DE1593303A1 - Verfahren zur Herstellung von OEstr-5(10)-en3,17-dion - Google Patents
Verfahren zur Herstellung von OEstr-5(10)-en3,17-dionInfo
- Publication number
- DE1593303A1 DE1593303A1 DE19661593303 DE1593303A DE1593303A1 DE 1593303 A1 DE1593303 A1 DE 1593303A1 DE 19661593303 DE19661593303 DE 19661593303 DE 1593303 A DE1593303 A DE 1593303A DE 1593303 A1 DE1593303 A1 DE 1593303A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- group
- dione
- oestr
- solvents
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 13
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000010494 dissociation reaction Methods 0.000 claims description 4
- 230000005593 dissociations Effects 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- JMYVDDWUJYTUEY-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C([C@H]1[C@@H]2CCC[C@]2(CC[C@@H]11)C)CC2=C1CCCC2 JMYVDDWUJYTUEY-BDXSIMOUSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000002167 estrones Chemical class 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000005656 rearomatization reaction Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- RORYLAUXKSWMQL-CBZIJGRNSA-N (8r,9s,13s,14s)-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound C1CC(=O)CC2=C1[C@H]1CC[C@](C)(C(CC3)=O)[C@@H]3[C@@H]1CC2 RORYLAUXKSWMQL-CBZIJGRNSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000006027 Birch reduction reaction Methods 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100226146 Drosophila mojavensis Est-5 gene Proteins 0.000 description 1
- 101150064205 ESR1 gene Proteins 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002875 norsteroids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000284 | 1965-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593303A1 true DE1593303A1 (de) | 1970-07-16 |
Family
ID=11000805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593303 Withdrawn DE1593303A1 (de) | 1965-05-22 | 1966-05-12 | Verfahren zur Herstellung von OEstr-5(10)-en3,17-dion |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT267084B (enrdf_load_stackoverflow) |
| CH (1) | CH479571A (enrdf_load_stackoverflow) |
| DE (1) | DE1593303A1 (enrdf_load_stackoverflow) |
| DK (1) | DK117702B (enrdf_load_stackoverflow) |
| GB (1) | GB1133154A (enrdf_load_stackoverflow) |
| NL (1) | NL6607002A (enrdf_load_stackoverflow) |
| SE (1) | SE314369B (enrdf_load_stackoverflow) |
| YU (1) | YU32137B (enrdf_load_stackoverflow) |
-
1966
- 1966-05-12 DE DE19661593303 patent/DE1593303A1/de not_active Withdrawn
- 1966-05-12 AT AT449466A patent/AT267084B/de active
- 1966-05-13 CH CH697766A patent/CH479571A/de not_active IP Right Cessation
- 1966-05-17 SE SE684166A patent/SE314369B/xx unknown
- 1966-05-18 DK DK255666A patent/DK117702B/da unknown
- 1966-05-18 GB GB2205066A patent/GB1133154A/en not_active Expired
- 1966-05-20 YU YU93766A patent/YU32137B/xx unknown
- 1966-05-20 NL NL6607002A patent/NL6607002A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU93766A (en) | 1973-08-31 |
| SE314369B (enrdf_load_stackoverflow) | 1969-09-08 |
| NL6607002A (enrdf_load_stackoverflow) | 1966-11-23 |
| AT267084B (de) | 1968-12-10 |
| DK117702B (da) | 1970-05-25 |
| CH479571A (de) | 1969-10-15 |
| GB1133154A (en) | 1968-11-13 |
| YU32137B (en) | 1974-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |