DE2056512C3 - - Google Patents
Info
- Publication number
- DE2056512C3 DE2056512C3 DE19702056512 DE2056512A DE2056512C3 DE 2056512 C3 DE2056512 C3 DE 2056512C3 DE 19702056512 DE19702056512 DE 19702056512 DE 2056512 A DE2056512 A DE 2056512A DE 2056512 C3 DE2056512 C3 DE 2056512C3
- Authority
- DE
- Germany
- Prior art keywords
- pregnen
- dimethyl
- dione
- hydroxy
- acid
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000003152 gestagenic effect Effects 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000016087 ovulation Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000003433 contraceptive agent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006567 deketalization reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 231100000546 inhibition of ovulation Toxicity 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FCYQTGCEDUOHLT-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 FCYQTGCEDUOHLT-LEKSSAKUSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- AFQMZFUQXHANDQ-ZQOQTTQJSA-N CC[C@@]12CC[C@@H]3[C@]4(CCC(C=C4CC[C@H]3[C@@H]2CC=C1C(C)=O)=O)C Chemical compound CC[C@@]12CC[C@@H]3[C@]4(CCC(C=C4CC[C@H]3[C@@H]2CC=C1C(C)=O)=O)C AFQMZFUQXHANDQ-ZQOQTTQJSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- XLTYXMRRKLJRNE-UHFFFAOYSA-N acetyl acetate;ethyl acetate Chemical compound CCOC(C)=O.CC(=O)OC(C)=O XLTYXMRRKLJRNE-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 229960001566 methyltestosterone Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702056512 DE2056512A1 (de) | 1970-11-10 | 1970-11-10 | 17 alpha-Hydroxy-16 alpha, 18-dimethyl-4-pregnen-3,20-dion und seine Ester |
| CS691073A CS166291B2 (en, 2012) | 1970-11-10 | 1971-08-31 | |
| CS690971A CS166290B2 (en, 2012) | 1970-11-10 | 1971-08-31 | |
| CS622471A CS166289B2 (en, 2012) | 1970-11-10 | 1971-08-31 | |
| DK433271A DK127851B (da) | 1970-11-10 | 1971-09-03 | Analogifremgangsmåde til fremstilling af 17α-hydroxy-16α, 18-dimethyl-4-pregnen-3,20-dion eller estere deraf. |
| ES394771A ES394771A1 (es) | 1970-11-10 | 1971-09-03 | Procedimiento para la preparacion de 17 alfa - hidroxi -16 alfa, 18 - dimetil-4-pregnen-3,20-diona y sus 17 alfa-mono- esteres o 9-enol - 17 alfa - diesteres. |
| CH1287375A CH601348A5 (en, 2012) | 1970-11-10 | 1971-11-01 | |
| CH1287475A CH591519A5 (en, 2012) | 1970-11-10 | 1971-11-01 | |
| CH1588371A CH590886A5 (en, 2012) | 1970-11-10 | 1971-11-01 | |
| HUSE000360 HU163628B (en, 2012) | 1970-11-10 | 1971-11-08 | |
| GB5173971A GB1377975A (en) | 1970-11-10 | 1971-11-08 | 17alpha-hydroxy-16alpha,18-dimethyl-delta4-pregnene-3,20-dione and its esters |
| AT585072A AT319489B (de) | 1970-11-10 | 1971-11-09 | Verfahren zur Herstellung von neuen 16α, 18-Dimethylpregnenen |
| NL7115418A NL7115418A (en, 2012) | 1970-11-10 | 1971-11-09 | |
| AT966571A AT308985B (de) | 1970-11-10 | 1971-11-09 | Verfahren zur Herstellung von neuen 16α18-Dimethylpregnenen |
| AT585172A AT319490B (de) | 1970-11-10 | 1971-11-09 | Verfahren zur Herstellung von neuen 16α, 18-Dimethylpregnenen |
| FR7140076A FR2113873B1 (en, 2012) | 1970-11-10 | 1971-11-09 | |
| BE775190A BE775190A (fr) | 1970-11-10 | 1971-11-10 | 17 alpha-hydroxy-16 alpha, 18-dimethyl-4-pregnene-3,20-dione etses esters, et leur procede de preparation |
| DK89373A DK129767B (da) | 1970-11-10 | 1973-02-20 | Svangerskabsforebyggende middel, der indeholder 17α-hydroxy-16α,18-dimethyl-4-pregnen-3,20-dion eller 17α-monoestere eller 3-enol-17α-diestere deraf. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702056512 DE2056512A1 (de) | 1970-11-10 | 1970-11-10 | 17 alpha-Hydroxy-16 alpha, 18-dimethyl-4-pregnen-3,20-dion und seine Ester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2056512A1 DE2056512A1 (de) | 1972-05-18 |
| DE2056512B2 DE2056512B2 (en, 2012) | 1980-04-03 |
| DE2056512C3 true DE2056512C3 (en, 2012) | 1980-12-04 |
Family
ID=5788360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702056512 Granted DE2056512A1 (de) | 1970-11-10 | 1970-11-10 | 17 alpha-Hydroxy-16 alpha, 18-dimethyl-4-pregnen-3,20-dion und seine Ester |
Country Status (11)
| Country | Link |
|---|---|
| AT (3) | AT319490B (en, 2012) |
| BE (1) | BE775190A (en, 2012) |
| CH (3) | CH591519A5 (en, 2012) |
| CS (3) | CS166291B2 (en, 2012) |
| DE (1) | DE2056512A1 (en, 2012) |
| DK (1) | DK127851B (en, 2012) |
| ES (1) | ES394771A1 (en, 2012) |
| FR (1) | FR2113873B1 (en, 2012) |
| GB (1) | GB1377975A (en, 2012) |
| HU (1) | HU163628B (en, 2012) |
| NL (1) | NL7115418A (en, 2012) |
-
1970
- 1970-11-10 DE DE19702056512 patent/DE2056512A1/de active Granted
-
1971
- 1971-08-31 CS CS691073A patent/CS166291B2/cs unknown
- 1971-08-31 CS CS622471A patent/CS166289B2/cs unknown
- 1971-08-31 CS CS690971A patent/CS166290B2/cs unknown
- 1971-09-03 DK DK433271A patent/DK127851B/da unknown
- 1971-09-03 ES ES394771A patent/ES394771A1/es not_active Expired
- 1971-11-01 CH CH1287475A patent/CH591519A5/xx not_active IP Right Cessation
- 1971-11-01 CH CH1287375A patent/CH601348A5/xx not_active IP Right Cessation
- 1971-11-01 CH CH1588371A patent/CH590886A5/xx not_active IP Right Cessation
- 1971-11-08 HU HUSE000360 patent/HU163628B/hu unknown
- 1971-11-08 GB GB5173971A patent/GB1377975A/en not_active Expired
- 1971-11-09 AT AT585172A patent/AT319490B/de not_active IP Right Cessation
- 1971-11-09 NL NL7115418A patent/NL7115418A/xx unknown
- 1971-11-09 FR FR7140076A patent/FR2113873B1/fr not_active Expired
- 1971-11-09 AT AT585072A patent/AT319489B/de not_active IP Right Cessation
- 1971-11-09 AT AT966571A patent/AT308985B/de not_active IP Right Cessation
- 1971-11-10 BE BE775190A patent/BE775190A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH601348A5 (en, 2012) | 1978-07-14 |
| CS166289B2 (en, 2012) | 1976-02-27 |
| ES394771A1 (es) | 1974-03-01 |
| BE775190A (fr) | 1972-05-10 |
| FR2113873A1 (en, 2012) | 1972-06-30 |
| GB1377975A (en) | 1974-12-18 |
| DK127851B (da) | 1974-01-21 |
| CS166291B2 (en, 2012) | 1976-02-27 |
| CS166290B2 (en, 2012) | 1976-02-27 |
| AT308985B (de) | 1973-07-25 |
| DE2056512B2 (en, 2012) | 1980-04-03 |
| HU163628B (en, 2012) | 1973-09-27 |
| FR2113873B1 (en, 2012) | 1975-03-14 |
| AT319489B (de) | 1974-12-27 |
| AT319490B (de) | 1974-12-27 |
| NL7115418A (en, 2012) | 1972-05-15 |
| CH590886A5 (en, 2012) | 1977-08-31 |
| DE2056512A1 (de) | 1972-05-18 |
| CH591519A5 (en, 2012) | 1977-09-30 |
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