NO128976B - - Google Patents
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- Publication number
- NO128976B NO128976B NO410272A NO410272A NO128976B NO 128976 B NO128976 B NO 128976B NO 410272 A NO410272 A NO 410272A NO 410272 A NO410272 A NO 410272A NO 128976 B NO128976 B NO 128976B
- Authority
- NO
- Norway
- Prior art keywords
- oxo
- methyl
- hydroxy
- steroid
- acyloxy
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003431 steroids Chemical class 0.000 claims description 7
- 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 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 methylmagnesium halide Chemical class 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 150000003128 pregnanes Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001195 anabolic effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 230000001548 androgenic effect Effects 0.000 claims 1
- 230000001072 progestational effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- VMNRNUNYBVFVQI-UHFFFAOYSA-N 10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CCC2(C)C2C1C1CCCC1(C)CC2 VMNRNUNYBVFVQI-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229940117975 chromium trioxide Drugs 0.000 description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 5
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 5
- LPMDCPLRVPBTRF-DAELLWKTSA-N (8r,9s,10r,13s,14s)-6,10,13-trimethyl-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)CC(=O)C=C1C(C)=C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 LPMDCPLRVPBTRF-DAELLWKTSA-N 0.000 description 4
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000000583 progesterone congener Substances 0.000 description 3
- DWJQHNJCKUWONS-NTNOATJHSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-6,10,13-trimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound CC(=O)[C@H]1CC[C@H]2[C@@H]3C=C(C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C DWJQHNJCKUWONS-NTNOATJHSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical class O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 2
- 229960000445 ethisterone Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003270 steroid hormone Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GZSCFURMBHMSCE-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical class C([C@@]12C)CC(=O)C=C1C(C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 GZSCFURMBHMSCE-RTQNCGMRSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GNFABWAPJFOZSF-KTORGGLSSA-N 6alpha-Methylprogesterone Chemical class C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GNFABWAPJFOZSF-KTORGGLSSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 150000001441 androstanes Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 229950008604 mestanolone Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/68—Heating arrangements specially adapted for cooking plates or analogous hot-plates
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C15/00—Details
- F24C15/10—Tops, e.g. hot plates; Rings
- F24C15/102—Tops, e.g. hot plates; Rings electrically heated
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/68—Heating arrangements specially adapted for cooking plates or analogous hot-plates
- H05B3/72—Plates of sheet metal
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Resistance Heating (AREA)
- Surface Heating Bodies (AREA)
- Baking, Grill, Roasting (AREA)
- Central Heating Systems (AREA)
- Steroid Compounds (AREA)
- Cookers (AREA)
- Electric Stoves And Ranges (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO410272A NO128976B (xx) | 1972-11-13 | 1972-11-13 | |
| NL7314753A NL160698C (nl) | 1972-11-13 | 1973-10-26 | Elektrisch fornuis. |
| DE19732355345 DE2355345C3 (de) | 1972-11-13 | 1973-11-06 | Heizvorrichtung, insbesondere Herdoder Wärmeplatte |
| SE7315175A SE394785B (sv) | 1972-11-13 | 1973-11-08 | Vermeanordning med vermezoner omgivna av kallare zoner |
| IT5358873A IT996417B (it) | 1972-11-13 | 1973-11-09 | Dispositivo elettrico di riscalda mento particolarmente per cucine |
| GB5247073A GB1418819A (en) | 1972-11-13 | 1973-11-12 | Heating appliance |
| CH1585673A CH563098A5 (xx) | 1972-11-13 | 1973-11-12 | |
| JP12762473A JPS559794B2 (xx) | 1972-11-13 | 1973-11-13 | |
| FR7340335A FR2206643B1 (xx) | 1972-11-13 | 1973-11-13 | |
| BE137685A BE807248A (fr) | 1972-11-13 | 1973-11-13 | Dispositif de chauffage |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO410272A NO128976B (xx) | 1972-11-13 | 1972-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128976B true NO128976B (xx) | 1974-02-04 |
Family
ID=19880073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO410272A NO128976B (xx) | 1972-11-13 | 1972-11-13 |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS559794B2 (xx) |
| BE (1) | BE807248A (xx) |
| CH (1) | CH563098A5 (xx) |
| DE (1) | DE2355345C3 (xx) |
| FR (1) | FR2206643B1 (xx) |
| GB (1) | GB1418819A (xx) |
| IT (1) | IT996417B (xx) |
| NL (1) | NL160698C (xx) |
| NO (1) | NO128976B (xx) |
| SE (1) | SE394785B (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045654A (en) * | 1975-09-02 | 1977-08-30 | A/S Ardal Og Sunndal Verk | Electric hotplate with thermostat |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS562379Y2 (xx) * | 1976-04-28 | 1981-01-20 | ||
| DE3033828A1 (de) * | 1980-09-09 | 1982-04-29 | Fischer, Karl, 7519 Oberderdingen | Elektrokochplatte |
| EP0162620A3 (en) * | 1984-05-11 | 1987-05-13 | THORN EMI Patents Limited | A cooking arrangement |
| JPS61120674U (xx) * | 1985-01-18 | 1986-07-30 | ||
| DE3545442A1 (de) * | 1985-12-20 | 1987-06-25 | Bosch Siemens Hausgeraete | Heizelement fuer thermische hausgeraete, insbesondere fuer kochstellen |
| DE8717025U1 (xx) * | 1987-12-28 | 1988-06-23 | Jaksch, Adolf, 8000 Muenchen, De | |
| DE102004013045B4 (de) * | 2004-03-10 | 2006-06-29 | Alfred Kärcher Gmbh & Co. Kg | Vorrichtung zum Zubereiten von Speisen, insbesondere als mobile Feldküche |
| DE102013021356A1 (de) | 2012-12-29 | 2015-08-20 | Labetherm Limited Zweigniederlassung Deutschland | Gestaltung eines Tiegelbodens vom Gargerät und Verfahren zum Betreiben solch ein Gerätes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS442126Y1 (xx) * | 1965-02-05 | 1969-01-27 | ||
| DE1579652A1 (de) * | 1966-01-26 | 1970-10-29 | Stumpp & Schuele Kg | Elektrisch beheiztes Koch-,Brat- und Backgeraet |
| DE2030558A1 (de) * | 1970-06-20 | 1971-12-30 | Blanc & Co | Kochplatte |
-
1972
- 1972-11-13 NO NO410272A patent/NO128976B/no unknown
-
1973
- 1973-10-26 NL NL7314753A patent/NL160698C/xx not_active IP Right Cessation
- 1973-11-06 DE DE19732355345 patent/DE2355345C3/de not_active Expired
- 1973-11-08 SE SE7315175A patent/SE394785B/xx unknown
- 1973-11-09 IT IT5358873A patent/IT996417B/it active
- 1973-11-12 GB GB5247073A patent/GB1418819A/en not_active Expired
- 1973-11-12 CH CH1585673A patent/CH563098A5/xx not_active IP Right Cessation
- 1973-11-13 FR FR7340335A patent/FR2206643B1/fr not_active Expired
- 1973-11-13 BE BE137685A patent/BE807248A/xx unknown
- 1973-11-13 JP JP12762473A patent/JPS559794B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045654A (en) * | 1975-09-02 | 1977-08-30 | A/S Ardal Og Sunndal Verk | Electric hotplate with thermostat |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2206643B1 (xx) | 1977-06-03 |
| DE2355345C3 (de) | 1979-06-21 |
| GB1418819A (en) | 1975-12-24 |
| DE2355345A1 (de) | 1974-06-06 |
| JPS49108653A (xx) | 1974-10-16 |
| NL7314753A (xx) | 1974-05-15 |
| DE2355345B2 (de) | 1978-10-19 |
| NL160698C (nl) | 1979-11-15 |
| NL160698B (nl) | 1979-06-15 |
| FR2206643A1 (xx) | 1974-06-07 |
| IT996417B (it) | 1975-12-10 |
| BE807248A (fr) | 1974-03-01 |
| JPS559794B2 (xx) | 1980-03-12 |
| CH563098A5 (xx) | 1975-06-13 |
| SE394785B (sv) | 1977-07-04 |
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