DE1157609B - Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler Wirksamkeit - Google Patents
Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler WirksamkeitInfo
- Publication number
- DE1157609B DE1157609B DEM45602A DEM0045602A DE1157609B DE 1157609 B DE1157609 B DE 1157609B DE M45602 A DEM45602 A DE M45602A DE M0045602 A DEM0045602 A DE M0045602A DE 1157609 B DE1157609 B DE 1157609B
- Authority
- DE
- Germany
- Prior art keywords
- steroid
- enol
- pregnatrien
- dione
- gestagenic
- 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 14
- 150000003431 steroids Chemical class 0.000 title claims description 14
- 230000003152 gestagenic effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 2
- -1 aliphatic enol Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- 150000002085 enols Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DGAAGMXDUVMZHQ-OPLYSGQSSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-6-fluoro-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene Chemical compound FC1=C[C@H]2[C@@H]3CC[C@H](CC)[C@]3(CC[C@@H]2[C@]2(CCCC=C12)C)C DGAAGMXDUVMZHQ-OPLYSGQSSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- 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
- 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 |
|---|---|---|---|
| DEM45602A DE1157609B (de) | 1960-06-11 | 1960-06-11 | Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler Wirksamkeit |
| CH498861A CH388952A (de) | 1960-06-11 | 1961-04-28 | Verfahren zur Herstellung von Steroid-3-enolacylaten |
| BE604366A BE604366A (fr) | 1960-06-11 | 1961-05-30 | Procédé de préparation de stéroïde-3-énolacylates |
| NL265328A NL112740C (enExample) | 1960-06-11 | 1961-05-30 | |
| GB20433/61A GB949719A (en) | 1960-06-11 | 1961-06-06 | Steroid-3-enolacylates and the preparation thereof |
| FR864424A FR1319M (fr) | 1960-06-11 | 1961-06-09 | Stéroide-3-énolacylés. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM45602A DE1157609B (de) | 1960-06-11 | 1960-06-11 | Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler Wirksamkeit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1157609B true DE1157609B (de) | 1963-11-21 |
Family
ID=7305341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM45602A Pending DE1157609B (de) | 1960-06-11 | 1960-06-11 | Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler Wirksamkeit |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE604366A (enExample) |
| CH (1) | CH388952A (enExample) |
| DE (1) | DE1157609B (enExample) |
| FR (1) | FR1319M (enExample) |
| GB (1) | GB949719A (enExample) |
| NL (1) | NL112740C (enExample) |
-
1960
- 1960-06-11 DE DEM45602A patent/DE1157609B/de active Pending
-
1961
- 1961-04-28 CH CH498861A patent/CH388952A/de unknown
- 1961-05-30 NL NL265328A patent/NL112740C/xx active
- 1961-05-30 BE BE604366A patent/BE604366A/fr unknown
- 1961-06-06 GB GB20433/61A patent/GB949719A/en not_active Expired
- 1961-06-09 FR FR864424A patent/FR1319M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR1319M (fr) | 1962-05-21 |
| CH388952A (de) | 1965-03-15 |
| BE604366A (fr) | 1961-11-30 |
| GB949719A (en) | 1964-02-19 |
| NL112740C (enExample) | 1966-03-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH505802A (de) | Verfahren zur Herstellung von Estern von 17a-Hydroxysteroiden der Pregnanreihe | |
| DE1157609B (de) | Verfahren zur Herstellung von gestagenen Steroid-3-enolacylaten mit erhoehter oraler Wirksamkeit | |
| US3002969A (en) | 3beta-hydroxy-6-methyl-delta5-steroids and method of preparation | |
| DE1468905A1 (de) | Verfahren zur Herstellung von Steroidverbindungen | |
| DE1188079B (de) | Verfahren zur Herstellung von 17alpha, 21-Dioxysteroiden | |
| DE1468985A1 (de) | 17alpha-Alkyl-,17alpha-Alkenyl- und 17alpha-Alkinyl-4,5-epoxy-19-norandrostan-17beta-diole und deren Carbonsaeureester sowie Verfahren zur Herstellung dieser Verbindungen | |
| CH522622A (de) | Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons | |
| DE1793749C3 (de) | Verfahren zur Herstellung von 1,4-Diensteroiden | |
| DE1158507B (de) | Verfahren zur Herstellung von 6a-Methyl-16-methylen-steroiden | |
| AT232654B (de) | Verfahren zur Herstellung von 16α-Methyl-17α-hydroxy-20-ketonen der Allopregnan-Reihe | |
| DE2158260C3 (de) | 11-Alkoxysteroide, Verfahren zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen | |
| AT337372B (de) | Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen | |
| DE1643618C3 (de) | Verfahren zur Herstellung von 13 beta- Alkyl-3,11,17,20,21 -pentaoxylierten-18,19,-dinorpregnenen und 13-Alkyl-11 -oxylierten-18,19-dinorpregnanen | |
| DE2046640B2 (de) | Verfahren zur herstellung von delta hoch 4 -3-oxo-l alpha-methyl-steroiden | |
| DE1593448C (de) | 13beta-Äthyl-gon-4-en-3-on-thioketale, deren Herstellung und diese enthaltendes Mittel | |
| AT233184B (de) | Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden | |
| DE934591C (de) | Verfahren zur Herstellung von 17-Ketonen der Testan- und der Androstanreihe | |
| DE2056512C3 (enExample) | ||
| DE2057171A1 (de) | Verfahren zur Herstellung von neuen alpha-Hydroxy-11ss-nitro-oxysteroiden mit einem aromatischen A-Ring | |
| DE1668685B2 (de) | 17-Hydroxy-und 17-Acyloxy-6beta, 7 beta-epoxy-1 alpha, 2 alpha-methylen-4-pregnen-3,20-dione, Verfahren zu deren Herstellung sowie diese enthaltende Mittel | |
| DE1249270B (de) | Verfahien zur Herstellung von /114-16si-Methvlsteroiden | |
| CH377337A (de) | Verfahren zur Herstellung von 11B,18-Oxido-steroiden | |
| EP0040355A2 (de) | Verfahren zur partiellen Reduktion von C21-Steroidcarbonsäuren und ihren Estern zu C21-Steroidalkoholen | |
| DE1243682B (de) | Verfahren zur Herstellung von therapeutisch wirksamen Steroidverbindungen | |
| DE1793749A1 (de) | Verfahren zur herstellung von 1,4diensteroiden |