BE552150A - - Google Patents

Info

Publication number

BE552150A

BE552150A BE552150DA BE552150A BE 552150 A BE552150 A BE 552150A BE 552150D A BE552150D A BE 552150DA BE 552150 A BE552150 A BE 552150A

Authority

BE

Belgium

Prior art keywords

5alpha

4beta

hydroxy

allopregnano

chloro

Prior art date

Links

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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 6
• 150000001875 compounds Chemical class 0.000 claims description 6
• 239000003960 organic solvent Substances 0.000 claims description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
• 239000011707 mineral Substances 0.000 claims description 4
• 239000003270 steroid hormone Substances 0.000 claims description 3
• 150000003431 steroids Chemical group 0.000 claims description 3
• 230000015572 biosynthetic process Effects 0.000 claims description 2
• 230000000144 pharmacologic effect Effects 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 238000003786 synthesis reaction Methods 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 3
• VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims 1
• 239000012433 hydrogen halide Substances 0.000 claims 1
• 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
• 239000000543 intermediate Substances 0.000 claims 1
• 238000002844 melting Methods 0.000 description 18
• 230000008018 melting Effects 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 150000002009 diols Chemical class 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• 239000004593 Epoxy Substances 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• HAAYBYDROVFKPU-UHFFFAOYSA-N silver;azane;nitrate Chemical compound N.N.[Ag+].[O-][N+]([O-])=O HAAYBYDROVFKPU-UHFFFAOYSA-N 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1