CH518272A - Verfahren zur Herstellung neuer 4-Halogen-1,2a;6,7B-bismethylen- 4-3-ketosteroide - Google Patents
Verfahren zur Herstellung neuer 4-Halogen-1,2a;6,7B-bismethylen- 4-3-ketosteroideInfo
- Publication number
- CH518272A CH518272A CH1133367A CH1133367A CH518272A CH 518272 A CH518272 A CH 518272A CH 1133367 A CH1133367 A CH 1133367A CH 1133367 A CH1133367 A CH 1133367A CH 518272 A CH518272 A CH 518272A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- dione
- methylenated
- bismethylene
- acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- MNRGTYIVYMTMKH-UHFFFAOYSA-N 2-sulfinylpropane Chemical compound CC(C)=S=O MNRGTYIVYMTMKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 7
- RKYVNNGJYBJHDR-ZEHUYGQASA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-9,12,14,15,16,17-hexahydro-8H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound CC[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(C=C[C@]4(C)[C@H]3C(C[C@]12C)=O)=O RKYVNNGJYBJHDR-ZEHUYGQASA-N 0.000 claims 1
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000003152 gestagenic effect Effects 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000002280 anti-androgenic effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000016087 ovulation Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BNZIOELRSPHEDB-ZEHUYGQASA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2=O BNZIOELRSPHEDB-ZEHUYGQASA-N 0.000 description 1
- -1 1,2-methylene compounds Chemical class 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 231100000546 inhibition of ovulation Toxicity 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000005822 methylenation reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- 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
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1614571A CH527176A (de) | 1966-08-25 | 1967-08-11 | Verfahren zur Herstellung neuer 4-Halogen-1,2a;6,7B-bismethylen- 4-3-ketosteroide |
| CH210270A CH531489A (de) | 1967-08-11 | 1970-02-13 | Verfahren zur Herstellung von 4-Chlor-1a,2a;6a,7a-dimethylen-3-keto-4-pregnenen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC039449 | 1966-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH518272A true CH518272A (de) | 1972-01-31 |
Family
ID=7435178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1133367A CH518272A (de) | 1966-08-25 | 1967-08-11 | Verfahren zur Herstellung neuer 4-Halogen-1,2a;6,7B-bismethylen- 4-3-ketosteroide |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3480711A (en, 2012) |
| BE (1) | BE703084A (en, 2012) |
| CH (1) | CH518272A (en, 2012) |
| CS (1) | CS150193B2 (en, 2012) |
| DE (1) | DE1593516C3 (en, 2012) |
| DK (1) | DK114972B (en, 2012) |
| ES (1) | ES344167A1 (en, 2012) |
| FI (1) | FI45170C (en, 2012) |
| GB (1) | GB1136856A (en, 2012) |
| IL (1) | IL28466A (en, 2012) |
| NL (1) | NL152564B (en, 2012) |
| NO (1) | NO124688B (en, 2012) |
| SE (1) | SE325270B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5374035A (en) * | 1993-06-03 | 1994-12-20 | Santos; Jose C. | Winch with power train, manual operation option, and particular brake assembly |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643027B2 (de) * | 1967-06-09 | 1977-12-08 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 4,6-dichlor-delta hoch 4,6- steroide der pregnanreihe |
| DK123712B (da) * | 1969-02-13 | 1972-07-24 | Schering Ag | Analogifremgangsmåde til fremstilling af 4-chlor-1α, 2α, 6α, 7α-dimethylen-4-pregnen-17α-ol-3,20-dion eller estere deraf. |
| DE102007027635A1 (de) * | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17ß-Cyano-19-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1183500B (de) * | 1962-10-12 | 1964-12-17 | Schering Ag | Verfahren zur Herstellung von alpha, beta-Methylenketonen der Steroidreihe |
-
1966
- 1966-08-25 DE DE1593516A patent/DE1593516C3/de not_active Expired
-
1967
- 1967-06-30 SE SE10021/67*A patent/SE325270B/xx unknown
- 1967-07-18 CS CS5275A patent/CS150193B2/cs unknown
- 1967-08-02 US US657749A patent/US3480711A/en not_active Expired - Lifetime
- 1967-08-07 IL IL28466A patent/IL28466A/en unknown
- 1967-08-11 CH CH1133367A patent/CH518272A/de not_active IP Right Cessation
- 1967-08-11 DK DK409167AA patent/DK114972B/da unknown
- 1967-08-16 ES ES344167A patent/ES344167A1/es not_active Expired
- 1967-08-21 GB GB38441/67A patent/GB1136856A/en not_active Expired
- 1967-08-24 NO NO169490A patent/NO124688B/no unknown
- 1967-08-24 NL NL676711628A patent/NL152564B/xx not_active IP Right Cessation
- 1967-08-24 FI FI672277A patent/FI45170C/fi active
- 1967-08-25 BE BE703084D patent/BE703084A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5374035A (en) * | 1993-06-03 | 1994-12-20 | Santos; Jose C. | Winch with power train, manual operation option, and particular brake assembly |
Also Published As
| Publication number | Publication date |
|---|---|
| ES344167A1 (es) | 1968-09-16 |
| SE325270B (en, 2012) | 1970-06-29 |
| DE1593516B2 (de) | 1974-09-19 |
| CS150193B2 (en, 2012) | 1973-09-04 |
| BE703084A (en, 2012) | 1968-02-26 |
| NL152564B (nl) | 1977-03-15 |
| US3480711A (en) | 1969-11-25 |
| GB1136856A (en) | 1968-12-18 |
| NO124688B (en, 2012) | 1972-05-23 |
| FI45170C (fi) | 1972-04-10 |
| DE1593516C3 (de) | 1975-05-15 |
| DE1593516A1 (de) | 1970-12-03 |
| DK114972B (da) | 1969-08-25 |
| IL28466A (en) | 1971-11-29 |
| NL6711628A (en, 2012) | 1968-02-26 |
| FI45170B (en, 2012) | 1971-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |