CH507926A - Verfahren zur Herstellung von 19-Alkylsteroiden - Google Patents
Verfahren zur Herstellung von 19-AlkylsteroidenInfo
- Publication number
- CH507926A CH507926A CH1782270A CH1782270A CH507926A CH 507926 A CH507926 A CH 507926A CH 1782270 A CH1782270 A CH 1782270A CH 1782270 A CH1782270 A CH 1782270A CH 507926 A CH507926 A CH 507926A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- delta4
- hydroxy
- formula
- delta3
- Prior art date
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract description 4
- 230000035558 fertility Effects 0.000 abstract description 2
- 229960003387 progesterone Drugs 0.000 abstract description 2
- 239000000186 progesterone Substances 0.000 abstract description 2
- 101100241859 Mus musculus Oacyl gene Proteins 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000006771 Gonadotropins Human genes 0.000 description 1
- 108010086677 Gonadotropins Proteins 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000002622 gonadotropin Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- -1 methoxy, ethoxy Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1782270A CH507926A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1782270A CH507926A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH720068A CH502327A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507926A true CH507926A (de) | 1971-05-31 |
Family
ID=4321433
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1782270A CH507926A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH720068A CH502327A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782470A CH507923A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782370A CH507925A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782570A CH524585A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH720068A CH502327A (de) | 1968-05-15 | 1968-05-15 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782470A CH507923A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782370A CH507925A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
| CH1782570A CH524585A (de) | 1968-05-15 | 1969-04-25 | Verfahren zur Herstellung von 19-Alkylsteroiden |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT290027B (enrdf_load_html_response) |
| BE (1) | BE733017A (enrdf_load_html_response) |
| CH (5) | CH507926A (enrdf_load_html_response) |
| DE (1) | DE1924785A1 (enrdf_load_html_response) |
| ES (1) | ES367281A1 (enrdf_load_html_response) |
| FR (1) | FR2008589A1 (enrdf_load_html_response) |
| GB (1) | GB1269234A (enrdf_load_html_response) |
| IL (1) | IL32151A0 (enrdf_load_html_response) |
| NL (1) | NL6907136A (enrdf_load_html_response) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE632012A (enrdf_load_html_response) * |
-
1968
- 1968-05-15 CH CH1782270A patent/CH507926A/de not_active IP Right Cessation
- 1968-05-15 CH CH720068A patent/CH502327A/de not_active IP Right Cessation
-
1969
- 1969-04-25 CH CH1782470A patent/CH507923A/de not_active IP Right Cessation
- 1969-04-25 CH CH1782370A patent/CH507925A/de not_active IP Right Cessation
- 1969-04-25 CH CH1782570A patent/CH524585A/de not_active IP Right Cessation
- 1969-05-04 IL IL32151A patent/IL32151A0/xx unknown
- 1969-05-09 NL NL6907136A patent/NL6907136A/xx unknown
- 1969-05-13 GB GB24320/69A patent/GB1269234A/en not_active Expired
- 1969-05-14 AT AT460669A patent/AT290027B/de not_active IP Right Cessation
- 1969-05-14 FR FR6915700A patent/FR2008589A1/fr not_active Withdrawn
- 1969-05-14 DE DE19691924785 patent/DE1924785A1/de active Pending
- 1969-05-14 ES ES367281A patent/ES367281A1/es not_active Expired
- 1969-05-14 BE BE733017D patent/BE733017A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6907136A (enrdf_load_html_response) | 1969-11-18 |
| DE1924785A1 (de) | 1969-11-20 |
| FR2008589A1 (enrdf_load_html_response) | 1970-01-23 |
| CH502327A (de) | 1971-01-31 |
| AT290027B (de) | 1971-05-10 |
| CH507925A (de) | 1971-05-31 |
| GB1269234A (en) | 1972-04-06 |
| ES367281A1 (es) | 1973-03-16 |
| CH524585A (de) | 1972-06-30 |
| BE733017A (enrdf_load_html_response) | 1969-11-14 |
| IL32151A0 (en) | 1969-07-30 |
| CH507923A (de) | 1971-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |