NO304115B1 - FremgangsmÕte for fremstilling av 10<beta>-H-steroider - Google Patents

FremgangsmÕte for fremstilling av 10<beta>-H-steroider Download PDF

Info

Publication number: NO304115B1
Authority: NO; Norway
Prior art keywords: denotes; group; hydrogen atom; formula; atom
Prior art date: 1990-06-01

Application number

NO924617A

Other languages

English (en)

Norwegian (no)

Other versions

NO924617D0 (no

NO924617L (no

Inventor

Eckhard Ottow

G Nter Neef

Arwed Cleve

Rudolf Wiechert

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1990-06-01

Filing date

1992-11-30

Publication date

1998-10-26

1992-11-30 Application filed by Schering Ag filed Critical Schering Ag

1992-11-30 Publication of NO924617D0 publication Critical patent/NO924617D0/no

1992-11-30 Publication of NO924617L publication Critical patent/NO924617L/no

1998-10-26 Publication of NO304115B1 publication Critical patent/NO304115B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 32
230000008569 process Effects 0.000 title claims abstract description 4
238000002360 preparation method Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 49
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 12
229910052751 metal Inorganic materials 0.000 claims abstract description 8
239000002184 metal Substances 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims abstract description 8
150000003431 steroids Chemical class 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
-1 methyl- Chemical group 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
125000000468 ketone group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
229910052727 yttrium Inorganic materials 0.000 claims description 8
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 7
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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150000007524 organic acids Chemical class 0.000 claims description 3
235000006408 oxalic acid Nutrition 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
150000002739 metals Chemical class 0.000 claims 1
230000009467 reduction Effects 0.000 abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 31
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
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239000011541 reaction mixture Substances 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000012074 organic phase Substances 0.000 description 21
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
229910052938 sodium sulfate Inorganic materials 0.000 description 20
235000011152 sodium sulphate Nutrition 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
239000007789 gas Substances 0.000 description 9
230000001681 protective effect Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 7
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 6
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
238000006317 isomerization reaction Methods 0.000 description 5
BDGMZNTVBMVQNT-BLWDEEPMSA-N 17,17-bis-(ethylenedioxy)-5-estren11-one Chemical compound C1C2(OCCO3)OCCOC32[C@]2(C)[C@@H]1[C@H](CC=C1[C@@H]3CCCC1)[C@@H]3C(=O)C2 BDGMZNTVBMVQNT-BLWDEEPMSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
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UZFCEMSIKBQVQT-UUNRTTHMSA-N 17,17-bis-(ethylenedioxy)11-trifluoromethylsulfonyloxy-5,9(11)-estradiene Chemical compound C1C2(OCCO3)OCCOC32[C@]2(C)[C@@H]1[C@H](CC=C1[C@@H]3CCCC1)C3=C(OS(=O)(=O)C(F)(F)F)C2 UZFCEMSIKBQVQT-UUNRTTHMSA-N 0.000 description 3
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150000007513 acids Chemical class 0.000 description 3
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239000004305 biphenyl Substances 0.000 description 3
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238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
238000006567 deketalization reaction Methods 0.000 description 3
125000005265 dialkylamine group Chemical group 0.000 description 3
239000012467 final product Substances 0.000 description 3
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238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 2
238000006027 Birch reduction reaction Methods 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
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 description 2
239000001257 hydrogen Substances 0.000 description 2
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150000002440 hydroxy compounds Chemical class 0.000 description 2
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235000010755 mineral Nutrition 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
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150000003839 salts Chemical class 0.000 description 2
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
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HRKJTEONDBCWIV-USMWAVCTSA-N 17,17-bis-(ethylenedioxy)11-(4-methoxyphenyl)-5,9(11)-estradiene Chemical compound C1=CC(OC)=CC=C1C(C1)=C2[C@H]3CCCCC3=CC[C@H]2[C@H]2[C@@]1(C)C1(OCCO3)OCCOC13C2 HRKJTEONDBCWIV-USMWAVCTSA-N 0.000 description 1
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KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
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150000001204 N-oxides Chemical class 0.000 description 1
241001474977 Palla Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003418 antiprogestin Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
125000002837 carbocyclic group Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
OJKBCQOJVMAHDX-UHFFFAOYSA-N diethyl(pyridin-3-yl)borane Chemical compound CCB(CC)C1=CC=CN=C1 OJKBCQOJVMAHDX-UHFFFAOYSA-N 0.000 description 1
NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000005935 nucleophilic addition reaction Methods 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000011916 stereoselective reduction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
230000007306 turnover Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
HPQUOZITTSKGPY-UHFFFAOYSA-M zinc;2h-thiophen-2-ide;chloride Chemical compound [Zn+]Cl.C=1C=[C-]SC=1 HPQUOZITTSKGPY-UHFFFAOYSA-M 0.000 description 1

Classifications

- 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
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/008—Ketals at position 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
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- 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
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

NO924617A 1990-06-01 1992-11-30 FremgangsmÕte for fremstilling av 10<beta>-H-steroider NO304115B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4018167A DE4018167A1 (de)	1990-06-01	1990-06-01	Verfahren zur herstellung von 10(beta)-h-steroiden
PCT/EP1991/001018 WO1991018918A1 (de)	1990-06-01	1991-06-03	VERFAHREN ZUR HERSTELLUNG VON 10β-H-STEROIDEN

Publications (3)

Publication Number	Publication Date
NO924617D0 NO924617D0 (no)	1992-11-30
NO924617L NO924617L (no)	1992-11-30
NO304115B1 true NO304115B1 (no)	1998-10-26

Family

ID=6407912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO924617A NO304115B1 (no)	1990-06-01	1992-11-30	FremgangsmÕte for fremstilling av 10<beta>-H-steroider

Country Status (12)

Country	Link
US (1)	US5405979A (es)
EP (1)	EP0532562B1 (es)
JP (1)	JP2999258B2 (es)
AT (1)	ATE114317T1 (es)
CA (1)	CA2084313C (es)
DE (2)	DE4018167A1 (es)
DK (1)	DK0532562T3 (es)
ES (1)	ES2065039T3 (es)
FI (1)	FI111642B (es)
HU (1)	HU218484B (es)
NO (1)	NO304115B1 (es)
WO (1)	WO1991018918A1 (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4042007A1 (de) *	1990-12-22	1992-06-25	Schering Ag	6,7-modifizierte-11(beta)-aryl-4-estrene
DE19610667C2 (de) *	1996-03-08	1998-04-09	Schering Ag	(Z)-11ß-[4-(Dimethylamino)phenyl]17ß-hydroxy-17alpha-(3-hydroxy-1-propenyl)estr-4-en-3-on als kristallines Ansolvat
DE102011004899A1 (de)	2011-03-01	2012-09-06	Bayer Pharma Aktiengesellschaft	17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
JP6906525B2 (ja)	2015-12-23	2021-07-21	オリックファーマシューティカルズ，インク．	グルココルチコイド受容体の阻害剤
WO2017112904A1 (en)	2015-12-23	2017-06-29	Oric Pharmaceuticals, Inc.	Inhibitors of glucocorticoid receptor
CA3009525A1 (en) *	2015-12-23	2017-06-29	Oric Pharmaceuticals, Inc.	Inhibitors of glucocorticoid receptor
MX2019004030A (es)	2016-10-07	2019-09-16	Oric Pharmaceuticals Inc	Inhibidores del receptor de glucocorticoides.
CA3095042A1 (en) *	2018-04-11	2019-10-17	Oric Pharmaceuticals, Inc.	Solid forms and formulations comprising a glucocorticoid receptor antagonist and uses thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3014120A1 (de) *	1980-04-12	1981-10-29	Hoechst Ag, 6000 Frankfurt	Verfahren zur synthese von oestron bzw. oestronderivaten
AU572589B2 (en) *	1983-12-14	1988-05-12	Upjohn Company, The	11(alpha)-difluoromethyl and (e)-and (z)-11-fluoromethylene steroids
IE60780B1 (en) *	1987-01-23	1994-08-10	Akzo Nv	New 11-aryl steroid derivatives

1990
- 1990-06-01 DE DE4018167A patent/DE4018167A1/de not_active Withdrawn
1991
- 1991-06-03 AT AT91910189T patent/ATE114317T1/de not_active IP Right Cessation
- 1991-06-03 CA CA002084313A patent/CA2084313C/en not_active Expired - Fee Related
- 1991-06-03 JP JP3509553A patent/JP2999258B2/ja not_active Expired - Fee Related
- 1991-06-03 DK DK91910189.9T patent/DK0532562T3/da active
- 1991-06-03 WO PCT/EP1991/001018 patent/WO1991018918A1/de active IP Right Grant
- 1991-06-03 HU HU9203775A patent/HU218484B/hu not_active IP Right Cessation
- 1991-06-03 US US07/952,739 patent/US5405979A/en not_active Expired - Lifetime
- 1991-06-03 EP EP91910189A patent/EP0532562B1/de not_active Expired - Lifetime
- 1991-06-03 DE DE59103592T patent/DE59103592D1/de not_active Expired - Fee Related
- 1991-06-03 ES ES91910189T patent/ES2065039T3/es not_active Expired - Lifetime
1992
- 1992-11-30 FI FI925445A patent/FI111642B/fi active
- 1992-11-30 NO NO924617A patent/NO304115B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI925445A0 (fi)	1992-11-30
EP0532562A1 (de)	1993-03-24
CA2084313C (en)	2002-12-10
DE59103592D1 (de)	1995-01-12
JP2999258B2 (ja)	2000-01-17
NO924617D0 (no)	1992-11-30
NO924617L (no)	1992-11-30
EP0532562B1 (de)	1994-11-23
ATE114317T1 (de)	1994-12-15
WO1991018918A1 (de)	1991-12-12
HUT62596A (en)	1993-05-28
HU9203775D0 (en)	1993-03-29
ES2065039T3 (es)	1995-02-01
US5405979A (en)	1995-04-11
HU218484B (hu)	2000-09-28
CA2084313A1 (en)	1991-12-02
FI111642B (fi)	2003-08-29
FI925445A (fi)	1992-11-30
DE4018167A1 (de)	1991-12-05
DK0532562T3 (da)	1995-05-15
JPH05507271A (ja)	1993-10-21

Legal Events

Date	Code	Title	Description
2005-04-25	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
CA1334668C (en)	1995-03-07	13-alkyl-11beta-phenylgonanes
JP2588267B2 (ja)	1997-03-05	１９，１１β―架橋ステロイド，その製造法および該化合物を含有する製薬学的調剤
FI111844B (fi)	2003-09-30	Menetelmä terapeuttisesti käyttökelpoisten 11beta-aryyli-4-estreenijohdannaisten valmistamiseksi
NO168891B (no)	1992-01-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive 11beta-(4-isopropenylfenyl)-oestra-4,9-diener
NO169344B (no)	1992-03-02	11beta-substituerte steroider og antikonsepsjonsmidler inneholdende disse
IE893002L (en)	1990-03-20	11ß-phenyl-14ßH steroids
JP3202229B2 (ja)	2001-08-27	８−エン−１９，１１β−架橋したステロイド、その製造方法および該ステロイドを含有する製薬的製剤
NO304115B1 (no)	1998-10-26	FremgangsmÕte for fremstilling av 10<beta>-H-steroider
US5232915A (en)	1993-08-03	9α-hydroxy-19,11β-bridged steroids, their production and pharmaceutical preparations containing these steroids
US4464302A (en)	1984-08-07	17-[(Hydroxymethyl)formamido-methylene]-steroids
HUT65320A (en)	1994-05-02	Process for the production of 14-beta-h-, 14- or 15-en -11-beta-aryl-estrenes and of medical preparatives containing it
JP3181589B2 (ja)	2001-07-03	６、７−変性１１β−アリール−４−エステレン
EP0567472B1 (de)	1998-10-07	D-homo-(16-en)-11 beta-aryl-4-estrene,verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel.
US5446178A (en)	1995-08-29	Process for preparing 19,11β-bridged steroids
NO304116B1 (no)	1998-10-26	Utgangsforbindelser for fremstilling av 10<beta>-H-steroider, og en fremgangsmÕte for fremstilling av disse utgangsforbindelser
US7214808B2 (en)	2007-05-08	Method for the production of 4-(17α-substituted-3-oxoestra-4,9-dien-11β-yl)benzaldehyde-(1E)-oximes
FI110688B (fi)	2003-03-14	11 beta-aryyli-4-estreenejä ja menetelmä niiden valmistamiseksi
NO169345B (no)	1992-03-02	Analogifremgansmaate for fremstilling av terapeutisk aktive 11beta-substituerte steroider
NO177350B (no)	1995-05-22	Steroider med 19,11 skaper
PT100055B (pt)	1999-08-31	D-homo-(16-eno)-11b-aril-4-estrenos, processo para a sua preparacao bem como a sua utilizacao como medicamentos
CA2099017A1 (en)	1992-06-23	D-homo-(16-en)-11.beta.-aryl-4-estrenes, process for producing them and their use as medicaments
HU196433B (en)	1988-11-28	Process for producing new 20-amino-steroides