DE1593490A1 - Steroid-keto-Aldchyde - Google Patents
Steroid-keto-AldchydeInfo
- Publication number
- DE1593490A1 DE1593490A1 DE19661593490 DE1593490A DE1593490A1 DE 1593490 A1 DE1593490 A1 DE 1593490A1 DE 19661593490 DE19661593490 DE 19661593490 DE 1593490 A DE1593490 A DE 1593490A DE 1593490 A1 DE1593490 A1 DE 1593490A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- aldehyde group
- radical
- general formula
- carboxylic acid
- 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
- 229930194542 Keto Natural products 0.000 title 1
- 238000000034 method Methods 0.000 claims description 14
- 125000003172 aldehyde group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- -1 butyl-O Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QDXKHFDUSMXRGD-JWDKAUQWSA-N CC[C@H]1CC[C@H]2[C@@H]3CC([C@H]4CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)=O Chemical compound CC[C@H]1CC[C@H]2[C@@H]3CC([C@H]4CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)=O QDXKHFDUSMXRGD-JWDKAUQWSA-N 0.000 description 1
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC038384 | 1966-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593490A1 true DE1593490A1 (de) | 1970-10-22 |
Family
ID=7434681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593490 Pending DE1593490A1 (de) | 1966-01-27 | 1966-01-27 | Steroid-keto-Aldchyde |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE693274A (enrdf_load_stackoverflow) |
| CH (1) | CH484889A (enrdf_load_stackoverflow) |
| DE (1) | DE1593490A1 (enrdf_load_stackoverflow) |
| DK (1) | DK114407B (enrdf_load_stackoverflow) |
| ES (1) | ES336022A1 (enrdf_load_stackoverflow) |
| FI (1) | FI43074B (enrdf_load_stackoverflow) |
| FR (1) | FR1508947A (enrdf_load_stackoverflow) |
| GB (1) | GB1160212A (enrdf_load_stackoverflow) |
| IL (1) | IL27181A (enrdf_load_stackoverflow) |
| NL (1) | NL6701320A (enrdf_load_stackoverflow) |
| SE (1) | SE330886B (enrdf_load_stackoverflow) |
-
1966
- 1966-01-27 DE DE19661593490 patent/DE1593490A1/de active Pending
- 1966-12-29 IL IL2718166A patent/IL27181A/xx unknown
-
1967
- 1967-01-16 CH CH58167A patent/CH484889A/de not_active IP Right Cessation
- 1967-01-17 GB GB244767A patent/GB1160212A/en not_active Expired
- 1967-01-17 DK DK27467A patent/DK114407B/da unknown
- 1967-01-24 ES ES0336022A patent/ES336022A1/es not_active Expired
- 1967-01-26 FR FR92557A patent/FR1508947A/fr not_active Expired
- 1967-01-27 BE BE693274D patent/BE693274A/xx unknown
- 1967-01-27 SE SE124567A patent/SE330886B/xx unknown
- 1967-01-27 NL NL6701320A patent/NL6701320A/xx unknown
- 1967-01-27 FI FI24767A patent/FI43074B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| SE330886B (enrdf_load_stackoverflow) | 1970-12-07 |
| FR1508947A (fr) | 1968-01-05 |
| IL27181A (en) | 1970-11-30 |
| GB1160212A (en) | 1969-08-06 |
| DK114407B (da) | 1969-06-30 |
| NL6701320A (enrdf_load_stackoverflow) | 1967-07-28 |
| ES336022A1 (es) | 1967-12-16 |
| FI43074B (enrdf_load_stackoverflow) | 1970-10-01 |
| BE693274A (enrdf_load_stackoverflow) | 1967-07-27 |
| CH484889A (de) | 1970-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1152101B (de) | Verfahren zur Herstellung von mit einem Pyrazolring kondensierten Steroidverbindungen | |
| DE1593490A1 (de) | Steroid-keto-Aldchyde | |
| DE1793633C3 (de) | Verfahren zur Herstellung von Gona 4(5),9(10)dien3 onen Ausscheidung aus 1468642 | |
| EP0201452A2 (de) | Verfahren zur Herstellung von 17alpha-Ethinyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on und die neuen Ausgangsverbindungen für dieses Verfahren | |
| AT275056B (de) | Verfahren zur Herstellung von Steroid-ketoaldehyden | |
| AT267088B (de) | Verfahren zur Herstellung neuer 1,2α-Methylen-19-nor-testosterone | |
| DE1418945C3 (de) | Verfahren zur Herstellung von 16 alpha Methyl 17alpha hydroxy 20 oxo pregnandenvaten | |
| AT271759B (de) | Verfahren zur Herstellung von neuen 1,2β-Methylensteroiden | |
| DE974201C (de) | Verfahren zur Reduktion von Verbindungen der Cyclopentanopolyhydrophenanthren-Reihe | |
| DE935969C (de) | Verfahren zur Herstellung von ª‡, ª‰-ungesaettigten Steroidketonen | |
| AT206593B (de) | Verfahren zur Herstellung von 6-Methyl-3-oxo-Δ<4>-steroiden | |
| DE1593697C (de) | Verfahren zur Herstellung von 1 alpha Alkoxy , 1 alpha Alkenyloxy , 1 alpha Alkinyl oxy- oder 1 alpha Cycloalkyloxy 5 alpha steroiden | |
| DE1593448C (de) | 13beta-Äthyl-gon-4-en-3-on-thioketale, deren Herstellung und diese enthaltendes Mittel | |
| DE961536C (de) | Verfahren zur Herstellung von 20-Keto-21-formylsteroiden der Pregnanreihe | |
| AT235477B (de) | Verfahren zur Herstellung von neuen, mit einem Isoxazolring kondensierten Steroidverbindungen | |
| AT274257B (de) | Verfahren zur Herstellung von 17-oxygenierten 3-Oxo-Δ<4,9,11>-trienen der 19-Nor-androstanreihe | |
| DE1593686C (de) | Verfahren zur Herstellung von 3 Ketobenzo eckige Klammer auf d,e eckige Klammer zus steroiden | |
| DE964677C (de) | Verfahren zur Herstellung von Allopregnanen | |
| DE948974C (de) | Verfahren zur Herstellung von cyclischen 4-Halogenpregnan-3, 20-dion-3, 20-diketalen | |
| DE1593337C (de) | Verfahren zur Herstellung von 3 Oxo 7 alpha Methyl gona 4,9 dienen | |
| DE1668687B2 (de) | Neue 18-methyl-5alpha-h-androstane, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel | |
| CH497404A (de) | Verfahren zur Herstellung von in 22-Stellung substituierten 6-Ketosteroiden aus 20-Formyl-6-keto-steroiden der Pregnanreihe | |
| DE1230795B (de) | Verfahren zur Herstellung von Androstano [2, 3-c]furazan-derivaten | |
| DE1175232B (de) | Verfahren zur Herstellung von 6ª‡-Methyl-17ª‡-hydroxyprogesteron sowie von dessen Estern | |
| CH514563A (de) | Verfahren zur Herstellung von 6-Keto-20-hydroxysteroiden |