GB968206A - 17-oxygenated-2-oxa-3-oxosteroids - Google Patents
17-oxygenated-2-oxa-3-oxosteroidsInfo
- Publication number
- GB968206A GB968206A GB1781661A GB1781661A GB968206A GB 968206 A GB968206 A GB 968206A GB 1781661 A GB1781661 A GB 1781661A GB 1781661 A GB1781661 A GB 1781661A GB 968206 A GB968206 A GB 968206A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- compound
- general formula
- acid
- treating
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract 5
- 150000002596 lactones Chemical class 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 150000001340 alkali metals Chemical class 0.000 abstract 4
- -1 hydroxymethylene Chemical group 0.000 abstract 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000012285 osmium tetroxide Substances 0.000 abstract 3
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 3
- 230000001590 oxidative effect Effects 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- KIMPXLFTFHLCDB-GTTLQXADSA-N (1S,2S,5S,9S,10R,12R,13S)-5-methyl-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadecane-6,15-dione Chemical compound O1[C@@H]2C[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]3(CCC(C[C@H]23)=O)C1)=O KIMPXLFTFHLCDB-GTTLQXADSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910000510 noble metal Inorganic materials 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000012279 sodium borohydride Substances 0.000 abstract 2
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- OJCASCDNRIICEJ-GTTLQXADSA-N (1S,2S,5S,9S,10R,12R,13S)-5-methyl-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadec-16-ene-6,15-dione Chemical compound O1[C@@H]2C[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]3(C=CC(C[C@H]23)=O)C1)=O OJCASCDNRIICEJ-GTTLQXADSA-N 0.000 abstract 1
- PNAGQSCZPFXSPA-WLZFUECHSA-N (3aS,3bR,9aR,9bS,11aS)-11a-methyl-3,3a,3b,4,5,9,9a,9b,10,11-decahydro-2H-indeno[4,5-h]isochromene-1,7-dione Chemical compound C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(OC[C@@H]3[C@H]1CC2)=O)=O PNAGQSCZPFXSPA-WLZFUECHSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- PGIFZYYVLPNEAQ-DMCXBQQISA-N [(1S,2S,5S,6S,9S,10R,12R,13S,15S)-6-acetyloxy-5-methyl-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadecan-15-yl] acetate Chemical compound C(C)(=O)O[C@@H]1C[C@@H]2[C@H]3C[C@H]4[C@@H]5CC[C@@H]([C@@]5(C)CC[C@@H]4[C@]2(CC1)CO3)OC(C)=O PGIFZYYVLPNEAQ-DMCXBQQISA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000004703 alkoxides Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 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 abstract 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2959460A | 1960-05-17 | 1960-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB968206A true GB968206A (en) | 1964-08-26 |
Family
ID=21849854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1781661A Expired GB968206A (en) | 1960-05-17 | 1961-05-16 | 17-oxygenated-2-oxa-3-oxosteroids |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE603876A (enrdf_load_stackoverflow) |
| CH (1) | CH399448A (enrdf_load_stackoverflow) |
| DE (1) | DE1171425B (enrdf_load_stackoverflow) |
| FR (1) | FR1697M (enrdf_load_stackoverflow) |
| GB (1) | GB968206A (enrdf_load_stackoverflow) |
| NL (1) | NL110015C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100881A1 (en) * | 2001-05-15 | 2002-12-19 | Cedarburg Pharmaceuticals, Llc | Process for the synthesis of oxandrolone |
-
0
- NL NL110015D patent/NL110015C/xx active
-
1961
- 1961-05-12 DE DES73932A patent/DE1171425B/de active Pending
- 1961-05-16 BE BE603876A patent/BE603876A/fr unknown
- 1961-05-16 GB GB1781661A patent/GB968206A/en not_active Expired
- 1961-05-16 FR FR861947A patent/FR1697M/fr not_active Expired
- 1961-05-17 CH CH578461A patent/CH399448A/de unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100881A1 (en) * | 2001-05-15 | 2002-12-19 | Cedarburg Pharmaceuticals, Llc | Process for the synthesis of oxandrolone |
Also Published As
| Publication number | Publication date |
|---|---|
| NL110015C (enrdf_load_stackoverflow) | |
| BE603876A (fr) | 1961-11-16 |
| FR1697M (fr) | 1963-02-18 |
| DE1171425B (de) | 1964-06-04 |
| CH399448A (de) | 1965-09-30 |
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