BE553345A - - Google Patents
Info
- Publication number
- BE553345A BE553345A BE553345DA BE553345A BE 553345 A BE553345 A BE 553345A BE 553345D A BE553345D A BE 553345DA BE 553345 A BE553345 A BE 553345A
- Authority
- BE
- Belgium
- Prior art keywords
- lithium
- lithium carbonate
- couple
- hydroxy
- dibromo
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- AMXOYNBUYSYVKV-UHFFFAOYSA-M Lithium bromide Chemical group [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 24
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 21
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- AMRYDCQBDUCMCE-UHFFFAOYSA-K trilithium;bromide;carbonate Chemical compound [Li+].[Li+].[Li+].[Br-].[O-]C([O-])=O AMRYDCQBDUCMCE-UHFFFAOYSA-K 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 9
- -1 lithium halide Chemical class 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- YZZVVLUNOZJXCM-DADBAOPHSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-7,8,9,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O YZZVVLUNOZJXCM-DADBAOPHSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- IRGYNZPMSCRQNC-UHFFFAOYSA-L C([O-])(O)=O.[Li+].[Cl-].[Li+] Chemical compound C([O-])(O)=O.[Li+].[Cl-].[Li+] IRGYNZPMSCRQNC-UHFFFAOYSA-L 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M Lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims 2
- 230000001808 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 150000001993 dienes Chemical class 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241001342522 Vampyrum spectrum Species 0.000 description 5
- 125000000950 dibromo group Chemical group Br* 0.000 description 5
- JWMFYGXQPXQEEM-GCOKGBOCSA-N 5α-pregnane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-GCOKGBOCSA-N 0.000 description 4
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N Prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 238000005360 mashing Methods 0.000 description 3
- 150000003124 pregnadienes Chemical class 0.000 description 3
- 150000003128 pregnanes Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LKQVYBSBDWEBEM-VMXHOPILSA-N (8S,9S,10R,13S,14S)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LKQVYBSBDWEBEM-VMXHOPILSA-N 0.000 description 2
- AHRWWYGWQKBKBF-ZCFUGHDASA-N (8S,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O AHRWWYGWQKBKBF-ZCFUGHDASA-N 0.000 description 2
- 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
- XMRPGKVKISIQBV-BJMCWZGWSA-N 5α-Dihydroprogesterone Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 description 2
- QZLYKIGBANMMBK-DYKIIFRCSA-N 5β-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-DYKIIFRCSA-N 0.000 description 2
- GIRZGILISCUEPM-MWJYAYKCSA-N CC([C@H]1C(C=C2C3=CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O)=O Chemical class CC([C@H]1C(C=C2C3=CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O)=O GIRZGILISCUEPM-MWJYAYKCSA-N 0.000 description 2
- 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 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N Prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- YEXBXGXBJIUZBA-POMAFESVSA-N BrC1CC([C@@H]2CC[C@@H]3[C@H](CC[C@@]4(CCC[C@H]43)C)[C@]2(C1)C)Br Chemical compound BrC1CC([C@@H]2CC[C@@H]3[C@H](CC[C@@]4(CCC[C@H]43)C)[C@]2(C1)C)Br YEXBXGXBJIUZBA-POMAFESVSA-N 0.000 description 1
- NYGWTZLABYSHOP-FCYODTKKSA-N C([C@H]12)CC3CCCC[C@]3(C)[C@H]1CC[C@@]1(C)C2=CC=C1 Chemical compound C([C@H]12)CC3CCCC[C@]3(C)[C@H]1CC[C@@]1(C)C2=CC=C1 NYGWTZLABYSHOP-FCYODTKKSA-N 0.000 description 1
- 101710014056 CHT1 Proteins 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- 229940011871 Estrogens Drugs 0.000 description 1
- 229940030484 SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM ESTROGENS Drugs 0.000 description 1
- 101700028444 USO1 Proteins 0.000 description 1
- 101700061199 WNT1 Proteins 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940046080 endocrine therapy drugs Estrogens Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229960001067 hydrocortisone acetate Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002906 microbiologic Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 150000003126 pregnane derivatives Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE553345A true BE553345A (sv) |
Family
ID=178189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE553345D BE553345A (sv) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE553345A (sv) |
-
0
- BE BE553345D patent/BE553345A/fr unknown
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