GB929273A - Steroids and their production - Google Patents

Steroids and their production

Info

Publication number
GB929273A
GB929273A GB4814162A GB4814162A GB929273A GB 929273 A GB929273 A GB 929273A GB 4814162 A GB4814162 A GB 4814162A GB 4814162 A GB4814162 A GB 4814162A GB 929273 A GB929273 A GB 929273A
Authority
GB
United Kingdom
Prior art keywords
group
qiii
compounds
formula iii
hydrogen
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
GB4814162A
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 GB929273A publication Critical patent/GB929273A/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

<FORM:0929273/IV(a)/1> <FORM:0929273/IV(a)/2> <FORM:0929273/IV(a)/3> <FORM:0929273/IV(a)/4> <FORM:0929273/IV(a)/5> The invention comprises 10a -methyl-9a -steroids of the general formula III and IV shown in the Figure, wherein R2 represents no double bonds or one or more double bonds at one or more of the positions 1, 3, 4, 5 and 6, R4 represents a keto, hydroxy, etherified hydroxy or esterified hydroxy group, and QIII represents a hydrogen or halogen atom, or a hydroxy or O-alkyl group, QV represents a hydrogen atom and QIV represents a secondary amine residue (including cyclic amine), or an O-acyl, phenyl or alkyl group, or QIV and QV each represent a phenyl or alkyl group; the preparation of the compounds of formula III, wherein QIII represents a hydrogen atom or a hydroxy group, by oxidising 10a -methyl-9a -steroids of the general formula II shown in the Figure, wherein QI and QII each represent an aliphatic hydrocarbon group having from 1 to 6 carbon atoms or QI may represent a hydrogen atom and QII is as previously defined; the preparation of the compounds of formula IV, wherein QIV represents the secondary amino group and QV represents a hydrogen atom by reacting compounds of formula III, wherein QIII represents hydrogen, with a secondary amine; the preparation of the compounds of formula IV, wherein QIV represents an O-acyl group and QV represents hydrogen, by reacting compounds of formula III, wherein QIII represents hydrogen with an acid anhydride; the preparation of the compounds of formula IV wherein QIV and QV each represent the same alkyl or phenyl group or one represents such a group and the other hydrogen, by reacting compounds of the formula III, wherein QIII represents a hydrogen atom or an O-alkyl group, with a phenyl or alkyl Grignard reagent and decomposing the reaction product in an acidic or neutral medium; and the preparation of compounds of formula IV, wherein QIV represents a phenyl group and QV represents a phenyl or alkyl group, by reacting compounds of formula III, wherein QIII represents a halogen atom, with diphenyl cadmium, reacting the resulting intermediate ketone with a phenyl or alkyl Grignard reagent, and decomposing the reaction product in a neutral or acidic medium. The compounds of formula III, wherein QIII represents a halogen atom or an O-alkyl group, are prepared by halogenating or esterifying the corresponding compound of formula III, wherein QIII represents a hydroxy group. In the oxidation processes referred to above, it is preferably to protect a 4(5) double bond in the absence of a 3-keto group, for example, by conversion to a dibromide from which the bromine atoms can be removed at a later stage by the action of zinc dust in glacial acetic acid, or by conversion into an epoxide by reaction with hydrogen peroxide in alkaline medium and subsequent decomposition by reaction of the epoxide with potassium iodide in a weakly acidic medium. Oxidation with chromium trioxide, potassium or sodium dichromate, or potassium permanganate forms acids of the formula III, i.e. QIII represents a hydroxy group, or oxidation with ozone forms an ozonide which may be decomposed to form an acid or aldehyde of formula III, i.e. QIII represents a hydroxy group or a hydrogen atom, by means of oxidising or reducing agents, for example, oxidising agents such as hydrogen peroxide or an alkaline solution of potassium permanganate, and reducing agents such as zinc dust-glacial acetic acid, iron powder in sulphuric acid, and aldehydes. Following the above processes, a 3-hydroxy group may be oxidised to a 3-keto group, for example, by means of manganese dioxide. In the examples the compounds of the formulae XVI and XVII shown in the Figure are prepared. D 4,22-Pyrostadiene-3-one is prepared by oxidising pyrocalciferol with cyclohexanone and aluminium isopropylate to form D 4,7,22-pyrostatriene-3-one, treating this compound with dry hydrogen chloride in isopropanol to form D 4,6,22-pyrostratriene-3-one, reducing this compound with lithium in liquid ammonia to form D 5,22-pyrostadiene-3-one, and isomerising this compound in an alkaline or acidic medium. Specifications 929,271 and 929,275 also are referred to.
GB4814162A 1958-04-12 1959-04-12 Steroids and their production Expired GB929273A (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
GB929273A true GB929273A (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
GB4814162A Expired GB929273A (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
GB4814262A Expired GB929274A (en) 1958-04-12 1959-04-12 Steroids and their production

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB4841359A Expired GB929275A (en) 1958-04-12 1959-04-09 Steroids and their production

Family Applications After (2)

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

Country Status (2)

Country Link
CH (3) CH452517A (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
GB929274A (en) 1963-06-19
CH396894A (en) 1965-08-15
CH452517A (en) 1968-03-15
CH398576A (en) 1966-03-15
GB929275A (en) 1963-06-19
GB929272A (en) 1963-06-19

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