BE552153A - - Google Patents

Info

Publication number

BE552153A

BE552153A BE552153DA BE552153A BE 552153 A BE552153 A BE 552153A BE 552153D A BE552153D A BE 552153DA BE 552153 A BE552153 A BE 552153A

Authority

BE

Belgium

Prior art keywords

acetate

chloro

activity

17alpha

epoxy

Prior art date

Links

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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
• 230000001195 anabolic effect Effects 0.000 claims description 6
• 238000000034 method Methods 0.000 claims description 5
• 150000001875 compounds Chemical class 0.000 claims description 4
• 235000019441 ethanol Nutrition 0.000 claims description 4
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
• 230000001548 androgenic effect Effects 0.000 claims description 3
• 239000002253 acid Substances 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
• 238000002360 preparation method Methods 0.000 claims description 2
• 150000003431 steroids Chemical class 0.000 claims 2
• 125000002252 acyl group Chemical group 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 239000000203 mixture Substances 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 229960004719 nandrolone Drugs 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• MRKZAZMYXYSBDG-UHFFFAOYSA-N cyclopentyl propanoate Chemical compound CCC(=O)OC1CCCC1 MRKZAZMYXYSBDG-UHFFFAOYSA-N 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000004593 Epoxy Substances 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
• REWKEGSQGOSEES-FNKXXKKYSA-N 17beta-Hydroxyestr-4-en-3-one cyclopentanepropionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@H]4CCC(=O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 REWKEGSQGOSEES-FNKXXKKYSA-N 0.000 description 2
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 210000003205 muscle Anatomy 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
• 239000003208 petroleum Substances 0.000 description 2
• 125000002599 19-nortestosterone group Chemical group 0.000 description 1
• -1 4-chloro- cyclopentylpropionate Chemical compound 0.000 description 1
• 208000034657 Convalescence Diseases 0.000 description 1
• 241000065675 Cyclops Species 0.000 description 1
• 206010053759 Growth retardation Diseases 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• ZXSWTMLNIIZPET-ZOFHRBRSSA-N Normethandrolone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 ZXSWTMLNIIZPET-ZOFHRBRSSA-N 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• 208000037063 Thinness Diseases 0.000 description 1
• FNMAFGQVNCRKGS-JZQWUOKRSA-N [(8r,9s,10r,13s,14s,17s)-4-chloro-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=C(Cl)C(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 FNMAFGQVNCRKGS-JZQWUOKRSA-N 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
• UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 150000002118 epoxides Chemical class 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 231100000001 growth retardation Toxicity 0.000 description 1
• 231100000518 lethal Toxicity 0.000 description 1
• 230000001665 lethal effect Effects 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 210000001625 seminal vesicle Anatomy 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 235000011149 sulphuric acid Nutrition 0.000 description 1
• 201000010653 vesiculitis Diseases 0.000 description 1
• 238000005406 washing Methods 0.000 description 1