DE1243189B - Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-Reihe - Google Patents
Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-ReiheInfo
- Publication number
- DE1243189B DE1243189B DESCH35420A DESC035420A DE1243189B DE 1243189 B DE1243189 B DE 1243189B DE SCH35420 A DESCH35420 A DE SCH35420A DE SC035420 A DESC035420 A DE SC035420A DE 1243189 B DE1243189 B DE 1243189B
- Authority
- DE
- Germany
- Prior art keywords
- methylene
- acetate
- melting point
- androsten
- keto
- 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 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 claims description 4
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 methylene compound Chemical class 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- 238000002844 melting Methods 0.000 claims 8
- 230000008018 melting Effects 0.000 claims 8
- 238000004587 chromatography analysis Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- 238000001953 recrystallisation Methods 0.000 claims 4
- 239000000741 silica gel Substances 0.000 claims 4
- 229910002027 silica gel Inorganic materials 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000012043 crude product Substances 0.000 claims 2
- 239000000155 melt Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- SQGZFRITSMYKRH-QAGGRKNESA-N androst-5-ene-3,17-dione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 SQGZFRITSMYKRH-QAGGRKNESA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000006567 deketalization reaction Methods 0.000 claims 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- OZRGLPAXIYOWIG-HZPUXBNGSA-N 4-nitrobenzylamine Chemical compound CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CCCC[C@]4(C)[C@H]3CC[C@]12C)=O OZRGLPAXIYOWIG-HZPUXBNGSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 238000005822 methylenation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical class C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1053037D GB1053037A (enrdf_load_stackoverflow) | 1964-07-02 | ||
| BE666330D BE666330A (enrdf_load_stackoverflow) | 1964-07-02 | ||
| DESCH35420A DE1243189B (de) | 1964-07-02 | 1964-07-02 | Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-Reihe |
| CH611865A CH460751A (de) | 1964-07-02 | 1965-05-03 | Verfahren zur Herstellung von 1,2B-Methylen-3-keto-5B-steroiden |
| NL6506593A NL6506593A (enrdf_load_stackoverflow) | 1964-07-02 | 1965-05-25 | |
| DK303265A DK115258B (da) | 1964-07-02 | 1965-06-16 | Fremgangsmåde til fremstilling af 1,2β-methylen-3-keto-5β-steroider. |
| SE8324/65A SE323671B (enrdf_load_stackoverflow) | 1964-07-02 | 1965-06-23 | |
| BR17080365A BR6570803D0 (pt) | 1964-07-02 | 1965-06-28 | Processo para obtencao de alfa beta-metileno cetonas da serie esteroide |
| FR23240A FR1451363A (fr) | 1964-07-02 | 1965-07-02 | Nouvelles alpha.beta-méthylène-cétones de la série stéroïdique et leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH35420A DE1243189B (de) | 1964-07-02 | 1964-07-02 | Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-Reihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1243189B true DE1243189B (de) | 1967-06-29 |
Family
ID=7433483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH35420A Pending DE1243189B (de) | 1964-07-02 | 1964-07-02 | Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-Reihe |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE666330A (enrdf_load_stackoverflow) |
| BR (1) | BR6570803D0 (enrdf_load_stackoverflow) |
| CH (1) | CH460751A (enrdf_load_stackoverflow) |
| DE (1) | DE1243189B (enrdf_load_stackoverflow) |
| DK (1) | DK115258B (enrdf_load_stackoverflow) |
| GB (1) | GB1053037A (enrdf_load_stackoverflow) |
| NL (1) | NL6506593A (enrdf_load_stackoverflow) |
| SE (1) | SE323671B (enrdf_load_stackoverflow) |
-
0
- GB GB1053037D patent/GB1053037A/en active Active
- BE BE666330D patent/BE666330A/xx unknown
-
1964
- 1964-07-02 DE DESCH35420A patent/DE1243189B/de active Pending
-
1965
- 1965-05-03 CH CH611865A patent/CH460751A/de unknown
- 1965-05-25 NL NL6506593A patent/NL6506593A/xx unknown
- 1965-06-16 DK DK303265A patent/DK115258B/da unknown
- 1965-06-23 SE SE8324/65A patent/SE323671B/xx unknown
- 1965-06-28 BR BR17080365A patent/BR6570803D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1053037A (enrdf_load_stackoverflow) | |
| DK115258B (da) | 1969-09-22 |
| NL6506593A (enrdf_load_stackoverflow) | 1966-01-03 |
| SE323671B (enrdf_load_stackoverflow) | 1970-05-11 |
| BR6570803D0 (pt) | 1973-08-16 |
| BE666330A (enrdf_load_stackoverflow) | |
| CH460751A (de) | 1968-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2035738A1 (de) | Neue Androstandenvate und Verfahren zu ihrer Herstellung | |
| DE1593427A1 (de) | Verfahren zur Herstellung von Steroiden | |
| DE3410880A1 (de) | 17-substituierte estradiene und estratriene | |
| DE1243189B (de) | Verfahren zur Herstellung von 1, 2beta-Methylen-3-ketosteroiden der 5beta-Reihe | |
| DE1618871C3 (de) | Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988 | |
| AT253145B (de) | Verfahren zur Herstellung von neuen 1, 2β-Methylen-3-ketosteroiden | |
| DE1263000B (de) | Neues Verfahren zur Herstellung von Gemischen aus delta 1,3,5(10)-3-Oxysteroiden und delta 1,3,5(10)9(11)-3-Oxysteroiden bzw. von delta 1,3,5(10)-3-Oxysteroiden | |
| DE1593500C3 (de) | 15,16 beta-Methylensteroide sowie Verfahren zu deren Herstellung | |
| DE1593516B2 (de) | 4 Halogen-l,2alpha; 6,7beta-bismethylen-Delta hoch 4-3-ketosteroide, Verfahren zu ihrer Herstellung sowie diese Steroide enthaltende Mittel | |
| DE1938283A1 (de) | 6-subst.-13-Polycarbonalkyl-18,19-dinorpregn-4-en-3-one,ihre delta?-Dehydro-Analogen,Zwischenprodukte,Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung | |
| CH539621A (de) | Verfahren zur Herstellung von 15,16B-Methylensteroiden | |
| DE1793687C3 (de) | Verfahren zur Herstellung von Steroidverbindungen. Ausscheidung aus: 1493108 | |
| DE1493168C (de) | Verfahren zur Herstellung von 5alpha Androstanolon derivaten | |
| CH495965A (de) | Verfahren zur Herstellung von Steroiden der Östranreihe | |
| DE1223379B (de) | Verfahren zur Herstellung von 3-Hydroxy- bzw. 3-Alkoxy-1, 3, 5(10)-oestratrienen | |
| DE1568688C3 (de) | Verfahren zur Herstellung von 3-Oxo-4,6-dehydro-19-nor-steroiden, sowie 17 beta-Hydroxy-8 alpha, 10 alpha-östra-4,6-dien-3-on | |
| DE1961906A1 (de) | 7 alpha-Methyl-androstenolone | |
| DE1043333B (de) | Verfahren zur Herstellung von Methylsteroiden | |
| DE1568702C3 (de) | Verfahren zur Herstellung von 11 beta-Fluor-19-nor-steroiden, einige dieser Verbindungen und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE1493114C3 (enrdf_load_stackoverflow) | ||
| DE1643028C3 (de) | Neue 1,2 alpha -Methylensteroide, Verfahren zu ihrer Herstellung, sowie diese enthaltende Mittel | |
| DE1211193B (de) | Verfahren zur Herstellung von delta 17(20)-Pregnenen | |
| DE1215150B (de) | Verfahren zur Herstellung von 3-Keto-20-acyloxy-steroiden | |
| DE1210811B (de) | Verfahren zur Herstellung von delta 1,3,5(10)-3-Hydroxysteroidtrienen | |
| DE1241825B (de) | Ver fahren zur Herstellung von 6 Chlor 4 6diLirverbindungen der Pregnan-, Androstan oder Cholestanreihe |