COOR group, R having the above significance, by reacting 10a -methyl-9a -steroids of the general formula V, wherein R2 and R4 have the above significance, with a dialkyl oxalate in the presence of an alkali metal alkoxide as condensing agent to form 10a -methyl-9a -steroids of the general formula VB shown in the Figure, brominating these compounds and decomposing the dibrominated products with an alkali metal enolate (in this process the dialkyl oxalate may associate at the 2 and/or 4 positions of a 3-keto-compound unsubstituted at the 2 and/or 4 positions so that 2- and/or 4-bromo substitution takes place during the step of brominating and the process may require an additional step of removing the bromine atoms by reduction with zinc dust and glacial acetic acid). The first process above may be modified in that the 10a -methyl-9a -steroid reactants of the general formula IIIA in the Figure are prepared by a process described in Specification 929,274. The substituent at the 3-position of the 10a -methyl-9a -steroids of the general formula VI in the Figure may be varied, for example, a hydroxy group may be oxidised to keto-manganese dioxide being a suitable oxidising agent, or a hydroxy group may be esterified. In the examples the 10a -methyl-9a -steroids of the formulae XXI and XXII shown in the Figure are prepared. Specifications 929,271 and 929,273 also are referred to.
GB4841359A 1958-04-12 1959-04-09 Steroids and their production Expired GB929275A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
NL226774 1958-04-12
NL232312 1958-10-15
NL236884 1959-03-07
NL237103 1959-03-13

Publications (1)

Publication Number Publication Date
GB929275A true GB929275A (en) 1963-06-19

Family

ID=27483655

Family Applications (4)

Application Number Title Priority Date Filing Date
GB4841359A Expired GB929275A (en) 1958-04-12 1959-04-09 Steroids and their production
GB4814262A Expired GB929274A (en) 1958-04-12 1959-04-12 Steroids and their production
GB1202659A Expired GB929272A (en) 1958-04-12 1959-04-12 Steroids and their production
GB4814162A Expired GB929273A (en) 1958-04-12 1959-04-12 Steroids and their production

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB4814262A Expired GB929274A (en) 1958-04-12 1959-04-12 Steroids and their production
GB1202659A Expired GB929272A (en) 1958-04-12 1959-04-12 Steroids and their production
GB4814162A Expired GB929273A (en) 1958-04-12 1959-04-12 Steroids and their production

Country Status (2)

Country Link
CH (3) CH396894A (en)
GB (4) GB929275A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2994092B1 (en) * 2012-08-03 2014-11-28 Centre Nat Rech Scient NOVEL ENZYMA ACTIVITY COMPOUNDS OF SIRT1 AND PHARMACEUTICAL OR COSMETIC COMPOSITIONS COMPRISING THE SAME

Also Published As

Publication number Publication date
CH396894A (en) 1965-08-15
CH398576A (en) 1966-03-15
GB929273A (en) 1963-06-19
CH452517A (en) 1968-03-15
GB929272A (en) 1963-06-19
GB929274A (en) 1963-06-19

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