BE552152A - - Google Patents
Info
- Publication number
- BE552152A BE552152A BE552152DA BE552152A BE 552152 A BE552152 A BE 552152A BE 552152D A BE552152D A BE 552152DA BE 552152 A BE552152 A BE 552152A
- Authority
- BE
- Belgium
- Prior art keywords
- solution
- chlorotestosterone
- acetate
- steroids
- desc
- Prior art date
Links
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- KCZCIYZKSLLNNH-FBPKJDBXSA-N Clostebol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1Cl KCZCIYZKSLLNNH-FBPKJDBXSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- 230000001195 anabolic Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000001548 androgenic Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
- WNUBDFJMQBMNQB-DXODLALXSA-N [(8R,9S,10R,13S,14S,17S)-4-chloro-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] propanoate Chemical compound C1CC2=C(Cl)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 WNUBDFJMQBMNQB-DXODLALXSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 238000002844 melting Methods 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LUKFSWINVWQMNF-DXODLALXSA-N 4-Fluoro-17β-hydroxyandrost-4-en-3-one propionate Chemical compound C1CC2=C(F)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 LUKFSWINVWQMNF-DXODLALXSA-N 0.000 description 3
- 210000003205 Muscles Anatomy 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229960001712 Testosterone Propionate Drugs 0.000 description 3
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- -1 3-keto-4alpha, 5-epoxy-17beta hydroxy-androstane Chemical compound 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 210000002307 Prostate Anatomy 0.000 description 2
- 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 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting Effects 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical compound [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- SOMOGWLYTLQJGT-XMUHMHRVSA-N 4-Chloro-17α-methyl-17β-hydroxy-4-androsten-3-one Chemical compound C1CC2=C(Cl)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 SOMOGWLYTLQJGT-XMUHMHRVSA-N 0.000 description 1
- BQOIJSIMMIDHMO-FBPKJDBXSA-N 4-Hydroxytestosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1O BQOIJSIMMIDHMO-FBPKJDBXSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical group OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
- RZRPTBIGEANTGU-IRIMSJTPSA-N Adrenosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RZRPTBIGEANTGU-IRIMSJTPSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- FJUROQQZIRAFCX-IMLUXURESA-N C(CC)(=O)O[C@H]1CC([C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)Cl Chemical compound C(CC)(=O)O[C@H]1CC([C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)Cl FJUROQQZIRAFCX-IMLUXURESA-N 0.000 description 1
- VFHKWFWPZSMISG-MQDSLDMISA-N C1(=CC=CC=C1)C(C(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C(C(=O)CC[C@]12C)Cl)C Chemical compound C1(=CC=CC=C1)C(C(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C(C(=O)CC[C@]12C)Cl)C VFHKWFWPZSMISG-MQDSLDMISA-N 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-M CC([O-])=NO Chemical compound CC([O-])=NO RRUDCFGSUDOHDG-UHFFFAOYSA-M 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N Formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 101700057165 GPR6 Proteins 0.000 description 1
- RVFNTORTIFQPJB-YIJWYKPTSA-N O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4Cl)O)[C@@H]4[C@@H]3CCC2=C1 Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4Cl)O)[C@@H]4[C@@H]3CCC2=C1 RVFNTORTIFQPJB-YIJWYKPTSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 240000004546 Persea americana var. americana Species 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 210000001625 Seminal Vesicles Anatomy 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229960003604 Testosterone Drugs 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N Thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- NXQOQNROJJFYCJ-FZFXZXLVSA-N androst-16-ene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 NXQOQNROJJFYCJ-FZFXZXLVSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 201000005617 ovarian disease Diseases 0.000 description 1
- 235000005426 persea americana Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001568 sexual Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 230000004936 stimulating Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE552152A true BE552152A (da) |
Family
ID=177437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE552152D BE552152A (da) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE552152A (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007131737A2 (en) * | 2006-05-12 | 2007-11-22 | Alexander Tobias Teichmann | Medication against breast cancer and related diseases |
-
0
- BE BE552152D patent/BE552152A/fr unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007131737A2 (en) * | 2006-05-12 | 2007-11-22 | Alexander Tobias Teichmann | Medication against breast cancer and related diseases |
| WO2007131736A3 (en) * | 2006-05-12 | 2008-03-06 | Alexander Tobias Teichmann | Use of 4, 17 beta-dihydroxyandrost-4-ene-3-one for treating cancers |
| WO2007131737A3 (en) * | 2006-05-12 | 2008-05-02 | Alexander Tobias Teichmann | Medication against breast cancer and related diseases |
| JP2009536932A (ja) * | 2006-05-12 | 2009-10-22 | トビアス タイヒマン アレクサンダー | 乳癌及び関連疾患に対する薬剤 |
| JP2009536931A (ja) * | 2006-05-12 | 2009-10-22 | トビアス タイヒマン アレクサンダー | ４，１７β−ジヒドロキシアンドロスト−４−エン−３−オンの新規な使用 |
| AU2007251822B2 (en) * | 2006-05-12 | 2012-08-16 | Curadis Gmbh | Use of 4, 17 beta-dihydroxyandrost-4-ene-3-one for treating cancers |
| CN101443016B (zh) * | 2006-05-12 | 2012-09-05 | 梅伯尔有限公司 | 4,17β-二羟基雄-4-烯-3-酮在制备治疗癌症的药物中的应用 |
| AU2007251823B2 (en) * | 2006-05-12 | 2012-09-06 | Curadis Gmbh | Medication against breast cancer and related diseases |
| US9114163B2 (en) | 2006-05-12 | 2015-08-25 | Mabel Gmbh | Medication against breast cancer and related diseases |
| US9138477B2 (en) | 2006-05-12 | 2015-09-22 | Mabel Gmbh | Uses for 4,17β-dihydroxyandrost-4-ene-3-one |
| US9610292B2 (en) | 2006-05-12 | 2017-04-04 | Mabel Gmbh | Uses for 4,17β-dihydroxyandrost-4-ene-3-one |
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