IL42423A - O-(nitroaryl) oximes of 3-keto-androstanes their preparation and pharmaceutical compositions containing them - Google Patents
O-(nitroaryl) oximes of 3-keto-androstanes their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL42423A IL42423A IL42423A IL4242373A IL42423A IL 42423 A IL42423 A IL 42423A IL 42423 A IL42423 A IL 42423A IL 4242373 A IL4242373 A IL 4242373A IL 42423 A IL42423 A IL 42423A
- Authority
- IL
- Israel
- Prior art keywords
- acetoxy
- nitrophenoxy
- imino
- hydroxy
- nitrophenyl
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- VMNRNUNYBVFVQI-QYXZOKGRSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical class C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 11
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000001548 androgenic effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000001195 anabolic effect Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- -1 2-hydroxy- 5-nitrophenyl group Chemical group 0.000 claims 2
- NOLDGUAIRGYBAB-SVMUCYCZSA-N [(5R,8R,9S,10S,13R,14S)-10-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-13-yl]methanimine Chemical compound N=C[C@@]12CCC[C@H]1[C@@H]1CC[C@H]3CCCC[C@]3(C)[C@H]1CC2 NOLDGUAIRGYBAB-SVMUCYCZSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- MELMLGVHHOWYAX-ZFSNVMTLSA-N C[C@](CCCC1)([C@H]1CC1)[C@@H](CC2)[C@@H]1[C@H](CC1)[C@@]2(C=N)C1=O Chemical compound C[C@](CCCC1)([C@H]1CC1)[C@@H](CC2)[C@@H]1[C@H](CC1)[C@@]2(C=N)C1=O MELMLGVHHOWYAX-ZFSNVMTLSA-N 0.000 claims 1
- RJRHPWQKBQBCAD-OFELHODLSA-N [(5r,8r,9s,10s,13r,14s)-10-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-13-yl]methyl acetate Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(COC(=O)C)CC1 RJRHPWQKBQBCAD-OFELHODLSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 150000001502 aryl halides Chemical class 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 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
- 241001465754 Metazoa Species 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
- 241000700159 Rattus Species 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229960001566 methyltestosterone Drugs 0.000 description 5
- 210000002307 prostate Anatomy 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001113 coital effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US259092A US3862193A (en) | 1970-12-02 | 1972-06-02 | O-(nitroaryl) oximes of 3-keto steroids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42423A0 IL42423A0 (en) | 1973-08-29 |
| IL42423A true IL42423A (en) | 1977-02-28 |
Family
ID=22983493
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42423A IL42423A (en) | 1972-06-02 | 1973-06-01 | O-(nitroaryl) oximes of 3-keto-androstanes their preparation and pharmaceutical compositions containing them |
| IL50345A IL50345A (en) | 1972-06-02 | 1973-06-01 | 2alpha-chloro-5alpha-androstan-17beta-ol-3-one and its preparation |
| IL50345A IL50345A0 (en) | 1972-06-02 | 1976-08-24 | A novel androstane and its preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL50345A IL50345A (en) | 1972-06-02 | 1973-06-01 | 2alpha-chloro-5alpha-androstan-17beta-ol-3-one and its preparation |
| IL50345A IL50345A0 (en) | 1972-06-02 | 1976-08-24 | A novel androstane and its preparation |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE800405R (enrdf_load_stackoverflow) |
| CA (1) | CA998041A (enrdf_load_stackoverflow) |
| CH (1) | CH593303A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2327509A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2186263B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1429951A (enrdf_load_stackoverflow) |
| IL (3) | IL42423A (enrdf_load_stackoverflow) |
| NL (1) | NL7307703A (enrdf_load_stackoverflow) |
| ZA (1) | ZA733706B (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3211756A (en) * | 1963-07-23 | 1965-10-12 | Searle & Co | 3-hydroxyimino-17alpha-(lower alkyl)-5alpha-androstan-17beta-ols and the optionally substituted 3-acyloxyimino and 3-alkoxyimino derivatives corresponding |
| US3686237A (en) * | 1969-12-04 | 1972-08-22 | Ortho Pharma Corp | O-(nitroaryl)oximes of 3-keto steroids |
-
1973
- 1973-05-23 CA CA171,985A patent/CA998041A/en not_active Expired
- 1973-05-30 DE DE2327509A patent/DE2327509A1/de not_active Withdrawn
- 1973-05-30 FR FR7319809A patent/FR2186263B2/fr not_active Expired
- 1973-05-30 ZA ZA00733706A patent/ZA733706B/xx unknown
- 1973-06-01 NL NL7307703A patent/NL7307703A/xx not_active Application Discontinuation
- 1973-06-01 BE BE131839A patent/BE800405R/xx active
- 1973-06-01 IL IL42423A patent/IL42423A/en unknown
- 1973-06-01 GB GB2634873A patent/GB1429951A/en not_active Expired
- 1973-06-01 CH CH796273A patent/CH593303A5/xx not_active IP Right Cessation
- 1973-06-01 IL IL50345A patent/IL50345A/en unknown
-
1976
- 1976-08-24 IL IL50345A patent/IL50345A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH593303A5 (enrdf_load_stackoverflow) | 1977-11-30 |
| IL50345A0 (en) | 1976-10-31 |
| DE2327509A1 (de) | 1973-12-13 |
| GB1429951A (en) | 1976-03-31 |
| FR2186263A2 (enrdf_load_stackoverflow) | 1974-01-11 |
| ZA733706B (en) | 1975-01-29 |
| IL42423A0 (en) | 1973-08-29 |
| IL50345A (en) | 1977-02-28 |
| AU5642873A (en) | 1974-12-05 |
| BE800405R (fr) | 1973-12-03 |
| FR2186263B2 (enrdf_load_stackoverflow) | 1976-08-13 |
| CA998041A (en) | 1976-10-05 |
| NL7307703A (enrdf_load_stackoverflow) | 1973-12-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU682195B2 (en) | New 11-benzaldoxime-estradiene-derivatives, methods for their production and pharmaceuticals containing these substances | |
| US3492321A (en) | Cyclopropenyl estra, -1,3,5(10)-trienes | |
| EP1599493B1 (de) | Antitumor wirksame 2-substituierte estra-1,3,5(10)-trien-3-yl sulfamate | |
| US3200114A (en) | 17-tetrahydropyranyl ethers of (3, 2-c)-pyrazole and (2, 3-d)-isoxazole derivatives o the androstane and 19-norandrostane series | |
| DE69407057T2 (de) | 1,3.5 (10) - estratriene derivate mit oraler wirkung | |
| US3770780A (en) | O-(nitroaryl)oximes of 3-keto steroids | |
| RU2091019C1 (ru) | Контрацептивное средство для животных и способ его получения | |
| IL42423A (en) | O-(nitroaryl) oximes of 3-keto-androstanes their preparation and pharmaceutical compositions containing them | |
| JPS6355488B2 (enrdf_load_stackoverflow) | ||
| US3686237A (en) | O-(nitroaryl)oximes of 3-keto steroids | |
| US3862193A (en) | O-(nitroaryl) oximes of 3-keto steroids | |
| IL44903A (en) | 17beta-hydroxy-16,16-dimethylestr-4-en-3-one its preparation and pharmaceutical compositions containing it | |
| GB2025422A (en) | 17-acetylene derivatives of androst-4-ene | |
| US3167547A (en) | 17-tetrahydropyranyl ethers of 19-nor, 3-keto androstanes | |
| US20030100544A1 (en) | Antitumor wirksame 2-alkoxyestradiolsulfamate | |
| KR20100037593A (ko) | 선택적으로 활성인 에스트로겐으로서의 8-베타-치환된 에스트라트리엔 | |
| AU2002210470B2 (en) | 4-halogenated 17-methylene steroids, method for the production thereof and pharmaceutical compositions containing these compounds | |
| JP3754466B2 (ja) | ジエノゲストを有効成分とするホルモン療法用制癌剤 | |
| US3816406A (en) | O-aryl oximes of 3-keto steroids | |
| US3225072A (en) | Carbalkoxyhydrazones of the androstane series | |
| US5866559A (en) | 17α-cyanomethylestra-4,9-dien derivatives and pharmaceutical compositions containing same | |
| US3840568A (en) | Estratriene derivatives | |
| US3370071A (en) | 3-keto-13beta-alkyl-17beta-acetyl-gona-4, 9-dienes and process | |
| US3574690A (en) | Delta 4,9,11-gonatriene-3-ones | |
| KR790001897B1 (ko) | 17β-히드록시-16,16-디메틸에스트르-4-엔-3-온의 제조방법 |