ZA200101304B - Benzocycloheptenes, method for the production thereof pharmaceutical preparations containing these compounds, and their use for producing medicaments. - Google Patents
Benzocycloheptenes, method for the production thereof pharmaceutical preparations containing these compounds, and their use for producing medicaments. Download PDFInfo
- Publication number
- ZA200101304B ZA200101304B ZA200101304A ZA200101304A ZA200101304B ZA 200101304 B ZA200101304 B ZA 200101304B ZA 200101304 A ZA200101304 A ZA 200101304A ZA 200101304 A ZA200101304 A ZA 200101304A ZA 200101304 B ZA200101304 B ZA 200101304B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- dihydro
- benzocyclohepten
- pentyloxy
- methyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 70
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- ZVCPCZRXWGOICC-UHFFFAOYSA-N 1h-benzo[7]annulene Chemical class C1=CC=CC=C2CC=CC=C21 ZVCPCZRXWGOICC-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 2
- -1 heteroaryl radical Chemical class 0.000 claims description 94
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000008177 pharmaceutical agent Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- MEDJPTBHZLSBKF-UHFFFAOYSA-N 5-[4-[5-(4,4,5,5,5-pentafluoropentylsulfanyl)pentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulene Chemical compound C1=CC(OCCCCCSCCCC(F)(F)C(F)(F)F)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC=CC=C12 MEDJPTBHZLSBKF-UHFFFAOYSA-N 0.000 claims description 3
- MJNJMGLKTSBSRQ-UHFFFAOYSA-N 5-[4-[5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulene Chemical compound C1=CC(OCCCCCS(=O)CCCC(F)(F)C(F)(F)F)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC=CC=C12 MJNJMGLKTSBSRQ-UHFFFAOYSA-N 0.000 claims description 3
- HTVIORJSDMUILY-UHFFFAOYSA-N 5-[4-[6-(4,4,5,5,5-pentafluoropentylsulfanyl)hexoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCCSCCCC(F)(F)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 HTVIORJSDMUILY-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000006193 alkinyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
- UENBASOEUJIMKF-UHFFFAOYSA-N 5-[4-[5-[(4-methylphenyl)methylsulfanyl]pentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C1=CC(C)=CC=C1CSCCCCCOC1=CC=C(C=2C3=CC=C(O)C=C3CCCC=2C=2C=CC=CC=2)C=C1 UENBASOEUJIMKF-UHFFFAOYSA-N 0.000 claims description 2
- JKWOZLRGHIULAS-UHFFFAOYSA-N 5-[4-[6-(4,4,5,5,5-pentafluoropentylsulfinyl)hexoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 JKWOZLRGHIULAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HNTQXJSEQKSMOQ-UHFFFAOYSA-N n-butyl-2-[5-[4-(2-hydroxy-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl)phenoxy]pentylsulfanyl]-n-methylacetamide Chemical compound C1=CC(OCCCCCSCC(=O)N(C)CCCC)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(O)=CC=C12 HNTQXJSEQKSMOQ-UHFFFAOYSA-N 0.000 claims description 2
- GCEJBVXETSJTDC-UHFFFAOYSA-N n-butyl-2-[6-[4-(2-hydroxy-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl)phenoxy]hexylsulfanyl]-n-methylacetamide Chemical compound C1=CC(OCCCCCCSCC(=O)N(C)CCCC)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(O)=CC=C12 GCEJBVXETSJTDC-UHFFFAOYSA-N 0.000 claims description 2
- VHYKINZOPGMZJX-UHFFFAOYSA-N n-butyl-n-methyl-2-[5-[4-(6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl)phenoxy]pentylsulfinyl]acetamide Chemical compound C1=CC(OCCCCCS(=O)CC(=O)N(C)CCCC)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC=CC=C12 VHYKINZOPGMZJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- WXYJXAMRWMXVSI-UHFFFAOYSA-N 5-[4-(5-benzylsulfanylpentoxy)phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCSCC=4C=CC=CC=4)=CC=3)C=1CCCC=2C1=CC=CC=C1 WXYJXAMRWMXVSI-UHFFFAOYSA-N 0.000 claims 1
- RPYJOALLPHCEES-UHFFFAOYSA-N 5-[4-[2-[methyl-[3-(4,4,5,5,5-pentafluoropentylsulfinyl)propyl]amino]ethoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C1=CC(OCCN(CCCS(=O)CCCC(F)(F)C(F)(F)F)C)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(O)=CC=C12 RPYJOALLPHCEES-UHFFFAOYSA-N 0.000 claims 1
- UPTCURNURCNZTO-UHFFFAOYSA-N 5-[4-[5-(4-tert-butylphenyl)sulfinylpentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)CCCCCOC1=CC=C(C=2C3=CC=C(O)C=C3CCCC=2C=2C=CC=CC=2)C=C1 UPTCURNURCNZTO-UHFFFAOYSA-N 0.000 claims 1
- HCJOKOMWMXHTRR-UHFFFAOYSA-N 5-[4-[5-(benzenesulfonyl)pentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCS(=O)(=O)C=4C=CC=CC=4)=CC=3)C=1CCCC=2C1=CC=CC=C1 HCJOKOMWMXHTRR-UHFFFAOYSA-N 0.000 claims 1
- HWHAHNDRUYVXPF-UHFFFAOYSA-N 6-(4-hydroxyphenyl)-5-[4-[5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentoxy]phenyl]-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C1=CC(O)=CC=C1C(CCCC1=CC(O)=CC=C11)=C1C1=CC=C(OCCCCCS(=O)(=O)CCCC(F)(F)C(F)(F)F)C=C1 HWHAHNDRUYVXPF-UHFFFAOYSA-N 0.000 claims 1
- VBYRHYKOZSAZLE-UHFFFAOYSA-N 6-phenyl-5-[4-[5-(4,4,4-trifluorobutylsulfanyl)pentoxy]phenyl]-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCSCCCC(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 VBYRHYKOZSAZLE-UHFFFAOYSA-N 0.000 claims 1
- KMUCLKKTVMZWHN-UHFFFAOYSA-N 6-phenyl-5-[4-[5-[4-(trifluoromethyl)phenyl]sulfanylpentoxy]phenyl]-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCSC=4C=CC(=CC=4)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 KMUCLKKTVMZWHN-UHFFFAOYSA-N 0.000 claims 1
- FIXHKFIFIRDADK-UHFFFAOYSA-N 6-phenyl-5-[4-[5-[4-(trifluoromethyl)phenyl]sulfinylpentoxy]phenyl]-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCS(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 FIXHKFIFIRDADK-UHFFFAOYSA-N 0.000 claims 1
- NACJXNJIRVBZCJ-UHFFFAOYSA-N 6-phenyl-5-[4-[5-[4-(trifluoromethyl)phenyl]sulfonylpentoxy]phenyl]-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCS(=O)(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 NACJXNJIRVBZCJ-UHFFFAOYSA-N 0.000 claims 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 1
- UWZWTPGFJUBJAX-UHFFFAOYSA-N n-butyl-2-[2-[2-[4-(2-hydroxy-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl)phenoxy]ethyl-methylamino]ethylsulfinyl]-n-methylacetamide Chemical compound C1=CC(OCCN(C)CCS(=O)CC(=O)N(C)CCCC)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(O)=CC=C12 UWZWTPGFJUBJAX-UHFFFAOYSA-N 0.000 claims 1
- WYAHAWZIMAKAMZ-UHFFFAOYSA-N n-methyl-3-(4,4,5,5,5-pentafluoropentylsulfanyl)-n-[2-[4-(6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl)phenoxy]ethyl]propan-1-amine Chemical compound C1=CC(OCCN(CCCSCCCC(F)(F)C(F)(F)F)C)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC=CC=C12 WYAHAWZIMAKAMZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 249
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
- 239000000243 solution Substances 0.000 description 109
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 230000008018 melting Effects 0.000 description 72
- 238000002844 melting Methods 0.000 description 72
- 238000001704 evaporation Methods 0.000 description 71
- 230000008020 evaporation Effects 0.000 description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 239000013078 crystal Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
- 229910052938 sodium sulfate Inorganic materials 0.000 description 43
- 235000011152 sodium sulphate Nutrition 0.000 description 43
- 230000007935 neutral effect Effects 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 33
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 24
- 238000011282 treatment Methods 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 210000004291 uterus Anatomy 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 230000001833 anti-estrogenic effect Effects 0.000 description 11
- 235000009518 sodium iodide Nutrition 0.000 description 11
- 230000001076 estrogenic effect Effects 0.000 description 10
- 235000006408 oxalic acid Nutrition 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 229940011871 estrogen Drugs 0.000 description 8
- 239000000262 estrogen Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 7
- 210000000988 bone and bone Anatomy 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 230000002265 prevention Effects 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ADWGQXQZZVMNOW-UHFFFAOYSA-N 4-[2-(oxan-2-yloxy)-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-5-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(OC3OCCCC3)=CC=C12 ADWGQXQZZVMNOW-UHFFFAOYSA-N 0.000 description 6
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- 239000004480 active ingredient Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000328 estrogen antagonist Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 4
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- 230000003637 steroidlike Effects 0.000 description 4
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- 238000002560 therapeutic procedure Methods 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- VKSJZRFGKPVKNA-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-5-(5-iodopentylsulfonyl)pentane Chemical compound FC(F)(F)C(F)(F)CCCS(=O)(=O)CCCCCI VKSJZRFGKPVKNA-UHFFFAOYSA-N 0.000 description 3
- SGKVLOVVEDHSGR-UHFFFAOYSA-N 2-[[5-[4-(2-chloroethoxy)phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-yl]oxy]oxane Chemical compound C1=CC(OCCCl)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC(OC3OCCCC3)=CC=C12 SGKVLOVVEDHSGR-UHFFFAOYSA-N 0.000 description 3
- NFZHGBJOAXTFGR-UHFFFAOYSA-N 5-[4-(2-iodoethoxy)phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulene Chemical compound C1=CC(OCCI)=CC=C1C1=C(C=2C=CC=CC=2)CCCC2=CC=CC=C12 NFZHGBJOAXTFGR-UHFFFAOYSA-N 0.000 description 3
- AYESDTLULQWFPT-UHFFFAOYSA-N 6-bromo-5-(4-methoxyphenyl)-2-phenylmethoxy-8,9-dihydro-7h-benzo[7]annulene Chemical compound C1=CC(OC)=CC=C1C1=C(Br)CCCC2=CC(OCC=3C=CC=CC=3)=CC=C12 AYESDTLULQWFPT-UHFFFAOYSA-N 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
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- 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 1
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- GCZQHDFWKVMZOE-UHFFFAOYSA-N thiophen-2-ylmethanethiol Chemical compound SCC1=CC=CS1 GCZQHDFWKVMZOE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P5/32—Antioestrogens
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833786A DE19833786A1 (de) | 1998-07-18 | 1998-07-18 | Benzocycloheptene, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200101304B true ZA200101304B (en) | 2002-05-15 |
Family
ID=7875476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200101304A ZA200101304B (en) | 1998-07-18 | 2001-02-15 | Benzocycloheptenes, method for the production thereof pharmaceutical preparations containing these compounds, and their use for producing medicaments. |
Country Status (33)
Country | Link |
---|---|
US (3) | US6495607B2 (xx) |
EP (1) | EP1098874B1 (xx) |
JP (1) | JP2002520388A (xx) |
KR (1) | KR100642690B1 (xx) |
CN (1) | CN1309635A (xx) |
AR (1) | AR024505A1 (xx) |
AT (1) | ATE243193T1 (xx) |
AU (1) | AU763189B2 (xx) |
BG (1) | BG65098B1 (xx) |
BR (1) | BR9912240A (xx) |
CA (1) | CA2337991C (xx) |
CO (1) | CO5080743A1 (xx) |
CZ (1) | CZ299624B6 (xx) |
DE (2) | DE19833786A1 (xx) |
DK (1) | DK1098874T3 (xx) |
EA (1) | EA004182B1 (xx) |
EE (1) | EE04273B1 (xx) |
ES (1) | ES2201753T3 (xx) |
HR (1) | HRP20010115B1 (xx) |
HU (1) | HUP0102921A3 (xx) |
IL (1) | IL140897A (xx) |
NO (1) | NO20010277L (xx) |
NZ (1) | NZ508957A (xx) |
PE (1) | PE20000864A1 (xx) |
PL (1) | PL200116B1 (xx) |
PT (1) | PT1098874E (xx) |
RS (1) | RS49906B (xx) |
SK (1) | SK285262B6 (xx) |
TR (1) | TR200100105T2 (xx) |
TW (1) | TWI250143B (xx) |
UA (1) | UA67790C2 (xx) |
WO (1) | WO2000003979A1 (xx) |
ZA (1) | ZA200101304B (xx) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19833786A1 (de) * | 1998-07-18 | 2000-01-20 | Schering Ag | Benzocycloheptene, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
DE19916419B4 (de) * | 1999-04-08 | 2005-06-16 | Schering Ag | Kombinationspräparat aus Vitamin-D-Metaboliten oder Vitamin-D-Analoga und einem Östrogenpartialagonisten zur Behandlung von Osteoporose |
DE60239207D1 (de) * | 2001-08-10 | 2011-03-31 | Takeda Pharmaceutical | Gnrh-agonistische kombinationsmittel |
DE10151095A1 (de) * | 2001-10-12 | 2003-04-30 | Schering Ag | Synthese von Sauerstoff-substituierten Benzocycloheptenen als wertvolle Zwischenprodukte für die Herstellung gewebeselektiver Estrogene |
IL161322A0 (en) * | 2001-10-12 | 2004-09-27 | Schering Ag | Synthesis of oxygen-substituted benzocycloheptenes, used as valuable intermediate products for producing tissue-selective oestrogens |
CA2576747A1 (en) * | 2004-08-17 | 2006-03-02 | Janssen Pharmaceutica N.V. | Benzoxazepine derivatives as selective estrogen receptor modulators |
EP1951664A1 (en) | 2005-11-22 | 2008-08-06 | Sumitomo Chemical Company, Limited | Organic sulfur compounds and use thereof as arthropodicides |
DE102005057224A1 (de) | 2005-11-29 | 2007-05-31 | Bayer Schering Pharma Ag | Prodrugs ERß-selektiver Substanzen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
DE102007023614A1 (de) | 2007-05-21 | 2008-11-27 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
DE102007049630A1 (de) | 2007-10-11 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
AU2008219115A1 (en) * | 2007-02-16 | 2008-08-28 | Synta Pharmaceuticals Corp. | Substituted fused-ring compounds for inflammation and immune-related uses |
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 |
TW200904329A (en) | 2007-05-18 | 2009-02-01 | Sumitomo Chemical Co | Organic sulfur compound and its use for controlling harmful arthropod |
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 |
DE102007032800A1 (de) | 2007-07-10 | 2009-01-15 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
EP2048126A1 (de) * | 2007-10-11 | 2009-04-15 | Bayer Schering Pharma AG | Benzocycloheptanderivate als selektiv wirksame Estrogene |
DE102007058747A1 (de) | 2007-12-05 | 2009-06-10 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
EP2070909A1 (de) | 2007-12-15 | 2009-06-17 | Bayer Schering Pharma AG | Nichtsteroidale Progesteronrezeptor-Modulatoren |
DE102010030538A1 (de) | 2010-06-25 | 2011-12-29 | Bayer Schering Pharma Aktiengesellschaft | 6,7-Dihydro-5H-benzo[7]annulen-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
DE102011087987A1 (de) | 2011-12-08 | 2013-06-13 | Bayer Intellectual Property Gmbh | 6,7-Dihydro-5H-benzo[7]annulen-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
WO2015028409A1 (de) * | 2013-08-27 | 2015-03-05 | Bayer Pharma Aktiengesellschaft | 6,7-dihydro-5h-benzo[7]annulen-derivate, verfahren zu ihrer herstellung, pharmazeutische präparate die diese enthalten, sowie deren verwendung zur herstellung von arzneimitteln |
SG11201806829TA (en) * | 2016-02-15 | 2018-09-27 | Sanofi Sa | 6,7-dihydro-5h-benzo[7]annulene derivatives as estrogen receptor modulators |
RU2742278C2 (ru) * | 2016-11-17 | 2021-02-04 | Санофи | Новые соединения замещенного n-(3-фторпропил)пирролидина, способы их получения и их терапевтическое применение |
EP3434272A1 (en) | 2017-07-25 | 2019-01-30 | Sanofi | Combination comprising palbociclib and 6-(2,4-dichlorophenyl)-5-[4-[(3s)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulene-2-carboxylic acid |
CN107674051B (zh) * | 2017-09-20 | 2021-01-08 | 南京医科大学 | 4-羟基他莫昔酚环状衍生物乏氧活化前药及其药物用途 |
AR116300A1 (es) | 2018-09-07 | 2021-04-21 | Sanofi Sa | Proceso para la preparación de 6-(2,4-diclorofenil)-5-[4-[(3s)-1-(3-fluoropropil)pirrolidin-3-il]oxifenil]-8,9-dihidro-7h-benzo[7]anuleno-2-carboxilato de metilo |
WO2021063967A1 (en) * | 2019-10-01 | 2021-04-08 | Sanofi | Novel substituted 6,7-dihydro-5h-benzo[7]annulene compounds, processes for their preparation and therapeutic uses thereof |
TW202313558A (zh) * | 2021-07-08 | 2023-04-01 | 大陸商勤浩醫藥(蘇州)有限公司 | 一類苯并七元環類化合物及其應用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US5552412A (en) | 1995-01-09 | 1996-09-03 | Pfizer Inc | 5-substitued-6-cyclic-5,6,7,8-tetrahydronaphthalen2-ol compounds which are useful for treating osteoporosis |
DE19635525A1 (de) * | 1996-08-20 | 1998-02-26 | Schering Ag | 7alpha-(xi-Aminoalkyl)-estratriene, Verfahren zu deren Herstellung, pharmazeutische Präparate, die diese 7alpha(xi-Aminoalkyl-estratriene enthalten sowie deren Verwendung zur Herstellung von Arzneimitteln |
DE19806357A1 (de) * | 1998-02-10 | 1999-08-12 | Schering Ag | 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 |
DE19833786A1 (de) * | 1998-07-18 | 2000-01-20 | Schering Ag | Benzocycloheptene, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
-
1998
- 1998-07-18 DE DE19833786A patent/DE19833786A1/de not_active Withdrawn
-
1999
- 1999-07-16 PE PE1999000718A patent/PE20000864A1/es not_active Application Discontinuation
- 1999-07-16 AR ARP990103511A patent/AR024505A1/es active IP Right Grant
- 1999-07-17 TW TW088112168A patent/TWI250143B/zh not_active IP Right Cessation
- 1999-07-19 EE EEP200100037A patent/EE04273B1/xx not_active IP Right Cessation
- 1999-07-19 CZ CZ20010048A patent/CZ299624B6/cs not_active IP Right Cessation
- 1999-07-19 WO PCT/EP1999/005093 patent/WO2000003979A1/de active IP Right Grant
- 1999-07-19 NZ NZ508957A patent/NZ508957A/en unknown
- 1999-07-19 RS YUP-33/01A patent/RS49906B/sr unknown
- 1999-07-19 CO CO99045525A patent/CO5080743A1/es unknown
- 1999-07-19 UA UA2001021132A patent/UA67790C2/uk unknown
- 1999-07-19 HU HU0102921A patent/HUP0102921A3/hu unknown
- 1999-07-19 AU AU52843/99A patent/AU763189B2/en not_active Ceased
- 1999-07-19 EP EP99938277A patent/EP1098874B1/de not_active Expired - Lifetime
- 1999-07-19 PL PL345863A patent/PL200116B1/pl not_active IP Right Cessation
- 1999-07-19 JP JP2000560088A patent/JP2002520388A/ja active Pending
- 1999-07-19 PT PT99938277T patent/PT1098874E/pt unknown
- 1999-07-19 US US09/357,239 patent/US6495607B2/en not_active Expired - Fee Related
- 1999-07-19 CA CA002337991A patent/CA2337991C/en not_active Expired - Fee Related
- 1999-07-19 IL IL14089799A patent/IL140897A/xx not_active IP Right Cessation
- 1999-07-19 AT AT99938277T patent/ATE243193T1/de not_active IP Right Cessation
- 1999-07-19 DE DE59906017T patent/DE59906017D1/de not_active Expired - Fee Related
- 1999-07-19 CN CN99808794A patent/CN1309635A/zh active Pending
- 1999-07-19 KR KR1020017000731A patent/KR100642690B1/ko not_active IP Right Cessation
- 1999-07-19 SK SK53-2001A patent/SK285262B6/sk not_active IP Right Cessation
- 1999-07-19 DK DK99938277T patent/DK1098874T3/da active
- 1999-07-19 EA EA200100154A patent/EA004182B1/ru not_active IP Right Cessation
- 1999-07-19 ES ES99938277T patent/ES2201753T3/es not_active Expired - Lifetime
- 1999-07-19 TR TR2001/00105T patent/TR200100105T2/xx unknown
- 1999-07-19 BR BR9912240-5A patent/BR9912240A/pt not_active Application Discontinuation
-
2001
- 2001-01-17 NO NO20010277A patent/NO20010277L/no not_active Application Discontinuation
- 2001-01-17 BG BG105161A patent/BG65098B1/bg unknown
- 2001-02-15 ZA ZA200101304A patent/ZA200101304B/en unknown
- 2001-02-15 HR HR20010115A patent/HRP20010115B1/xx not_active IP Right Cessation
-
2002
- 2002-09-11 US US10/238,640 patent/US6878750B2/en not_active Expired - Fee Related
-
2005
- 2005-04-11 US US11/102,840 patent/US7145015B2/en not_active Expired - Fee Related
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