DE2053310C3 - Verfahren zur Herstellung von 14-Anhydrobufalin - Google Patents
Verfahren zur Herstellung von 14-AnhydrobufalinInfo
- Publication number
- DE2053310C3 DE2053310C3 DE2053310A DE2053310A DE2053310C3 DE 2053310 C3 DE2053310 C3 DE 2053310C3 DE 2053310 A DE2053310 A DE 2053310A DE 2053310 A DE2053310 A DE 2053310A DE 2053310 C3 DE2053310 C3 DE 2053310C3
- Authority
- DE
- Germany
- Prior art keywords
- ecm
- acid
- hydroxy
- anhydrobufalin
- lactone
- 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
- LPARRDGBTTTYTR-UHFFFAOYSA-N 5-(3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl)pyran-2-one Chemical compound CC12CCC(C3(CCC(O)CC3CC3)C)C3C1=CCC2C=1C=CC(=O)OC=1 LPARRDGBTTTYTR-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 4
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 2
- 229910052741 iridium Inorganic materials 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QEEBRPGZBVVINN-UHFFFAOYSA-N Desacetyl-bufotalin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 QEEBRPGZBVVINN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FFQCZYROKVPTGV-UHFFFAOYSA-N Cl.[Ir+4] Chemical compound Cl.[Ir+4] FFQCZYROKVPTGV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QEEBRPGZBVVINN-BMPKRDENSA-N bufalin Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 QEEBRPGZBVVINN-BMPKRDENSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XZTUSOXSLKTKJQ-UHFFFAOYSA-N Uzarigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 XZTUSOXSLKTKJQ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ATLJNLYIJOCWJE-CWMZOUAVSA-N bufogenin Chemical compound C=1([C@H]2C[C@H]3O[C@@]43[C@H]3[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC3)C)CC[C@@]42C)C=CC(=O)OC=1 ATLJNLYIJOCWJE-CWMZOUAVSA-N 0.000 description 1
- 229950006858 bufogenin Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- XZTUSOXSLKTKJQ-CESUGQOBSA-N digitoxigenin Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 XZTUSOXSLKTKJQ-CESUGQOBSA-N 0.000 description 1
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ATLJNLYIJOCWJE-UHFFFAOYSA-N resibufogenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C=1C=CC(=O)OC=1 ATLJNLYIJOCWJE-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2053310A DE2053310C3 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von 14-Anhydrobufalin |
| CA124,162,A CA951721A (en) | 1970-10-30 | 1971-10-01 | Process for the preparation of 14-anhydrobufaline |
| NL7114652A NL7114652A (enExample) | 1970-10-30 | 1971-10-25 | |
| CS7498A CS167333B2 (enExample) | 1970-10-30 | 1971-10-25 | |
| CH1565871A CH559217A5 (enExample) | 1970-10-30 | 1971-10-27 | |
| IL38029A IL38029A (en) | 1970-10-30 | 1971-10-28 | Process for the preparation of 14-anhydrobufaline |
| FI713079A FI48076C (fi) | 1970-10-30 | 1971-10-28 | Menetelmä 14-anhydrobufaliinin valmistamiseksi |
| BE774716A BE774716A (fr) | 1970-10-30 | 1971-10-29 | Procede de preparation de la 14-anhydro-bufaline |
| GB5050771A GB1363293A (en) | 1970-10-30 | 1971-10-29 | Process for the preparation of 14-anhydrobutalin |
| AT937871A AT310360B (de) | 1970-10-30 | 1971-10-29 | Verfahren zur Herstellung von 14-Anhydrobufalin |
| SE13757/71A SE364269B (enExample) | 1970-10-30 | 1971-10-29 | |
| PL1971151294A PL81407B1 (enExample) | 1970-10-30 | 1971-10-29 | |
| DK531171AA DK126939B (da) | 1970-10-30 | 1971-10-29 | Fremgangsmåde til fremstilling af 14-anhydrobufalin. |
| US00194003A US3753980A (en) | 1970-10-30 | 1971-10-29 | Process for the preparation of 14-anhydrobufaline |
| HUHO1429A HU162808B (enExample) | 1970-10-30 | 1971-10-29 | |
| FR7139199A FR2113458A5 (enExample) | 1970-10-30 | 1971-11-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2053310A DE2053310C3 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von 14-Anhydrobufalin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2053310A1 DE2053310A1 (de) | 1972-05-10 |
| DE2053310B2 DE2053310B2 (de) | 1973-07-05 |
| DE2053310C3 true DE2053310C3 (de) | 1974-02-28 |
Family
ID=5786619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2053310A Expired DE2053310C3 (de) | 1970-10-30 | 1970-10-30 | Verfahren zur Herstellung von 14-Anhydrobufalin |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3753980A (enExample) |
| AT (1) | AT310360B (enExample) |
| BE (1) | BE774716A (enExample) |
| CA (1) | CA951721A (enExample) |
| CH (1) | CH559217A5 (enExample) |
| CS (1) | CS167333B2 (enExample) |
| DE (1) | DE2053310C3 (enExample) |
| DK (1) | DK126939B (enExample) |
| FI (1) | FI48076C (enExample) |
| FR (1) | FR2113458A5 (enExample) |
| GB (1) | GB1363293A (enExample) |
| HU (1) | HU162808B (enExample) |
| IL (1) | IL38029A (enExample) |
| NL (1) | NL7114652A (enExample) |
| PL (1) | PL81407B1 (enExample) |
| SE (1) | SE364269B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4096142A (en) * | 1972-01-04 | 1978-06-20 | Steele Chemicals Co. Ltd. | 14,19-Dioxygenated steroid compounds and their 14-dehydro analogs and process for the preparation thereof |
-
1970
- 1970-10-30 DE DE2053310A patent/DE2053310C3/de not_active Expired
-
1971
- 1971-10-01 CA CA124,162,A patent/CA951721A/en not_active Expired
- 1971-10-25 NL NL7114652A patent/NL7114652A/xx unknown
- 1971-10-25 CS CS7498A patent/CS167333B2/cs unknown
- 1971-10-27 CH CH1565871A patent/CH559217A5/xx not_active IP Right Cessation
- 1971-10-28 FI FI713079A patent/FI48076C/fi active
- 1971-10-28 IL IL38029A patent/IL38029A/xx unknown
- 1971-10-29 SE SE13757/71A patent/SE364269B/xx unknown
- 1971-10-29 HU HUHO1429A patent/HU162808B/hu unknown
- 1971-10-29 PL PL1971151294A patent/PL81407B1/pl unknown
- 1971-10-29 GB GB5050771A patent/GB1363293A/en not_active Expired
- 1971-10-29 AT AT937871A patent/AT310360B/de not_active IP Right Cessation
- 1971-10-29 US US00194003A patent/US3753980A/en not_active Expired - Lifetime
- 1971-10-29 DK DK531171AA patent/DK126939B/da unknown
- 1971-10-29 BE BE774716A patent/BE774716A/xx unknown
- 1971-11-02 FR FR7139199A patent/FR2113458A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI48076B (enExample) | 1974-02-28 |
| AT310360B (de) | 1973-09-25 |
| FR2113458A5 (enExample) | 1972-06-23 |
| CH559217A5 (enExample) | 1975-02-28 |
| HU162808B (enExample) | 1973-04-28 |
| GB1363293A (en) | 1974-08-14 |
| PL81407B1 (enExample) | 1975-08-30 |
| DE2053310A1 (de) | 1972-05-10 |
| CA951721A (en) | 1974-07-23 |
| US3753980A (en) | 1973-08-21 |
| CS167333B2 (enExample) | 1976-04-29 |
| DE2053310B2 (de) | 1973-07-05 |
| DK126939B (da) | 1973-09-03 |
| NL7114652A (enExample) | 1972-05-03 |
| IL38029A (en) | 1974-07-31 |
| SE364269B (enExample) | 1974-02-18 |
| FI48076C (fi) | 1974-06-10 |
| BE774716A (fr) | 1972-05-02 |
| IL38029A0 (en) | 1971-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |