SK142495A3 - Carbazole derivatives, process for preparing the same, pharmaceutical compositions containing the same and their use - Google Patents
Carbazole derivatives, process for preparing the same, pharmaceutical compositions containing the same and their use Download PDFInfo
- Publication number
- SK142495A3 SK142495A3 SK1424-95A SK142495A SK142495A3 SK 142495 A3 SK142495 A3 SK 142495A3 SK 142495 A SK142495 A SK 142495A SK 142495 A3 SK142495 A3 SK 142495A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- carbazole
- ylmethyl
- formula
- compound according
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 239000003098 androgen Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 12
- 239000000262 estrogen Substances 0.000 claims abstract description 12
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 21
- -1 2-fluoro-7- [1,2,4] triazol-l-ylmethyl-9H-carbazole 2-fluoro-7-pyridin-3-ylmethyl-9H-carbazole 2-fluoro-7-pyridin-4-ylmethyl-9H-carbazole Chemical compound 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- 229940011871 estrogen Drugs 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 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 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 229940030486 androgens Drugs 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 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 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 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
- 125000000468 ketone group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture 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 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
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- 229910052757 nitrogen Inorganic materials 0.000 description 23
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
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- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 description 12
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 229960003604 testosterone Drugs 0.000 description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000010410 layer Substances 0.000 description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 102000011022 Chorionic Gonadotropin Human genes 0.000 description 5
- 108010062540 Chorionic Gonadotropin Proteins 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 5
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- 241000700159 Rattus Species 0.000 description 5
- UMYBPELCCZPPOD-UHFFFAOYSA-N [4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]boronic acid Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(B(O)O)C=C1 UMYBPELCCZPPOD-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 4
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- 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 description 3
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- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
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- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940100640 transdermal system Drugs 0.000 description 1
- 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
- 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
- 238000005550 wet granulation 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939310635A GB9310635D0 (en) | 1993-05-21 | 1993-05-21 | Chemical compounds |
| 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 |
|---|---|
| SK142495A3 true SK142495A3 (en) | 1996-06-05 |
Family
ID=10736007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1424-95A SK142495A3 (en) | 1993-05-21 | 1994-05-19 | Carbazole derivatives, process for preparing the same, pharmaceutical compositions containing the same and their use |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0699196A1 (cs) |
| JP (1) | JPH08510455A (cs) |
| CN (1) | CN1126473A (cs) |
| AU (1) | AU6928794A (cs) |
| BG (1) | BG100154A (cs) |
| CA (1) | CA2162921A1 (cs) |
| CZ (1) | CZ305195A3 (cs) |
| FI (1) | FI955587A0 (cs) |
| GB (1) | GB9310635D0 (cs) |
| HU (1) | HUT73790A (cs) |
| IL (1) | IL109703A0 (cs) |
| NO (1) | NO954681D0 (cs) |
| OA (1) | OA10195A (cs) |
| PE (1) | PE31195A1 (cs) |
| PL (1) | PL311702A1 (cs) |
| SK (1) | SK142495A3 (cs) |
| TW (1) | TW279866B (cs) |
| WO (1) | WO1994027989A1 (cs) |
| ZA (1) | ZA943494B (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995009157A1 (en) * | 1993-09-30 | 1995-04-06 | Yamanouchi Pharmaceutical Co., Ltd. | Azole derivative and pharmaceutical composition thereof |
| WO1996014090A1 (en) * | 1994-11-07 | 1996-05-17 | Janssen Pharmaceutica N.V. | Compositions comprising carbazoles and cyclodextrins |
| EP0820989A4 (en) * | 1995-03-01 | 1998-05-06 | Yamanouchi Pharma Co Ltd | IMIDAZOLE DERIVATIVES AND MEDICINAL COMPOSITION BASED ON SAID DERIVATIVES |
| DE69810760T2 (de) * | 1997-02-21 | 2003-11-20 | Takeda Chemical Industries, Ltd. | Verbindungen mit kondensierten ringen, verfahren zu ihrer herstellung und ihre anwendung |
| DE60119963T2 (de) | 2000-11-17 | 2006-10-05 | Takeda Pharmaceutical Co. Ltd. | Imidazol derivate, ihre herstellung und ihre verwendung |
| ATE502030T1 (de) | 2000-11-20 | 2011-04-15 | Takeda Pharmaceutical | Imidazolderivate, verfahren zu deren herstellung und deren verwendung |
| EP1348706B1 (en) | 2000-12-08 | 2009-08-19 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| WO2007002181A2 (en) * | 2005-06-24 | 2007-01-04 | 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 |
| EA021011B1 (ru) | 2009-06-26 | 2015-03-31 | Новартис Аг | 1,3-ДИЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ ИМИДАЗОЛИДИН-2-ОНА В КАЧЕСТВЕ ИНГИБИТОРОВ Cyp 17 |
| 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 |
| PT2568806T (pt) | 2010-05-12 | 2016-08-05 | Radius Health Inc | Regimes terapêuticos |
| WO2012018948A2 (en) | 2010-08-04 | 2012-02-09 | Pellficure Pharmaceuticals, Inc. | Novel treatment of prostate carcinoma |
| JP2013537210A (ja) | 2010-09-16 | 2013-09-30 | ノバルティス アーゲー | １７α−ヒドロキシラーゼ／Ｃ１７，２０−リアーゼ阻害剤 |
| WO2012047617A1 (en) | 2010-09-28 | 2012-04-12 | Radius Health, Inc. | Selective androgen receptor modulators |
| CN103649073B (zh) | 2011-04-28 | 2016-04-13 | 诺瓦提斯公司 | 17α-羟化酶/C17,20-裂合酶抑制剂 |
| US9492460B2 (en) * | 2013-02-27 | 2016-11-15 | Bristol-Myers Squibb Company | Carbazole compounds useful as bromodomain inhibitors |
| US20160022606A1 (en) | 2013-03-14 | 2016-01-28 | 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 |
| LT3122426T (lt) | 2014-03-28 | 2023-03-10 | Duke University | Krūties vėžio gydymas, naudojant selektyvius estrogenų receptorių moduliatorius |
| EP3191087A1 (en) | 2014-09-12 | 2017-07-19 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| PL3474841T3 (pl) | 2016-06-22 | 2022-07-11 | Ellipses Pharma Ltd | Sposoby leczenia nowotworu złośliwego piersi ar+ |
| AU2017350690A1 (en) | 2016-10-24 | 2019-06-13 | Pellficure Pharmaceuticals Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| KR102557321B1 (ko) | 2017-01-05 | 2023-07-18 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
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 SK SK1424-95A patent/SK142495A3/sk unknown
- 1994-05-19 CZ CZ953051A patent/CZ305195A3/cs unknown
- 1994-05-19 HU HU9503321A patent/HUT73790A/hu unknown
- 1994-05-19 PL PL94311702A patent/PL311702A1/xx unknown
- 1994-05-19 WO PCT/EP1994/001613 patent/WO1994027989A1/en not_active Ceased
- 1994-05-19 JP JP7500181A patent/JPH08510455A/ja active Pending
- 1994-05-19 CN CN94192683A patent/CN1126473A/zh active Pending
- 1994-05-19 AU AU69287/94A patent/AU6928794A/en not_active Abandoned
- 1994-05-19 CA CA002162921A patent/CA2162921A1/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
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1995
- 1995-11-17 OA OA60742A patent/OA10195A/en unknown
- 1995-11-20 FI FI955587A patent/FI955587A0/fi not_active Application Discontinuation
- 1995-11-20 NO NO954681A patent/NO954681D0/no unknown
- 1995-11-21 BG BG100154A patent/BG100154A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA10195A (en) | 1996-12-18 |
| EP0699196A1 (en) | 1996-03-06 |
| FI955587A7 (fi) | 1995-11-20 |
| FI955587A0 (fi) | 1995-11-20 |
| ZA943494B (en) | 1995-01-23 |
| WO1994027989A1 (en) | 1994-12-08 |
| CN1126473A (zh) | 1996-07-10 |
| NO954681L (no) | 1995-11-20 |
| CZ305195A3 (en) | 1996-06-12 |
| GB9310635D0 (en) | 1993-07-07 |
| BG100154A (en) | 1996-07-31 |
| HUT73790A (en) | 1996-09-30 |
| HU9503321D0 (en) | 1996-01-29 |
| NO954681D0 (no) | 1995-11-20 |
| TW279866B (cs) | 1996-07-01 |
| PL311702A1 (en) | 1996-03-04 |
| JPH08510455A (ja) | 1996-11-05 |
| CA2162921A1 (en) | 1994-12-08 |
| AU6928794A (en) | 1994-12-20 |
| IL109703A0 (en) | 1994-08-26 |
| PE31195A1 (es) | 1995-10-18 |
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