DE1229526B - Verfahren zur Herstellung von delta 4,1-3-Oxo-11beta-hydroxy-19-nor-steroiden-durch Einfuehrung von Sauerstoff in 11-Stellung auf chemischem Wege - Google Patents
Verfahren zur Herstellung von delta 4,1-3-Oxo-11beta-hydroxy-19-nor-steroiden-durch Einfuehrung von Sauerstoff in 11-Stellung auf chemischem WegeInfo
- Publication number
- DE1229526B DE1229526B DER38097A DER0038097A DE1229526B DE 1229526 B DE1229526 B DE 1229526B DE R38097 A DER38097 A DE R38097A DE R0038097 A DER0038097 A DE R0038097A DE 1229526 B DE1229526 B DE 1229526B
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- hydroxy
- estradiene
- radical
- methanol
- 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 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 17
- 229910052760 oxygen Inorganic materials 0.000 title claims description 17
- 239000001301 oxygen Substances 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000126 substance Substances 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- -1 alkyl radical Chemical class 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 8
- HWCYISVQOIISSU-HULBTWJISA-N (8R,9R,10S,13R)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrocyclopenta[a]phenanthrene Chemical compound C([C@@H]12)CCCC1CC[C@@H]1[C@@H]2CC[C@@]2(C)C1=CC=C2 HWCYISVQOIISSU-HULBTWJISA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 150000003431 steroids Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000000871 hypocholesterolemic effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- APLGXMKUJWCEBP-UHFFFAOYSA-N 1-butoxy-4-[(4-methylphenyl)methoxy]benzene Chemical compound C1=CC(OCCCC)=CC=C1OCC1=CC=C(C)C=C1 APLGXMKUJWCEBP-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
-
- 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
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR941004A FR1375078A (fr) | 1963-07-10 | 1963-07-10 | Procédé d'introduction d'une fonction oxygénée en position 11 de certains 19-norstéroïdes et produits en résultant |
| FR951379A FR1468639A (fr) | 1963-07-10 | 1963-10-22 | Nouveau stéroïde diénique 11-oxygéné et procédé de préparation |
| FR960726A FR5089M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-07-10 | 1964-01-17 | |
| FR971005A FR3845M (fr) | 1963-07-10 | 1964-04-15 | Nouveau médicament notamment pour le traitement de l'hypercholestérolémie et des troubles en résultant. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1229526B true DE1229526B (de) | 1966-12-01 |
Family
ID=27445615
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38097A Pending DE1229526B (de) | 1963-07-10 | 1964-06-08 | Verfahren zur Herstellung von delta 4,1-3-Oxo-11beta-hydroxy-19-nor-steroiden-durch Einfuehrung von Sauerstoff in 11-Stellung auf chemischem Wege |
| DER38098A Pending DE1232577B (de) | 1963-07-10 | 1964-06-08 | Verfahren zur Herstellung von delta 4,9-3-Oxo-11beta-hydroperoxy-19-nor-steroiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38098A Pending DE1232577B (de) | 1963-07-10 | 1964-06-08 | Verfahren zur Herstellung von delta 4,9-3-Oxo-11beta-hydroperoxy-19-nor-steroiden |
Country Status (10)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE663534A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-05-13 | |||
| US3389153A (en) * | 1965-08-13 | 1968-06-18 | Merck & Co Inc | 3-enol ethers of 17alpha-haloethynyl-estra 3, 5(10), 9(11)-trien-17beta-ols |
| FR205F (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-10-22 | |||
| NL129874C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-03-15 | |||
| US3475469A (en) * | 1967-06-27 | 1969-10-28 | American Home Prod | 13 - alkyl - 9 - chloromethylgon - 4-en-17beta-ol-3-ones and intermediates therefor |
| KR101356296B1 (ko) * | 2005-06-28 | 2014-02-06 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 높은 일 함수의 투명한 도체 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3211764A (en) * | 1963-09-25 | 1965-10-12 | American Cyanamid Co | 19-norandrostadienes and method of preparing the same |
-
0
- NL NL121957D patent/NL121957C/xx active
- BE BE649224D patent/BE649224A/xx unknown
- BE BE649223D patent/BE649223A/xx unknown
-
1963
- 1963-07-10 FR FR941004A patent/FR1375078A/fr not_active Expired
- 1963-10-22 FR FR951379A patent/FR1468639A/fr not_active Expired
-
1964
- 1964-01-17 FR FR960726A patent/FR5089M/fr not_active Expired
- 1964-04-15 FR FR971005A patent/FR3845M/fr active Active
- 1964-06-05 US US373116A patent/US3301756A/en not_active Expired - Lifetime
- 1964-06-05 US US373048A patent/US3282785A/en not_active Expired - Lifetime
- 1964-06-08 DE DER38097A patent/DE1229526B/de active Pending
- 1964-06-08 DE DER38098A patent/DE1232577B/de active Pending
- 1964-06-09 CH CH752964A patent/CH432504A/fr unknown
- 1964-06-09 CH CH753064A patent/CH433276A/fr unknown
- 1964-06-10 BR BR159890/64A patent/BR6459890D0/pt unknown
- 1964-06-10 DK DK289764AA patent/DK112796B/da unknown
- 1964-06-10 BR BR159891/64A patent/BR6459891D0/pt unknown
- 1964-06-10 DK DK289864AA patent/DK119107B/da unknown
- 1964-06-12 NL NL6406711A patent/NL6406711A/xx unknown
- 1964-06-12 GB GB24614/64A patent/GB1074491A/en not_active Expired
- 1964-06-12 NL NL6406712A patent/NL6406712A/xx unknown
- 1964-06-12 SE SE7232/64A patent/SE316172B/xx unknown
- 1964-06-12 SE SE7231/64A patent/SE316170B/xx unknown
- 1964-06-12 GB GB56702/66A patent/GB1074495A/en not_active Expired
- 1964-06-12 GB GB24615/64A patent/GB1074492A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6459890D0 (pt) | 1973-08-09 |
| DE1232577B (de) | 1967-01-19 |
| FR5089M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-22 |
| BE649224A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| SE316172B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-20 |
| BE649223A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| BR6459891D0 (pt) | 1973-09-11 |
| GB1074491A (en) | 1967-07-05 |
| DK119107B (da) | 1970-11-16 |
| NL121957C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| FR1375078A (fr) | 1964-10-16 |
| FR1468639A (fr) | 1967-02-10 |
| CH433276A (fr) | 1967-04-15 |
| FR3845M (fr) | 1966-01-17 |
| GB1074492A (en) | 1967-07-05 |
| NL6406711A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-01-11 |
| US3301756A (en) | 1967-01-31 |
| GB1074495A (en) | 1967-07-05 |
| SE316170B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-20 |
| US3282785A (en) | 1966-11-01 |
| DK112796B (da) | 1969-01-20 |
| NL6406712A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-01-11 |
| CH432504A (fr) | 1967-03-31 |
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