GB1202521A - 01beta-CHLORO-19-NOR-STEROIDS - Google Patents

01beta-CHLORO-19-NOR-STEROIDS

Info

Publication number
GB1202521A
GB1202521A GB23066/67A GB2306667A GB1202521A GB 1202521 A GB1202521 A GB 1202521A GB 23066/67 A GB23066/67 A GB 23066/67A GB 2306667 A GB2306667 A GB 2306667A GB 1202521 A GB1202521 A GB 1202521A
Authority
GB
United Kingdom
Prior art keywords
prepared
dione
steroid
reaction
chloro
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
GB23066/67A
Inventor
Joseph Elks
Gordon Hanley Phillips
Alan Tulley
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB23066/67A priority Critical patent/GB1202521A/en
Priority to PL1967121900A priority patent/PL79253B1/pl
Priority to BE702023D priority patent/BE702023A/xx
Priority to IL28411A priority patent/IL28411A/en
Priority to AT706867A priority patent/AT301766B/en
Priority to JP42048203A priority patent/JPS5021469B1/ja
Priority to AT851569A priority patent/AT311564B/en
Priority to DE1967G0050758 priority patent/DE1668124B2/en
Priority to DK389767AA priority patent/DK129004B/en
Priority to FR1565340D priority patent/FR1565340A/fr
Priority to SE10939/67*A priority patent/SE349025B/xx
Priority to NL6710459A priority patent/NL6710459A/xx
Priority to CH1075067A priority patent/CH580644A5/xx
Priority to FR125405A priority patent/FR7812M/fr
Priority to US846975A priority patent/US3665021A/en
Priority to DK483769AA priority patent/DK131295B/en
Priority to SE06851/70A priority patent/SE350488B/xx
Publication of GB1202521A publication Critical patent/GB1202521A/en
Priority to JP45075642A priority patent/JPS5224013B1/ja
Priority to CH1075067A priority patent/CH584724A5/xx
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
    • 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
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine 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
    • 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
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,202,521. 9α - Unsubstituted - 11# - chloro - 19 - nor - steroids. GLAXO LABORATORIES Ltd. 8 Aug., 1967 [29 July, 1966; 18 May, 1967], Nos. 34275/66 and 23066/67. Heading C2U. [Also in Division A5] Novel 9α - unsubstituted 11# - chloro - 19 - nor-steroids are prepared (1) by reaction of the corresponding 11α-ols with a reagent of the formula (in which R<SP>1</SP> and R<SP>2</SP> are each C 1-8 alkyl, aralkyl or aryl, or NR<SP>1</SP>R<SP>2</SP> is a heterocycle which may contain further hetero atoms, R<SP>3</SP> is Cl or F, R<SP>4</SP> is Cl or F and R<SP>5</SP> is H or R<SP>4</SP> and R<SP>5</SP> together represent a carbon-carbon bond, R<SP>6</SP> is Cl or F and R<SP>7</SP> is Cl, F or CF 3 ) the reaction being effected in the presence of chloride ions when neither nor R<SP>4</SP> is Cl, other reactive OH groups preferably being protected; or (2) by reaction of the corresponding 11α - alkyl or aryl - sulphonyloxy compounds with a source of chloride ions; or (3) by reaction of the 11α-ols with a triaryl - phosphine or - phosphite and chlorine or a chloroalkane. In the products 3- and 17- keto groups may be reduced, 3- and 17-hydroxy groups may be acylated or etherified or the corresponding keto groups may be enolacylated or -etherified, a 17-keto group may be reacted with an aliphatic or araliphatic organometallic compound to introduce an aliphatic or araliphatic group and form the 17-ol, a 3-acyloxy or -alkoxy steroid 3,5-diene may be chlorinated to give a 6# - chloro - 3 - oxo - #<SP>4</SP> - steroid and this may be epimerized by enol acylation or alkylation followed by hydrolysis, a #<SP>3'5</SP> - 3 - enol acylate or ether may be converted into the #<SP>4'6</SP> - 3 - ketone e.g. with chloranil or manganese dioxide, and a 3,17α - diacyloxy - #<SP>3'5</SP> - steroid may be selectively hydrolysed to the 17α - acyloxy - #<SP>4</SP> - 3 - keto - steroid. Other standard processes are also referred to. 11α,17α - Dihydroxy - 19 - norpregn - 4 - ene - 3,20 - dione is prepared from 21 - iodo - pregna - 1,4 - diene - 11#,17α - diol - 3,20 - dione by conversion to the 21 - unsubstituted compound, then to the #<SP>9</SP>(11) - compound, then to 3,17α - dihydroxy - 19 - norpregna - 1,3,5(10),9(11) - tetraen - 20 - one, then to the 3 - alkoxy compound, then to the 20 - ketal, hydroboration to the 11α - ol and Birch reduction and hydrolysis to the required product. 11α - Hydroxy - estra - 4,6 - diene - 3,17 - dione is prepared by the action of chloranil on 3- ethoxy - 11α - hydroxyestra - 3,5 - dien - 17 - one, prepared by enol etherification of the #<SP>4</SP>-3-one. 11α - Hydroxy - 19 - nor - pregn - 4 - ene - 3,20 - dione, is prepared by Birch reduction and hydrolysis of 20,20 - ethylenedioxy - 3 - methoxy - 19 - nor - pregna - 1,3,5(10) - trien - 11α - ol. 11α - Mesyloxyestr - 4 - ene - 3,11 - dione is prepared from the 11α-ol.
GB23066/67A 1966-07-29 1966-07-29 01beta-CHLORO-19-NOR-STEROIDS Expired GB1202521A (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
GB23066/67A GB1202521A (en) 1966-07-29 1966-07-29 01beta-CHLORO-19-NOR-STEROIDS
PL1967121900A PL79253B1 (en) 1966-07-29 1967-07-27
FR1565340D FR1565340A (en) 1966-07-29 1967-07-28
NL6710459A NL6710459A (en) 1966-07-29 1967-07-28
AT706867A AT301766B (en) 1966-07-29 1967-07-28 Process for the production of new 9α-unsubstituted 11β-chloro-19-nor-steroids
JP42048203A JPS5021469B1 (en) 1966-07-29 1967-07-28
AT851569A AT311564B (en) 1966-07-29 1967-07-28 Process for the preparation of new 6,11β-dichloro-19-norsteroid-4-en (or 4,6-diene) -3-ones unsubstituted in the 9α-position
DE1967G0050758 DE1668124B2 (en) 1966-07-29 1967-07-28 9 ALPHA-UNSUBSTITUTED 11 BETA-CHLORINE-19-NORSTEROIDS, PROCESS FOR THEIR PRODUCTION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINED
DK389767AA DK129004B (en) 1966-07-29 1967-07-28 Analogous process for the preparation of 9α-unsubstituted 11β-chloro-19-norsteroids of the estrane or 19-norpregane series.
BE702023D BE702023A (en) 1966-07-29 1967-07-28
SE10939/67*A SE349025B (en) 1966-07-29 1967-07-28
IL28411A IL28411A (en) 1966-07-29 1967-07-28 9alpha-unsubstituted 11beta-chloro-19-nor-steroids and their preparation
CH1075067A CH580644A5 (en) 1966-07-29 1967-07-28
FR125405A FR7812M (en) 1966-07-29 1967-08-23
US846975A US3665021A (en) 1966-07-29 1969-08-01 9alpha-unsubstituted-11beta-chloro-l9 nos-steroids
DK483769AA DK131295B (en) 1966-07-29 1969-09-10 Steroids of the estrane or 19-norpregnan series for use as contraceptives.
SE06851/70A SE350488B (en) 1966-07-29 1970-05-19
JP45075642A JPS5224013B1 (en) 1966-07-29 1970-08-31
CH1075067A CH584724A5 (en) 1966-07-29 1975-08-15

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB23066/67A GB1202521A (en) 1966-07-29 1966-07-29 01beta-CHLORO-19-NOR-STEROIDS
GB3427566 1966-07-29

Publications (1)

Publication Number Publication Date
GB1202521A true GB1202521A (en) 1970-08-19

Family

ID=26256295

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23066/67A Expired GB1202521A (en) 1966-07-29 1966-07-29 01beta-CHLORO-19-NOR-STEROIDS

Country Status (12)

Country Link
JP (2) JPS5021469B1 (en)
AT (2) AT311564B (en)
BE (1) BE702023A (en)
CH (2) CH580644A5 (en)
DE (1) DE1668124B2 (en)
DK (2) DK129004B (en)
FR (2) FR1565340A (en)
GB (1) GB1202521A (en)
IL (1) IL28411A (en)
NL (1) NL6710459A (en)
PL (1) PL79253B1 (en)
SE (2) SE349025B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1289521A (en) * 1969-01-23 1972-09-20
GB1313659A (en) * 1969-07-25 1973-04-18 Glaxo Lab Ltd 9alpha-unsubstituted-11beta-chloro-19-norpregnane compounds
JPS5090184A (en) * 1973-12-14 1975-07-19
JPS5090183A (en) * 1973-12-14 1975-07-19

Also Published As

Publication number Publication date
JPS5021469B1 (en) 1975-07-23
CH584724A5 (en) 1977-02-15
DK131295B (en) 1975-06-23
PL79253B1 (en) 1975-06-30
SE350488B (en) 1972-10-30
BE702023A (en) 1968-01-29
IL28411A (en) 1972-07-26
DE1668124A1 (en) 1971-05-06
SE349025B (en) 1972-09-18
FR1565340A (en) 1969-05-02
JPS5224013B1 (en) 1977-06-28
FR7812M (en) 1970-05-20
NL6710459A (en) 1968-01-30
DK131295C (en) 1975-11-17
DK129004B (en) 1974-08-05
CH580644A5 (en) 1976-10-15
AT311564B (en) 1973-11-26
DE1668124B2 (en) 1976-10-07
AT301766B (en) 1972-09-25

Similar Documents

Publication Publication Date Title
GB1434919A (en) 3alpha-hydroxy androstanes
GB1202521A (en) 01beta-CHLORO-19-NOR-STEROIDS
GB1127749A (en) A 19-nor-pregnane steroid and its preparation
GB1469575A (en) Preparation of 16,17-cyclic acetals and ketals of 9alpha-halo steroids
GB1277266A (en) 07-acetylgonanes and derivatives therefor
GB957953A (en) Steroids and their production
IE38074L (en) Delta 8(9)-steroids of the pregnane series.
GB1528212A (en) Estrogen derivatives
GB1038917A (en) Novel steroid derivatives and a process for their production
GB1280570A (en) Preparation of 6-methylene steroids
GB1304395A (en)
GB1259305A (en)
GB978540A (en) Improvements in or relating to the production of 16ª‰-alkylthio-17-oxo-steroids
IL39090A (en) Estradiol diethers and their preparation
GB1081307A (en) Improvements in or relating to the preparation of steroids
GB1008271A (en) Process for the manufacture of 19-nor-steroids
GB1193366A (en) Gona-4,9,11-Trienes, Process for their Preparation, and Compositions Incorporating them
GB1206816A (en) Novel 4-oxa steroids, processes for their preparation and conversion into other steroids, and the steroids thus produced
GB1066705A (en) Improved process for the preparation of steroidal tertiary ether glycols and compounds produced thereby
GB1101117A (en) Steroidal 2ª‡-carbonylhydrazones
GB1228211A (en)
GB554940A (en) Manufacture of androstanolones substituted in 17-position and derivatives thereof
GB1138460A (en) Steroid compounds
GB1111320A (en) 11ª‰-(hydroxy or esterified hydroxy)-9ª‰,10ª‡-steroids
GB1303008A (en)

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee