DE2529521C2 - Verfahren zur Gewinnung von 3-Hydroxysteroiden und 3-Oxosteroiden - Google Patents
Verfahren zur Gewinnung von 3-Hydroxysteroiden und 3-OxosteroidenInfo
- Publication number
- DE2529521C2 DE2529521C2 DE2529521A DE2529521A DE2529521C2 DE 2529521 C2 DE2529521 C2 DE 2529521C2 DE 2529521 A DE2529521 A DE 2529521A DE 2529521 A DE2529521 A DE 2529521A DE 2529521 C2 DE2529521 C2 DE 2529521C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl isobutyl
- calcium bromide
- isobutyl ketone
- mixture
- adduct
- 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
- 238000000034 method Methods 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 21
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 18
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 18
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 18
- 229910001622 calcium bromide Inorganic materials 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims 1
- 229930182558 Sterol Natural products 0.000 description 7
- 150000003431 steroids Chemical class 0.000 description 7
- 150000003432 sterols Chemical class 0.000 description 7
- 235000003702 sterols Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 4
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 4
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 4
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 4
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 4
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 4
- 235000015500 sitosterol Nutrition 0.000 description 4
- 229950005143 sitosterol Drugs 0.000 description 4
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 3
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 3
- LUJVUUWNAPIQQI-UHFFFAOYSA-N (+)-androsta-1,4-diene-3,17-dione Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 LUJVUUWNAPIQQI-UHFFFAOYSA-N 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- LUJVUUWNAPIQQI-QAGGRKNESA-N androsta-1,4-diene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LUJVUUWNAPIQQI-QAGGRKNESA-N 0.000 description 2
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 2
- 235000000431 campesterol Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000016831 stigmasterol Nutrition 0.000 description 2
- 229940032091 stigmasterol Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- NLDBCFRIELDMRO-UHFFFAOYSA-N Stigmasterin Natural products CCCC(CC)C=CC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C NLDBCFRIELDMRO-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
- 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
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- -1 methyl isobutyl Chemical group 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- JXWLYDNHVXFBJA-UHFFFAOYSA-N solasodine Natural products CC1CCC2(NC1)NC3CC4C5CC=C6CC(O)CCC6(C)C5CCC4(C)C3C2C JXWLYDNHVXFBJA-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2529521A DE2529521C2 (de) | 1975-06-30 | 1975-06-30 | Verfahren zur Gewinnung von 3-Hydroxysteroiden und 3-Oxosteroiden |
| DK285076A DK144377C (da) | 1975-06-30 | 1976-06-24 | Fremgangsmaade til isolering af 3-hydroxysteroider og 3-oxosteroider |
| US05/699,790 US4057541A (en) | 1975-06-30 | 1976-06-25 | Method for isolation of 3-hydroxy steroids and 3-keto steroids |
| CH817976A CH598286A5 (enExample) | 1975-06-30 | 1976-06-25 | |
| DD193602A DD124989A5 (enExample) | 1975-06-30 | 1976-06-28 | |
| HU76SCHE571A HU173782B (hu) | 1975-06-30 | 1976-06-29 | Sposob razdelenija 3 - gidroksi - steroidov i/ili 3 - okso - steroidov |
| NL7607150A NL7607150A (nl) | 1975-06-30 | 1976-06-30 | Werkwijze voor het isoleren van 3-hydroxy- steroiden en 3-oxosteroiden. |
| GB27191/76A GB1555968A (en) | 1975-06-30 | 1976-06-30 | Process for the isolation of 3-hydroxy steroids and 3-oxo teroids |
| FR7619925A FR2316247A1 (fr) | 1975-06-30 | 1976-06-30 | Procede pour isoler des 3-hydroxysteroides et des 3-oxosteroides de melanges contenant ces composes |
| JP51077698A JPS6019320B2 (ja) | 1975-06-30 | 1976-06-30 | ３―ヒドロキシステロイド及び３―オクソステロイドの単離法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2529521A DE2529521C2 (de) | 1975-06-30 | 1975-06-30 | Verfahren zur Gewinnung von 3-Hydroxysteroiden und 3-Oxosteroiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2529521A1 DE2529521A1 (de) | 1977-01-27 |
| DE2529521C2 true DE2529521C2 (de) | 1984-11-29 |
Family
ID=5950507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2529521A Expired DE2529521C2 (de) | 1975-06-30 | 1975-06-30 | Verfahren zur Gewinnung von 3-Hydroxysteroiden und 3-Oxosteroiden |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4057541A (enExample) |
| JP (1) | JPS6019320B2 (enExample) |
| CH (1) | CH598286A5 (enExample) |
| DD (1) | DD124989A5 (enExample) |
| DE (1) | DE2529521C2 (enExample) |
| DK (1) | DK144377C (enExample) |
| FR (1) | FR2316247A1 (enExample) |
| GB (1) | GB1555968A (enExample) |
| HU (1) | HU173782B (enExample) |
| NL (1) | NL7607150A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226785A (en) * | 1979-10-04 | 1980-10-07 | Eastman Kodak Company | Process for dehydrogenation of sterols to produce Δ4-3-ketosteroids |
| US4279828A (en) * | 1980-06-13 | 1981-07-21 | Eastman Kodak Company | Process for separating 3-hydroxy steroids or sterols from mixtures such as lipids |
| US4452994A (en) * | 1981-03-02 | 1984-06-05 | G. D. Searle & Co. | Process for isolating organic compounds and lithium salt complexes useful in said process |
| US4425275A (en) | 1982-07-12 | 1984-01-10 | Eastman Kodak Company | Process for separating 3-hydroxy steroids or sterols from mixtures such as lipids |
| US5045242A (en) * | 1990-01-11 | 1991-09-03 | Steven Roczniak | Removal of cholesterol from edible fats |
| GB2338234B (en) * | 1998-06-10 | 2000-05-03 | Torcan Chemical Ltd | Preparation of finasteride |
| US6677453B1 (en) | 1999-11-01 | 2004-01-13 | Torcan Chemical Ltd | Production of polymorphic forms I and II of finasteride by complexation with group I or II metal salts |
| CN100387611C (zh) * | 2006-02-23 | 2008-05-14 | 中国科学院上海有机化学研究所 | 一类16α-溴代甾体化合物及其合成方法 |
| CN101250211B (zh) * | 2008-04-02 | 2010-12-22 | 中国科学院上海有机化学研究所 | 一类孕甾-16-烯-20s-乙酸酯化合物及其合成方法 |
| FR2978452B1 (fr) * | 2011-07-28 | 2015-01-30 | Expanscience Lab | Extraction liquide / liquide avec un solvant comprenant au moins 5 atomes de carbone et 1 ou 2 atomes d'oxygene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2568202A (en) * | 1941-11-28 | 1951-09-18 | Veenendaalsche Sajet En Vijfsc | Process for recovering sterols from mixtures thereof |
| US3450541A (en) * | 1966-06-29 | 1969-06-17 | Us Agriculture | Rapid quantitative removal of natural sterols from lipids |
| NL127423C (enExample) * | 1967-05-11 | |||
| US3983147A (en) * | 1973-06-12 | 1976-09-28 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Separation of wool fatty acid |
-
1975
- 1975-06-30 DE DE2529521A patent/DE2529521C2/de not_active Expired
-
1976
- 1976-06-24 DK DK285076A patent/DK144377C/da active
- 1976-06-25 US US05/699,790 patent/US4057541A/en not_active Expired - Lifetime
- 1976-06-25 CH CH817976A patent/CH598286A5/xx not_active IP Right Cessation
- 1976-06-28 DD DD193602A patent/DD124989A5/xx unknown
- 1976-06-29 HU HU76SCHE571A patent/HU173782B/hu unknown
- 1976-06-30 FR FR7619925A patent/FR2316247A1/fr active Granted
- 1976-06-30 GB GB27191/76A patent/GB1555968A/en not_active Expired
- 1976-06-30 NL NL7607150A patent/NL7607150A/xx not_active Application Discontinuation
- 1976-06-30 JP JP51077698A patent/JPS6019320B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK144377C (da) | 1982-07-26 |
| DD124989A5 (enExample) | 1977-03-23 |
| NL7607150A (nl) | 1977-01-03 |
| DE2529521A1 (de) | 1977-01-27 |
| DK144377B (da) | 1982-03-01 |
| JPS527951A (en) | 1977-01-21 |
| JPS6019320B2 (ja) | 1985-05-15 |
| FR2316247B1 (enExample) | 1980-05-09 |
| US4057541A (en) | 1977-11-08 |
| GB1555968A (en) | 1979-11-14 |
| HU173782B (hu) | 1979-08-28 |
| DK285076A (da) | 1976-12-31 |
| CH598286A5 (enExample) | 1978-04-28 |
| FR2316247A1 (fr) | 1977-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |