JPH08510455A - １７，２０―リアーゼ阻害活性を有するカルバゾール誘導体 - Google Patents
１７，２０―リアーゼ阻害活性を有するカルバゾール誘導体Info
- Publication number
- JPH08510455A JPH08510455A JP7500181A JP50018195A JPH08510455A JP H08510455 A JPH08510455 A JP H08510455A JP 7500181 A JP7500181 A JP 7500181A JP 50018195 A JP50018195 A JP 50018195A JP H08510455 A JPH08510455 A JP H08510455A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- carbazole
- ylmethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 2
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 title description 13
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 title description 13
- 230000002401 inhibitory effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 239000003098 androgen Substances 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 10
- 229940011871 estrogen Drugs 0.000 claims abstract description 9
- 239000000262 estrogen Substances 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 33
- -1 triazol-1-ylmethyl -9H- carbazole Chemical compound 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- LFCQNAOJQWIHSR-UHFFFAOYSA-N 2-fluoro-7-(pyridin-3-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=CN=C1 LFCQNAOJQWIHSR-UHFFFAOYSA-N 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- CJKAHOZICMOBTA-UHFFFAOYSA-N 2-fluoro-7-(pyridin-4-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=NC=C1 CJKAHOZICMOBTA-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000011200 topical administration Methods 0.000 claims description 4
- GJYDAAIUCZMZGI-UHFFFAOYSA-N 1,7-difluoro-2-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=C(F)C=3CN1C=NC=N1 GJYDAAIUCZMZGI-UHFFFAOYSA-N 0.000 claims description 3
- UUNNIGZLLLUITE-UHFFFAOYSA-N 2,4-difluoro-7-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC(F)=C(C2=CC=3)C=1NC2=CC=3CN1C=NC=N1 UUNNIGZLLLUITE-UHFFFAOYSA-N 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 241000282412 Homo Species 0.000 claims description 3
- 229940030486 androgens Drugs 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- CDFBRMQNNCVRSY-UHFFFAOYSA-N 2-fluoro-7-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CN1C=NC=N1 CDFBRMQNNCVRSY-UHFFFAOYSA-N 0.000 claims description 2
- AXUGYCMGYYRNSE-UHFFFAOYSA-N 2-fluoro-7-[(3-fluoropyridin-4-yl)methyl]-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=NC=C1F AXUGYCMGYYRNSE-UHFFFAOYSA-N 0.000 claims description 2
- BEEQFMQHLNPVKA-UHFFFAOYSA-N 2-fluoro-7-[(3-methoxypyridin-4-yl)methyl]-9h-carbazole Chemical compound COC1=CN=CC=C1CC1=CC=C2C3=CC=C(F)C=C3NC2=C1 BEEQFMQHLNPVKA-UHFFFAOYSA-N 0.000 claims description 2
- LXCHEUMJSPFNAY-UHFFFAOYSA-N 2-fluoro-7-[(3-methylpyridin-4-yl)methyl]-9h-carbazole Chemical compound CC1=CN=CC=C1CC1=CC=C2C3=CC=C(F)C=C3NC2=C1 LXCHEUMJSPFNAY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000003635 deoxygenating effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000012298 atmosphere Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 28
- 239000012265 solid product Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 238000005406 washing Methods 0.000 description 17
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
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- 239000002253 acid Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 229960003604 testosterone Drugs 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
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- 239000007788 liquid Substances 0.000 description 7
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
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- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
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- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 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
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 150000003852 triazoles Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939310635A GB9310635D0 (en) | 1993-05-21 | 1993-05-21 | Chemical compounds |
| GB9310635.9 | 1993-05-21 | ||
| PCT/EP1994/001613 WO1994027989A1 (en) | 1993-05-21 | 1994-05-19 | Carbazole derivatives with 17,20-lyase-inhibiting activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08510455A true JPH08510455A (ja) | 1996-11-05 |
Family
ID=10736007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7500181A Pending JPH08510455A (ja) | 1993-05-21 | 1994-05-19 | １７，２０―リアーゼ阻害活性を有するカルバゾール誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0699196A1 (enExample) |
| JP (1) | JPH08510455A (enExample) |
| CN (1) | CN1126473A (enExample) |
| AU (1) | AU6928794A (enExample) |
| BG (1) | BG100154A (enExample) |
| CA (1) | CA2162921A1 (enExample) |
| CZ (1) | CZ305195A3 (enExample) |
| FI (1) | FI955587A7 (enExample) |
| GB (1) | GB9310635D0 (enExample) |
| HU (1) | HUT73790A (enExample) |
| IL (1) | IL109703A0 (enExample) |
| NO (1) | NO954681L (enExample) |
| OA (1) | OA10195A (enExample) |
| PE (1) | PE31195A1 (enExample) |
| PL (1) | PL311702A1 (enExample) |
| SK (1) | SK142495A3 (enExample) |
| TW (1) | TW279866B (enExample) |
| WO (1) | WO1994027989A1 (enExample) |
| ZA (1) | ZA943494B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016515098A (ja) * | 2013-02-27 | 2016-05-26 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ブロモドメイン阻害剤として有用なカルバゾール化合物 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0721943A4 (en) * | 1993-09-30 | 1996-09-04 | Yamanouchi Pharma Co Ltd | AZOL DERIVATIVES AND PHARMACEUTICAL PREPARATIONS |
| WO1996014090A1 (en) * | 1994-11-07 | 1996-05-17 | Janssen Pharmaceutica N.V. | Compositions comprising carbazoles and cyclodextrins |
| NZ302392A (en) * | 1995-03-01 | 1998-08-26 | Yamanouchi Pharma Co Ltd | Tricyclic substituted imidazole derivatives and medicaments thereof |
| CN1251577A (zh) * | 1997-02-21 | 2000-04-26 | 武田药品工业株式会社 | 稠环化合物及其生产和应用 |
| CA2429133C (en) | 2000-11-17 | 2009-08-18 | Takeda Chemical Industries, Ltd. | Novel imidazole derivatives, production method thereof and use thereof |
| DE60144246D1 (de) | 2000-11-20 | 2011-04-28 | Takeda Pharmaceutical | Imidazolderivate, verfahren zu deren herstellung und deren verwendung |
| WO2002046186A1 (en) | 2000-12-08 | 2002-06-13 | Takeda Chemical Industries, Ltd. | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| AU2006262283B2 (en) * | 2005-06-24 | 2011-10-13 | Eli Lilly And Company | Tetrahydrocarbazole derivatives useful as androgen receptor modulators (SARM) |
| GB0525323D0 (en) | 2005-12-13 | 2006-01-18 | Sterix Ltd | Compound |
| US8093279B2 (en) | 2005-12-13 | 2012-01-10 | Gillian Reed, legal representative | Compound |
| CN100586932C (zh) * | 2007-01-26 | 2010-02-03 | 中国医学科学院医药生物技术研究所 | 抗肿瘤化合物及其制备方法 |
| PE20121048A1 (es) | 2009-06-26 | 2012-08-25 | Novartis Ag | Derivados de imidazolidin-2-ona 1,3-disustituida como inhibidores de cyp17 |
| JP5964756B2 (ja) * | 2010-02-04 | 2016-08-03 | ラジウス ヘルス，インコーポレイテッド | 選択的アンドロゲン受容体モジュレーター |
| PL2568806T3 (pl) | 2010-05-12 | 2017-03-31 | Radius Health, Inc. | Schematy lecznicze |
| KR101594660B1 (ko) | 2010-08-04 | 2016-02-16 | 펠피큐어 파마슈티걸즈 아이엔씨 | 전립선 암종의 치료를 위한 병용 요법 |
| EP2627648A1 (en) | 2010-09-16 | 2013-08-21 | Novartis AG | 17aHYDROXYLASE/C17,20-LYASE INHIBITORS |
| AU2011312490B2 (en) | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| MX359399B (es) | 2011-04-28 | 2018-09-27 | Novartis Ag | Inhibidores de 17alfa-hidroxilasa/c17-20-liasa. |
| AU2014241816B9 (en) | 2013-03-14 | 2019-02-14 | Pellficure Pharmaceuticals Inc. | Novel therapy for prostate carcinoma |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| ES2939940T3 (es) | 2014-03-28 | 2023-04-28 | Univ Duke | Tratamiento del cáncer de mama utilizando moduladores selectivos de los receptores de estrógenos |
| WO2016040896A1 (en) | 2014-09-12 | 2016-03-17 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| WO2017223115A1 (en) | 2016-06-22 | 2017-12-28 | Radius Health, Inc. | Ar+ breast cancer treatment methods |
| WO2018080933A1 (en) | 2016-10-24 | 2018-05-03 | Pellficure Pharmaceuticals Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| EP3565542B1 (en) | 2017-01-05 | 2024-04-10 | Radius Pharmaceuticals, Inc. | Polymorphic forms of rad1901-2hcl |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS229934B2 (en) * | 1981-07-07 | 1984-07-16 | Pfizer | Production method subst.indolylacryte acid derivative |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
-
1993
- 1993-05-21 GB GB939310635A patent/GB9310635D0/en active Pending
-
1994
- 1994-05-02 ZA ZA943494A patent/ZA943494B/xx unknown
- 1994-05-17 TW TW083104441A patent/TW279866B/zh active
- 1994-05-19 CN CN94192683A patent/CN1126473A/zh active Pending
- 1994-05-19 JP JP7500181A patent/JPH08510455A/ja active Pending
- 1994-05-19 HU HU9503321A patent/HUT73790A/hu unknown
- 1994-05-19 PL PL94311702A patent/PL311702A1/xx unknown
- 1994-05-19 SK SK1424-95A patent/SK142495A3/sk unknown
- 1994-05-19 CA CA002162921A patent/CA2162921A1/en not_active Abandoned
- 1994-05-19 CZ CZ953051A patent/CZ305195A3/cs unknown
- 1994-05-19 WO PCT/EP1994/001613 patent/WO1994027989A1/en not_active Ceased
- 1994-05-19 AU AU69287/94A patent/AU6928794A/en not_active Abandoned
- 1994-05-19 EP EP94917647A patent/EP0699196A1/en not_active Withdrawn
- 1994-05-20 IL IL10970394A patent/IL109703A0/xx unknown
- 1994-11-18 PE PE1994255110A patent/PE31195A1/es not_active Application Discontinuation
-
1995
- 1995-11-17 OA OA60742A patent/OA10195A/en unknown
- 1995-11-20 NO NO954681A patent/NO954681L/no unknown
- 1995-11-20 FI FI955587A patent/FI955587A7/fi not_active Application Discontinuation
- 1995-11-21 BG BG100154A patent/BG100154A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016515098A (ja) * | 2013-02-27 | 2016-05-26 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ブロモドメイン阻害剤として有用なカルバゾール化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO954681D0 (no) | 1995-11-20 |
| PE31195A1 (es) | 1995-10-18 |
| FI955587A0 (fi) | 1995-11-20 |
| IL109703A0 (en) | 1994-08-26 |
| WO1994027989A1 (en) | 1994-12-08 |
| NO954681L (no) | 1995-11-20 |
| CZ305195A3 (en) | 1996-06-12 |
| OA10195A (en) | 1996-12-18 |
| AU6928794A (en) | 1994-12-20 |
| HUT73790A (en) | 1996-09-30 |
| PL311702A1 (en) | 1996-03-04 |
| CA2162921A1 (en) | 1994-12-08 |
| TW279866B (enExample) | 1996-07-01 |
| ZA943494B (en) | 1995-01-23 |
| FI955587A7 (fi) | 1995-11-20 |
| EP0699196A1 (en) | 1996-03-06 |
| GB9310635D0 (en) | 1993-07-07 |
| BG100154A (en) | 1996-07-31 |
| SK142495A3 (en) | 1996-06-05 |
| CN1126473A (zh) | 1996-07-10 |
| HU9503321D0 (en) | 1996-01-29 |
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