GB938638A - New enol ethers of 3-keto-5ª -androstanes - Google Patents
New enol ethers of 3-keto-5ª -androstanesInfo
- Publication number
- GB938638A GB938638A GB36390/61A GB3639061A GB938638A GB 938638 A GB938638 A GB 938638A GB 36390/61 A GB36390/61 A GB 36390/61A GB 3639061 A GB3639061 A GB 3639061A GB 938638 A GB938638 A GB 938638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- testosterone
- carbon atoms
- represents hydrogen
- formula
- 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
Links
- VMNRNUNYBVFVQI-QYXZOKGRSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical class C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 title 1
- 150000002084 enol ethers Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000003500 enol ether group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960001566 methyltestosterone Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960004719 nandrolone Drugs 0.000 abstract 1
- 230000001613 neoplastic effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 229920006395 saturated elastomer Chemical group 0.000 abstract 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229960003604 testosterone Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises steroids of the general formula <FORM:0938638/IV(a)/1> wherein R represents an aliphatic, cycloaliphatic or arylaliphatic hydrocarbon radical containing from 5 to 18 carbon atoms, R1 and R2 represent hydrogen or methyl and R3 represents ketonic oxygen or a group of the formula <FORM:0938638/IV(a)/2> wherein X represents hydrogen or the acyl residue of an alkanoic acid and R4 represents hydrogen or a saturated or unsaturated hydrocarbon radical containing 1, 2 or 3 carbon atoms, and the preparation thereof by subjecting 3-ethyl enol ethers of the general formula <FORM:0938638/IV(a)/3> wherein R, R1, R2, R3, R4 and X have the above significance, to the following reactions in either order:-(a) reaction with an alcohol ROH wherein R has the above significance, and (b) catalytic hydrogenation to hydrogenate one double bond. Products containing a 17-keto substituent may be reduced to products containing a 17BETA-OH substituent which may then be acylated, or treated with an R4-halide Grignard reagent or with an alkali metal acetylide to form compounds having at the 17-position the group of the formula <FORM:0938638/IV(a)/4> wherein R4 has the above signficance and X represents hydrogen. 2a -Methyl-testosterone is prepared by condensing testosterone with diethyloxalate and treating the product with methyl iodide and then alkali. 2a -Methyl-19-nor-testosterone is prepared by a similar method. Therapeutic compositions suitable for oral or parenteral administration in the treatment of neoplastic diseases contain as the active ingredient alkyl D 2-enol ethers of 5a -androstan-17b -ol-3-one and 19-nor-5a -androstan-17b -ol-3-one wherein the alkyl radical in the enol ether group contains 7 to 14 carbon atoms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1768060 | 1960-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB938638A true GB938638A (en) | 1963-10-02 |
Family
ID=11150545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36390/61A Expired GB938638A (en) | 1960-10-12 | 1961-10-10 | New enol ethers of 3-keto-5ª -androstanes |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH415616A (en) |
| FR (1) | FR1449M (en) |
| GB (1) | GB938638A (en) |
-
1961
- 1961-10-03 FR FR874918A patent/FR1449M/en active Active
- 1961-10-10 GB GB36390/61A patent/GB938638A/en not_active Expired
- 1961-10-10 CH CH1172561A patent/CH415616A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH415616A (en) | 1966-06-30 |
| FR1449M (en) | 1962-08-20 |
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