GB1100441A - 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives - Google Patents

13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives

Info

Publication number
GB1100441A
GB1100441A GB3206463A GB3206463A GB1100441A GB 1100441 A GB1100441 A GB 1100441A GB 3206463 A GB3206463 A GB 3206463A GB 3206463 A GB3206463 A GB 3206463A GB 1100441 A GB1100441 A GB 1100441A
Authority
GB
United Kingdom
Prior art keywords
group
trans
followed
compounds
hydrogen atom
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
GB3206463A
Inventor
Gordon Alan Hughes
Herchel Smith
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.)
Individual
Original Assignee
Individual
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 to BE651797D priority Critical patent/BE651797A/xx
Application filed by Individual filed Critical Individual
Priority to GB3206463A priority patent/GB1100441A/en
Priority to GB4001667A priority patent/GB1100443A/en
Priority to GB4001767A priority patent/GB1100444A/en
Priority to IL2182664A priority patent/IL21826A/en
Priority to IN95058A priority patent/IN95058B/en
Priority to NO15427664A priority patent/NO126016B/no
Priority to DE19641618871 priority patent/DE1618871C3/en
Priority to DE19641793641 priority patent/DE1793641C2/en
Priority to DE19641618872 priority patent/DE1618872C3/en
Priority to BR16164364A priority patent/BR6461643D0/en
Priority to DE19641468988 priority patent/DE1468988B1/en
Priority to CH1052964A priority patent/CH498819A/en
Priority to CH1742068A priority patent/CH498820A/en
Priority to CH381370A priority patent/CH499510A/en
Priority to CH1742168A priority patent/CH498821A/en
Priority to CH1387870A priority patent/CH507225A/en
Priority to AT696964A priority patent/AT269376B/en
Priority to AT292768A priority patent/AT301039B/en
Priority to AT227470A priority patent/AT301045B/en
Priority to ES0303113A priority patent/ES303113A1/en
Priority to FR1566154D priority patent/FR1566154A/fr
Priority to DK400464A priority patent/DK134161B/en
Priority to SE983464A priority patent/SE331470B/xx
Priority to SE843170A priority patent/SE350256B/xx
Priority to NL6409391A priority patent/NL139307B/en
Priority to FR994684A priority patent/FR4915M/fr
Priority to NO16575266A priority patent/NO132762C/no
Priority to NO16575366A priority patent/NO127193B/no
Publication of GB1100441A publication Critical patent/GB1100441A/en
Priority to SE04239/68A priority patent/SE334879B/xx
Priority to SE04238/68A priority patent/SE335120B/xx
Priority to SE04237/68A priority patent/SE335119B/xx
Priority to DK655269A priority patent/DK127598B/en
Priority to JP5758471A priority patent/JPS4837029B1/ja
Priority to DK395771A priority patent/DK132031C/en
Priority to NO495971A priority patent/NO129905B/no
Priority to DK220272A priority patent/DK127475B/en
Priority to DK38273A priority patent/DK131020B/en
Priority to DK84773A priority patent/DK131367B/en
Priority to DK286173A priority patent/DK134264B/en
Priority to NL7308508A priority patent/NL7308508A/xx
Priority to NL737308507A priority patent/NL145559B/en
Priority to IN1000/CAL/74A priority patent/IN137556B/en
Priority to IN137555A priority patent/IN137555B/en
Priority to IN1001/CAL/74A priority patent/IN137557B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • 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
    • A61K31/567—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 position 17 alpha, e.g. mestranol, norethandrolone
    • 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
    • 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

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 (a) compounds of formulae <FORM:1100441/C2/1> and <FORM:1100441/C2/2> each having an ethylenic bond terminating at the 50-position, wherein each group R is a hydrogen atom or an alkyl group, R1 is an alkyl group having at least 2 carbon atoms, -OR3 is a free, etherified or esterified hydroxy group, R2 is a haloalk-1-ynyl group trans to R1, Q is a methylene or ethylene group, X is a group hydrolysable by acid to a keto-group, the hydrogen atoms H and the group R1 at the junctions of ring C having the trans-anti-transconfiguration, and the hydrogen atom at the 10-position, if present, being antito that at the 9-position, with a disclaimer to 17a -chloroethynyl - 13b - ethyl - gon - 4 - en - 17b - ol - 3-one except when prepared by the processes described below; and (b) their preparation by reaction of the corresponding 3-X-substituted 17-ketone with a haloalkynyl organometallic reagent, followed, if desired, by (a) hydrolysis of a group X, (b) 17-etherification, or (c) 17-esterification, with formation of a 3-enol acetate, followed by partial hydrolysis, if desired. The compounds of the invention have progestational, pituitary-gonadotrophic blocking and anti-estrogenic activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral, parenteral or rectal administration.
GB3206463A 1961-10-19 1963-08-14 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives Expired GB1100441A (en)

Priority Applications (45)

Application Number Priority Date Filing Date Title
BE651797D BE651797A (en) 1962-10-17
GB3206463A GB1100441A (en) 1963-08-14 1963-08-14 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives
GB4001667A GB1100443A (en) 1962-10-17 1963-08-14 17ª‡-chloroethynyl-13ª‰-ethylgonenolone
GB4001767A GB1100444A (en) 1962-10-17 1963-08-14 13-alkyl 17-halogenoalkynyl steroid 3-alcohols and their esters
IL2182664A IL21826A (en) 1962-10-17 1964-08-03 Steroid ketones and their derivatives
IN95058A IN95058B (en) 1962-10-17 1964-08-05
NO15427664A NO126016B (en) 1962-10-17 1964-08-05
DE19641468988 DE1468988B1 (en) 1962-10-17 1964-08-10 17alpha-chloroethynyl-13beta-ethyl-4- or -5 (10) -gon-3-ketones
DE19641793641 DE1793641C2 (en) 1962-10-17 1964-08-10 Process for the preparation of 17-haloalkynyl 3-ketogones and their use. Eliminated from: 1468988
DE19641618872 DE1618872C3 (en) 1962-10-17 1964-08-10 Process for the preparation of 13-ethylgonane compounds and certain 13-ethylgonane compounds. Eliminated from: 1468988
BR16164364A BR6461643D0 (en) 1962-10-17 1964-08-10 PROCESS OF PREPARATION OF STEROID KETONES AND THEIR DERIVATIVES
DE19641618871 DE1618871C3 (en) 1962-10-17 1964-08-10 Process for the production of a steroid ketone derivative. Eliminated from: 1468988
CH381370A CH499510A (en) 1962-10-17 1964-08-12 Process for the preparation of steroid ketone derivatives with 17- or 17a-haloalkynyl groups
CH1742068A CH498820A (en) 1961-10-19 1964-08-12 Steroid ketones
CH1052964A CH498819A (en) 1962-10-17 1964-08-12 Steroid ketones
CH1742168A CH498821A (en) 1962-10-17 1964-08-12 Steroid ketones
CH1387870A CH507225A (en) 1962-10-17 1964-08-12 Process for the preparation of steroid ketones with 17- or 17a-haloalkynyl groups
AT696964A AT269376B (en) 1962-10-17 1964-08-13 Process for the production of new steroid ketones
AT292768A AT301039B (en) 1962-10-17 1964-08-13 Process for the manufacture of new steroids
AT227470A AT301045B (en) 1962-10-17 1964-08-13 Process for the manufacture of new steroids
ES0303113A ES303113A1 (en) 1963-08-14 1964-08-13 Procedure for preparing steroid ketones and their derivatives. (Machine-translation by Google Translate, not legally binding)
FR1566154D FR1566154A (en) 1962-10-17 1964-08-13
DK400464A DK134161B (en) 1962-10-17 1964-08-13 Analogous method for the production of steroid ketones.
SE983464A SE331470B (en) 1962-10-17 1964-08-14
NL6409391A NL139307B (en) 1962-10-17 1964-08-14 METHOD OF PREPARING A MEDICINAL PRODUCT WITH A HORMONE ACTIVITY.
SE843170A SE350256B (en) 1962-10-17 1964-08-14
FR994684A FR4915M (en) 1962-10-17 1964-11-12
NO16575266A NO132762C (en) 1962-10-17 1966-11-25
NO16575366A NO127193B (en) 1962-10-17 1966-11-25
SE04239/68A SE334879B (en) 1962-10-17 1968-03-29
SE04238/68A SE335120B (en) 1962-10-17 1968-03-29
SE04237/68A SE335119B (en) 1962-10-17 1968-03-29
DK655269A DK127598B (en) 1962-10-17 1969-12-10 Analogous process for the preparation of 17-haloalkynyl-3,17-dihydroxy-13-ethylgonenes or -D-homogens or esters or ethers thereof.
JP5758471A JPS4837029B1 (en) 1962-10-17 1971-08-02
DK395771A DK132031C (en) 1962-10-17 1971-08-12 ANALOGICAL PROCEDURE FOR THE PREPARATION OF 17-HALOALKYNYL-17-HYDROXY-13-ETHYL-GONEN-3-ONES OR THE CORRESPONDING D-HOMO COMPOUNDS
NO495971A NO129905B (en) 1962-10-17 1971-12-30
DK220272A DK127475B (en) 1962-10-17 1972-05-03 Analogous process for the preparation of 17-haloalkynyl-17-hydroxy-13-ethylgonenes or -D-homogonens or esters or ethers thereof.
DK38273A DK131020B (en) 1962-10-17 1973-01-24 Contraceptives.
DK84773A DK131367B (en) 1962-10-17 1973-02-16 Contraceptives.
DK286173A DK134264B (en) 1962-10-17 1973-05-24 Contraceptives.
NL7308508A NL7308508A (en) 1962-10-17 1973-06-19
NL737308507A NL145559B (en) 1962-10-17 1973-06-19 PROCESS FOR PREPARING A PREPARATION WITH PROGESTATIVE AND ANTI-OESTROGEN ACTIVITY, FORMED MEDICINAL PRODUCT AND PROCEDURE FOR PREPARING PROGESTATIVE AND ANTI-OESTROGEN ACTIVE COMPOUNDS.
IN1000/CAL/74A IN137556B (en) 1962-10-17 1974-05-03
IN137555A IN137555B (en) 1962-10-17 1974-05-03
IN1001/CAL/74A IN137557B (en) 1962-10-17 1974-05-03

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3206463A GB1100441A (en) 1963-08-14 1963-08-14 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives

Publications (1)

Publication Number Publication Date
GB1100441A true GB1100441A (en) 1968-01-24

Family

ID=10332630

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3206463A Expired GB1100441A (en) 1961-10-19 1963-08-14 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives

Country Status (2)

Country Link
ES (1) ES303113A1 (en)
GB (1) GB1100441A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984476A (en) * 1974-10-18 1976-10-05 Andor Furst D-homo-19-norsteroids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984476A (en) * 1974-10-18 1976-10-05 Andor Furst D-homo-19-norsteroids

Also Published As

Publication number Publication date
ES303113A1 (en) 1965-01-01

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