BE560182A - - Google Patents

Info

Publication number

BE560182A

BE560182A BE560182DA BE560182A BE 560182 A BE560182 A BE 560182A BE 560182D A BE560182D A BE 560182DA BE 560182 A BE560182 A BE 560182A

Authority

BE

Belgium

Prior art keywords

alpha

pregnene

trione

halo

fluoro

Prior art date

Links

• Espacenet
• Global Dossier
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• WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
• 150000001875 compounds Chemical class 0.000 claims description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 239000002904 solvent Substances 0.000 claims description 4
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
• 239000012442 inert solvent Substances 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 7
• 150000003431 steroids Chemical class 0.000 claims 2
• FUFLCEKSBBHCMO-KJQYFISQSA-N 11-dehydrocorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 FUFLCEKSBBHCMO-KJQYFISQSA-N 0.000 claims 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
• 241000575946 Ione Species 0.000 claims 1
• GFNANZIMVAIWHM-OBYCQNJPSA-N Triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 229940072033 potash Drugs 0.000 claims 1
• 235000015320 potassium carbonate Nutrition 0.000 claims 1
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
• AOJFQRQNPXYVLM-UHFFFAOYSA-M pyridine;chloride Chemical group [Cl-].C1=CC=NC=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-M 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• 230000000694 effects Effects 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 239000003208 petroleum Substances 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 3
• 230000005712 crystallization Effects 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• BHDHELFREODRJK-XRYUJSLGSA-N (8S,9R,10S,13S,14S,17R)-9-fluoro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound O=C1CC[C@]2(C)[C@@]3(F)C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 BHDHELFREODRJK-XRYUJSLGSA-N 0.000 description 2
• -1 9 alpha-halo-11 beta Chemical class 0.000 description 2
• 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 2
• 206010041277 Sodium retention Diseases 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 229960004544 cortisone Drugs 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• SUPOKHOQAKXOHJ-BYZMTCBYSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical class C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 SUPOKHOQAKXOHJ-BYZMTCBYSA-N 0.000 description 1
• 208000006673 Asthma Diseases 0.000 description 1
• 206010006811 Bursitis Diseases 0.000 description 1
• JYGXADMDTFJGBT-VWUMJDOOSA-N Cortisol Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 1
• 206010012438 Dermatitis atopic Diseases 0.000 description 1
• BYSGBSNPRWKUQH-UJDJLXLFSA-N Glycogen Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)O1 BYSGBSNPRWKUQH-UJDJLXLFSA-N 0.000 description 1
• 229940096919 Glycogen Drugs 0.000 description 1
• 229920002527 Glycogen Polymers 0.000 description 1
• 210000004185 Liver Anatomy 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 201000008937 atopic dermatitis Diseases 0.000 description 1
• 239000012267 brine Substances 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 229960000890 hydrocortisone Drugs 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 230000003287 optical Effects 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 201000003068 rheumatic fever Diseases 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 230000000699 topical Effects 0.000 description 1