DE1179201B - Verfahren zur Herstellung von in 1ª- und/oder 7ª-Stellung durch die Acetylthiogruppe substituierten 17ª-Methyl-testosteron-derivaten - Google Patents
Verfahren zur Herstellung von in 1ª- und/oder 7ª-Stellung durch die Acetylthiogruppe substituierten 17ª-Methyl-testosteron-derivatenInfo
- Publication number
- DE1179201B DE1179201B DEM46979A DEM0046979A DE1179201B DE 1179201 B DE1179201 B DE 1179201B DE M46979 A DEM46979 A DE M46979A DE M0046979 A DEM0046979 A DE M0046979A DE 1179201 B DE1179201 B DE 1179201B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- testosterone
- acetylthio
- preparation
- testosterone derivatives
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 title claims description 8
- -1 acetylthio group Chemical group 0.000 title description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 2
- 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 description 14
- 230000001195 anabolic effect Effects 0.000 description 11
- 230000001548 androgenic effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229960003604 testosterone Drugs 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 210000001625 seminal vesicle Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 201000010653 vesiculitis Diseases 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000003263 anabolic agent Substances 0.000 description 1
- 229940070021 anabolic steroids Drugs 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
- 229960005471 androstenedione Drugs 0.000 description 1
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- 229960001566 methyltestosterone Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- 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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM46979A DE1179201B (de) | 1960-10-29 | 1960-10-29 | Verfahren zur Herstellung von in 1ª- und/oder 7ª-Stellung durch die Acetylthiogruppe substituierten 17ª-Methyl-testosteron-derivaten |
| CH918661A CH393315A (de) | 1960-10-29 | 1961-08-04 | Verfahren zur Herstellung neuer 17a-Methyl-testosteronderivate |
| NL268993A NL106985C (member.php) | 1960-10-29 | 1961-09-06 | |
| FR873189A FR1363M (fr) | 1960-10-29 | 1961-09-14 | Nouveaux dérivés de la 17 alpha-méthyl-testostérone. |
| GB35382/61A GB928864A (en) | 1960-10-29 | 1961-09-29 | New 17ª -methyl-testosterone derivatives |
| US147469A US3087942A (en) | 1960-10-29 | 1961-10-25 | Preparation of anabolic agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM46979A DE1179201B (de) | 1960-10-29 | 1960-10-29 | Verfahren zur Herstellung von in 1ª- und/oder 7ª-Stellung durch die Acetylthiogruppe substituierten 17ª-Methyl-testosteron-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1179201B true DE1179201B (de) | 1964-10-08 |
Family
ID=7305775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM46979A Pending DE1179201B (de) | 1960-10-29 | 1960-10-29 | Verfahren zur Herstellung von in 1ª- und/oder 7ª-Stellung durch die Acetylthiogruppe substituierten 17ª-Methyl-testosteron-derivaten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3087942A (member.php) |
| CH (1) | CH393315A (member.php) |
| DE (1) | DE1179201B (member.php) |
| FR (1) | FR1363M (member.php) |
| GB (1) | GB928864A (member.php) |
| NL (1) | NL106985C (member.php) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837535A (en) * | 1957-01-16 | 1958-06-03 | Searle & Co | 1-acylthio substitution products of 17alpha-oxa-d-homo-4-androstene-3, 17-dione |
| US2859222A (en) * | 1957-12-31 | 1958-11-04 | Searle & Co | 7alpha-acylthio substitution products of 4-androsten-3-ones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929763A (en) * | 1955-02-07 | 1960-03-22 | Ciba Pharm Prod Inc | Increasing anabolic activity with 1-de-hydro-17alpha-methyl-testosterone |
| US2875215A (en) * | 1957-05-24 | 1959-02-24 | Searle & Co | 1-acylthio substitution products of 3, 17-dioxygenated androstane derivatives |
-
1960
- 1960-10-29 DE DEM46979A patent/DE1179201B/de active Pending
-
1961
- 1961-08-04 CH CH918661A patent/CH393315A/de unknown
- 1961-09-06 NL NL268993A patent/NL106985C/xx active
- 1961-09-14 FR FR873189A patent/FR1363M/fr active Active
- 1961-09-29 GB GB35382/61A patent/GB928864A/en not_active Expired
- 1961-10-25 US US147469A patent/US3087942A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837535A (en) * | 1957-01-16 | 1958-06-03 | Searle & Co | 1-acylthio substitution products of 17alpha-oxa-d-homo-4-androstene-3, 17-dione |
| US2859222A (en) * | 1957-12-31 | 1958-11-04 | Searle & Co | 7alpha-acylthio substitution products of 4-androsten-3-ones |
Also Published As
| Publication number | Publication date |
|---|---|
| US3087942A (en) | 1963-04-30 |
| GB928864A (en) | 1963-06-19 |
| NL106985C (member.php) | 1963-11-16 |
| CH393315A (de) | 1965-06-15 |
| FR1363M (fr) | 1962-06-18 |
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