IL40433A - De a-steroids and their manufacture - Google Patents

De a-steroids and their manufacture

Info

Publication number
IL40433A
IL40433A IL40433A IL4043372A IL40433A IL 40433 A IL40433 A IL 40433A IL 40433 A IL40433 A IL 40433A IL 4043372 A IL4043372 A IL 4043372A IL 40433 A IL40433 A IL 40433A
Authority
IL
Israel
Prior art keywords
methyl
dea
dimethyl
butoxy
tert
Prior art date
Application number
IL40433A
Other versions
IL40433A0 (en
Original Assignee
Sparamedica 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 Sparamedica Ag filed Critical Sparamedica Ag
Publication of IL40433A0 publication Critical patent/IL40433A0/en
Publication of IL40433A publication Critical patent/IL40433A/en

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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. [GB1374850A]

Claims (14)

1. A process for the manufacture of ΙΟβ-methyl deA-st wherein R represents a ketalized 3-oxobutyl group or (3 , 5-dimethyl-4-isoxazolyl)-methyl and R 2 is lower alkoxy or 1-acetoxyethyl, ' ' which process comprises treating a deA-steroid of the general wherein R and R have the significance given earlier in this claim, . at a temperature below -50°C with a methylation. agent.
2. A process according to claim 1, wherein the treatment is carried out at -70°C to -110°C.
3. ) A process according to claim 1 or claim 2, wherein the treatment is carried out using a methyl halide and a base.
4. ) A process according to claim 3, wherein said methyl halide is methyl iodide and said base is sodium hydride.
5. ) A process according to any one of claims 1 to inclusive, wherein there is used a deA-steroid starting material of formula II in which the ketal group is ethylen.ediox , 1,2-phenylenediox , 2 , 2-dimethyl-l , 3-propylenedioxy , . ,1 > 4- (2-butenyl-ene)-dioxy and 2,2-pentamethylene-lj3-propylenedioxy.
6. ) A process for the manufacture of the lO -methyl-^^11^--deA-steroids of formula I given in claim 1, substantially as hereinbefore described with reference to the foregoing Examples.
7. ) 10P-Mehtyl-A9^i:L^-deA-steroids, when manufactured by the process claimed in any one of claims 1 to 6 inclusive or by an obvious chemical equivalent thereof.
8. ) ΙΟβ-Methyl- ^i:L^-deA-steroids of the formula wherein R represents a ketalized 3-oxobutyl group or (3 ,5-dimethyl-4-isoxazolyl)-methyl and 2 R is lower alkoxy or 1-acetox ethyl.
9. ) 17 -tert.-Butoxy-10a-[ (3, 5-dimethyl-4-isoxazolyl) -methyl]- - - - - - -
10. )' 20P-Acetoxy-10a-[ (3,5-dimethyl-4-isoxazolyl)-Kiethyl]- -deA-pregn-9(ll)-en-5-one.
11. ) 17 -tertButoxy'r-,5-seco-androst-9(ll)-ene-3 ,5-dione.
12. ) 3,3-(2,2-Dimethyl-l,3-propylenedioxy)-17 -tert.-"butoxy-4, 5-secoandrost-9(ll)-en-5-one .
13. ) 3,3-[l,4-(2-Butenylene)-dioxy]-17 -tert.-butoxy-4, 5-secoandrost-9(ll) -en-5-one.
14. ) 17P-tert .-Butoxy-3 , 3-( o-phenylenediox ) -4 , 5-secoand'rost--9(ll)-en-5-one . 15 ) 17 -tert .-Butoxy-3 , 3-(2 , 2-pentamethylene-l , 3-propyl-enediox )-4 , 5-secoandrost-9(ll) -en-5-one . :OHN AND PARTNERS
IL40433A 1971-11-12 1972-09-25 De a-steroids and their manufacture IL40433A (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
IL40433A0 IL40433A0 (en) 1972-11-28
IL40433A true IL40433A (en) 1976-05-31

Family

ID=4418045

Family Applications (1)

Application Number Title Priority Date Filing Date
IL40433A IL40433A (en) 1971-11-12 1972-09-25 De a-steroids and their manufacture

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
AT323908B (en) 1975-08-11
FR2160178A5 (en) 1973-06-22
ZA726400B (en) 1973-07-25
JPS4857964A (en) 1973-08-14
DE2250426A1 (en) 1973-05-17
SE386451B (en) 1976-08-09
GB1374850A (en) 1974-11-20
BE791184A (en) 1973-05-10
CH586174A5 (en) 1977-03-31
NL7213810A (en) 1973-05-15
AU465178B2 (en) 1975-09-18
AU4695472A (en) 1974-03-28
SE7512007L (en) 1975-10-27

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