DD281809A5 - Verfahren zur herstellung neuer 11 beta-phenyl-4,9,15-estratriene - Google Patents

Verfahren zur herstellung neuer 11 beta-phenyl-4,9,15-estratriene Download PDF

Info

Publication number: DD281809A5
Authority: DD; German Democratic Republic
Prior art keywords: group; hydrogen atom; carbon atoms; meaning; alkyl
Prior art date: 1987-07-16

Application number

DD88317992A

Other languages

German (de)

English (en)

Inventor

Eckhard Ottow

Guenter Neef

Helmut Hofmeister

Stefan Scholz

Walter Elger

Sybille Beier

Krysztof Chwalisz

Original Assignee

��@��@��@��@��k��

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.)

1987-07-16

Filing date

1988-07-15

Publication date

1990-08-22

1988-07-15 Application filed by ��@��@��@��@��k�� filed Critical ��@��@��@��@��k��

1990-08-22 Publication of DD281809A5 publication Critical patent/DD281809A5/de

Links

238000000034 method Methods 0.000 title description 6
-1 hydroxyimino Chemical group 0.000 claims abstract description 55
150000001875 compounds Chemical class 0.000 claims abstract description 50
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000002252 acyl group Chemical group 0.000 claims abstract description 8
239000000460 chlorine Substances 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 4
125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000002355 alkine group Chemical group 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 15
230000000380 anti-gestagenic effect Effects 0.000 abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
239000011737 fluorine Substances 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
239000011630 iodine Substances 0.000 abstract description 2
229910052740 iodine Inorganic materials 0.000 abstract description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000000186 progesterone Substances 0.000 description 8
229960003387 progesterone Drugs 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 6
206010000210 abortion Diseases 0.000 description 5
231100000176 abortion Toxicity 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
239000006260 foam Substances 0.000 description 4
230000006698 induction Effects 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
239000000583 progesterone congener Substances 0.000 description 4
102000003998 progesterone receptors Human genes 0.000 description 4
108090000468 progesterone receptors Proteins 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
102100021869 Tyrosine aminotransferase Human genes 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
230000035558 fertility Effects 0.000 description 3
239000003862 glucocorticoid Substances 0.000 description 3
230000003054 hormonal effect Effects 0.000 description 3
239000007943 implant Substances 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000035935 pregnancy Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
229940037128 systemic glucocorticoids Drugs 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
KKADPXVIOXHVKN-UHFFFAOYSA-N 4-hydroxyphenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=C(O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-N 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
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241000700198 Cavia Species 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
208000001132 Osteoporosis Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
108010042606 Tyrosine transaminase Proteins 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000003470 adrenal cortex hormone Substances 0.000 description 2
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000002800 anti-glucocorticoid effect Effects 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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 2
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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231100000673 dose–response relationship Toxicity 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
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229940088597 hormone Drugs 0.000 description 2
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JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone 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 2
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150000002500 ions Chemical class 0.000 description 2
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229910052744 lithium Inorganic materials 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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150000002923 oximes Chemical class 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
239000013558 reference substance Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
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238000006467 substitution reaction Methods 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
239000005051 trimethylchlorosilane Substances 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
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UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
150000001987 diarylethers Chemical class 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 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
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000013011 mating Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000002175 menstrual effect Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002687 nonaqueous vehicle Chemical class 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000012188 paraffin wax Chemical class 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920000136 polysorbate Polymers 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
239000003755 preservative agent Substances 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
229910001958 silver carbonate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
238000011121 vaginal smear Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- 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
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD88317992A 1987-07-16 1988-07-15 Verfahren zur herstellung neuer 11 beta-phenyl-4,9,15-estratriene DD281809A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873723788 DE3723788A1 (de)	1987-07-16	1987-07-16	11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate

Publications (1)

Publication Number	Publication Date
DD281809A5 true DD281809A5 (de)	1990-08-22

Family

ID=6331846

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88317992A DD281809A5 (de)	1987-07-16	1988-07-15	Verfahren zur herstellung neuer 11 beta-phenyl-4,9,15-estratriene

Country Status (12)

Country	Link
US (1)	US5132299A (da)
EP (1)	EP0299913B1 (da)
JP (1)	JP2792876B2 (da)
AT (1)	ATE87631T1 (da)
CA (1)	CA1320946C (da)
DD (1)	DD281809A5 (da)
DE (2)	DE3723788A1 (da)
DK (1)	DK43189D0 (da)
ES (1)	ES2054859T3 (da)
FI (1)	FI94349C (da)
HU (1)	HU203764B (da)
WO (1)	WO1989000578A1 (da)

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DE3917274A1 (de) *	1989-05-24	1990-11-29	Schering Ag	9(alpha)-hydroxy-19, 11(beta)-ueberbrueckte steroide, deren herstellung und diese enthaltende pharmazeutische praeparate
JP3202224B2 (ja) *	1989-08-04	2001-08-27	シエーリングアクチエンゲゼルシヤフト	１１β―アリール―ゴナ―４，９―ジエン―３―オン、その製造方法及びそれを含有する調剤学的調製剤
DE4042004A1 (de) *	1990-12-22	1992-06-25	Schering Ag	14(beta)-h-, 14- u. 15-en-11(beta)-aryl-4-estrene
US5407928A (en) *	1990-08-15	1995-04-18	Schering Aktiengesellschaft	11β-aryl-gona-4,9-dien-3-ones
US5780220A (en) *	1994-05-19	1998-07-14	Trustees Of The University Of Pennsylvania	Methods and compositions for inhibiting HIV replication
US5639598A (en) *	1994-05-19	1997-06-17	The Trustees Of The University Of Pennsylvania	Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions
US5767113A (en) *	1995-05-10	1998-06-16	The Salk Institute For Biological Studies	Compounds useful for concurrently activating glucocorticoid-induced response and reducing multidrug resistance
IL118974A (en) *	1995-08-17	2001-09-13	Akzo Nobel Nv	History 11 - (Transformed Phenyl) - Astra - 4, 9 - Diane, their preparation and pharmaceutical preparations containing them
DE19706061A1 (de) *	1997-02-07	1998-08-13	Schering Ag	Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette
US6090798A (en) *	1997-12-19	2000-07-18	Alcon Laboratories, Inc.	Treatment of GLC1A glaucoma with glucocorticoid antagonists
DE102004059880A1 (de) *	2004-12-10	2006-06-14	Grünenthal GmbH	Stabiles, hormonhaltiges (Zwischen-)Produkt
EP2576582B1 (en)	2010-05-26	2019-09-18	Corcept Therapeutics, Inc.	Treatment of muscular dystrophy
CN107530435A (zh)	2015-03-02	2018-01-02	科赛普特治疗学股份有限公司	使用糖皮质激素受体拮抗剂和生长抑素治疗acth分泌型肿瘤
CN107530339B (zh)	2015-03-30	2021-03-16	科赛普特治疗学股份有限公司	糖皮质激素受体拮抗剂联合糖皮质激素用于治疗肾上腺功能不全
MX383318B (es)	2015-08-13	2025-03-13	Corcept Therapeutics Inc	Metodo para diagnosticar de manera diferencial el sindrome de cushing dependiente de la corticotropina.
KR102197526B1 (ko)	2016-01-19	2020-12-31	코어셉트 쎄라퓨틱스 인코포레이티드	이소성 쿠싱 증후군의 감별 진단
US10413540B2 (en)	2017-03-31	2019-09-17	Corcept Therapeutics, Inc.	Glucocorticoid receptor modulators to treat cervical cancer
MX393313B (es)	2017-06-20	2025-03-24	Corcept Therapeutics Inc	Metodos de tratamiento de tumores neuroepiteliales usando moduladores selectivos del receptor de glucocorticoide.
EP3713086A1 (de)	2019-03-18	2020-09-23	Siemens Aktiengesellschaft	Schutzschaltung für einen halbleiterschalter
EP4263807A2 (en)	2020-12-18	2023-10-25	Instil Bio (Uk) Limited	Processing of tumor infiltrating lymphocytes

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Publication number	Priority date	Publication date	Assignee	Title
US2530817A (en) *	1948-05-19	1950-11-21	Univ Pennsylvania	13-monomethyl steroids
US2940968A (en) *	1958-10-01	1960-06-14	Merck & Co Inc	Dimethylated steroids and processes for producing same
CH558346A (de) *	1971-06-17	1975-01-31	Sandoz Ag	Verfahren zur herstellung neuer 3-oximino-17(alpha)-propadienyl-substituierter steroide.
DE3042529A1 (de) *	1980-11-07	1982-06-24	Schering Ag, 1000 Berlin Und 4619 Bergkamen	11-methylen- (delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch)5(pfeil hoch) -steroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
FR2522328B1 (fr) *	1982-03-01	1986-02-14	Roussel Uclaf	Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments
EP0116974B1 (de) *	1983-02-18	1986-10-29	Schering Aktiengesellschaft	11-Beta-Aryl-Estradiene, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE3347126A1 (de) *	1983-12-22	1985-07-11	Schering AG, 1000 Berlin und 4709 Bergkamen	11ss-aryl-estradiene, deren herstellung und diese enthaltende pharmazeutische praeparate
NZ214998A (en) *	1985-02-07	1989-06-28	Schering Ag	13-(methyl or ethyl)-11-beta-phenyl-gonane derivatives; preparatory processes and pharmaceutical compositions

1987
- 1987-07-16 DE DE19873723788 patent/DE3723788A1/de not_active Withdrawn
1988
- 1988-07-15 EP EP88730161A patent/EP0299913B1/de not_active Expired - Lifetime
- 1988-07-15 WO PCT/DE1988/000447 patent/WO1989000578A1/de not_active Ceased
- 1988-07-15 JP JP63505988A patent/JP2792876B2/ja not_active Expired - Lifetime
- 1988-07-15 DE DE8888730161T patent/DE3879787D1/de not_active Expired - Fee Related
- 1988-07-15 US US07/458,668 patent/US5132299A/en not_active Expired - Fee Related
- 1988-07-15 DD DD88317992A patent/DD281809A5/de not_active IP Right Cessation
- 1988-07-15 ES ES88730161T patent/ES2054859T3/es not_active Expired - Lifetime
- 1988-07-15 CA CA000572238A patent/CA1320946C/en not_active Expired - Fee Related
- 1988-07-15 HU HU884582A patent/HU203764B/hu not_active IP Right Cessation
- 1988-07-15 AT AT88730161T patent/ATE87631T1/de not_active IP Right Cessation
1989
- 1989-01-31 DK DK043189A patent/DK43189D0/da not_active Application Discontinuation
1990
- 1990-01-15 FI FI900217A patent/FI94349C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3723788A1 (de)	1989-01-26
CA1320946C (en)	1993-08-03
JPH03500642A (ja)	1991-02-14
EP0299913B1 (de)	1993-03-31
WO1989000578A1 (fr)	1989-01-26
ES2054859T3 (es)	1994-08-16
EP0299913A1 (de)	1989-01-18
FI94349B (fi)	1995-05-15
FI94349C (fi)	1995-08-25
HUT52112A (en)	1990-06-28
JP2792876B2 (ja)	1998-09-03
ATE87631T1 (de)	1993-04-15
DE3879787D1 (de)	1993-05-06
HU203764B (en)	1991-09-30
DK43189A (da)	1989-01-31
DK43189D0 (da)	1989-01-31
US5132299A (en)	1992-07-21
FI900217A0 (fi)	1990-01-15

Legal Events

Date	Code	Title	Description
1999-12-09	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0254670B1 (de)	1989-11-15	11beta-(4-Isopropenylphenyl)-estra-4,9-diene, deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0299913B1 (de)	1993-03-31	11Beta-Phenyl-4,9,15-Estratriene, deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0192598B1 (de)	1989-12-13	11 Beta-N,N-Dimethylaminophenyl-Estradiene, deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0349481B1 (de)	1995-11-02	13-Alkyl-11Beta-phenylgonane
EP0648778B1 (de)	1997-08-13	Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0116974B1 (de)	1986-10-29	11-Beta-Aryl-Estradiene, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0360369B1 (de)	1995-05-03	11Beta-phenyl-14betaH-steroide
DE19706061A1 (de)	1998-08-13	Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette
DE4332284C2 (de)	1997-05-28	11-Benzaldoxim-17beta-methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP1060187B1 (de)	2003-04-16	S-substituierte 11beta-benzaldoxim-estra-4,9-dien-kohlensäurethiolester, verfahren zu deren herstellung und diese verbindungen enthaltene pharmazeutische zubereitungen
EP0404283A2 (de)	1990-12-27	11-Beta-aryl-4-estrene, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel
WO2011009533A2 (de)	2011-01-27	17-hydroxy-17-pentafluorethyl-estra-4,9(10) -dien-11-ethinylphenyl-derivate, verfahren zu deren herstellung und deren verwendung zur behandlung von krankheiten
EP0559690B1 (de)	1997-06-04	8-EN-19, 11 beta-ÜBERBRÜCKTE STEROIDE, DEREN HERSTELLUNG UND DIESE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE
DE3504421A1 (de)	1986-08-07	Neue 11ss-phenyl-gonane, deren herstellung und diese enthaltende pharmazeutische praeparate
WO1992011278A1 (de)	1992-07-09	14β-H-, 14- UND 15-EN-11β-ARYL-4-ESTRENE
EP0567472B1 (de)	1998-10-07	D-homo-(16-en)-11 beta-aryl-4-estrene,verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel.
DE602005003564T2 (de)	2008-10-23	Progesteronrezeptormodulatoren
WO2001044267A1 (de)	2001-06-21	11-β-PHENYLESTRADIEN-DERIVATE MIT FLUORALKYLGRUPPEN IN DER AROMATISCHEN SEITENKETTE, DEREN HERSTELLUNG UND DIESE VERBINDUNGEN ENTHALTENDE PHARMAZEUTISCHE ZUSAMMENSETZUNGEN
AU625450B2 (en)	1992-07-09	11beta-phenyl-4,9,15-estratrienes, their manufacture, and pharmaceutical preparations containing them
EP0034114A1 (de)	1981-08-19	3-Desoxy-delta-15-Steroide, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate
DE3527517A1 (de)	1987-01-29	11ss-phenyl-gonane, deren herstellung und diese enthaltende pharmazeutische praeparate