NO121103B - - Google Patents
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- Publication number
- NO121103B NO121103B NO16781167A NO16781167A NO121103B NO 121103 B NO121103 B NO 121103B NO 16781167 A NO16781167 A NO 16781167A NO 16781167 A NO16781167 A NO 16781167A NO 121103 B NO121103 B NO 121103B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- hydroxy
- general formula
- androstane
- oxo
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims description 11
- 150000003128 pregnanes Chemical class 0.000 claims description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 150000003431 steroids Chemical class 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 229940117975 chromium trioxide Drugs 0.000 claims description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 6
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229960001566 methyltestosterone Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GNFABWAPJFOZSF-RTDHNQHTSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)CC(=O)C=C1C(C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GNFABWAPJFOZSF-RTDHNQHTSA-N 0.000 description 1
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H13/00—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch
- H01H13/02—Details
- H01H13/26—Snap-action arrangements depending upon deformation of elastic members
- H01H13/28—Snap-action arrangements depending upon deformation of elastic members using compression or extension of coil springs
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H33/00—High-tension or heavy-current switches with arc-extinguishing or arc-preventing means
- H01H33/02—Details
- H01H33/04—Means for extinguishing or preventing arc between current-carrying parts
- H01H33/06—Insulating body insertable between contacts
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H33/00—High-tension or heavy-current switches with arc-extinguishing or arc-preventing means
- H01H33/70—Switches with separate means for directing, obtaining, or increasing flow of arc-extinguishing fluid
- H01H33/76—Switches with separate means for directing, obtaining, or increasing flow of arc-extinguishing fluid wherein arc-extinguishing gas is evolved from stationary parts; Selection of material therefor
- H01H33/77—Switches with separate means for directing, obtaining, or increasing flow of arc-extinguishing fluid wherein arc-extinguishing gas is evolved from stationary parts; Selection of material therefor wherein the break is in air at atmospheric pressure
Landscapes
- Steroid Compounds (AREA)
- Arc-Extinguishing Devices That Are Switches (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0049914 | 1966-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121103B true NO121103B (de) | 1971-01-18 |
Family
ID=7052255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16781167A NO121103B (de) | 1966-04-21 | 1967-04-20 |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE697327A (de) |
| DE (1) | DE1590296B1 (de) |
| NL (1) | NL148734B (de) |
| NO (1) | NO121103B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2511185A1 (fr) * | 1981-08-07 | 1983-02-11 | Telemecanique Electrique | Dispositif automatique de limitation de courants de court-circuit |
| DE3723538A1 (de) * | 1987-07-16 | 1989-01-26 | Sachsenwerk Ag | Loeschkammer zur unterbrechung von laststromkreisen |
| DE59009511D1 (de) * | 1990-03-28 | 1995-09-14 | Siemens Ag | Schnellschalter. |
| WO2000022641A1 (de) * | 1998-10-09 | 2000-04-20 | Siemens Aktiengesellschaft | Mittelspannungsschalter |
| DE102014226131B4 (de) | 2014-12-16 | 2021-06-24 | Volkswagen Aktiengesellschaft | Vorrichtung zum Schalten einer Hochvolt-Verbindung für ein Fahrzeug und Fahrzeug mit einer derartigen Vorrichtung |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE616194C (de) * | 1931-07-26 | 1935-07-22 | Sachsenwerk Licht & Kraft Ag | Elektrischer Schalter |
| DE652800C (de) * | 1934-09-02 | 1937-11-08 | Frida Strauss Geb Ruppel | Schalter mit Lichtbogenloeschung durch stroemendes Druckgas |
| DE672867C (de) * | 1934-09-29 | 1939-03-13 | Frida Strauss Geb Ruppel | Schalter mit Lichtbogenloeschung durch stroemendes Druckgas |
| DE660024C (de) * | 1935-06-22 | 1938-05-14 | Frida Strauss Geb Ruppel | Elektrischer Schalter mit Haupt- und Nebenkontakten |
| DE678744C (de) * | 1937-07-17 | 1939-07-20 | Aeg | Elektrischer Schalter, insbesondere Installationsselbstschalter |
| DE690203C (de) * | 1937-10-01 | 1940-04-18 | Aeg | Installationsselbstschalter, insbesondere zum Abschalten von Kurzschlussstromkreisen |
| DE696787C (de) * | 1938-12-21 | 1940-09-30 | Aeg | Elektrischer Gasschalter |
| DE698559C (de) * | 1939-02-02 | 1940-11-13 | Aeg | Hochspannungsschalter, bestehend aus einem Gasschalter und einem Schubtrennschalter |
| DE921512C (de) * | 1940-06-04 | 1954-12-20 | Siemens Ag | Schalter |
| CH299057A (fr) * | 1951-10-12 | 1954-05-31 | Pagan Laurent | Interrupteur électrique. |
| DE1105028B (de) * | 1959-07-01 | 1961-04-20 | Concordia Maschinen U Elek Zit | Last- und Leistungsschalter mit Loeschkammer aus organischem Werkstoff |
| BE639853A (de) * | 1962-02-23 |
-
1966
- 1966-04-21 DE DE19661590296 patent/DE1590296B1/de active Pending
-
1967
- 1967-04-20 BE BE697327D patent/BE697327A/xx not_active IP Right Cessation
- 1967-04-20 NO NO16781167A patent/NO121103B/no unknown
- 1967-04-21 NL NL6705661A patent/NL148734B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL148734B (nl) | 1976-02-16 |
| DE1590296B1 (de) | 1971-01-28 |
| BE697327A (de) | 1967-10-02 |
| NL6705661A (de) | 1967-10-23 |
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