CH579592A5 - 3-ketosteroid oximes anabolic androgenic - antifertility - Google Patents
3-ketosteroid oximes anabolic androgenic - antifertilityInfo
- Publication number
- CH579592A5 CH579592A5 CH56671A CH56671A CH579592A5 CH 579592 A5 CH579592 A5 CH 579592A5 CH 56671 A CH56671 A CH 56671A CH 56671 A CH56671 A CH 56671A CH 579592 A5 CH579592 A5 CH 579592A5
- Authority
- CH
- Switzerland
- Prior art keywords
- imino
- nitrophenoxy
- hydroxylamine
- reacting
- keto
- Prior art date
Links
- 230000001195 anabolic effect Effects 0.000 title abstract description 6
- 150000002923 oximes Chemical class 0.000 title abstract description 6
- 230000001548 androgenic effect Effects 0.000 title abstract description 4
- 230000003509 anti-fertility effect Effects 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229930194542 Keto Natural products 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 37
- -1 dinitrophenoxy Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- OOHKBWPOLBTKMR-UHFFFAOYSA-N o-(4-nitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1 OOHKBWPOLBTKMR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 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 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229960003604 testosterone Drugs 0.000 claims description 3
- VIDCBERQJMHDKJ-GUZBXJAVSA-N (8R,9S,10R,13S,14S)-15-imino-10,13-dimethyl-3-(4-nitrophenoxy)-1,2,3,6,7,8,9,11,12,14-decahydrocyclopenta[a]phenanthren-17-one Chemical compound [N+](=O)([O-])C1=CC=C(OC2C=C3CC[C@@H]4[C@H](CC[C@@]5(C(CC([C@H]54)=N)=O)C)[C@]3(CC2)C)C=C1 VIDCBERQJMHDKJ-GUZBXJAVSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 241000124008 Mammalia Species 0.000 abstract 1
- 230000035558 fertility Effects 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 128
- 235000019441 ethanol Nutrition 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 238000000921 elemental analysis Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 238000002844 melting Methods 0.000 description 27
- 230000007717 exclusion Effects 0.000 description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 5
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 5
- 229960001566 methyltestosterone Drugs 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003433 contraceptive agent Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 210000002307 prostate Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- NSCDVPILOBBYIK-GLYPSPDYSA-N [N+](=O)([O-])C1=CC=C(OC2C[C@@H]3CC[C@H]4[C@@H]5CCC([C@@]5(C=N)CC[C@@H]4[C@]3(CC2)C)=O)C=C1 Chemical compound [N+](=O)([O-])C1=CC=C(OC2C[C@@H]3CC[C@H]4[C@@H]5CCC([C@@]5(C=N)CC[C@@H]4[C@]3(CC2)C)=O)C=C1 NSCDVPILOBBYIK-GLYPSPDYSA-N 0.000 description 2
- 239000003263 anabolic agent Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 230000002254 contraceptive effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 2
- 229960004719 nandrolone Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- IUFOPOQNYKRRML-AMZOQCFUSA-N (8s,10s,13s,14s)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CCC2=C1 IUFOPOQNYKRRML-AMZOQCFUSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- XYGMEFJSKQEBTO-KUJXMBTLSA-N Clostebol acetate Chemical compound C1CC2=C(Cl)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 XYGMEFJSKQEBTO-KUJXMBTLSA-N 0.000 description 1
- ILCTUFVQFCIIDS-NGFSFWIMSA-N [(5s,8r,9s,10s,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)C)[C@@]2(C)CC1 ILCTUFVQFCIIDS-NGFSFWIMSA-N 0.000 description 1
- SRELIFBKQILPBM-DAHLPWLQSA-N [(8R,9S,10R,13S,14S)-4-chloro-10,13-dimethyl-3-(4-nitrophenoxy)-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound [N+](=O)([O-])C1=CC=C(OC2C(=C3CC[C@@H]4[C@H](CC[C@@]5(C(CC[C@H]54)OC(C)=O)C)[C@]3(CC2)C)Cl)C=C1 SRELIFBKQILPBM-DAHLPWLQSA-N 0.000 description 1
- 229940124325 anabolic agent Drugs 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
- 229960005471 androstenedione Drugs 0.000 description 1
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
- RSIHSRDYCUFFLA-DYKIIFRCSA-N boldenone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 RSIHSRDYCUFFLA-DYKIIFRCSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- RSIHSRDYCUFFLA-UHFFFAOYSA-N dehydrotestosterone Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)O)C4C3CCC2=C1 RSIHSRDYCUFFLA-UHFFFAOYSA-N 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 1
- 229960000445 ethisterone Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ZDHCJEIGTNNEMY-XGXHKTLJSA-N norethandrolone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(C)CC2 ZDHCJEIGTNNEMY-XGXHKTLJSA-N 0.000 description 1
- 229940053934 norethindrone Drugs 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux 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
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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 |
|---|---|---|---|
| CA154,525A CA976916A (en) | 1971-01-14 | 1972-10-18 | Container closure particularly for sealing bottles having a gas emitting content |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9453070A | 1970-12-02 | 1970-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH579592A5 true CH579592A5 (en) | 1976-09-15 |
Family
ID=22245740
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH56671A CH579592A5 (en) | 1970-12-02 | 1971-01-14 | 3-ketosteroid oximes anabolic androgenic - antifertility |
| CH390176A CH579594A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-02 | 1976-03-29 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH390176A CH579594A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-02 | 1976-03-29 |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH579592A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1971
- 1971-01-14 CH CH56671A patent/CH579592A5/de not_active IP Right Cessation
-
1976
- 1976-03-29 CH CH390176A patent/CH579594A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH579594A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |