DEL0018685MA - - Google Patents

Info

Publication number: DEL0018685MA
Authority: DE; Germany
Prior art keywords: alcohol; bromination; water; bromine; moles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

Other languages

German (de)

English (en)

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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 26
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 21
238000005893 bromination reaction Methods 0.000 claims description 19
230000031709 bromination Effects 0.000 claims description 18
238000007254 oxidation reaction Methods 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
230000003647 oxidation Effects 0.000 claims description 16
230000008569 process Effects 0.000 claims description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
235000019445 benzyl alcohol Nutrition 0.000 claims description 7
229950001336 bromamide Drugs 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims 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 claims description 2
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-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-NUNROCCHSA-N 0.000 claims 1
JWMFYGXQPXQEEM-IVSMBDLYSA-N [2H]C1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CCC2C1)CC[C@@H]4C([2H])C)C)C Chemical compound [2H]C1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CCC2C1)CC[C@@H]4C([2H])C)C)C JWMFYGXQPXQEEM-IVSMBDLYSA-N 0.000 claims 1
FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 22
229910052794 bromium Inorganic materials 0.000 description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 18
239000000047 product Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 11
229910000042 hydrogen bromide Inorganic materials 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000011630 iodine Substances 0.000 description 6
125000000468 ketone group Chemical group 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229930194542 Keto Natural products 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000008107 starch Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
-1 Keto steroids Chemical group 0.000 description 4
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 3
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 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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 3
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
229960004544 cortisone Drugs 0.000 description 3
125000000950 dibromo group Chemical group Br* 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
229940011871 estrogen Drugs 0.000 description 3
239000000262 estrogen Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
OXBIPVXLRIVPOH-VUNLOTMMSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-4-bromo-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2C(Br)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OXBIPVXLRIVPOH-VUNLOTMMSA-N 0.000 description 2
PBQJFYWCFSNZAL-UHFFFAOYSA-N 1-bromoimidazolidine-2,4-dione Chemical compound BrN1CC(=O)NC1=O PBQJFYWCFSNZAL-UHFFFAOYSA-N 0.000 description 2
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 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
125000000217 alkyl group Chemical group 0.000 description 2
239000003098 androgen Substances 0.000 description 2
229940030486 androgens Drugs 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
229960003290 cortisone acetate Drugs 0.000 description 2
230000029087 digestion Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229960003399 estrone Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229960003387 progesterone Drugs 0.000 description 2
239000000186 progesterone Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
VPJQKYVRISQHDC-FRZRYRDQSA-N (5R,8R,9S,10R,13S,14S)-2,4-dibromo-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione Chemical compound BrC1C(C([C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(C1)C)Br)=O VPJQKYVRISQHDC-FRZRYRDQSA-N 0.000 description 1
ZIJIAIPOTIQLNT-LBMGVPKBSA-N (5R,8S,9S,10R,13S,14S)-2,4-dibromo-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical class BrC1C(C([C@@H]2CC[C@@H]3[C@H](CC[C@@]4(CCC[C@H]43)C)[C@]2(C1)C)Br)=O ZIJIAIPOTIQLNT-LBMGVPKBSA-N 0.000 description 1
DJTOLSNIKJIDFF-LEAFODBOSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol 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 DJTOLSNIKJIDFF-LEAFODBOSA-N 0.000 description 1
VPJQKYVRISQHDC-KOKUEQTASA-N (8R,9S,10R,13S,14S)-2,4-dibromo-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione Chemical compound BrC1C(C(C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(C1)C)=O)Br)=O VPJQKYVRISQHDC-KOKUEQTASA-N 0.000 description 1
XZHKZJXZRWFLCJ-RKFIYKRSSA-N (8R,9S,10S,13R,14S,17R)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,17-dodecahydro-1H-cyclopenta[a]phenanthrene-15,16-dione Chemical compound [C@@H]12C(C([C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C)=O)=O XZHKZJXZRWFLCJ-RKFIYKRSSA-N 0.000 description 1
KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 description 1
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
XMRPGKVKISIQBV-CVHNGYJVSA-N 5-α-pregnan-3,20-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 XMRPGKVKISIQBV-CVHNGYJVSA-N 0.000 description 1
CBMYJHIOYJEBSB-YSZCXEEOSA-N 5alpha-androstane-3beta,17beta-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 CBMYJHIOYJEBSB-YSZCXEEOSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
101100005631 Mus musculus Ccni gene Proteins 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
210000004404 adrenal cortex Anatomy 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001441 androstanes Chemical class 0.000 description 1
229960003473 androstanolone Drugs 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000003613 bile acid Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
229960003964 deoxycholic acid Drugs 0.000 description 1
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
229940119740 deoxycorticosterone Drugs 0.000 description 1
CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960005309 estradiol Drugs 0.000 description 1
229930182833 estradiol Natural products 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000003337 fertilizer Substances 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
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
MZMRZONIDDFOGF-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCCC[N+](C)(C)C MZMRZONIDDFOGF-UHFFFAOYSA-M 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000003198 secondary alcohol group Chemical group 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Publication	Publication Date	Title
US2768189A (en)	1956-10-23	Method of producing alpha-brominated keto steroid compounds
DE1468035A1 (de)	1968-12-12	Verfahren zur Herstellung von 19-Alkylsteroiden
DE963875C (de)	1957-05-16	Verfahren zur Herstellung von ª‡-Brom-3-ketosteroiden
DE1468410A1 (de)	1969-11-20	Verfahren zur Herstellung von 16-Methylensteroiden
DEL0018685MA (fr)
DE3338212C2 (de)	1995-05-18	1-Methyl-androsta-1,4,6-trien-3,17-dione, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
US2684376A (en)	1954-07-20	Process for the simultaneous oxidation and halogenation of steroids and compounds obtained thereby
DE1618871C3 (de)	1974-02-21	Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988
DE2046640C3 (de)	1973-10-18	Verfahren zur Herstellung von Delta hoch 4 -3-Oxo-l alpha-methyl·Steroiden
CH494213A (de)	1970-07-31	Verfahren zur Herstellung von Gonadienonen
DE1643028C3 (de)	1975-01-09	Neue 1,2 alpha -Methylensteroide, Verfahren zu ihrer Herstellung, sowie diese enthaltende Mittel
DE1593052B2 (de)	1974-08-15	Verfahren zur Herstellung von 16-Methylen-19-norprogesteron-derivaten
AT233175B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>- und 3-Oxo-Δ<1,4,6>-steroiden
DE1468604B1 (de)	1970-07-02	Verfahren zur Herstellung von 17alpha-Alkyl-,-Alkenyl- oder -Alkinyl-13beta-alkylgon-4-oder-5(10)-en-17beta-ol-3-onen
AT269378B (de)	1969-03-10	Verfahren zur Herstellung von neuen 6-Hydroxy- oder -Acyloxymethyl-3-oxo-4,6-dien-steroiden
AT228410B (de)	1963-07-10	Verfahren zur Herstellung neuer 6-Methyl-3-oxo-4, 6-dien-steroide
DE1468423A1 (de)	1969-01-09	Verfahren zur Herstellung von 7-Alkyl-19-norsteroiden
DE1792310A1 (de)	1971-12-16	Oxydationsmittel und Oxydationsverfahren
DE1468227C (de)	1972-11-02	Verfahren zur Herstellung von Delta hoch 4 - bzw. Delta hoch 5 -ungesättigten Steroiden der Androstan-, Pregnan- und Sapogeninreihe mit einer freien oder veresterten Hydroxygruppe in 19-Stellung
CH495965A (de)	1970-09-15	Verfahren zur Herstellung von Steroiden der Östranreihe
DE1236501B (de)	1967-03-16	Verfahren zur Herstellung von 10alpha- und 9beta, 10alpha-Steroiden der Androstan- bzw. Pregnanreihe
DE1215147B (de)	1966-04-28	Verfahren zur Herstellung von 19-Norsteroiden der Androstanreihe
DE1493108C (de)	1972-08-10	Steroidverbindungen
DE2211817C3 (de)	1976-12-02	Verfahren zur Herstellung von Dinorcholestan-Derivaten und dazu eingesetzte Verbindungen
DE1241825B (de)	1975-10-16	Ver fahren zur Herstellung von 6 Chlor 4 6diLirverbindungen der Pregnan-, Androstan oder Cholestanreihe

DEL0018685MA - - Google Patents

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