GB1374850A - De-a-steroids - Google Patents

De-a-steroids

Info

Publication number
GB1374850A
GB1374850A GB5202772A GB5202772A GB1374850A GB 1374850 A GB1374850 A GB 1374850A GB 5202772 A GB5202772 A GB 5202772A GB 5202772 A GB5202772 A GB 5202772A GB 1374850 A GB1374850 A GB 1374850A
Authority
GB
United Kingdom
Prior art keywords
oxobutyl
butenyl
esterified
compounds
etherified
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
GB5202772A
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 GB1374850A publication Critical patent/GB1374850A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Abstract

1374850 De-A-steroids, 4,5-secosteroids F HOFFMANN-LA ROCHE & CO AG 10 Nov 1972 [12 Nov 1971] 52027/72 Heading C2C The invention relates to compounds of formula wherein R<SP>1</SP> is 3-oxobutyl, ketalized 3-oxobutyl, 3-chloro-2-butenyl, 3-methyl-2-butenyl, 3- (C 1 -C 6 alkoxy)-2-butenyl, 3-hydroxybutyl (or an ester or ether thereof), 2-carboxyethyl, 2-cyanoethyl, 2-(C 2 -C 6 alkoxycarbonyl)-ethyl or a 4-isoxazolylmethyl group bearing a C 1 -C 6 alkyl substituent in at least one of positions 3 and 5; and D is a group of formula wherein m is 1 or 2; R<SP>2</SP> is free, esterified or etherified hydroxy; R<SP>3</SP> is H, C 1 -C 6 alkyl or C 2 -C 6 alkynyl; or R<SP>2</SP> and R<SP>3</SP> together represent a ketal, ethylidene, 1-(C 1 -C 6 alkanoyloxy)- ethylidene or bis-(methylenedioxy)ethyl group; R<SP>4</SP> is H or OH; R<SP>5</SP> is oxo, ketal, (H, OH), (H, esterified OH) or (H, etherified OH); R<SP>6</SP> is H or free, esterified or etherified OH; or R<SP>4</SP> and R<SP>6</SP> may together represent C 1 -C 6 alkylidenedioxy when R<SP>5</SP> is oxo; and R<SP>7</SP> is H or Me. The invention comprises (A) compounds I (with the exception of those in which, simultaneously, m is 1; R<SP>1</SP> is 3-oxobutyl, ketalized 3-oxobutyl or 3-chloro-2-butenyl; R<SP>2</SP> is esterified hydroxy; and R<SP>3</SP> is H); and (B) the preparation of compounds I by methylating the corresponding #<SP>9(10)</SP>-10-demethyl compounds (steroid numbering) below - 50‹ C. The minor proportion of 10x-methyl epimer also formed may be removed from the 10#-methyl product by chromatography. Any ketal groups in the product may be hydrolysed.
GB5202772A 1971-11-12 1972-11-10 De-a-steroids Expired GB1374850A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1651671A CH586174A5 (en) 1971-11-12 1971-11-12

Publications (1)

Publication Number Publication Date
GB1374850A true GB1374850A (en) 1974-11-20

Family

ID=4418045

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5202772A Expired GB1374850A (en) 1971-11-12 1972-11-10 De-a-steroids

Country Status (12)

Country Link
JP (1) JPS4857964A (en)
AT (1) AT323908B (en)
AU (1) AU465178B2 (en)
BE (1) BE791184A (en)
CH (1) CH586174A5 (en)
DE (1) DE2250426A1 (en)
FR (1) FR2160178A5 (en)
GB (1) GB1374850A (en)
IL (1) IL40433A (en)
NL (1) NL7213810A (en)
SE (2) SE386451B (en)
ZA (1) ZA726400B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2500440A1 (en) * 1981-02-23 1982-08-27 Roussel Uclaf NEW MEDICAMENTS DERIVED FROM 3-HYDROXY DODECAHYDRO BENZ (E) INDEN-7-ONE DISUBSTITUTED IN POSITION 6, PRODUCTS DERIVED FROM 3-HYDROXY DODECAHYDRO BENZ (E) INDEN-7-ONE DISUBSTITUTED IN POSITION 6, AND PROCESS FOR THEIR PREPARATION AND INTERMEDIATE PRODUCTS

Also Published As

Publication number Publication date
IL40433A0 (en) 1972-11-28
NL7213810A (en) 1973-05-15
BE791184A (en) 1973-05-10
CH586174A5 (en) 1977-03-31
AT323908B (en) 1975-08-11
AU4695472A (en) 1974-03-28
SE7512007L (en) 1975-10-27
AU465178B2 (en) 1975-09-18
DE2250426A1 (en) 1973-05-17
ZA726400B (en) 1973-07-25
IL40433A (en) 1976-05-31
SE386451B (en) 1976-08-09
FR2160178A5 (en) 1973-06-22
JPS4857964A (en) 1973-08-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee