NO133696B - - Google Patents

Info

Publication number

NO133696B

NO133696B NO336073A NO336073A NO133696B NO 133696 B NO133696 B NO 133696B NO 336073 A NO336073 A NO 336073A NO 336073 A NO336073 A NO 336073A NO 133696 B NO133696 B NO 133696B

Authority

NO

Norway

Prior art keywords

dione

oxido

pregnadiene

fluoro

dihydroxy

Prior art date

1973-08-27

Links

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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 21
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
• 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 19
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 150000003128 pregnanes Chemical class 0.000 claims description 11
• 239000003513 alkali Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 239000000047 product Substances 0.000 description 20
• 239000002904 solvent Substances 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 7
• -1 steroid alcohols Chemical class 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 150000003431 steroids Chemical class 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• 150000001298 alcohols Chemical class 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 238000003682 fluorination reaction Methods 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 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 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• 239000004698 Polyethylene Substances 0.000 description 2
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
• 150000008041 alkali metal carbonates Chemical class 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 229910052739 hydrogen Inorganic materials 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 229920000573 polyethylene Polymers 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 229960005205 prednisolone Drugs 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• UPTAPIKFKZGAGM-OKKWSIRNSA-N 1-[(8R,9S,10S,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical class C1C(O)CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC21 UPTAPIKFKZGAGM-OKKWSIRNSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
• NJCJHGJZWVIYPY-ACXQXYJUSA-N [2-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 NJCJHGJZWVIYPY-ACXQXYJUSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• 238000009739 binding Methods 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 229960003290 cortisone acetate Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
• 125000000369 oxido group Chemical group [*]=O 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• RJKFOVLPORLFTN-UHFFFAOYSA-N progesterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 RJKFOVLPORLFTN-UHFFFAOYSA-N 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1