CH626379A5 - - Google Patents
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- Publication number
- CH626379A5 CH626379A5 CH910976A CH910976A CH626379A5 CH 626379 A5 CH626379 A5 CH 626379A5 CH 910976 A CH910976 A CH 910976A CH 910976 A CH910976 A CH 910976A CH 626379 A5 CH626379 A5 CH 626379A5
- Authority
- CH
- Switzerland
- Prior art keywords
- derivative
- formula
- double bond
- defined above
- halogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- -1 alkanesulfonyl halide Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 2
- 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 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- WLOIWTCOFHCSCL-SXYSDOLCSA-N (8S,9S,10R,13R,14S)-3-ethoxy-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1C[C@@H]2[C@](CCC(OCC)=C3)(C)C3=CC[C@H]2[C@@H]2CC=C[C@]21C WLOIWTCOFHCSCL-SXYSDOLCSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 4
- 229960001566 methyltestosterone Drugs 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 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 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002280 anti-androgenic effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HJSRLNOJUZKKRW-YRJWVXGYSA-N (8S,9S,10R,13R,14S)-6-chloro-3-ethoxy-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1C[C@@H]2[C@](CCC(OCC)=C3)(C)C3=C(Cl)C[C@H]2[C@@H]2CC=C[C@]21C HJSRLNOJUZKKRW-YRJWVXGYSA-N 0.000 description 2
- FBDVOEZFUNNGND-CXQPBAHBSA-N (8S,9S,10R,13S,14S)-10,13,16-trimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@]4(C)C=C(C)C[C@H]4[C@@H]3CCC2=C1 FBDVOEZFUNNGND-CXQPBAHBSA-N 0.000 description 2
- HNDHDMOSWUAEAW-UHFFFAOYSA-N (8alpha,9beta,10alpha,13alpha,14beta)-Androsta-4,6-dien-3-one Natural products O=C1CCC2(C)C3CCC(C)(C=CC4)C4C3CCC2=C1 HNDHDMOSWUAEAW-UHFFFAOYSA-N 0.000 description 2
- VSVZWJKDKUJVBS-VMXHOPILSA-N (8s,9s,10r,13r,14s)-10,13-dimethyl-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3C=CC2=C1 VSVZWJKDKUJVBS-VMXHOPILSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- HNDHDMOSWUAEAW-VMXHOPILSA-N androstadienone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC2=C1 HNDHDMOSWUAEAW-VMXHOPILSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- DRNHYGPENBSWNC-KEPBYGSZSA-N (6S,8S,9S,10R,13R,14S)-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C[C@H]1C[C@H]2[C@@H]3CC=C[C@@]3(C)CC[C@@H]2[C@]2(CCC(C=C12)=O)C DRNHYGPENBSWNC-KEPBYGSZSA-N 0.000 description 1
- MIQXIGLLXUPVNF-XNPNQNQESA-N (6S,8S,9S,10R,13R,14S)-6-bromo-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound Br[C@H]1C[C@H]2[C@@H]3CC=C[C@@]3(C)CC[C@@H]2[C@]2(CCC(C=C12)=O)C MIQXIGLLXUPVNF-XNPNQNQESA-N 0.000 description 1
- LRDIHAYEPKUHKE-ZHAUUAPESA-N (6S,8S,9S,10R,13S,14S)-6-chloro-10,13,16-trimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound Cl[C@H]1C[C@H]2[C@@H]3CC(=C[C@@]3(C)CC[C@@H]2[C@]2(CCC(C=C12)=O)C)C LRDIHAYEPKUHKE-ZHAUUAPESA-N 0.000 description 1
- CFOFPRNYBQSOAT-VMXHOPILSA-N (8S,9S,10R,13R,14S)-10,13-dimethyl-8,9,11,12,14,15-hexahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3C=CC2=C1 CFOFPRNYBQSOAT-VMXHOPILSA-N 0.000 description 1
- PLOPWAVSHLCAKI-CTWRKMMKSA-N (8S,9S,10R,13S,14S)-10,13-dimethyl-16-propan-2-yl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@]4(C)C=C(C(C)C)C[C@H]4[C@@H]3CCC2=C1 PLOPWAVSHLCAKI-CTWRKMMKSA-N 0.000 description 1
- RHIAYXPWNAXIJV-IFLJBQAJSA-N (8S,9S,10R,13S,14S)-16-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@]4(C)C=C(CC)C[C@H]4[C@@H]3CCC2=C1 RHIAYXPWNAXIJV-IFLJBQAJSA-N 0.000 description 1
- NGYDAURHEQWDMO-VMXHOPILSA-N (8s,9s,10r,13r,14s)-10,13-dimethyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC2=C1 NGYDAURHEQWDMO-VMXHOPILSA-N 0.000 description 1
- QRHBXQAFGLVWFW-BEQVDIJNSA-N 17beta-Hydroxy-6beta-methylandrost-4-en-3-one Chemical compound C([C@@]12C)CC(=O)C=C1[C@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@H]21 QRHBXQAFGLVWFW-BEQVDIJNSA-N 0.000 description 1
- HZWZHWTZLZZBFF-UQYBFTDGSA-N 17beta-Hydroxy-7alpha-methylandrost-4-en-3-one Chemical compound C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2[C@H](C)CC3=CC(=O)CC[C@]3(C)[C@H]21 HZWZHWTZLZZBFF-UQYBFTDGSA-N 0.000 description 1
- QNDGAROPZNKYNK-UHFFFAOYSA-N 4,5-dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=C(Cl)C(Cl)=C(O)C(C#N)=C1C#N QNDGAROPZNKYNK-UHFFFAOYSA-N 0.000 description 1
- UMDCOKNNLDEKJB-DYKIIFRCSA-N 6-dehydrotestosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3C=CC2=C1 UMDCOKNNLDEKJB-DYKIIFRCSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000203720 Pimelobacter simplex Species 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testosterone Natural products 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 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical class 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
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/005—3 membered carbocyclic rings in position 12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/007—3 membered carbocyclic rings in position 6-7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29898/75A GB1550343A (en) | 1975-07-16 | 1975-07-16 | Androstane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626379A5 true CH626379A5 (fi) | 1981-11-13 |
Family
ID=10298992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH910976A CH626379A5 (fi) | 1975-07-16 | 1976-07-15 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4075233A (fi) |
| JP (1) | JPS5212159A (fi) |
| AT (1) | AT362085B (fi) |
| AU (1) | AU506101B2 (fi) |
| BE (1) | BE844169A (fi) |
| CH (1) | CH626379A5 (fi) |
| DE (1) | DE2631915A1 (fi) |
| DK (1) | DK142877B (fi) |
| FI (1) | FI55851C (fi) |
| FR (1) | FR2317934A1 (fi) |
| GB (1) | GB1550343A (fi) |
| HU (1) | HU175369B (fi) |
| IE (1) | IE43693B1 (fi) |
| IT (1) | IT1063150B (fi) |
| LU (1) | LU75394A1 (fi) |
| NL (1) | NL7607824A (fi) |
| NO (1) | NO146865C (fi) |
| NZ (1) | NZ181482A (fi) |
| SE (1) | SE7608092L (fi) |
| ZA (1) | ZA764195B (fi) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1566905A (en) * | 1977-03-28 | 1980-05-08 | Gist Brocades Nv | Steroids of the a-nor-androstane and a-nor-estrane series |
| DE3115995A1 (de) * | 1981-04-13 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | D-homo-4,17-androstadien-3-on, verfahren zu seiner herstellung und diese verbindung enthaltende pharmazeutische praeparate |
| JPS58185406A (ja) * | 1982-04-20 | 1983-10-29 | Mitsubishi Gas Chem Co Inc | 過硼酸塩の製造方法 |
| ES8706717A1 (es) * | 1983-08-02 | 1987-07-01 | Research Corp | Metodo de preparar esteroides |
| DE3514272A1 (de) * | 1985-04-17 | 1986-10-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dermatica |
| US5175154A (en) * | 1987-11-25 | 1992-12-29 | Research Corporation Technologies, Inc. | 5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds |
| US4898694A (en) * | 1987-11-25 | 1990-02-06 | Schwartz Arthur G | 17-Hydroxy-steroids |
| US5001119A (en) * | 1987-11-25 | 1991-03-19 | Schwartz Arthur G | 16-substituted androstanes and 16-substituted androstenes |
| US5028631A (en) * | 1987-11-25 | 1991-07-02 | Schwartz Arthur G | Homoandrostan-17-one and homoandrosten-17-ones |
| US5883087A (en) * | 1991-01-07 | 1999-03-16 | Pherin Corporation | Androstane steroids as neurochemical initiators of change in human hypothalamic function and related pharmaceutical compositions and methods |
| US5969168A (en) * | 1991-01-07 | 1999-10-19 | Pherin Corporation | Androstanes for inducing hypothalamic effects |
| US5925774A (en) | 1991-01-07 | 1999-07-20 | Pherin Corporation | Estrenes for inducing hypothalamic effects |
| EP1340502A3 (en) * | 1993-06-15 | 2004-01-21 | Pherin Corporation | Androstane steroids as neurochemical initiators of change in human hypothalamic function and related pharmaceutical compositions and methods |
| US6066627A (en) * | 1994-08-04 | 2000-05-23 | Pherin Corporation | Steroids as neurochemical initiators of change in human blood levels of LH |
| US6331534B1 (en) | 1994-08-04 | 2001-12-18 | Pherin Pharmaceuticals, Inc. | Steroids as neurochemical stimulators of the VNO to alleviate pain |
| US6117860A (en) * | 1994-08-04 | 2000-09-12 | Pherin Pharmaceuticals, Inc. | Steroids as neurochemical stimulators of the VNO to treat paroxistic tachycardia |
| US6057439A (en) * | 1994-08-04 | 2000-05-02 | Pherin Corporation | Steroids as neurochemical stimulators of the VNO to alleviate symptoms of PMS and anxiety |
| CN112778390B (zh) * | 2021-01-22 | 2022-09-30 | 厦门欧瑞捷生物科技有限公司 | 一种雄烯酮的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3501462A (en) * | 1966-05-02 | 1970-03-17 | Sterling Drug Inc | 17-cyclopropyl steroids |
-
1975
- 1975-07-16 GB GB29898/75A patent/GB1550343A/en not_active Expired
-
1976
- 1976-07-15 JP JP51084455A patent/JPS5212159A/ja active Pending
- 1976-07-15 BE BE168949A patent/BE844169A/xx unknown
- 1976-07-15 SE SE7608092A patent/SE7608092L/ not_active Application Discontinuation
- 1976-07-15 DE DE19762631915 patent/DE2631915A1/de not_active Withdrawn
- 1976-07-15 AU AU15938/76A patent/AU506101B2/en not_active Expired
- 1976-07-15 IE IE1572/76A patent/IE43693B1/en unknown
- 1976-07-15 AT AT519776A patent/AT362085B/de active
- 1976-07-15 IT IT68774/76A patent/IT1063150B/it active
- 1976-07-15 HU HU76GI247A patent/HU175369B/hu unknown
- 1976-07-15 FI FI762058A patent/FI55851C/fi not_active IP Right Cessation
- 1976-07-15 ZA ZA764195A patent/ZA764195B/xx unknown
- 1976-07-15 FR FR7621674A patent/FR2317934A1/fr active Granted
- 1976-07-15 CH CH910976A patent/CH626379A5/de not_active IP Right Cessation
- 1976-07-15 LU LU75394A patent/LU75394A1/xx unknown
- 1976-07-15 DK DK321676AA patent/DK142877B/da unknown
- 1976-07-15 NO NO762483A patent/NO146865C/no unknown
- 1976-07-15 US US05/705,446 patent/US4075233A/en not_active Expired - Lifetime
- 1976-07-15 NL NL7607824A patent/NL7607824A/xx not_active Application Discontinuation
- 1976-07-15 NZ NZ181482A patent/NZ181482A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU75394A1 (fi) | 1977-02-28 |
| NO146865B (no) | 1982-09-13 |
| FR2317934B1 (fi) | 1980-11-07 |
| IE43693B1 (en) | 1981-05-06 |
| IE43693L (en) | 1977-01-16 |
| ATA519776A (de) | 1980-09-15 |
| GB1550343A (en) | 1979-08-15 |
| DK142877B (da) | 1981-02-16 |
| FI55851B (fi) | 1979-06-29 |
| FI55851C (fi) | 1979-10-10 |
| NO146865C (no) | 1982-12-22 |
| IT1063150B (it) | 1985-02-11 |
| AT362085B (de) | 1981-04-27 |
| DK142877C (fi) | 1981-09-28 |
| NO762483L (fi) | 1977-01-18 |
| DE2631915A1 (de) | 1977-02-03 |
| AU506101B2 (en) | 1979-12-13 |
| US4075233A (en) | 1978-02-21 |
| AU1593876A (en) | 1978-01-19 |
| HU175369B (hu) | 1980-07-28 |
| DK321676A (fi) | 1977-01-17 |
| BE844169A (fr) | 1977-01-17 |
| FI762058A (fi) | 1977-01-17 |
| JPS5212159A (en) | 1977-01-29 |
| ZA764195B (en) | 1977-07-27 |
| NZ181482A (en) | 1978-12-18 |
| SE7608092L (sv) | 1977-01-17 |
| FR2317934A1 (fr) | 1977-02-11 |
| NL7607824A (nl) | 1977-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |