NO770560L - Steroidderivater, samt fremgangsm}te ved fremstilling av disse. - Google Patents
Steroidderivater, samt fremgangsm}te ved fremstilling av disse.Info
- Publication number
- NO770560L NO770560L NO770560A NO770560A NO770560L NO 770560 L NO770560 L NO 770560L NO 770560 A NO770560 A NO 770560A NO 770560 A NO770560 A NO 770560A NO 770560 L NO770560 L NO 770560L
- Authority
- NO
- Norway
- Prior art keywords
- diene
- steroid
- dien
- trien
- acid
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title claims description 63
- 238000000034 method Methods 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 steroid enol ester Chemical class 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000007519 polyprotic acids Polymers 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- HFJJFVWDQNSUGH-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HFJJFVWDQNSUGH-VMXHOPILSA-N 0.000 claims description 4
- XNOGVXAXZQINLI-ZPOLXVRWSA-N (8s,9s,10r,13s,14s,17r)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,7,8,9,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-11-one Chemical compound C1=CCC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC=C21 XNOGVXAXZQINLI-ZPOLXVRWSA-N 0.000 claims description 4
- HIQVDECUIIZANU-ZPOLXVRWSA-N (8s,9s,10r,13s,14s,17r)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,7,8,9,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-11-one Chemical compound C1=C(O)CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC=C21 HIQVDECUIIZANU-ZPOLXVRWSA-N 0.000 claims description 4
- LFGPOYRCQQAAEF-YFWFAHHUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1=CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC=C21 LFGPOYRCQQAAEF-YFWFAHHUSA-N 0.000 claims description 4
- HYSDKFPHBHMBJZ-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2C=C(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 HYSDKFPHBHMBJZ-LEKSSAKUSA-N 0.000 claims description 4
- JVQRIUUIJIGHDM-YFWFAHHUSA-N 2-hydroxy-1-[(8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1=C(O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC=C21 JVQRIUUIJIGHDM-YFWFAHHUSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- DHYMIGDMHYMJAQ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 DHYMIGDMHYMJAQ-BYZMTCBYSA-N 0.000 claims description 3
- WGBUTJCBIKWVDA-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C([C@H]1[C@@H]2CCC[C@]2(CC[C@@H]11)C)CC2=C1CCC=C2 WGBUTJCBIKWVDA-BDXSIMOUSA-N 0.000 claims description 3
- KNYFHPYFRDKBIT-CEGNMAFCSA-N 1-[(8r,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 KNYFHPYFRDKBIT-CEGNMAFCSA-N 0.000 claims description 3
- YXRFQWKNFFQPAQ-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 YXRFQWKNFFQPAQ-LEKSSAKUSA-N 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- SHHRTQZHYMJFPS-QAGGRKNESA-N (8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1=C(O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 SHHRTQZHYMJFPS-QAGGRKNESA-N 0.000 claims description 2
- XMZASOTWFOTBQO-QXUSFIETSA-N (8r,9s,10r,13s,14s)-3-hydroxy-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1=C(O)CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 XMZASOTWFOTBQO-QXUSFIETSA-N 0.000 claims description 2
- NCULQPYCKPJVEO-CBZIJGRNSA-N (8r,9s,13s,14s)-3-hydroxy-13-methyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1CC(O)=CC2=C1[C@H]1CC[C@](C)(C(CC3)=O)[C@@H]3[C@@H]1CC2 NCULQPYCKPJVEO-CBZIJGRNSA-N 0.000 claims description 2
- GNHAWRYSMNHFTJ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CC=CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 GNHAWRYSMNHFTJ-BYZMTCBYSA-N 0.000 claims description 2
- JBFVIKZAURYSRE-KJQYFISQSA-N (8s,9s,10r,13s,14s,17s)-3-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,7,8,9,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-11-one Chemical compound C1=C(O)CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC=C21 JBFVIKZAURYSRE-KJQYFISQSA-N 0.000 claims description 2
- IGJGDNGVVSKWKG-DXUGQKIESA-N (9s,10r,13r,14r,17s)-17-ethyl-10,13-dimethyl-2,9,11,12,14,15,16,17-octahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CCC[C@]2(C)[C@@H](CC[C@@]3([C@@H](CC)CC[C@H]33)C)C3=CC=C21 IGJGDNGVVSKWKG-DXUGQKIESA-N 0.000 claims description 2
- LFHJOEACXVPKCX-CEGNMAFCSA-N 1-[(8r,9s,10r,13s,14s,17r)-3,17-dihydroxy-10,13-dimethyl-1,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1=CC2=CC(O)=CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 LFHJOEACXVPKCX-CEGNMAFCSA-N 0.000 claims description 2
- ZKTSKPGFWLVJPX-SXYSDOLCSA-N 1-[(9s,10r,13s,14s,17r)-3,17-dihydroxy-10,13-dimethyl-1,2,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1=C(O)CC[C@]2(C)[C@@H](CC[C@@]3([C@](C(=O)C)(O)CC[C@H]33)C)C3=CC=C21 ZKTSKPGFWLVJPX-SXYSDOLCSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims 2
- XOFOOPVNDALPEZ-UXMGNZLBSA-N (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC=1C[C@@H]2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC=1)C)O XOFOOPVNDALPEZ-UXMGNZLBSA-N 0.000 claims 1
- JWYFBDXKKQXBKW-GCOKGBOCSA-N (5S,8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound CC[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3CC[C@]12C JWYFBDXKKQXBKW-GCOKGBOCSA-N 0.000 claims 1
- UPVNJOUINDANKT-UGCZWRCOSA-N (5S,8S,9S,10S,13S,14S)-10,13-dimethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C([C@@H]1CC2)=CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 UPVNJOUINDANKT-UGCZWRCOSA-N 0.000 claims 1
- MBKYAJNPVNKMIP-IMRIKWHGSA-N (5r,8r,9r,10r,13s,14s)-3-hydroxy-13-methyl-2,5,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1=C(O)CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 MBKYAJNPVNKMIP-IMRIKWHGSA-N 0.000 claims 1
- SHNZTMPRCBXYMT-WZNAKSSCSA-N (5s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1=C(O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 SHNZTMPRCBXYMT-WZNAKSSCSA-N 0.000 claims 1
- REWRPWNDGYFELW-WZNAKSSCSA-N (5s,8r,9s,10s,13s,14s)-3-hydroxy-10,13-dimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C(O)=CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 REWRPWNDGYFELW-WZNAKSSCSA-N 0.000 claims 1
- FOAWKLBWEPTYCP-GCOKGBOCSA-N (5s,8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene 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 FOAWKLBWEPTYCP-GCOKGBOCSA-N 0.000 claims 1
- NTDNQJMXFXTZLE-UGCZWRCOSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C([C@@H]1CC2)C=CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 NTDNQJMXFXTZLE-UGCZWRCOSA-N 0.000 claims 1
- MHPLORJVSXEWIZ-ZPOLXVRWSA-N (8s,9s,10r,13s,14s,17r)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-8,9,12,14,15,16-hexahydro-7h-cyclopenta[a]phenanthren-11-one Chemical compound C1=CC=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC=C21 MHPLORJVSXEWIZ-ZPOLXVRWSA-N 0.000 claims 1
- BLYDDOAEUXLBIG-ZPOLXVRWSA-N (8s,9s,10r,13s,14s,17r)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-8,9,12,14,15,16-hexahydro-7h-cyclopenta[a]phenanthren-11-one Chemical compound C1=C(O)C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC=C21 BLYDDOAEUXLBIG-ZPOLXVRWSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 229910001411 inorganic cation Inorganic materials 0.000 claims 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- UZTMUWPZCPYSEB-PNKHAZJDSA-N (8R,9S,10R,13S,14S)-13-methyl-1,2,7,8,9,10,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol Chemical compound OC1=CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@H]2CC1 UZTMUWPZCPYSEB-PNKHAZJDSA-N 0.000 description 5
- 239000003470 adrenal cortex hormone Substances 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- 239000008188 pellet Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003128 pregnanes Chemical class 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB6512/76A GB1527161A (en) | 1976-02-19 | 1976-02-19 | Enol esters of steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO770560L true NO770560L (no) | 1977-08-22 |
Family
ID=9815869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770560A NO770560L (no) | 1976-02-19 | 1977-02-18 | Steroidderivater, samt fremgangsm}te ved fremstilling av disse. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4150126A (xx) |
| JP (1) | JPS52100458A (xx) |
| AT (1) | AT358200B (xx) |
| AU (1) | AU511532B2 (xx) |
| BE (1) | BE851649A (xx) |
| CA (1) | CA1087167A (xx) |
| DE (1) | DE2707121A1 (xx) |
| DK (1) | DK71977A (xx) |
| ES (1) | ES456057A1 (xx) |
| FI (1) | FI57114C (xx) |
| FR (1) | FR2341594A1 (xx) |
| GB (1) | GB1527161A (xx) |
| HU (1) | HU176558B (xx) |
| LU (1) | LU76795A1 (xx) |
| NL (1) | NL7701585A (xx) |
| NO (1) | NO770560L (xx) |
| NZ (1) | NZ183376A (xx) |
| SE (1) | SE7700170L (xx) |
| SU (1) | SU828970A3 (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261910A (en) * | 1978-08-14 | 1981-04-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the preparation of Chlorambucil derivatives |
| US4260736A (en) * | 1978-08-14 | 1981-04-07 | Kureha Kagaku Kogyo Kabushiki Kaisha | Steroid hormone-antitumor derivatives |
| US4512986A (en) * | 1983-07-26 | 1985-04-23 | Research Triangle Institute | Progrestationally active steroids |
| JPS61293993A (ja) * | 1985-06-21 | 1986-12-24 | Kureha Chem Ind Co Ltd | 新規な螢光物質，その製造方法及び薬剤 |
| JPH0621072B2 (ja) * | 1986-11-12 | 1994-03-23 | 呉羽化学工業株式会社 | エストラジオ−ル誘導体よりなる免疫調節剤 |
| GB9003939D0 (en) * | 1990-02-21 | 1990-04-18 | Imperial College | Sulphatase inhibitors |
| ATE190622T1 (de) * | 1990-08-18 | 2000-04-15 | Schering Ag | Verfahren zur herstellung von 20-methyl-5,7- pregnadien-3$g(b),21-diol-derivativen |
| GB9118465D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| GB0304927D0 (en) | 2003-03-04 | 2003-04-09 | Resolution Chemicals Ltd | Process for the production of tibolone |
| MX369930B (es) * | 2015-06-29 | 2019-11-26 | Galenica S A | Esteres de lactama esteroidal y derivados de acido bis(2-cloroetil)aminofenoxi propanoico. |
-
1976
- 1976-02-19 GB GB6512/76A patent/GB1527161A/en not_active Expired
-
1977
- 1977-01-10 SE SE7700170A patent/SE7700170L/ not_active Application Discontinuation
- 1977-01-17 US US05/760,151 patent/US4150126A/en not_active Expired - Lifetime
- 1977-01-28 FI FI770296A patent/FI57114C/fi not_active IP Right Cessation
- 1977-02-09 AU AU22091/77A patent/AU511532B2/en not_active Expired
- 1977-02-14 SU SU772451700A patent/SU828970A3/ru active
- 1977-02-15 NL NL7701585A patent/NL7701585A/xx not_active Application Discontinuation
- 1977-02-17 LU LU76795A patent/LU76795A1/xx unknown
- 1977-02-17 HU HU77LE801A patent/HU176558B/hu unknown
- 1977-02-17 CA CA271,963A patent/CA1087167A/en not_active Expired
- 1977-02-18 NO NO770560A patent/NO770560L/no unknown
- 1977-02-18 DK DK71977A patent/DK71977A/da unknown
- 1977-02-18 JP JP1633477A patent/JPS52100458A/ja active Pending
- 1977-02-18 DE DE19772707121 patent/DE2707121A1/de not_active Withdrawn
- 1977-02-18 NZ NZ183376A patent/NZ183376A/xx unknown
- 1977-02-18 ES ES456057A patent/ES456057A1/es not_active Expired
- 1977-02-18 AT AT111977A patent/AT358200B/de not_active IP Right Cessation
- 1977-02-21 FR FR7704960A patent/FR2341594A1/fr active Granted
- 1977-02-21 BE BE175104A patent/BE851649A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU176558B (en) | 1981-03-28 |
| NL7701585A (nl) | 1977-08-23 |
| SE7700170L (sv) | 1977-08-20 |
| AU2209177A (en) | 1978-08-17 |
| AU511532B2 (en) | 1980-08-21 |
| BE851649A (fr) | 1977-08-22 |
| DK71977A (da) | 1977-08-20 |
| ES456057A1 (es) | 1978-06-01 |
| SU828970A3 (ru) | 1981-05-07 |
| US4150126A (en) | 1979-04-17 |
| AT358200B (de) | 1980-08-25 |
| FI57114B (fi) | 1980-02-29 |
| CA1087167A (en) | 1980-10-07 |
| GB1527161A (en) | 1978-10-04 |
| JPS52100458A (en) | 1977-08-23 |
| LU76795A1 (xx) | 1978-10-18 |
| ATA111977A (de) | 1980-01-15 |
| FR2341594A1 (fr) | 1977-09-16 |
| FI770296A (xx) | 1977-08-20 |
| FR2341594B1 (xx) | 1980-09-19 |
| DE2707121A1 (de) | 1977-09-01 |
| FI57114C (fi) | 1980-06-10 |
| NZ183376A (en) | 1980-04-28 |
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