ES250249A1 - Un procedimiento para producir esteroides 9,11-dihalogenados de la sere de pregnano y del androstano - Google Patents
Un procedimiento para producir esteroides 9,11-dihalogenados de la sere de pregnano y del androstanoInfo
- Publication number
- ES250249A1 ES250249A1 ES0250249A ES250249A ES250249A1 ES 250249 A1 ES250249 A1 ES 250249A1 ES 0250249 A ES0250249 A ES 0250249A ES 250249 A ES250249 A ES 250249A ES 250249 A1 ES250249 A1 ES 250249A1
- Authority
- ES
- Spain
- Prior art keywords
- prepared
- dione
- methyl
- hydroxy
- reacting
- 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.)
- Expired
Links
- 150000003431 steroids Chemical class 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 238000000034 method Methods 0.000 abstract 9
- -1 nitrosyl halide Chemical class 0.000 abstract 9
- 150000002367 halogens Chemical group 0.000 abstract 7
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 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 abstract 5
- 239000007858 starting material Substances 0.000 abstract 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 4
- LPXQXCAQINZRGR-UHFFFAOYSA-N CC(C=C1)=CC=C1I.Cl.Cl Chemical compound CC(C=C1)=CC=C1I.Cl.Cl LPXQXCAQINZRGR-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 3
- 230000032050 esterification Effects 0.000 abstract 3
- 238000005886 esterification reaction Methods 0.000 abstract 3
- 230000026030 halogenation Effects 0.000 abstract 3
- 238000005658 halogenation reaction Methods 0.000 abstract 3
- 150000003128 pregnanes Chemical class 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 229960003387 progesterone Drugs 0.000 abstract 3
- 239000000186 progesterone Substances 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 241000025946 Chaetoceros simplex Species 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 abstract 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 230000033444 hydroxylation Effects 0.000 abstract 2
- 238000005805 hydroxylation reaction Methods 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 230000002906 microbiologic effect Effects 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 2
- 235000009518 sodium iodide Nutrition 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- SMIDAKVWLSXXKQ-GOMVOUAHSA-N (5S,6R,8R,9S,10R,13S,14S,17R)-17-acetyl-17-bromo-5-hydroxy-6,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O[C@]12[C@@H](C[C@H]3[C@@H]4CC[C@](C(C)=O)([C@]4(CC[C@@H]3[C@]2(CCC(C1)=O)C)C)Br)C SMIDAKVWLSXXKQ-GOMVOUAHSA-N 0.000 abstract 1
- YJDYCULVYZDESB-HKQXQEGQSA-N (5r,8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 YJDYCULVYZDESB-HKQXQEGQSA-N 0.000 abstract 1
- QUKZBUCPOSYYFO-FPRQENGNSA-N (5r,8r,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-17-ol Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CC[C@H]21 QUKZBUCPOSYYFO-FPRQENGNSA-N 0.000 abstract 1
- SMBOUCWJBJUHDR-CTVGIFIDSA-N (6S,8S,10R,13S,14S,17R)-17-(2-fluoroacetyl)-17-hydroxy-6,10,13-trimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound C[C@H]1C[C@H]2[C@@H]3CC[C@](C(CF)=O)([C@]3(CC=C2[C@]2(CCC(C=C12)=O)C)C)O SMBOUCWJBJUHDR-CTVGIFIDSA-N 0.000 abstract 1
- OTSPHSRSIAIVOY-JRMUFCLDSA-N (6s,8s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1C2=CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 OTSPHSRSIAIVOY-JRMUFCLDSA-N 0.000 abstract 1
- LTLZKGMWZNNLBR-CTVGIFIDSA-N (6s,8s,10r,13s,14s,17r)-17-hydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1C2=CC[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 LTLZKGMWZNNLBR-CTVGIFIDSA-N 0.000 abstract 1
- PGWDPYGLSQZOMQ-NMKBPFOZSA-N (8s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,12,14,15,16,17-octahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1C=C[C@]2(C)C3=CC[C@]4(C)[C@@H](CC)CC[C@H]4[C@@H]3CCC2=C1 PGWDPYGLSQZOMQ-NMKBPFOZSA-N 0.000 abstract 1
- KTDNJCHWPZHOFC-XFNFOBRPSA-N (8s,9s,10s,13r,14s,17r)-17-(2-fluoroethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CCF)[C@@H]4[C@@H]3CCC21 KTDNJCHWPZHOFC-XFNFOBRPSA-N 0.000 abstract 1
- POYNBBXYPFXQRC-XFNFOBRPSA-N (8s,9s,10s,13r,14s,17r)-17-(2-iodoethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CCI)[C@@H]4[C@@H]3CCC21 POYNBBXYPFXQRC-XFNFOBRPSA-N 0.000 abstract 1
- AUWGBTUZQWKWRS-WISGCMSASA-N 1-[(3S,8S,9S,10R,13S,14S,16R,17S)-16-ethyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]([C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)CC AUWGBTUZQWKWRS-WISGCMSASA-N 0.000 abstract 1
- RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 abstract 1
- YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 abstract 1
- TZJKBFRUMZLUME-UHFFFAOYSA-N 2,2-dibromo-1,4-dioxane Chemical compound BrC1(Br)COCCO1 TZJKBFRUMZLUME-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 241000134727 Agromyces mediolanus Species 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 abstract 1
- 241000223211 Curvularia lunata Species 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 1
- CRRKVZVYZQXICQ-RJJCNJEVSA-N Pregnenolone acetate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H](C(C)=O)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 CRRKVZVYZQXICQ-RJJCNJEVSA-N 0.000 abstract 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Natural products 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 abstract 1
- 241000235546 Rhizopus stolonifer Species 0.000 abstract 1
- DQHKOPGHSPUDFM-ABVATSDPSA-N [(3S,8R,9S,10R,13S,14S)-17-(1-acetyloxyethylidene)-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC(=C(C)OC(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C DQHKOPGHSPUDFM-ABVATSDPSA-N 0.000 abstract 1
- LGMLPGOANOZALY-KIYFCUGLSA-N [(3S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-chloro-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@](C(C)=O)([C@]4(CC[C@@H]3[C@]2(CC1)C)C)Cl LGMLPGOANOZALY-KIYFCUGLSA-N 0.000 abstract 1
- PYBGGSNABBXWHO-QJCZYOOHSA-N [(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-5,6-dichloro-10,13,16-trimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2(C(C[C@H]3[C@@H]4C[C@H]([C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)C)Cl)Cl PYBGGSNABBXWHO-QJCZYOOHSA-N 0.000 abstract 1
- SFNSGHUMGYWJGF-AWGTVLFOSA-N [(3s,8s,9s,10r,13s,14s,16r,17s)-17-acetyl-10,13,16-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1C=C2C[C@@H](OC(C)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(C)=O)[C@@]1(C)CC2 SFNSGHUMGYWJGF-AWGTVLFOSA-N 0.000 abstract 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 230000000382 dechlorinating effect Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 239000012025 fluorinating agent Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- XRURPHMPXJDCOO-UHFFFAOYSA-N iodine heptafluoride Chemical compound FI(F)(F)(F)(F)(F)F XRURPHMPXJDCOO-UHFFFAOYSA-N 0.000 abstract 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 abstract 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US743492A US2894963A (en) | 1958-06-20 | 1958-06-20 | 9,11-dihalogeno-4-pregnenes and 1,4-pregnadienes |
| CA775651 | 1959-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES250249A1 true ES250249A1 (es) | 1960-01-16 |
Family
ID=25673299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0250249A Expired ES250249A1 (es) | 1958-06-20 | 1959-06-19 | Un procedimiento para producir esteroides 9,11-dihalogenados de la sere de pregnano y del androstano |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE579900A (fi) |
| CH (1) | CH386415A (fi) |
| DK (1) | DK118874B (fi) |
| ES (1) | ES250249A1 (fi) |
| FR (1) | FR564M (fi) |
| GB (2) | GB928301A (fi) |
| NL (1) | NL106036C (fi) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397213A (en) * | 1966-01-12 | 1968-08-13 | Squibb & Sons Inc | 12 methyl-9, 11-dihaloprogesterones |
| FR2342738A1 (fr) * | 1976-03-02 | 1977-09-30 | Roussel Uclaf | Nouveaux derives halogenes de la serie du 16a-methyl pregnane |
| EP3656385A1 (en) | 2008-05-28 | 2020-05-27 | ReveraGen BioPharma, Inc. | Non-hormonal steroid modulators of nf-kb for treatment of disease |
| WO2011127048A2 (en) | 2010-04-05 | 2011-10-13 | Validus Biopharma | NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
-
1959
- 1959-06-11 GB GB20033/59A patent/GB928301A/en not_active Expired
- 1959-06-11 GB GB43100/61A patent/GB928302A/en not_active Expired
- 1959-06-18 CH CH7465759A patent/CH386415A/fr unknown
- 1959-06-18 NL NL240357A patent/NL106036C/xx active
- 1959-06-19 ES ES0250249A patent/ES250249A1/es not_active Expired
- 1959-06-19 DK DK220659AA patent/DK118874B/da unknown
- 1959-06-20 BE BE579900A patent/BE579900A/fr unknown
-
1960
- 1960-08-30 FR FR837195A patent/FR564M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DK118874B (da) | 1970-10-19 |
| NL106036C (fi) | 1963-09-16 |
| BE579900A (fr) | 1959-10-16 |
| CH386415A (fr) | 1965-01-15 |
| FR564M (fi) | 1961-06-05 |
| GB928302A (en) | 1963-06-12 |
| GB928301A (en) | 1963-06-12 |
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