NO125273B - - Google Patents
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- Publication number
- NO125273B NO125273B NO157467A NO15746765A NO125273B NO 125273 B NO125273 B NO 125273B NO 157467 A NO157467 A NO 157467A NO 15746765 A NO15746765 A NO 15746765A NO 125273 B NO125273 B NO 125273B
- Authority
- NO
- Norway
- Prior art keywords
- group
- dioxy
- free
- aldehyde
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003470 adrenal cortex hormone Substances 0.000 claims 1
- 150000002373 hemiacetals Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 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
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 3
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229960002478 aldosterone Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCJKXXMOOMBBPY-IEJDVFFQSA-N [2-[(8s,9s,10r,11s,13r,14s,17s)-13-formyl-11-hydroxy-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C=O)C[C@@H]2O HCJKXXMOOMBBPY-IEJDVFFQSA-N 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006567 deketalization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001976 hemiacetal group Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO16594166A NO124595B (fr) | 1964-09-29 | 1966-12-09 | |
| NO16594066A NO124596B (fr) | 1964-09-29 | 1966-12-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US400206A US3412107A (en) | 1964-09-29 | 1964-09-29 | 11-hydroxy-5-oxo-3, 5-seco-a-nor-androstan-3-oic acid 3, 11-lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125273B true NO125273B (fr) | 1972-08-14 |
Family
ID=23582655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157467A NO125273B (fr) | 1964-09-29 | 1965-03-30 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3412107A (fr) |
| AT (1) | AT280489B (fr) |
| BE (1) | BE663197A (fr) |
| CH (1) | CH577446A5 (fr) |
| DE (3) | DE1518980C3 (fr) |
| DK (3) | DK126031B (fr) |
| ES (1) | ES311225A1 (fr) |
| FI (6) | FI42552B (fr) |
| GB (8) | GB1103983A (fr) |
| IL (3) | IL31353A (fr) |
| MY (8) | MY6900083A (fr) |
| NL (2) | NL6901812A (fr) |
| NO (1) | NO125273B (fr) |
| SE (3) | SE353905B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3761503A (en) * | 1964-09-29 | 1973-09-25 | Hoffmann La Roche | Substituted-3,5-seco-a-nor-pregnan-3-oic-acids |
| DE2331997A1 (de) * | 1973-06-21 | 1975-01-16 | Schering Ag | Verfahren zur herstellung von bicycloalkan-derivaten |
| CA1195997A (fr) * | 1979-02-23 | 1985-10-29 | Andor Furst | Dea-steroides |
| FR2500441A1 (fr) * | 1981-02-23 | 1982-08-27 | Roussel Uclaf | Nouveaux medicaments derives de la 3-hydroxy dodecahydro benz (e) inden-7-one, produits derives de la 3-hydroxy dodecahydro benz (e) inden-7-one et leur procede de preparation |
| DE3434451A1 (de) * | 1984-09-20 | 1986-03-27 | Austgen, René, 6625 Püttlingen | Dieselkraftstoff-filter |
-
1964
- 1964-09-29 US US400206A patent/US3412107A/en not_active Expired - Lifetime
-
1965
- 1965-03-18 IL IL31353A patent/IL31353A/en unknown
- 1965-03-18 IL IL23180A patent/IL23180A/en unknown
- 1965-03-18 IL IL31354A patent/IL31354A/en unknown
- 1965-03-25 CH CH760568A patent/CH577446A5/de not_active IP Right Cessation
- 1965-03-27 DE DE1518980A patent/DE1518980C3/de not_active Expired
- 1965-03-27 DE DE1618507A patent/DE1618507C3/de not_active Expired
- 1965-03-27 DE DE19651618508 patent/DE1618508A1/de active Pending
- 1965-03-29 GB GB36701/67A patent/GB1103983A/en not_active Expired
- 1965-03-29 GB GB36700/67A patent/GB1103982A/en not_active Expired
- 1965-03-29 GB GB13173/65A patent/GB1103574A/en not_active Expired
- 1965-03-29 GB GB36703/67A patent/GB1103985A/en not_active Expired
- 1965-03-29 GB GB36705/67A patent/GB1103987A/en not_active Expired
- 1965-03-29 SE SE10751/69A patent/SE353905B/xx unknown
- 1965-03-29 AT AT282365A patent/AT280489B/de active
- 1965-03-29 SE SE4026/65A patent/SE317968B/xx unknown
- 1965-03-29 GB GB36706/67A patent/GB1103988A/en not_active Expired
- 1965-03-29 GB GB36704/67A patent/GB1103986A/en not_active Expired
- 1965-03-29 SE SE10752/69A patent/SE353904B/xx unknown
- 1965-03-29 GB GB36702/67A patent/GB1103984A/en not_active Expired
- 1965-03-30 FI FI0765/65A patent/FI42552B/fi active
- 1965-03-30 ES ES0311225A patent/ES311225A1/es not_active Expired
- 1965-03-30 NO NO157467A patent/NO125273B/no unknown
- 1965-04-29 BE BE663197A patent/BE663197A/fr unknown
-
1968
- 1968-12-13 DK DK609968AA patent/DK126031B/da unknown
- 1968-12-13 DK DK610268AA patent/DK123235B/da unknown
- 1968-12-13 DK DK610168AA patent/DK123234B/da unknown
-
1969
- 1969-02-05 NL NL6901812A patent/NL6901812A/xx unknown
- 1969-02-05 NL NL6901813A patent/NL6901813A/xx unknown
- 1969-03-24 FI FI0857/69A patent/FI43592B/fi active
- 1969-03-24 FI FI0856/69A patent/FI43591B/fi active
- 1969-03-24 FI FI0858/69A patent/FI43593B/fi active
- 1969-03-24 FI FI0859/69A patent/FI43594B/fi active
- 1969-03-24 FI FI0854/69A patent/FI43590B/fi active
- 1969-12-31 MY MY196983A patent/MY6900083A/xx unknown
- 1969-12-31 MY MY196981A patent/MY6900081A/xx unknown
- 1969-12-31 MY MY196979A patent/MY6900079A/xx unknown
- 1969-12-31 MY MY196982A patent/MY6900082A/xx unknown
- 1969-12-31 MY MY196977A patent/MY6900077A/xx unknown
- 1969-12-31 MY MY196978A patent/MY6900078A/xx unknown
- 1969-12-31 MY MY196976A patent/MY6900076A/xx unknown
- 1969-12-31 MY MY196980A patent/MY6900080A/xx unknown
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