DE1543012B2 - 2-CHLORINE-9BETA, 10ALPHA-PREGNA-1,4,6TRIEN-3,20-Dione, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE - Google Patents

2-CHLORINE-9BETA, 10ALPHA-PREGNA-1,4,6TRIEN-3,20-Dione, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE

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Publication number
DE1543012B2
DE1543012B2 DE19651543012 DE1543012A DE1543012B2 DE 1543012 B2 DE1543012 B2 DE 1543012B2 DE 19651543012 DE19651543012 DE 19651543012 DE 1543012 A DE1543012 A DE 1543012A DE 1543012 B2 DE1543012 B2 DE 1543012B2
Authority
DE
Germany
Prior art keywords
dione
pregna
pharmaceutical preparations
chlorine
6trien
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.)
Granted
Application number
DE19651543012
Other languages
German (de)
Other versions
DE1543012A1 (en
DE1543012C3 (en
Inventor
Engbert Härmen Bussum Scholer Hendrik Frederick Louis Leiden Westerhof Pieter Bussum Reennk, (Niederlande)
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of DE1543012A1 publication Critical patent/DE1543012A1/en
Publication of DE1543012B2 publication Critical patent/DE1543012B2/en
Application granted granted Critical
Publication of DE1543012C3 publication Critical patent/DE1543012C3/en
Expired legal-status Critical Current

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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
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (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)

Description

Die Erfindung betrifft 2-Chlor-9ftl0a-pregna-l,4, 6-trien-3,20-dion, ein Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Präparate.The invention relates to 2-chloro-9ftl0a-pregna-l, 4, 6-triene-3,20-dione, a process for its production and pharmaceutical preparations containing it.

Das neue 2-Chlor-9/?,10a-pregna-l,4,6-trien-3,20-dion kann nach Methoden erhalten werden, wie sie aus der Chemie der Steroid-Normalreihe an sich bekannt sind, beispielsweise dadurch, daß man 9/?,10a-Pregnal,4,6-trien-3,20-dion mit Chlor behandelt und anschließend dehydrochloriert (vgl. J. Chem. Soc. 1958, S. 1324).The new 2-chloro-9 / ?, 10a-pregna-l, 4,6-triene-3,20-dione can be obtained by methods such as those known per se from the chemistry of the normal steroid series are, for example, by using 9 / ?, 10a-pregnal, 4,6-triene-3,20-dione treated with chlorine and then dehydrochlorinated (cf. J. Chem. Soc. 1958, P. 1324).

Die erfindungsgemäße Verbindung ist hormonal wirksam. Sie hat eine testosteronantagonisierende Wirkung sowie Eigenschaften, die eine Verwendung als Kontrazeptivum möglich erscheinen lassen. Das Verfahrensprodukt. kann daher als Heilmittel, z. B. in Form pharmazeutischer Präparate, Verwendung finden, die es in Mischung mit einem für die enterale oder parenteral Applikation geeigneten organischen oder anorganischen inerten Trägermaterial, wie ζ. Β. Wasser, Gelatine, Milchzucker, Stärke, Magnesiumstearat, Talk, pflanzliche Öle, Gummi, Polyalkylenglykole, Vaseline usw., enthalten. Die pharmazeutischen Präparate können in fester Form, z. B. als Tabletten, Dragees, Suppositorien, Kapseln, oder in flüssiger Form, z. B. als Lösungen, Suspensionen oder Emulsionen, vorliegen. Gegebenenfalls ίο sind sie sterilisiert und bzw. oder enthalten Hilfsstoffe, wie Konservierungs-, Stabilisierungs-, Netzoder Emulgiermittel, Salze zur Veränderung des osmotischen Druckes oder Puffer. Sie können auch noch andere therapeutisch wertvolle Stoffe enthalten.The compound according to the invention is hormonally active. She has a testosterone antagonist Effect and properties that make it possible to use it as a contraceptive. The process product. can therefore be used as a remedy, e.g. B. in the form of pharmaceutical preparations, use find that it is mixed with an organic compound suitable for enteral or parenteral application or inorganic inert support material, such as ζ. Β. Water, gelatin, milk sugar, starch, Magnesium stearate, talc, vegetable oils, rubber, polyalkylene glycols, petroleum jelly, etc. the pharmaceutical preparations can be in solid form, e.g. B. as tablets, coated tablets, suppositories, capsules, or in liquid form, e.g. B. as solutions, suspensions or emulsions. Possibly ίο are they sterilized and / or contain auxiliary materials, such as preservatives, stabilizers, wetting agents or emulsifiers, salts to change the osmotic pressure or buffer. They can also contain other therapeutically valuable substances.

Beispiel t'v Example t'v

Zu einer Lösung von 1,50 g 9/?,10a-Pregna-l-,4,6-trien-3,20-dion in 3 ml Methylenchlorid und 40 ml Äther wurde bei — 200C eine Lösung von 370 mg Chlor in 5 ml Eisessig gegeben. Die Mischung wurde 5 Stunden bei — 200C gehalten, dann auf Wasser gegossen und mit Methylenchlorid extrahiert. Der mit Wasser neutral gewaschene Extrakt wurde getrocknet, eingedampft und der Rückstand mit 10 ml Pyridin 30 Minuten bei Zimmertemperatur gehalten. Es wurde auf Eiswasser verdünnte Salzsäure gegossen und mit Äther extrahiert Durch Umkristallisieren des Rohproduktes aus Äther wurde 2-Chlor-9/?,10«-pregnal,4,6-trien-3,20-dion erhalten. Schmelzpunkt: 122 bis 123° C; [«]£ = 332 (in Dioxan);'To a solution of 1.50 g of 9 / ?, 10a-pregna-l, 4,6-triene-3,20-dione in 3 ml of methylene chloride and 40 ml of ether was added at - 20 0 C, a solution of 370 mg of chloroauric given in 5 ml of glacial acetic acid. The mixture was for 5 hours at - 20 kept 0 C, then poured into water and extracted with methylene chloride. The extract, washed neutral with water, was dried and evaporated, and the residue was kept at room temperature with 10 ml of pyridine for 30 minutes. Dilute hydrochloric acid was poured onto ice water and extracted with ether. Recrystallization of the crude product from ether gave 2-chloro-9 / ?, 10 "-pregnal, 4,6-triene-3,20-dione. Melting point: 122 to 123 ° C; [«] £ = 332 (in dioxane); '

UV: ;.max 212 nm (ε.= 15 000),
263 nm (ε = 10 850),
309 nm (ε = 10 100).UV:; .max 212 nm (ε. = 15,000),
263 nm (ε = 10 850),
309 nm (ε = 10 100).

Claims (3)

Patentansprüche:Patent claims: 1. 2-Chlor-9/9,10«-pregna-l,4,6-trien-3,20-dion:1. 2-chloro-9 / 9,10 «-pregna-l, 4,6-triene-3,20-dione: 2. Verfahren zur Herstellung von 2-Chlor-9/2,10a-pregna-l,4,6-trien-3,20-dion, dadurch gekennzeichnet, daß man in an sich bekannter Weise 9/?,10a-Pregna-l,4,6-trien-3,20-dionmitChlor behandelt und anschließend dehydrochloriert.2. Process for the production of 2-chloro-9 / 2,10a-pregna-l, 4,6-triene-3,20-dione, characterized in that 9 / ?, 10a-Pregna-l, 4,6-triene-3,20-dione with chlorine treated and then dehydrochlorinated. 3. Pharmazeutische Präparate, dadurch gekennzeichnet, daß sie als Wirkstoff 2-Chlor-9/S,10«-pregna-l,4,6-trien-3,20-dion in Mischung mit üblichen Trägerstoffen enthalten.'3. Pharmaceutical preparations, characterized in that they contain 2-chloro-9 / S, 10 «-pregna-l, 4,6-triene-3,20-dione as the active ingredient contained in a mixture with common carriers. '
DE19651543012 1965-07-09 1965-07-09 2 chlorine 9beta, 10alpha pregna 1,4,6 tnen 3,20 dione, process for its manufacture and pharmaceutical preparations containing them Expired DE1543012C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH0056533 1965-07-09

Publications (3)

Publication Number Publication Date
DE1543012A1 DE1543012A1 (en) 1969-08-14
DE1543012B2 true DE1543012B2 (en) 1973-03-15
DE1543012C3 DE1543012C3 (en) 1973-10-31

Family

ID=7159416

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19651543012 Expired DE1543012C3 (en) 1965-07-09 1965-07-09 2 chlorine 9beta, 10alpha pregna 1,4,6 tnen 3,20 dione, process for its manufacture and pharmaceutical preparations containing them

Country Status (1)

Country Link
DE (1) DE1543012C3 (en)

Also Published As

Publication number Publication date
DE1543012A1 (en) 1969-08-14
DE1543012C3 (en) 1973-10-31

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