SK9442000A3 - 11beta-halogen-7alpha-substituted estratrienes, method for producing pharmaceutical preparations containing said 11beta-halogen-7alpha-substituted estratrienes and use of the same for producing medicaments - Google Patents

11beta-halogen-7alpha-substituted estratrienes, method for producing pharmaceutical preparations containing said 11beta-halogen-7alpha-substituted estratrienes and use of the same for producing medicaments Download PDF

Info

Publication number: SK9442000A3
Authority: SK; Slovakia
Prior art keywords: fluoro; estra; trien; dihydroxy; pentyl
Prior art date: 1997-12-23

Application number

SK944-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Rolf Bohlmann

Nikolaus Heinrich

Helmut Hofmeister

Jorg Kroll

Hermann Kunzer

Gerhard Sauer

Ludwig Zorn

Karl-Heinrich Fritzemeier

Monika Lessl

Rosemarie Lichtner

Yukishige Nishino

Karsten Parczyk

Martin Schneider

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.)

1997-12-23

Filing date

1998-12-23

Publication date

2001-04-09

1997-12-23 Priority claimed from DE1997158390 external-priority patent/DE19758390A1/de

1998-02-10 Priority claimed from DE1998106357 external-priority patent/DE19806357A1/de

1998-12-23 Application filed by Schering Ag filed Critical Schering Ag

2001-04-09 Publication of SK9442000A3 publication Critical patent/SK9442000A3/sk

Links

150000002164 estratrienes Chemical class 0.000 title claims abstract description 16
239000003814 drug Substances 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title claims description 21
239000000825 pharmaceutical preparation Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 75
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
239000011737 fluorine Substances 0.000 claims abstract description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
-1 hydrocarbon radical Chemical class 0.000 claims description 225
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 92
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
229940080818 propionamide Drugs 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 22
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
150000003254 radicals Chemical class 0.000 claims description 16
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 15
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17beta-estradiol Natural products OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 11
230000036961 partial effect Effects 0.000 claims description 11
125000004450 alkenylene group Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
125000004419 alkynylene group Chemical group 0.000 claims description 10
150000003431 steroids Chemical class 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
229930195733 hydrocarbon Natural products 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
229910052717 sulfur Chemical group 0.000 claims description 9
229930182833 estradiol Natural products 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Chemical group 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
125000006308 propyl amino group Chemical group 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004344 phenylpropyl group Chemical group 0.000 claims description 2
ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims 10
CVKMCTKUFWPCBY-UHFFFAOYSA-N n-(2-methoxyethyl)propanamide Chemical compound CCC(=O)NCCOC CVKMCTKUFWPCBY-UHFFFAOYSA-N 0.000 claims 3
ZGSSPVLYRUIEMY-UHFFFAOYSA-N 2-methyl-5-phenylpentanamide Chemical compound NC(=O)C(C)CCCC1=CC=CC=C1 ZGSSPVLYRUIEMY-UHFFFAOYSA-N 0.000 claims 2
MLDQPOXOWLCOEC-UHFFFAOYSA-N n-hexylbenzamide Chemical compound CCCCCCNC(=O)C1=CC=CC=C1 MLDQPOXOWLCOEC-UHFFFAOYSA-N 0.000 claims 2
QVFQOSQPCCDXMX-UHFFFAOYSA-N n-octylbenzamide Chemical compound CCCCCCCCNC(=O)C1=CC=CC=C1 QVFQOSQPCCDXMX-UHFFFAOYSA-N 0.000 claims 2
HLCRYAZDZCJZFG-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HLCRYAZDZCJZFG-BDXSIMOUSA-N 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
125000005418 aryl aryl group Chemical group 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
ZZKSAVUXOUDMGW-UHFFFAOYSA-N n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=CC=C1 ZZKSAVUXOUDMGW-UHFFFAOYSA-N 0.000 claims 1
WWHBQLKTQNBYQG-UHFFFAOYSA-N n-(3-phenylpropyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCC1=CC=CC=C1 WWHBQLKTQNBYQG-UHFFFAOYSA-N 0.000 claims 1
AMHHACRZBSECQT-UHFFFAOYSA-N n-(3-phenylpropyl)propanamide Chemical compound CCC(=O)NCCCC1=CC=CC=C1 AMHHACRZBSECQT-UHFFFAOYSA-N 0.000 claims 1
WVNFFHLXDXOSGO-UHFFFAOYSA-N n-hexylpropanamide Chemical compound CCCCCCNC(=O)CC WVNFFHLXDXOSGO-UHFFFAOYSA-N 0.000 claims 1
RCNSZOSXOKUSCL-UHFFFAOYSA-N n-octylpropanamide Chemical compound CCCCCCCCNC(=O)CC RCNSZOSXOKUSCL-UHFFFAOYSA-N 0.000 claims 1
230000001833 anti-estrogenic effect Effects 0.000 abstract description 24
229940046836 anti-estrogen Drugs 0.000 abstract description 14
239000000328 estrogen antagonist Substances 0.000 abstract description 14
230000001076 estrogenic effect Effects 0.000 abstract description 11
125000001424 substituent group Chemical group 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 315
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 259
239000000243 solution Substances 0.000 description 192
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 123
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 100
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 78
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 76
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
239000012043 crude product Substances 0.000 description 73
239000000741 silica gel Substances 0.000 description 72
229910002027 silica gel Inorganic materials 0.000 description 72
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 65
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 46
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 37
238000004587 chromatography analysis Methods 0.000 description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
239000006260 foam Substances 0.000 description 26
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
229910052938 sodium sulfate Inorganic materials 0.000 description 20
235000011152 sodium sulphate Nutrition 0.000 description 20
239000000203 mixture Substances 0.000 description 19
239000007858 starting material Substances 0.000 description 19
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000012279 sodium borohydride Substances 0.000 description 18
229910000033 sodium borohydride Inorganic materials 0.000 description 18
238000003756 stirring Methods 0.000 description 18
230000007935 neutral effect Effects 0.000 description 17
239000007788 liquid Substances 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
235000002639 sodium chloride Nutrition 0.000 description 16
239000000126 substance Substances 0.000 description 16
238000001819 mass spectrum Methods 0.000 description 15
238000000746 purification Methods 0.000 description 15
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 14
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000262 estrogen Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
229940011871 estrogen Drugs 0.000 description 9
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000012267 brine Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
235000009518 sodium iodide Nutrition 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
239000000725 suspension Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
238000010626 work up procedure Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000000556 agonist Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
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 7
239000005457 ice water Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
125000003710 aryl alkyl group Chemical class 0.000 description 6
238000000034 method Methods 0.000 description 6
238000000039 preparative column chromatography Methods 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
UYIFTLBWAOGQBI-BZDYCCQFSA-N Benzhormovarine Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-BZDYCCQFSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
230000001419 dependent effect Effects 0.000 description 5
229950002007 estradiol benzoate Drugs 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
238000002560 therapeutic procedure Methods 0.000 description 5
WRVYBYOOIQYCJI-UHFFFAOYSA-N 7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-heptadecafluoro-n-methyltetradecan-1-amine Chemical compound CNCCCCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WRVYBYOOIQYCJI-UHFFFAOYSA-N 0.000 description 4
KVINJMCLWSOHNP-UHFFFAOYSA-N 9,9,10,10,10-pentafluorodecyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCCCCCCC(F)(F)C(F)(F)F)C=C1 KVINJMCLWSOHNP-UHFFFAOYSA-N 0.000 description 4
229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
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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
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens
- 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
- 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
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Toxicology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK944-2000A 1997-12-23 1998-12-23 11beta-halogen-7alpha-substituted estratrienes, method for producing pharmaceutical preparations containing said 11beta-halogen-7alpha-substituted estratrienes and use of the same for producing medicaments SK9442000A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE1997158390 DE19758390A1 (de)	1997-12-23	1997-12-23	11ß-Halogen-7alpha-substituierte-Estratriene, Verfahren zur Herstellung pharmazeutischer Präparate, die diese 11ß-Halogen-7alpha-substituierte Estratriene enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln
DE1998106357 DE19806357A1 (de)	1998-02-10	1998-02-10	11beta-Halogen-7alpha-substituierte-Estratriene, Verfahren zur Herstellung pharmazeutischer Präparate, die diese 11beta-Halogen-7alpha-substituierte Estratriene enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln
PCT/EP1998/008470 WO1999033855A1 (de)	1997-12-23	1998-12-23	11β-HALOGEN-7α-SUBSTITUIERTE-ESTRATRIENE, VERFAHREN ZUR HERSTELLUNG PHARMAZEUTISCHER PRÄPARATE, DIE DIESE 11β-HALOGEN-7α-SUBSTITUIERTE-ESTRATRIENE ENTHALTEN, SOWIE DEREN VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN

Publications (1)

Publication Number	Publication Date
SK9442000A3 true SK9442000A3 (en)	2001-04-09

Family

ID=26042916

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK944-2000A SK9442000A3 (en)	1997-12-23	1998-12-23	11beta-halogen-7alpha-substituted estratrienes, method for producing pharmaceutical preparations containing said 11beta-halogen-7alpha-substituted estratrienes and use of the same for producing medicaments

Country Status (27)

Country	Link
US (1)	US6780855B2 (no)
EP (1)	EP1042355B1 (no)
JP (1)	JP2001527088A (no)
KR (1)	KR20010024806A (no)
CN (1)	CN1131235C (no)
AR (1)	AR015500A1 (no)
AT (1)	ATE232543T1 (no)
AU (1)	AU750801B2 (no)
BG (1)	BG104553A (no)
BR (1)	BR9814416A (no)
CA (1)	CA2316444A1 (no)
DE (1)	DE59807213D1 (no)
DK (1)	DK1042355T3 (no)
EA (1)	EA002623B1 (no)
EE (1)	EE200000380A (no)
ES (1)	ES2191371T3 (no)
HU (1)	HUP0100568A3 (no)
ID (1)	ID26207A (no)
IL (1)	IL136938A0 (no)
IS (1)	IS5526A (no)
NO (1)	NO20003286L (no)
NZ (1)	NZ505348A (no)
PE (1)	PE20000129A1 (no)
PL (1)	PL341299A1 (no)
SK (1)	SK9442000A3 (no)
TR (1)	TR200001973T2 (no)
WO (1)	WO1999033855A1 (no)

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AU2002215958B2 (en) *	2000-10-18	2006-08-17	Schering Ag	Use of inhibitors of progesterone receptor for treating cancer
DE10159217A1 (de) *	2001-11-27	2003-06-05	Schering Ag	17alpha-Alkyl-17ß-oxy-estratriene und Zwischenprodukte zu deren Herstellung, Verwendung der 17alpha-Alkyl-17ß-oxy-estratriene zur Herstellung von Arzneimitteln sowie pharmazeutische Präparate
AU2006202187B2 (en) *	2001-11-27	2008-11-06	Bayer Schering Pharma Aktiengesellschaft	17alpah-alkyl-17beta-oxy-estratrienes and intermediate products for their production, uses thereof and pharmaceutical preparations
US20040242551A1 (en) *	2003-05-28	2004-12-02	Schering Ag	Composition comprising antiprogestins and pure antiestrogens for prophylaxis and treatment of hormone-dependent diseases
EP1675843A1 (en) *	2003-10-14	2006-07-05	Council of Scientific and Industrial Research	(3r, 4r) -trans-3,4-diarylchroman derivatives with estrogenic activity
JP2007506805A (ja) *	2004-07-27	2007-03-22	シコールインコーポレイティド	７α−アルキル化された１９−ノルステロイドの調製方法
AU2006317486B9 (en)	2005-11-22	2011-08-04	Sumitomo Chemical Company, Limited	Organic sulfur compounds and use thereof as arthropodicides
DE102007049630A1 (de)	2007-10-11	2009-10-29	Bayer Schering Pharma Aktiengesellschaft	Nichtsteroidale Progesteronrezeptor-Modulatoren
DE102007023614A1 (de)	2007-05-21	2008-11-27	Bayer Schering Pharma Aktiengesellschaft	Nichtsteroidale Progesteronrezeptor-Modulatoren
JP2009001551A (ja)	2007-05-18	2009-01-08	Sumitomo Chemical Co Ltd	有機硫黄化合物及びその有害節足動物防除用途
TW200904329A (en)	2007-05-18	2009-02-01	Sumitomo Chemical Co	Organic sulfur compound and its use for controlling harmful arthropod
JP5298631B2 (ja)	2007-05-18	2013-09-25	住友化学株式会社	有機硫黄化合物及びその有害節足動物防除用途
DE102007032800A1 (de)	2007-07-10	2009-01-15	Bayer Schering Pharma Aktiengesellschaft	Nichtsteroidale Progesteronrezeptor-Modulatoren
EP2033948A1 (en) *	2007-08-30	2009-03-11	Bayer Schering Pharma Aktiengesellschaft	Process for preparing Estrogen-antagonistic 11beta-Fluoro-17alpha-alkylestra-1,3,5 (10)-triene-3, 17-diols having a 7alpha-(xi-Alkylamino-omega-perfluoroalkyl)alkyl side chain and alpha-Alkyl(amino)-omega-perfluoro(alkyl)alkanes and processes for their preparation
SG185311A1 (en)	2007-10-16	2012-11-29	Repros Therapeutics Inc	Trans-clomiphene for metabolic syndrome
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1998
- 1998-12-18 AR ARP980106471A patent/AR015500A1/es not_active Application Discontinuation
- 1998-12-18 PE PE1998001246A patent/PE20000129A1/es not_active Application Discontinuation
- 1998-12-23 EA EA200000711A patent/EA002623B1/ru not_active IP Right Cessation
- 1998-12-23 BR BR9814416-2A patent/BR9814416A/pt not_active IP Right Cessation
- 1998-12-23 DE DE59807213T patent/DE59807213D1/de not_active Expired - Fee Related
- 1998-12-23 US US09/380,413 patent/US6780855B2/en not_active Expired - Fee Related
- 1998-12-23 CN CN98812631A patent/CN1131235C/zh not_active Expired - Fee Related
- 1998-12-23 AU AU22763/99A patent/AU750801B2/en not_active Ceased
- 1998-12-23 EP EP98966410A patent/EP1042355B1/de not_active Expired - Lifetime
- 1998-12-23 JP JP2000526531A patent/JP2001527088A/ja active Pending
- 1998-12-23 ES ES98966410T patent/ES2191371T3/es not_active Expired - Lifetime
- 1998-12-23 ID IDW20001234A patent/ID26207A/id unknown
- 1998-12-23 EE EEP200000380A patent/EE200000380A/xx unknown
- 1998-12-23 CA CA002316444A patent/CA2316444A1/en not_active Abandoned
- 1998-12-23 HU HU0100568A patent/HUP0100568A3/hu unknown
- 1998-12-23 DK DK98966410T patent/DK1042355T3/da active
- 1998-12-23 KR KR1020007006955A patent/KR20010024806A/ko not_active Withdrawn
- 1998-12-23 NZ NZ505348A patent/NZ505348A/xx unknown
- 1998-12-23 WO PCT/EP1998/008470 patent/WO1999033855A1/de not_active Ceased
- 1998-12-23 AT AT98966410T patent/ATE232543T1/de not_active IP Right Cessation
- 1998-12-23 TR TR2000/01973T patent/TR200001973T2/xx unknown
- 1998-12-23 SK SK944-2000A patent/SK9442000A3/sk unknown
- 1998-12-23 PL PL98341299A patent/PL341299A1/xx unknown
- 1998-12-23 IL IL13693898A patent/IL136938A0/xx unknown
2000
- 2000-06-09 IS IS5526A patent/IS5526A/is unknown
- 2000-06-22 NO NO20003286A patent/NO20003286L/no not_active Application Discontinuation
- 2000-06-23 BG BG104553A patent/BG104553A/bg unknown

Also Published As

Publication number	Publication date
AU750801B2 (en)	2002-07-25
JP2001527088A (ja)	2001-12-25
DK1042355T3 (da)	2003-04-22
NO20003286L (no)	2000-08-23
EA002623B1 (ru)	2002-06-27
HUP0100568A3 (en)	2002-01-28
TR200001973T2 (tr)	2001-01-22
EP1042355A1 (de)	2000-10-11
CN1286693A (zh)	2001-03-07
ID26207A (id)	2000-12-07
AR015500A1 (es)	2001-05-02
NZ505348A (en)	2002-10-25
ATE232543T1 (de)	2003-02-15
EE200000380A (et)	2001-12-17
HUP0100568A2 (hu)	2001-08-28
EA200000711A1 (ru)	2001-02-26
EP1042355B1 (de)	2003-02-12
CN1131235C (zh)	2003-12-17
BR9814416A (pt)	2000-10-10
IL136938A0 (en)	2001-06-14
KR20010024806A (ko)	2001-03-26
DE59807213D1 (de)	2003-03-20
BG104553A (bg)	2001-02-28
WO1999033855A1 (de)	1999-07-08
NO20003286D0 (no)	2000-06-22
ES2191371T3 (es)	2003-09-01
CA2316444A1 (en)	1999-07-08
PL341299A1 (en)	2001-04-09
AU2276399A (en)	1999-07-19
US6780855B2 (en)	2004-08-24
US20030069434A1 (en)	2003-04-10
PE20000129A1 (es)	2000-03-11
IS5526A (is)	2000-06-09

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