DE1174314B - Verfahren zur Herstellung von 16-Methylen-9ª-fluor-11ª-hydroxy-17ª-acetoxy-progesteron-derivaten - Google Patents
Verfahren zur Herstellung von 16-Methylen-9ª-fluor-11ª-hydroxy-17ª-acetoxy-progesteron-derivatenInfo
- Publication number
- DE1174314B DE1174314B DEM44160A DEM0044160A DE1174314B DE 1174314 B DE1174314 B DE 1174314B DE M44160 A DEM44160 A DE M44160A DE M0044160 A DEM0044160 A DE M0044160A DE 1174314 B DE1174314 B DE 1174314B
- Authority
- DE
- Germany
- Prior art keywords
- acetoxy
- methylene
- progesterone
- hydroxy
- fluoro
- 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 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229960003387 progesterone Drugs 0.000 description 3
- 239000000186 progesterone Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- XSNMCQGNVPSIQM-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 XSNMCQGNVPSIQM-CKOZHMEPSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
-
- 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
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM51304A DE1176133B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51305A DE1176134B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 1-Dehydro-16-methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51303A DE1176132B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von ungesaettigten 16-Methylen-17ª-acetoxy-progesteron-derivaten |
| DEM44160A DE1174314B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-9ª-fluor-11ª-hydroxy-17ª-acetoxy-progesteron-derivaten |
| BR125904/61A BR6125904D0 (pt) | 1960-01-30 | 1961-01-16 | Processo de produzir derivados de 16-metileno-17 alfaace toxi-progesterona |
| FR850037A FR881M (OSRAM) | 1960-01-30 | 1961-01-18 | |
| CH593165A CH395082A (de) | 1960-01-30 | 1961-01-20 | Verfahren zur Herstellung von 1-Dehydro-progesteron-derivaten |
| CH68961A CH393316A (de) | 1960-01-30 | 1961-01-20 | Verfahren zur Herstellung von 9a-Halogen-steroiden |
| CH592965A CH393317A (de) | 1960-01-30 | 1961-01-20 | Verfahren zur Herstellung von ungesättigten 16-Methylen-progesteron-derivaten |
| CH593065A CH395081A (de) | 1960-01-30 | 1961-01-20 | Verfahren zur Herstellung von 16-Methylen-17a-acetoxy-progesteron-derivaten |
| GB26066/61D GB963427A (en) | 1960-01-30 | 1961-01-23 | 16-methylene-17ª -acetoxy-progesterone-derivatives and the preparation thereof |
| DK98062AA DK115180B (da) | 1960-01-30 | 1962-03-01 | Analogifremgangsmåde til fremstilling af 1-dehydro-16-methylen-17α-acetoxy-progesteronforbindelser. |
| SE1410862A SE302123B (OSRAM) | 1960-01-30 | 1962-12-28 | |
| SE1410762A SE301800B (OSRAM) | 1960-01-30 | 1962-12-28 | |
| SE14106/62A SE310675B (OSRAM) | 1960-01-30 | 1962-12-28 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM44160A DE1174314B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-9ª-fluor-11ª-hydroxy-17ª-acetoxy-progesteron-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1174314B true DE1174314B (de) | 1964-07-23 |
Family
ID=7304892
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM51305A Pending DE1176134B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 1-Dehydro-16-methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51303A Pending DE1176132B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von ungesaettigten 16-Methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51304A Pending DE1176133B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-17ª-acetoxy-progesteron-derivaten |
| DEM44160A Pending DE1174314B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-9ª-fluor-11ª-hydroxy-17ª-acetoxy-progesteron-derivaten |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM51305A Pending DE1176134B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 1-Dehydro-16-methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51303A Pending DE1176132B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von ungesaettigten 16-Methylen-17ª-acetoxy-progesteron-derivaten |
| DEM51304A Pending DE1176133B (de) | 1960-01-30 | 1960-01-30 | Verfahren zur Herstellung von 16-Methylen-17ª-acetoxy-progesteron-derivaten |
Country Status (7)
| Country | Link |
|---|---|
| BR (1) | BR6125904D0 (OSRAM) |
| CH (4) | CH395081A (OSRAM) |
| DE (4) | DE1176134B (OSRAM) |
| DK (1) | DK115180B (OSRAM) |
| FR (1) | FR881M (OSRAM) |
| GB (1) | GB963427A (OSRAM) |
| SE (3) | SE302123B (OSRAM) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2865808A (en) * | 1958-06-09 | 1958-12-23 | Pfizer & Co C | 16-methylene pregnene derivatives |
-
1960
- 1960-01-30 DE DEM51305A patent/DE1176134B/de active Pending
- 1960-01-30 DE DEM51303A patent/DE1176132B/de active Pending
- 1960-01-30 DE DEM51304A patent/DE1176133B/de active Pending
- 1960-01-30 DE DEM44160A patent/DE1174314B/de active Pending
-
1961
- 1961-01-16 BR BR125904/61A patent/BR6125904D0/pt unknown
- 1961-01-18 FR FR850037A patent/FR881M/fr active Active
- 1961-01-20 CH CH593065A patent/CH395081A/de unknown
- 1961-01-20 CH CH593165A patent/CH395082A/de unknown
- 1961-01-20 CH CH68961A patent/CH393316A/de unknown
- 1961-01-20 CH CH592965A patent/CH393317A/de unknown
- 1961-01-23 GB GB26066/61D patent/GB963427A/en not_active Expired
-
1962
- 1962-03-01 DK DK98062AA patent/DK115180B/da unknown
- 1962-12-28 SE SE1410862A patent/SE302123B/xx unknown
- 1962-12-28 SE SE1410762A patent/SE301800B/xx unknown
- 1962-12-28 SE SE14106/62A patent/SE310675B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2865808A (en) * | 1958-06-09 | 1958-12-23 | Pfizer & Co C | 16-methylene pregnene derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH395082A (de) | 1965-07-15 |
| DE1176134B (de) | 1964-08-20 |
| CH393317A (de) | 1965-06-15 |
| DE1176132B (de) | 1964-08-20 |
| SE302123B (OSRAM) | 1968-07-08 |
| BR6125904D0 (pt) | 1973-05-29 |
| SE301800B (OSRAM) | 1968-06-24 |
| CH393316A (de) | 1965-06-15 |
| CH395081A (de) | 1965-07-15 |
| GB963427A (en) | 1964-07-08 |
| DK115180B (da) | 1969-09-15 |
| FR881M (OSRAM) | 1961-10-23 |
| SE310675B (OSRAM) | 1969-05-12 |
| DE1176133B (de) | 1964-08-20 |
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