CA2461363A1 - Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors - Google Patents
Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors Download PDFInfo
- Publication number
- CA2461363A1 CA2461363A1 CA002461363A CA2461363A CA2461363A1 CA 2461363 A1 CA2461363 A1 CA 2461363A1 CA 002461363 A CA002461363 A CA 002461363A CA 2461363 A CA2461363 A CA 2461363A CA 2461363 A1 CA2461363 A1 CA 2461363A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- indole
- alkyl
- bromo
- methyl
- 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.)
- Abandoned
Links
- 150000002473 indoazoles Chemical class 0.000 title abstract description 12
- KDWAJWXWMMNKHA-UHFFFAOYSA-N 2-pyridin-3-yl-1h-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CN=C1 KDWAJWXWMMNKHA-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000002697 lyase inhibitor Substances 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 89
- 102000004317 Lyases Human genes 0.000 claims abstract description 41
- 108090000856 Lyases Proteins 0.000 claims abstract description 41
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 26
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 20
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 127
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 241000282465 Canis Species 0.000 claims description 4
- 241000283073 Equus caballus Species 0.000 claims description 4
- 241000282324 Felis Species 0.000 claims description 4
- 241000288906 Primates Species 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 35
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 20
- 102000004190 Enzymes Human genes 0.000 abstract description 17
- 108090000790 Enzymes Proteins 0.000 abstract description 17
- 239000003112 inhibitor Substances 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- 238000005160 1H NMR spectroscopy Methods 0.000 description 58
- 239000000203 mixture Substances 0.000 description 56
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 53
- 125000000217 alkyl group Chemical group 0.000 description 51
- -1 cortisol) Chemical compound 0.000 description 49
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 41
- 230000000694 effects Effects 0.000 description 41
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 38
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 36
- 239000003098 androgen Substances 0.000 description 34
- 238000004128 high performance liquid chromatography Methods 0.000 description 31
- CSDIPVWFZZEUMT-UHFFFAOYSA-N 5-bromo-1-pyridin-3-ylindole Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CN=C1 CSDIPVWFZZEUMT-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 29
- 201000010099 disease Diseases 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- 101150041968 CDC13 gene Proteins 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 22
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- RAIRKTKYHPQVQZ-UHFFFAOYSA-N 1-pyridin-3-ylindol-5-amine Chemical compound C1=CC2=CC(N)=CC=C2N1C1=CC=CN=C1 RAIRKTKYHPQVQZ-UHFFFAOYSA-N 0.000 description 20
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 20
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 20
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
- 239000000499 gel Substances 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 19
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 18
- 229960002847 prasterone Drugs 0.000 description 18
- WPGZNPGXADYGMZ-UHFFFAOYSA-N 5-bromo-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(Br)C=C2C=C1 WPGZNPGXADYGMZ-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 description 16
- 239000000262 estrogen Substances 0.000 description 16
- 229940011871 estrogen Drugs 0.000 description 16
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
- 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 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 229940030486 androgens Drugs 0.000 description 14
- 230000001419 dependent effect Effects 0.000 description 14
- 238000004809 thin layer chromatography Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 238000003556 assay Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
- 239000002207 metabolite Substances 0.000 description 12
- 238000002821 scintillation proximity assay Methods 0.000 description 12
- 229940079593 drug Drugs 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 239000000186 progesterone Substances 0.000 description 10
- 229960003387 progesterone Drugs 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- KOUOYJYRICGOSC-UHFFFAOYSA-N 5-pyridin-3-yl-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C1=CC=CN=C1 KOUOYJYRICGOSC-UHFFFAOYSA-N 0.000 description 9
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 9
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 229960002478 aldosterone Drugs 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 229940088597 hormone Drugs 0.000 description 9
- 239000005556 hormone Substances 0.000 description 9
- 229960000890 hydrocortisone Drugs 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000002395 mineralocorticoid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ASXFMIDIRZPCGK-UHFFFAOYSA-N (4-methylpyridin-3-yl)boronic acid Chemical compound CC1=CC=NC=C1B(O)O ASXFMIDIRZPCGK-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- 238000000423 cell based assay Methods 0.000 description 7
- 239000003862 glucocorticoid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 231100000252 nontoxic Toxicity 0.000 description 7
- 230000003000 nontoxic effect Effects 0.000 description 7
- 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 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000003431 steroids Chemical class 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 229960003604 testosterone Drugs 0.000 description 7
- GSQZOLXWFQQJHJ-UHFFFAOYSA-N 3-bromo-4-methylpyridine Chemical compound CC1=CC=NC=C1Br GSQZOLXWFQQJHJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010256 biochemical assay Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 150000002475 indoles Chemical class 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229960000249 pregnenolone Drugs 0.000 description 6
- 210000002307 prostate Anatomy 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 5
- STVHMYNPQCLUNJ-UHFFFAOYSA-N 5-bromo-1h-indazole Chemical compound BrC1=CC=C2NN=CC2=C1 STVHMYNPQCLUNJ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000001919 adrenal effect Effects 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 230000004075 alteration Effects 0.000 description 5
- 108010080146 androgen receptors Proteins 0.000 description 5
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- 229940037128 systemic glucocorticoids Drugs 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 4
- CELKOWQJPVJKIL-UHFFFAOYSA-N 3-fluoropyridine Chemical compound FC1=CC=CN=C1 CELKOWQJPVJKIL-UHFFFAOYSA-N 0.000 description 4
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 4
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
- 102100032187 Androgen receptor Human genes 0.000 description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 4
- 229940122014 Lyase inhibitor Drugs 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 4
- 230000002159 abnormal effect Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 230000002280 anti-androgenic effect Effects 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 4
- 229940035638 gonadotropin-releasing hormone Drugs 0.000 description 4
- 238000005805 hydroxylation reaction Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000002611 ovarian Effects 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- OZZAYJQNMKMUSD-DMISRAGPSA-N pregnenolone succinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OZZAYJQNMKMUSD-DMISRAGPSA-N 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000003270 steroid hormone Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 3
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 3
- JERGUCIJOXJXHF-UHFFFAOYSA-N 17alpha-Hydroxypregnenolone Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 JERGUCIJOXJXHF-UHFFFAOYSA-N 0.000 description 3
- JERGUCIJOXJXHF-TVWVXWENSA-N 17alpha-hydroxypregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JERGUCIJOXJXHF-TVWVXWENSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- JNAKJYAPSODBSS-UHFFFAOYSA-N 3-(5-bromoindol-1-yl)benzonitrile Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CC(C#N)=C1 JNAKJYAPSODBSS-UHFFFAOYSA-N 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- WKZMJMOBFMQGPE-UHFFFAOYSA-N 5-bromo-1-(2-methylpyridin-3-yl)indole Chemical compound CC1=NC=CC=C1N1C2=CC=C(Br)C=C2C=C1 WKZMJMOBFMQGPE-UHFFFAOYSA-N 0.000 description 3
- AGAPJSSFXAYNSD-UHFFFAOYSA-N 5-bromo-1-(6-methylpyridin-3-yl)indole Chemical compound C1=NC(C)=CC=C1N1C2=CC=C(Br)C=C2C=C1 AGAPJSSFXAYNSD-UHFFFAOYSA-N 0.000 description 3
- WRDPGCJEFRKLTA-UHFFFAOYSA-N 5-bromo-1-pyridin-3-ylindazole Chemical compound N1=CC2=CC(Br)=CC=C2N1C1=CC=CN=C1 WRDPGCJEFRKLTA-UHFFFAOYSA-N 0.000 description 3
- JVIXGGITTVDVRY-UHFFFAOYSA-N 5-bromo-2,3-dimethyl-1-pyridin-3-ylindole Chemical compound CC1=C(C)C2=CC(Br)=CC=C2N1C1=CC=CN=C1 JVIXGGITTVDVRY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 229960003473 androstanolone Drugs 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- 210000000481 breast Anatomy 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229940127089 cytotoxic agent Drugs 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229960005309 estradiol Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000001794 hormone therapy Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 238000006977 lyase reaction Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 238000011474 orchiectomy Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229940037129 plain mineralocorticoids for systemic use Drugs 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000003127 radioimmunoassay Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
- KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 2
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 2
- ZWCCRMIIWIMBJB-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-pyridin-3-ylindazole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC1=CC=NC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=N1 ZWCCRMIIWIMBJB-UHFFFAOYSA-N 0.000 description 2
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- QMMHNYYHQRUFGR-UHFFFAOYSA-N 1-pyridin-3-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 QMMHNYYHQRUFGR-UHFFFAOYSA-N 0.000 description 2
- YIDSZXZHWLAVEN-UHFFFAOYSA-N 1-pyridin-3-ylindol-5-amine;dihydrochloride Chemical compound Cl.Cl.C1=CC2=CC(N)=CC=C2N1C1=CC=CN=C1 YIDSZXZHWLAVEN-UHFFFAOYSA-N 0.000 description 2
- DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 description 2
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 2
- VPEDVSRGXXVBOT-UHFFFAOYSA-N 2-(5-bromoindol-1-yl)benzonitrile Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CC=C1C#N VPEDVSRGXXVBOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HTFXWAOSQODIBI-UHFFFAOYSA-N 2-benzyl-1,3-dihydropyrrolo[3,4-c]pyridine Chemical compound C1C2=CC=NC=C2CN1CC1=CC=CC=C1 HTFXWAOSQODIBI-UHFFFAOYSA-N 0.000 description 2
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 2
- JTIUHNWNGZLXNJ-UHFFFAOYSA-N 3-(5-bromoindol-1-yl)benzamide Chemical compound NC(=O)C1=CC=CC(N2C3=CC=C(Br)C=C3C=C2)=C1 JTIUHNWNGZLXNJ-UHFFFAOYSA-N 0.000 description 2
- AIPWPTPHMIYYOX-UHFFFAOYSA-N 3-bromo-2-methylpyridine Chemical compound CC1=NC=CC=C1Br AIPWPTPHMIYYOX-UHFFFAOYSA-N 0.000 description 2
- OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- ZNRGSYUVFVNSAW-UHFFFAOYSA-N 3-nitrophenylboronic acid Chemical compound OB(O)C1=CC=CC([N+]([O-])=O)=C1 ZNRGSYUVFVNSAW-UHFFFAOYSA-N 0.000 description 2
- AFPRGNMUIDCSDU-UHFFFAOYSA-N 4-(1-pyridin-3-ylindol-5-yl)morpholine Chemical compound C1COCCN1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 AFPRGNMUIDCSDU-UHFFFAOYSA-N 0.000 description 2
- ASOVBFDJDGPYJS-UHFFFAOYSA-N 5-bromo-1-phenylindole Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CC=C1 ASOVBFDJDGPYJS-UHFFFAOYSA-N 0.000 description 2
- GZHMGISVFCQZPX-UHFFFAOYSA-N 5-bromo-1-pyridin-2-ylindazole Chemical compound N1=CC2=CC(Br)=CC=C2N1C1=CC=CC=N1 GZHMGISVFCQZPX-UHFFFAOYSA-N 0.000 description 2
- OFKWIQJLYCKDNY-UHFFFAOYSA-N 5-bromo-2-methylpyridine Chemical compound CC1=CC=C(Br)C=N1 OFKWIQJLYCKDNY-UHFFFAOYSA-N 0.000 description 2
- VJZLJWQCBKNJAT-UHFFFAOYSA-N 5-bromo-2-pyridin-2-ylindazole Chemical compound C1=C2C=C(Br)C=CC2=NN1C1=CC=CC=N1 VJZLJWQCBKNJAT-UHFFFAOYSA-N 0.000 description 2
- JCYXZFZCAIZEHZ-UHFFFAOYSA-N 5-pyrimidin-5-yl-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C1=CN=CN=C1 JCYXZFZCAIZEHZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 235000003911 Arachis Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 102000014654 Aromatase Human genes 0.000 description 2
- 108010078554 Aromatase Proteins 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 208000008448 Congenital adrenal hyperplasia Diseases 0.000 description 2
- 208000016998 Conn syndrome Diseases 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229940124766 Cyp17 inhibitor Drugs 0.000 description 2
- 108010007167 Cytochromes b5 Proteins 0.000 description 2
- 102000007605 Cytochromes b5 Human genes 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 206010072079 Glucocorticoid deficiency Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010033128 Ovarian cancer Diseases 0.000 description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 description 2
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102100028255 Renin Human genes 0.000 description 2
- 108090000783 Renin Proteins 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 206010041277 Sodium retention Diseases 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 210000004404 adrenal cortex Anatomy 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229960005471 androstenedione Drugs 0.000 description 2
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000036983 biotransformation Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000009261 endocrine therapy Methods 0.000 description 2
- 229940034984 endocrine therapy antineoplastic and immunomodulating agent Drugs 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000001952 enzyme assay Methods 0.000 description 2
- 229960003399 estrone Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 2
- 229960004039 finasteride Drugs 0.000 description 2
- 229960002074 flutamide Drugs 0.000 description 2
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000003163 gonadal steroid hormone Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 229960002899 hydroxyprogesterone Drugs 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229960004125 ketoconazole Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 125000005151 nonafluorobutanesulfonyl group Chemical group FC(C(C(S(=O)(=O)*)(F)F)(F)F)(C(F)(F)F)F 0.000 description 2
- 239000003956 nonsteroidal anti androgen Substances 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 208000013846 primary aldosteronism Diseases 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 235000011069 sorbitan monooleate Nutrition 0.000 description 2
- 239000001593 sorbitan monooleate Substances 0.000 description 2
- 229940035049 sorbitan monooleate Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000002381 testicular Effects 0.000 description 2
- 210000001550 testis Anatomy 0.000 description 2
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 210000005239 tubule Anatomy 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- ZKAOVABYLXQUTI-UHFFFAOYSA-N (2-acetylphenyl)boronic acid Chemical compound CC(=O)C1=CC=CC=C1B(O)O ZKAOVABYLXQUTI-UHFFFAOYSA-N 0.000 description 1
- NPLZNDDFVCGRAG-UHFFFAOYSA-N (2-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C#N NPLZNDDFVCGRAG-UHFFFAOYSA-N 0.000 description 1
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- CHCWUTJYLUBETR-UHFFFAOYSA-N (3-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC(B(O)O)=C1 CHCWUTJYLUBETR-UHFFFAOYSA-N 0.000 description 1
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 1
- BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- WRQNDLDUNQMTCL-UHFFFAOYSA-N (4-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=C1 WRQNDLDUNQMTCL-UHFFFAOYSA-N 0.000 description 1
- RZCPLOMUUCFPQA-UHFFFAOYSA-N (4-ethylphenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C=C1 RZCPLOMUUCFPQA-UHFFFAOYSA-N 0.000 description 1
- PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 1
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- POVISIHLNLVTGJ-UHFFFAOYSA-N 1,4-bis(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1C1=CC=CC2=C1C=CN2C1=CN=CC=C1C POVISIHLNLVTGJ-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- CXZOADKFUPMQOZ-UHFFFAOYSA-N 1,5-bis(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3C(=CC=NC=3)C)C2=C1 CXZOADKFUPMQOZ-UHFFFAOYSA-N 0.000 description 1
- MSWMGNWCQQRYSY-UHFFFAOYSA-N 1,5-bis(4-methylpyridin-3-yl)indole-3-carbonitrile Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2C#N)C=3C(=CC=NC=3)C)C2=C1 MSWMGNWCQQRYSY-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- MQRZNQDJMZMURX-UHFFFAOYSA-N 1,5-dipyridin-3-ylindazole Chemical compound C12=CC=C(C=3C=NC=CC=3)C=C2C=NN1C1=CC=CN=C1 MQRZNQDJMZMURX-UHFFFAOYSA-N 0.000 description 1
- GSGXWIJZLLUAMC-UHFFFAOYSA-N 1,5-dipyridin-3-ylindole Chemical compound C1=CC2=CC(C=3C=NC=CC=3)=CC=C2N1C1=CC=CN=C1 GSGXWIJZLLUAMC-UHFFFAOYSA-N 0.000 description 1
- WBSTVYXLCKZFLU-UHFFFAOYSA-N 1,6-bis(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1C1=CC=C(C=CN2C=3C(=CC=NC=3)C)C2=C1 WBSTVYXLCKZFLU-UHFFFAOYSA-N 0.000 description 1
- YFVKHKCZBSGZPE-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(propylamino)propan-1-one Chemical compound CCCNC(C)C(=O)C1=CC=C2OCOC2=C1 YFVKHKCZBSGZPE-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- KSZCAOXXPXQKFH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-pyridin-3-ylindole Chemical compound ClC1=CC=CC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=C1 KSZCAOXXPXQKFH-UHFFFAOYSA-N 0.000 description 1
- UMEQNMOBERTGOX-UHFFFAOYSA-N 1-(2-chlorophenyl)-6-pyridin-3-ylindole Chemical compound ClC1=CC=CC=C1N1C2=CC(C=3C=NC=CC=3)=CC=C2C=C1 UMEQNMOBERTGOX-UHFFFAOYSA-N 0.000 description 1
- WXEYKYCXRPAAJT-UHFFFAOYSA-N 1-(2-fluorophenyl)-4-pyridin-3-ylindole Chemical compound FC1=CC=CC=C1N1C2=CC=CC(C=3C=NC=CC=3)=C2C=C1 WXEYKYCXRPAAJT-UHFFFAOYSA-N 0.000 description 1
- DBALRPYRMRDWSM-UHFFFAOYSA-N 1-(2-fluorophenyl)-5-pyridin-3-ylindole Chemical compound FC1=CC=CC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=C1 DBALRPYRMRDWSM-UHFFFAOYSA-N 0.000 description 1
- VQQKEPPGYGFIQB-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-5-pyridin-3-ylindole Chemical compound CC1=NC=CC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=C1 VQQKEPPGYGFIQB-UHFFFAOYSA-N 0.000 description 1
- TYJMAKMGQQFOIB-UHFFFAOYSA-N 1-(3-bromophenyl)-4-pyridin-3-ylindole Chemical compound BrC1=CC=CC(N2C3=CC=CC(=C3C=C2)C=2C=NC=CC=2)=C1 TYJMAKMGQQFOIB-UHFFFAOYSA-N 0.000 description 1
- IRCGCYZSRHSIOS-UHFFFAOYSA-N 1-(3-bromophenyl)-5-pyridin-3-ylindole Chemical compound BrC1=CC=CC(N2C3=CC=C(C=C3C=C2)C=2C=NC=CC=2)=C1 IRCGCYZSRHSIOS-UHFFFAOYSA-N 0.000 description 1
- ZZRPAVQVVOKXBB-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-pyridin-3-ylindole Chemical compound ClC1=CC=CC(N2C3=CC=C(C=C3C=C2)C=2C=NC=CC=2)=C1 ZZRPAVQVVOKXBB-UHFFFAOYSA-N 0.000 description 1
- NRQWKBXSPCUXLV-UHFFFAOYSA-N 1-(3-chlorophenyl)-6-pyridin-3-ylindole Chemical compound ClC1=CC=CC(N2C3=CC(=CC=C3C=C2)C=2C=NC=CC=2)=C1 NRQWKBXSPCUXLV-UHFFFAOYSA-N 0.000 description 1
- AXWOLFBUQIKTDT-UHFFFAOYSA-N 1-(3-fluorophenyl)-4-pyridin-3-ylindole Chemical compound FC1=CC=CC(N2C3=CC=CC(=C3C=C2)C=2C=NC=CC=2)=C1 AXWOLFBUQIKTDT-UHFFFAOYSA-N 0.000 description 1
- CVHZBZJJXORCIR-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-pyridin-3-ylindole Chemical compound FC1=CC=CC(N2C3=CC=C(C=C3C=C2)C=2C=NC=CC=2)=C1 CVHZBZJJXORCIR-UHFFFAOYSA-N 0.000 description 1
- UAUXWJLPMNHIDR-UHFFFAOYSA-N 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole Chemical compound O1C(C)(C)C(C)(C)OB1N1C2=CC=CC=C2C=C1 UAUXWJLPMNHIDR-UHFFFAOYSA-N 0.000 description 1
- XUJLJAQVBUSSAH-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-4-(3-nitrophenyl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C=C(C=CC=3)[N+]([O-])=O)=C2C=C1 XUJLJAQVBUSSAH-UHFFFAOYSA-N 0.000 description 1
- YBVWADRVNCNIKK-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-4-phenylindole Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C=CC=CC=3)=C2C=C1 YBVWADRVNCNIKK-UHFFFAOYSA-N 0.000 description 1
- LFCFPCRIVAHNMN-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-(2h-pyrimidin-1-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(N3C=CC=NC3)C=C2C=C1 LFCFPCRIVAHNMN-UHFFFAOYSA-N 0.000 description 1
- YSQKCYQFQVGAOH-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-(3-nitrophenyl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(C=CC=3)[N+]([O-])=O)C=C2C=C1 YSQKCYQFQVGAOH-UHFFFAOYSA-N 0.000 description 1
- FSYHCSCGMYZMOY-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-[4-(trifluoromethyl)phenyl]indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CC(=CC=3)C(F)(F)F)C=C2C=C1 FSYHCSCGMYZMOY-UHFFFAOYSA-N 0.000 description 1
- PKKZOKIBHHPTCT-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-phenylindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CC=CC=3)C=C2C=C1 PKKZOKIBHHPTCT-UHFFFAOYSA-N 0.000 description 1
- SPHQJEAODAUOER-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-phenylmethoxyindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(OCC=3C=CC=CC=3)C=C2C=C1 SPHQJEAODAUOER-UHFFFAOYSA-N 0.000 description 1
- UHJZOGXNAASMRV-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-pyridin-3-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=C1 UHJZOGXNAASMRV-UHFFFAOYSA-N 0.000 description 1
- ISPWMUGGLJQWJE-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-pyridin-4-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CN=CC=3)C=C2C=C1 ISPWMUGGLJQWJE-UHFFFAOYSA-N 0.000 description 1
- SEOPICPBSHMUPB-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-pyrimidin-5-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=NC=NC=3)C=C2C=C1 SEOPICPBSHMUPB-UHFFFAOYSA-N 0.000 description 1
- NCFKROUHOLCPNT-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-5-thiophen-3-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C3=CSC=C3)C=C2C=C1 NCFKROUHOLCPNT-UHFFFAOYSA-N 0.000 description 1
- ZKYANEKLBRTBLX-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-6-(2h-pyrimidin-1-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(N3C=CC=NC3)=CC=C2C=C1 ZKYANEKLBRTBLX-UHFFFAOYSA-N 0.000 description 1
- KDSAJUUIEIRBTE-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-6-pyridin-4-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC(C=3C=CN=CC=3)=CC=C2C=C1 KDSAJUUIEIRBTE-UHFFFAOYSA-N 0.000 description 1
- FICJBVAPYYLDSH-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)-6-thiophen-3-ylindole Chemical compound CC1=CC=NC=C1N1C2=CC(C3=CSC=C3)=CC=C2C=C1 FICJBVAPYYLDSH-UHFFFAOYSA-N 0.000 description 1
- JUYPSRLWPMZZNG-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)indole-5-carbonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C#N)C=C2C=C1 JUYPSRLWPMZZNG-UHFFFAOYSA-N 0.000 description 1
- FNBLCKGMFOGQSI-UHFFFAOYSA-N 1-[2-(1-pyridin-3-ylindol-5-yl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 FNBLCKGMFOGQSI-UHFFFAOYSA-N 0.000 description 1
- ZCJAYDKWZAWMPR-UHFFFAOYSA-N 1-chloro-2-fluorobenzene Chemical compound FC1=CC=CC=C1Cl ZCJAYDKWZAWMPR-UHFFFAOYSA-N 0.000 description 1
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- QDSJDCZPXBRXLG-UHFFFAOYSA-N 1-phenyl-4-pyridin-3-ylindole Chemical compound C1=CC2=C(C=3C=NC=CC=3)C=CC=C2N1C1=CC=CC=C1 QDSJDCZPXBRXLG-UHFFFAOYSA-N 0.000 description 1
- WUNZZEYYEMOHCQ-UHFFFAOYSA-N 1-phenyl-5-pyridin-3-ylindole Chemical compound C1=CC2=CC(C=3C=NC=CC=3)=CC=C2N1C1=CC=CC=C1 WUNZZEYYEMOHCQ-UHFFFAOYSA-N 0.000 description 1
- PWCNZJRYKBBZHQ-UHFFFAOYSA-N 1-phenyl-n-(1-pyridin-3-ylindol-5-yl)methanesulfonamide Chemical compound C=1C=C2N(C=3C=NC=CC=3)C=CC2=CC=1NS(=O)(=O)CC1=CC=CC=C1 PWCNZJRYKBBZHQ-UHFFFAOYSA-N 0.000 description 1
- ZTEHKKQOQJEVBN-UHFFFAOYSA-N 1-pyridin-2-yl-5-pyridin-3-ylindole Chemical compound C1=CC2=CC(C=3C=NC=CC=3)=CC=C2N1C1=CC=CC=N1 ZTEHKKQOQJEVBN-UHFFFAOYSA-N 0.000 description 1
- GNOZXDYEFCNKMP-UHFFFAOYSA-N 1-pyridin-3-yl-4-[3-(trifluoromethyl)phenyl]indole Chemical compound FC(F)(F)C1=CC=CC(C=2C=3C=CN(C=3C=CC=2)C=2C=NC=CC=2)=C1 GNOZXDYEFCNKMP-UHFFFAOYSA-N 0.000 description 1
- OBJIBKHULYPSAV-UHFFFAOYSA-N 1-pyridin-3-yl-5-[2-(trifluoromethyl)phenyl]indole Chemical compound FC(F)(F)C1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 OBJIBKHULYPSAV-UHFFFAOYSA-N 0.000 description 1
- QYPDYAPHKYJZSH-UHFFFAOYSA-N 1-pyridin-3-yl-5-[3-(trifluoromethyl)phenyl]indole Chemical compound FC(F)(F)C1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 QYPDYAPHKYJZSH-UHFFFAOYSA-N 0.000 description 1
- YQAUACPJUGHPGL-UHFFFAOYSA-N 1-pyridin-3-yl-5-[4-(trifluoromethyl)phenyl]indole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 YQAUACPJUGHPGL-UHFFFAOYSA-N 0.000 description 1
- DKTQNVLSXDWNBT-UHFFFAOYSA-N 1-pyridin-3-yl-5-pyridin-4-ylindole Chemical compound C1=CC2=CC(C=3C=CN=CC=3)=CC=C2N1C1=CC=CN=C1 DKTQNVLSXDWNBT-UHFFFAOYSA-N 0.000 description 1
- FIDJETJNCYKENG-UHFFFAOYSA-N 1-pyridin-3-yl-5-pyrrolidin-1-ylindole Chemical compound C1CCCN1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 FIDJETJNCYKENG-UHFFFAOYSA-N 0.000 description 1
- FKQLBRCBPGPBND-UHFFFAOYSA-N 1-pyridin-3-yl-5-thiophen-3-ylindole Chemical compound S1C=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 FKQLBRCBPGPBND-UHFFFAOYSA-N 0.000 description 1
- QJNUQDCNQMKTBA-UHFFFAOYSA-N 1-pyridin-3-yl-6-[4-(trifluoromethyl)phenyl]indole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C=CN2C=3C=NC=CC=3)C2=C1 QJNUQDCNQMKTBA-UHFFFAOYSA-N 0.000 description 1
- GPLWZTFTXZZINB-UHFFFAOYSA-N 1-pyridin-3-yl-6-thiophen-3-ylindole Chemical compound S1C=CC(C=2C=C3N(C=4C=NC=CC=4)C=CC3=CC=2)=C1 GPLWZTFTXZZINB-UHFFFAOYSA-N 0.000 description 1
- VLRCKMRUGUJPQJ-UHFFFAOYSA-N 1-pyridin-3-ylindol-5-amine;hydrochloride Chemical compound Cl.C1=CC2=CC(N)=CC=C2N1C1=CC=CN=C1 VLRCKMRUGUJPQJ-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- 101150016096 17 gene Proteins 0.000 description 1
- 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 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 description 1
- VHADYSUJZAPXOW-UHFFFAOYSA-N 1h-indol-5-ylboronic acid Chemical compound OB(O)C1=CC=C2NC=CC2=C1 VHADYSUJZAPXOW-UHFFFAOYSA-N 0.000 description 1
- YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 1
- ZPGBWZITAJVCLV-UHFFFAOYSA-N 2,3-dimethyl-1,5-dipyridin-3-ylindole Chemical compound CC1=C(C)C2=CC(C=3C=NC=CC=3)=CC=C2N1C1=CC=CN=C1 ZPGBWZITAJVCLV-UHFFFAOYSA-N 0.000 description 1
- CELLJWUVMKEJDY-UHFFFAOYSA-N 2,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(F)C(S(Cl)(=O)=O)=C1 CELLJWUVMKEJDY-UHFFFAOYSA-N 0.000 description 1
- ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 1
- RWEYGHQNAVUYSL-UHFFFAOYSA-N 2-(5-pyridin-3-ylindol-1-yl)benzonitrile Chemical compound N#CC1=CC=CC=C1N1C2=CC=C(C=3C=NC=CC=3)C=C2C=C1 RWEYGHQNAVUYSL-UHFFFAOYSA-N 0.000 description 1
- OTEJAVHQRMYZJQ-UHFFFAOYSA-N 2-(6-pyridin-3-ylindol-1-yl)benzonitrile Chemical compound N#CC1=CC=CC=C1N1C2=CC(C=3C=NC=CC=3)=CC=C2C=C1 OTEJAVHQRMYZJQ-UHFFFAOYSA-N 0.000 description 1
- ZIZGWNOAHUCACM-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1S(Cl)(=O)=O ZIZGWNOAHUCACM-UHFFFAOYSA-N 0.000 description 1
- FHLQLDPMINSWRK-UHFFFAOYSA-N 2-[1-(4-methylpyridin-3-yl)indol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C(=CC=CC=3)C#N)=C2C=C1 FHLQLDPMINSWRK-UHFFFAOYSA-N 0.000 description 1
- XWWUNESZUGTKTM-UHFFFAOYSA-N 2-[1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C(=CC=CC=3)C#N)C=C2C=C1 XWWUNESZUGTKTM-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- PRCWZOFUAHTIMR-UHFFFAOYSA-N 2-[5-(4-methylpyridin-3-yl)indol-1-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3C(=CC=CC=3)C#N)C2=C1 PRCWZOFUAHTIMR-UHFFFAOYSA-N 0.000 description 1
- RFPYLCKOVLRFSX-UHFFFAOYSA-N 2-[6-(4-methylpyridin-3-yl)indol-1-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=CC=C(C=CN2C=3C(=CC=CC=3)C#N)C2=C1 RFPYLCKOVLRFSX-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- ZSZKAQCISWFDCQ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC=C1S(Cl)(=O)=O ZSZKAQCISWFDCQ-UHFFFAOYSA-N 0.000 description 1
- VDMLOEVKJPETTN-UHFFFAOYSA-N 2-methyl-1,5-bis(4-methylpyridin-3-yl)indole Chemical compound CC1=CC2=CC(C=3C(=CC=NC=3)C)=CC=C2N1C1=CN=CC=C1C VDMLOEVKJPETTN-UHFFFAOYSA-N 0.000 description 1
- NSITWKWRZZOYQJ-UHFFFAOYSA-N 2-methyl-5-phenyl-1-pyridin-3-ylindole Chemical compound CC1=CC2=CC(C=3C=CC=CC=3)=CC=C2N1C1=CC=CN=C1 NSITWKWRZZOYQJ-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- FSGLUBQENACWCC-UHFFFAOYSA-N 3,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1F FSGLUBQENACWCC-UHFFFAOYSA-N 0.000 description 1
- HUINQEZEJHXLJI-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=3C=CN(C=3C=CC=2)C=2C=NC=CC=2)=C1 HUINQEZEJHXLJI-UHFFFAOYSA-N 0.000 description 1
- MZOUHRRKFCULSZ-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 MZOUHRRKFCULSZ-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- LXYWKTOJORWCCQ-UHFFFAOYSA-N 3-(5-pyridin-3-ylindol-1-yl)benzonitrile Chemical compound N#CC1=CC=CC(N2C3=CC=C(C=C3C=C2)C=2C=NC=CC=2)=C1 LXYWKTOJORWCCQ-UHFFFAOYSA-N 0.000 description 1
- WAZXDRIRAZKKBQ-UHFFFAOYSA-N 3-(6-pyridin-3-ylindol-1-yl)benzonitrile Chemical compound N#CC1=CC=CC(N2C3=CC(=CC=C3C=C2)C=2C=NC=CC=2)=C1 WAZXDRIRAZKKBQ-UHFFFAOYSA-N 0.000 description 1
- KHCXGFNZZRXOND-UHFFFAOYSA-N 3-(bromomethyl)pyridine Chemical compound BrCC1=CC=CN=C1 KHCXGFNZZRXOND-UHFFFAOYSA-N 0.000 description 1
- BVTNOPKAHPIQER-UHFFFAOYSA-N 3-[1-(4-methylpyridin-3-yl)-3-propan-2-ylindol-5-yl]benzonitrile Chemical compound C12=CC=C(C=3C=C(C=CC=3)C#N)C=C2C(C(C)C)=CN1C1=CN=CC=C1C BVTNOPKAHPIQER-UHFFFAOYSA-N 0.000 description 1
- PHAFZIFJXJPAFJ-UHFFFAOYSA-N 3-[1-(4-methylpyridin-3-yl)indol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C=C(C=CC=3)C#N)=C2C=C1 PHAFZIFJXJPAFJ-UHFFFAOYSA-N 0.000 description 1
- MZBLWMRUTKRAEH-UHFFFAOYSA-N 3-[1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(C=CC=3)C#N)C=C2C=C1 MZBLWMRUTKRAEH-UHFFFAOYSA-N 0.000 description 1
- HPQOOBNCGIYQIJ-UHFFFAOYSA-N 3-[1-(6-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound C1=NC(C)=CC=C1N1C2=CC=C(C=3C=C(C=CC=3)C#N)C=C2C=C1 HPQOOBNCGIYQIJ-UHFFFAOYSA-N 0.000 description 1
- AUKFWGFZXUDBKL-UHFFFAOYSA-N 3-[2-methyl-1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2N1C1=CN=CC=C1C AUKFWGFZXUDBKL-UHFFFAOYSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- SEVKLDHWHBTQNZ-UHFFFAOYSA-N 3-[3-methyl-1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound C12=CC=C(C=3C=C(C=CC=3)C#N)C=C2C(C)=CN1C1=CN=CC=C1C SEVKLDHWHBTQNZ-UHFFFAOYSA-N 0.000 description 1
- MMNQTRVTARCOAY-UHFFFAOYSA-N 3-[4-(4-methylpyridin-3-yl)indol-1-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=CC=CC2=C1C=CN2C1=CC=CC(C#N)=C1 MMNQTRVTARCOAY-UHFFFAOYSA-N 0.000 description 1
- SKCSTTOTFMLXQJ-UHFFFAOYSA-N 3-[4-fluoro-1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(C=CC=3)C#N)C(F)=C2C=C1 SKCSTTOTFMLXQJ-UHFFFAOYSA-N 0.000 description 1
- AZINAVOCUUUHIC-UHFFFAOYSA-N 3-[5-(4-methylpyridin-3-yl)indol-1-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3C=C(C=CC=3)C#N)C2=C1 AZINAVOCUUUHIC-UHFFFAOYSA-N 0.000 description 1
- JGYQHCSUGBXIOL-UHFFFAOYSA-N 3-[7-chloro-1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=C(Cl)C=C(C=3C=C(C=CC=3)C#N)C=C2C=C1 JGYQHCSUGBXIOL-UHFFFAOYSA-N 0.000 description 1
- AKDOZAHGNXWARZ-UHFFFAOYSA-N 3-[7-methyl-1-(4-methylpyridin-3-yl)indazol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=C(C)C=C(C=3C=C(C=CC=3)C#N)C=C2C=N1 AKDOZAHGNXWARZ-UHFFFAOYSA-N 0.000 description 1
- GNMJGHVURSAEGR-UHFFFAOYSA-N 3-[7-methyl-1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=C(C)C=C(C=3C=C(C=CC=3)C#N)C=C2C=C1 GNMJGHVURSAEGR-UHFFFAOYSA-N 0.000 description 1
- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
- JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 1
- QXJUKWOEXLHWHN-UHFFFAOYSA-N 3-methyl-5-phenyl-1-pyridin-3-ylindole Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C(C)=CN1C1=CC=CN=C1 QXJUKWOEXLHWHN-UHFFFAOYSA-N 0.000 description 1
- VECRYHRUPCYWCZ-UHFFFAOYSA-N 3-propan-2-yl-1,5-dipyridin-3-ylindole Chemical compound C12=CC=C(C=3C=NC=CC=3)C=C2C(C(C)C)=CN1C1=CC=CN=C1 VECRYHRUPCYWCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 1
- BTSDVPPCZKTLFR-UHFFFAOYSA-N 4-(1-pyridin-3-ylindol-5-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 BTSDVPPCZKTLFR-UHFFFAOYSA-N 0.000 description 1
- BPTZGJVVGFAKDV-UHFFFAOYSA-N 4-(2-chlorophenyl)-1-pyridin-3-ylindole Chemical compound ClC1=CC=CC=C1C1=CC=CC2=C1C=CN2C1=CC=CN=C1 BPTZGJVVGFAKDV-UHFFFAOYSA-N 0.000 description 1
- YZHUROQQKWHGCT-UHFFFAOYSA-N 4-(3-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C=C(F)C=CC=3)=C2C=C1 YZHUROQQKWHGCT-UHFFFAOYSA-N 0.000 description 1
- HWIZKXOVUACPTH-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(OC)=CC=C1C1=CC=CC2=C1C=CN2C1=CC=CN=C1 HWIZKXOVUACPTH-UHFFFAOYSA-N 0.000 description 1
- YNVQWRXHXAYOPS-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC2=C1C=CN2C1=CC=CN=C1 YNVQWRXHXAYOPS-UHFFFAOYSA-N 0.000 description 1
- CKGLLFKNYUOLFQ-UHFFFAOYSA-N 4-(furan-3-yl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C3=COC=C3)=C2C=C1 CKGLLFKNYUOLFQ-UHFFFAOYSA-N 0.000 description 1
- GWECNMIFBLRDKP-UHFFFAOYSA-N 4-(furan-3-yl)-1-pyridin-3-ylindole Chemical compound O1C=CC(C=2C=3C=CN(C=3C=CC=2)C=2C=NC=CC=2)=C1 GWECNMIFBLRDKP-UHFFFAOYSA-N 0.000 description 1
- OZDCZHDOIBUGAJ-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)C=C1 OZDCZHDOIBUGAJ-UHFFFAOYSA-N 0.000 description 1
- BACURKVQLVEZHK-UHFFFAOYSA-N 4-[1-(4-methylpyridin-3-yl)indol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=CC(C=3C=CC(=CC=3)C#N)=C2C=C1 BACURKVQLVEZHK-UHFFFAOYSA-N 0.000 description 1
- OBKSSNHSRWUKNI-UHFFFAOYSA-N 4-[1-(4-methylpyridin-3-yl)indol-5-yl]benzonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CC(=CC=3)C#N)C=C2C=C1 OBKSSNHSRWUKNI-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- KJTYZDORHCDZPS-UHFFFAOYSA-N 4-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(C=NN2)C=2C3=CC=CC=C3N=CC=2)=N1 KJTYZDORHCDZPS-UHFFFAOYSA-N 0.000 description 1
- FXVDNCRTKXMSEZ-UHFFFAOYSA-N 4-acetylbenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 FXVDNCRTKXMSEZ-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 1
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 1
- SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 1
- DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
- NLPQBCDTVGOEHF-UHFFFAOYSA-N 4-fluoro-1,5-bis(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3C(=CC=NC=3)C)C2=C1F NLPQBCDTVGOEHF-UHFFFAOYSA-N 0.000 description 1
- FQBPEBWAYPFLQL-UHFFFAOYSA-N 4-fluoro-1,5-dipyridin-3-ylindole Chemical compound C1=CC=2C(F)=C(C=3C=NC=CC=3)C=CC=2N1C1=CC=CN=C1 FQBPEBWAYPFLQL-UHFFFAOYSA-N 0.000 description 1
- GJWWFHOBFZOSGG-UHFFFAOYSA-N 4-fluoro-1-pyridin-3-yl-5-thiophen-3-ylindole Chemical compound C1=CC=2C(F)=C(C3=CSC=C3)C=CC=2N1C1=CC=CN=C1 GJWWFHOBFZOSGG-UHFFFAOYSA-N 0.000 description 1
- XYUDPZRAOHEEDD-UHFFFAOYSA-N 4-fluoro-5-(2-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C(=CC=CC=3)F)C(F)=C2C=C1 XYUDPZRAOHEEDD-UHFFFAOYSA-N 0.000 description 1
- PHTUDVZHJHLOIS-UHFFFAOYSA-N 4-fluoro-5-phenyl-1-pyridin-3-ylindole Chemical compound C1=CC=2C(F)=C(C=3C=CC=CC=3)C=CC=2N1C1=CC=CN=C1 PHTUDVZHJHLOIS-UHFFFAOYSA-N 0.000 description 1
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- VFVQQKKPYJMHRI-UHFFFAOYSA-N 4-phenyl-1-pyridin-3-ylindole Chemical compound C1=CC2=C(C=3C=CC=CC=3)C=CC=C2N1C1=CC=CN=C1 VFVQQKKPYJMHRI-UHFFFAOYSA-N 0.000 description 1
- CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 1
- ZNTFRCQHRDYINF-UHFFFAOYSA-N 4-pyridin-2-yl-1-pyridin-3-ylindole Chemical compound C1=CC2=C(C=3N=CC=CC=3)C=CC=C2N1C1=CC=CN=C1 ZNTFRCQHRDYINF-UHFFFAOYSA-N 0.000 description 1
- YEZADZMMVHWFIY-UHFFFAOYSA-N 4-tert-butylbenzenesulfonyl chloride Chemical compound CC(C)(C)C1=CC=C(S(Cl)(=O)=O)C=C1 YEZADZMMVHWFIY-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- BYEJVGRULOVXJF-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C(=CC=CC=3)Cl)C=C2C=C1 BYEJVGRULOVXJF-UHFFFAOYSA-N 0.000 description 1
- MHJKFEPUMUMFAU-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-pyridin-3-ylindole Chemical compound ClC1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 MHJKFEPUMUMFAU-UHFFFAOYSA-N 0.000 description 1
- LEMBJPZSXVJBGV-UHFFFAOYSA-N 5-(2-chlorophenyl)-2,3-dimethyl-1-pyridin-3-ylindole Chemical compound CC1=C(C)C2=CC(C=3C(=CC=CC=3)Cl)=CC=C2N1C1=CC=CN=C1 LEMBJPZSXVJBGV-UHFFFAOYSA-N 0.000 description 1
- QRPRKNFVKYPXOQ-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C(=CC=CC=3)F)C=C2C=C1 QRPRKNFVKYPXOQ-UHFFFAOYSA-N 0.000 description 1
- ZAAZRNTTWAYCEJ-UHFFFAOYSA-N 5-(2-methoxyphenyl)-1-pyridin-3-ylindole Chemical compound COC1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 ZAAZRNTTWAYCEJ-UHFFFAOYSA-N 0.000 description 1
- ZKAXPCRHQYTFCM-UHFFFAOYSA-N 5-(2-methylphenyl)-1-pyridin-3-ylindole Chemical compound CC1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 ZKAXPCRHQYTFCM-UHFFFAOYSA-N 0.000 description 1
- GHIVPSFIDUIPOR-UHFFFAOYSA-N 5-(2-methylpyridin-3-yl)-1-pyridin-3-ylindole Chemical compound CC1=NC=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 GHIVPSFIDUIPOR-UHFFFAOYSA-N 0.000 description 1
- HODYZNBGFVNCJG-UHFFFAOYSA-N 5-(3-chlorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(Cl)C=CC=3)C=C2C=C1 HODYZNBGFVNCJG-UHFFFAOYSA-N 0.000 description 1
- YBLYOIWSXAZJGX-UHFFFAOYSA-N 5-(3-chlorophenyl)-1-pyridin-3-ylindole Chemical compound ClC1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 YBLYOIWSXAZJGX-UHFFFAOYSA-N 0.000 description 1
- YKPLDSAGAZNYFP-UHFFFAOYSA-N 5-(3-cyanophenyl)-1-(4-methylpyridin-3-yl)indole-3-carbonitrile Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(C=CC=3)C#N)C=C2C(C#N)=C1 YKPLDSAGAZNYFP-UHFFFAOYSA-N 0.000 description 1
- FKNJFTVJQBUEKI-UHFFFAOYSA-N 5-(3-ethoxyphenyl)-1-pyridin-3-ylindole Chemical compound CCOC1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 FKNJFTVJQBUEKI-UHFFFAOYSA-N 0.000 description 1
- MHCVCYVMEDMPHM-UHFFFAOYSA-N 5-(3-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=C(F)C=CC=3)C=C2C=C1 MHCVCYVMEDMPHM-UHFFFAOYSA-N 0.000 description 1
- MNKVAJVPBFZDTC-UHFFFAOYSA-N 5-(3-fluorophenyl)-1-pyridin-3-ylindole Chemical compound FC1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 MNKVAJVPBFZDTC-UHFFFAOYSA-N 0.000 description 1
- AGPPGSORLZJKAX-UHFFFAOYSA-N 5-(3-methylphenyl)-1-pyridin-3-ylindole Chemical compound CC1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 AGPPGSORLZJKAX-UHFFFAOYSA-N 0.000 description 1
- ACUPSKJUHCSUNX-UHFFFAOYSA-N 5-(3-nitrophenyl)-1-pyridin-3-ylindole Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C3C=CN(C3=CC=2)C=2C=NC=CC=2)=C1 ACUPSKJUHCSUNX-UHFFFAOYSA-N 0.000 description 1
- MCKFVPPRFFQZTN-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CC(Cl)=CC=3)C=C2C=C1 MCKFVPPRFFQZTN-UHFFFAOYSA-N 0.000 description 1
- RDXRXXKHQRTWIW-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 RDXRXXKHQRTWIW-UHFFFAOYSA-N 0.000 description 1
- GVESVYRONSIFLK-UHFFFAOYSA-N 5-(4-ethoxyphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 GVESVYRONSIFLK-UHFFFAOYSA-N 0.000 description 1
- RZNUUKRCOSSJAS-UHFFFAOYSA-N 5-(4-ethylphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(CC)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 RZNUUKRCOSSJAS-UHFFFAOYSA-N 0.000 description 1
- KUXSNVDEVSQSKS-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-(2-methylpyridin-3-yl)indole Chemical compound CC1=NC=CC=C1N1C2=CC=C(C=3C=CC(F)=CC=3)C=C2C=C1 KUXSNVDEVSQSKS-UHFFFAOYSA-N 0.000 description 1
- LTBUQKSQGPITDH-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C=3C=CC(F)=CC=3)C=C2C=C1 LTBUQKSQGPITDH-UHFFFAOYSA-N 0.000 description 1
- ZHESLPIODWKCHK-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-pyridin-3-ylindazole Chemical compound C1=CC(F)=CC=C1C1=CC=C(N(N=C2)C=3C=NC=CC=3)C2=C1 ZHESLPIODWKCHK-UHFFFAOYSA-N 0.000 description 1
- AMWBWPKLNFHKBO-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(F)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 AMWBWPKLNFHKBO-UHFFFAOYSA-N 0.000 description 1
- DNBXGFHXBYPAAU-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=C2)C=3C(=CC=NC=3)C)C2=C1 DNBXGFHXBYPAAU-UHFFFAOYSA-N 0.000 description 1
- SACDORSIGXDGOQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 SACDORSIGXDGOQ-UHFFFAOYSA-N 0.000 description 1
- OZBCSFKFQSRCNL-UHFFFAOYSA-N 5-(4-methylphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(C)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 OZBCSFKFQSRCNL-UHFFFAOYSA-N 0.000 description 1
- BZWOQXMOFGETMY-UHFFFAOYSA-N 5-(4-methylpyridin-3-yl)-1-pyridin-2-ylindazole Chemical compound CC1=CC=NC=C1C1=CC=C(N(N=C2)C=3N=CC=CC=3)C2=C1 BZWOQXMOFGETMY-UHFFFAOYSA-N 0.000 description 1
- JXLTVMMMXBGGIF-UHFFFAOYSA-N 5-(4-methylpyridin-3-yl)-1-pyridin-2-ylindole Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3N=CC=CC=3)C2=C1 JXLTVMMMXBGGIF-UHFFFAOYSA-N 0.000 description 1
- VDQISTYPBWHHMZ-UHFFFAOYSA-N 5-(4-methylpyridin-3-yl)-1-pyridin-3-ylindole Chemical compound CC1=CC=NC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 VDQISTYPBWHHMZ-UHFFFAOYSA-N 0.000 description 1
- IWMJIIATRFACRJ-UHFFFAOYSA-N 5-(4-methylpyridin-3-yl)-2-pyridin-2-ylindazole Chemical compound CC1=CC=NC=C1C1=CC2=CN(C=3N=CC=CC=3)N=C2C=C1 IWMJIIATRFACRJ-UHFFFAOYSA-N 0.000 description 1
- BCNBJAYUFQZWIG-UHFFFAOYSA-N 5-(4-tert-butylphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 BCNBJAYUFQZWIG-UHFFFAOYSA-N 0.000 description 1
- BCRSDRGYRMVALP-UHFFFAOYSA-N 5-(6-methylpyridin-3-yl)-1-pyridin-3-ylindole Chemical compound C1=NC(C)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 BCRSDRGYRMVALP-UHFFFAOYSA-N 0.000 description 1
- XHHMQFOGKACSCC-UHFFFAOYSA-N 5-(furan-3-yl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(C3=COC=C3)C=C2C=C1 XHHMQFOGKACSCC-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- HJDJFMQCLCCSGL-UHFFFAOYSA-N 5-bromo-1-(4-methylpyridin-3-yl)indazole Chemical compound CC1=CC=NC=C1N1C2=CC=C(Br)C=C2C=N1 HJDJFMQCLCCSGL-UHFFFAOYSA-N 0.000 description 1
- YCEJRISUHXJIPD-UHFFFAOYSA-N 5-bromo-1-pyridin-2-ylindole Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CC=N1 YCEJRISUHXJIPD-UHFFFAOYSA-N 0.000 description 1
- ZPUQCVKBNRGSAP-UHFFFAOYSA-N 5-bromo-1h-indole-3-carbonitrile Chemical compound BrC1=CC=C2NC=C(C#N)C2=C1 ZPUQCVKBNRGSAP-UHFFFAOYSA-N 0.000 description 1
- IOGAIEWEHFPGNO-UHFFFAOYSA-N 5-bromo-2,3-dimethyl-1h-indole Chemical compound C1=C(Br)C=C2C(C)=C(C)NC2=C1 IOGAIEWEHFPGNO-UHFFFAOYSA-N 0.000 description 1
- BJUZAZKEDCDGRW-UHFFFAOYSA-N 5-bromo-2-methyl-1h-indole Chemical compound BrC1=CC=C2NC(C)=CC2=C1 BJUZAZKEDCDGRW-UHFFFAOYSA-N 0.000 description 1
- GDQXDVJFMLNXHX-UHFFFAOYSA-N 5-bromo-3-methyl-1h-indole Chemical compound C1=C(Br)C=C2C(C)=CNC2=C1 GDQXDVJFMLNXHX-UHFFFAOYSA-N 0.000 description 1
- FBNRLQRIMLEPOY-UHFFFAOYSA-N 5-bromo-3-propan-2-yl-1h-indole Chemical compound C1=C(Br)C=C2C(C(C)C)=CNC2=C1 FBNRLQRIMLEPOY-UHFFFAOYSA-N 0.000 description 1
- OBGNVOLKFFCMAM-UHFFFAOYSA-N 5-bromo-4-fluoro-1h-indole Chemical compound FC1=C(Br)C=CC2=C1C=CN2 OBGNVOLKFFCMAM-UHFFFAOYSA-N 0.000 description 1
- HAKIMTKXOCVWRH-UHFFFAOYSA-N 5-bromo-6-fluoro-1h-indole Chemical compound C1=C(Br)C(F)=CC2=C1C=CN2 HAKIMTKXOCVWRH-UHFFFAOYSA-N 0.000 description 1
- NWHWSVLYUXYJFU-UHFFFAOYSA-N 5-bromo-6-methoxy-1h-indole Chemical compound C1=C(Br)C(OC)=CC2=C1C=CN2 NWHWSVLYUXYJFU-UHFFFAOYSA-N 0.000 description 1
- NBSOYBSYOOJMPE-UHFFFAOYSA-N 5-bromo-7-chloro-1h-indole Chemical compound ClC1=CC(Br)=CC2=C1NC=C2 NBSOYBSYOOJMPE-UHFFFAOYSA-N 0.000 description 1
- OUNQFZFHLJLFAR-UHFFFAOYSA-N 5-bromo-7-methyl-1h-indazole Chemical compound CC1=CC(Br)=CC2=C1NN=C2 OUNQFZFHLJLFAR-UHFFFAOYSA-N 0.000 description 1
- HOUJSOAXJSBNRH-UHFFFAOYSA-N 5-bromo-7-methyl-1h-indole Chemical compound CC1=CC(Br)=CC2=C1NC=C2 HOUJSOAXJSBNRH-UHFFFAOYSA-N 0.000 description 1
- FTFFHWWIPOQCBC-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile Chemical compound BrC1=CN=CC(C#N)=C1 FTFFHWWIPOQCBC-UHFFFAOYSA-N 0.000 description 1
- GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
- MIVTUOHYGIEYGC-UHFFFAOYSA-N 5-phenyl-1-pyridin-3-ylindole Chemical compound C1=CC2=CC(C=3C=CC=CC=3)=CC=C2N1C1=CC=CN=C1 MIVTUOHYGIEYGC-UHFFFAOYSA-N 0.000 description 1
- VZMIHGYOAGECNX-UHFFFAOYSA-N 5-phenyl-1-pyridin-3-ylindole-3-carbonitrile Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C(C#N)=CN1C1=CC=CN=C1 VZMIHGYOAGECNX-UHFFFAOYSA-N 0.000 description 1
- JCQLPDZCNSVBMS-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1OCC1=CC=CC=C1 JCQLPDZCNSVBMS-UHFFFAOYSA-N 0.000 description 1
- YFAUPZQNWIXPIW-UHFFFAOYSA-N 5-piperidin-1-yl-1-pyridin-3-ylindole Chemical compound C1CCCCN1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 YFAUPZQNWIXPIW-UHFFFAOYSA-N 0.000 description 1
- OIIPPPGEKJJMCG-UHFFFAOYSA-N 5-pyridin-2-yl-1-pyridin-3-ylindole Chemical compound C1=CC2=CC(C=3N=CC=CC=3)=CC=C2N1C1=CC=CN=C1 OIIPPPGEKJJMCG-UHFFFAOYSA-N 0.000 description 1
- RISNTYZTMRJOOW-UHFFFAOYSA-N 6-(2-chlorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(C=3C(=CC=CC=3)Cl)=CC=C2C=C1 RISNTYZTMRJOOW-UHFFFAOYSA-N 0.000 description 1
- JWHUYSVROKYESI-UHFFFAOYSA-N 6-(2-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(C=3C(=CC=CC=3)F)=CC=C2C=C1 JWHUYSVROKYESI-UHFFFAOYSA-N 0.000 description 1
- GCNLAYJHYQGDQM-UHFFFAOYSA-N 6-(2-methylphenyl)-1-pyridin-3-ylindole Chemical compound CC1=CC=CC=C1C1=CC=C(C=CN2C=3C=NC=CC=3)C2=C1 GCNLAYJHYQGDQM-UHFFFAOYSA-N 0.000 description 1
- XAVKCYNXZNHETQ-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(C=3C=C(Cl)C=CC=3)=CC=C2C=C1 XAVKCYNXZNHETQ-UHFFFAOYSA-N 0.000 description 1
- JMKTVCOPBNKLMC-UHFFFAOYSA-N 6-(3-fluorophenyl)-1-pyridin-3-ylindole Chemical compound FC1=CC=CC(C=2C=C3N(C=4C=NC=CC=4)C=CC3=CC=2)=C1 JMKTVCOPBNKLMC-UHFFFAOYSA-N 0.000 description 1
- QCSFEUAGDDIJNX-UHFFFAOYSA-N 6-(3-nitrophenyl)-1-pyridin-3-ylindole Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C3N(C=4C=NC=CC=4)C=CC3=CC=2)=C1 QCSFEUAGDDIJNX-UHFFFAOYSA-N 0.000 description 1
- RSMWUMBSZQGZQJ-UHFFFAOYSA-N 6-(4-chlorophenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C=CN2C=3C=NC=CC=3)C2=C1 RSMWUMBSZQGZQJ-UHFFFAOYSA-N 0.000 description 1
- HCTZVQOJSIVHHI-UHFFFAOYSA-N 6-(4-ethoxyphenyl)-1-pyridin-3-ylindole Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C=CN2C=3C=NC=CC=3)C2=C1 HCTZVQOJSIVHHI-UHFFFAOYSA-N 0.000 description 1
- LWFMXQYEJIZBBH-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(C=3C=CC(F)=CC=3)=CC=C2C=C1 LWFMXQYEJIZBBH-UHFFFAOYSA-N 0.000 description 1
- QMXJBJXYZYCWQE-UHFFFAOYSA-N 6-(4-methylpyridin-3-yl)-1-pyridin-2-ylindole Chemical compound CC1=CC=NC=C1C1=CC=C(C=CN2C=3N=CC=CC=3)C2=C1 QMXJBJXYZYCWQE-UHFFFAOYSA-N 0.000 description 1
- MAWGHOPSCKCTPA-UHFFFAOYSA-N 6-bromo-1h-indole Chemical compound BrC1=CC=C2C=CNC2=C1 MAWGHOPSCKCTPA-UHFFFAOYSA-N 0.000 description 1
- SPROIPHKWRJLPX-UHFFFAOYSA-N 6-fluoro-5-(2-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC(F)=C(C=3C(=CC=CC=3)F)C=C2C=C1 SPROIPHKWRJLPX-UHFFFAOYSA-N 0.000 description 1
- OKGGTPRDPXXUNP-UHFFFAOYSA-N 6-methoxy-1-(4-methylpyridin-3-yl)-5-phenylindole Chemical compound COC1=CC=2N(C=3C(=CC=NC=3)C)C=CC=2C=C1C1=CC=CC=C1 OKGGTPRDPXXUNP-UHFFFAOYSA-N 0.000 description 1
- PTSFYEJYSNRYCS-UHFFFAOYSA-N 6-methoxy-1-(4-methylpyridin-3-yl)-5-pyridin-3-ylindole Chemical compound COC1=CC=2N(C=3C(=CC=NC=3)C)C=CC=2C=C1C1=CC=CN=C1 PTSFYEJYSNRYCS-UHFFFAOYSA-N 0.000 description 1
- VPSICJRRHYFMAK-UHFFFAOYSA-N 6-phenyl-1-pyridin-3-ylindole Chemical compound C1=CC2=CC=C(C=3C=CC=CC=3)C=C2N1C1=CC=CN=C1 VPSICJRRHYFMAK-UHFFFAOYSA-N 0.000 description 1
- VGBMNKCWUCKZCQ-UHFFFAOYSA-N 7-chloro-1,5-dipyridin-3-ylindole Chemical compound C1=2C(Cl)=CC(C=3C=NC=CC=3)=CC=2C=CN1C1=CC=CN=C1 VGBMNKCWUCKZCQ-UHFFFAOYSA-N 0.000 description 1
- DHBCIBGGCPWGDY-UHFFFAOYSA-N 7-chloro-1-pyridin-3-yl-5-thiophen-3-ylindole Chemical compound C1=2C(Cl)=CC(C3=CSC=C3)=CC=2C=CN1C1=CC=CN=C1 DHBCIBGGCPWGDY-UHFFFAOYSA-N 0.000 description 1
- MEHLMCGNZVKOCH-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=C(Cl)C=C(C=3C(=CC=CC=3)F)C=C2C=C1 MEHLMCGNZVKOCH-UHFFFAOYSA-N 0.000 description 1
- AHUQNTPWHWENGZ-UHFFFAOYSA-N 7-chloro-5-phenyl-1-pyridin-3-ylindole Chemical compound C1=2C(Cl)=CC(C=3C=CC=CC=3)=CC=2C=CN1C1=CC=CN=C1 AHUQNTPWHWENGZ-UHFFFAOYSA-N 0.000 description 1
- AACCZQDGENADIE-UHFFFAOYSA-N 7-methyl-1,5-dipyridin-3-ylindole Chemical compound C1=2C(C)=CC(C=3C=NC=CC=3)=CC=2C=CN1C1=CC=CN=C1 AACCZQDGENADIE-UHFFFAOYSA-N 0.000 description 1
- LXZWZQGJZWDCSX-UHFFFAOYSA-N 7-methyl-1-(4-methylpyridin-3-yl)-5-pyridin-3-ylindazole Chemical compound CC1=CC=NC=C1N1C2=C(C)C=C(C=3C=NC=CC=3)C=C2C=N1 LXZWZQGJZWDCSX-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 208000005676 Adrenogenital syndrome Diseases 0.000 description 1
- 241001209177 Akis Species 0.000 description 1
- 108700028369 Alleles Proteins 0.000 description 1
- 235000001270 Allium sibiricum Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- BLJCSKCOZUDGPE-UHFFFAOYSA-N CCCCCC.CCCCCC.CCCCCC.CCCCCC.CCCCCC.CCCCCC.OCCN1CCN(CCS(O)(=O)=O)CC1 Chemical compound CCCCCC.CCCCCC.CCCCCC.CCCCCC.CCCCCC.CCCCCC.OCCN1CCN(CCS(O)(=O)=O)CC1 BLJCSKCOZUDGPE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- MBYXEBXZARTUSS-QLWBXOBMSA-N Emetamine Natural products O(C)c1c(OC)cc2c(c(C[C@@H]3[C@H](CC)CN4[C@H](c5c(cc(OC)c(OC)c5)CC4)C3)ncc2)c1 MBYXEBXZARTUSS-QLWBXOBMSA-N 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108700011498 Glucocorticoid Receptor Deficiency Proteins 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 108010026389 Gramicidin Proteins 0.000 description 1
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 101000922386 Homo sapiens Cytochrome b5 Proteins 0.000 description 1
- 101000938351 Homo sapiens Ephrin type-A receptor 3 Proteins 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020571 Hyperaldosteronism Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 208000026709 Liddle syndrome Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930126263 Maytansine Natural products 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000009905 Neurofibromatoses Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- AUVVAXYIELKVAI-UHFFFAOYSA-N SJ000285215 Natural products N1CCC2=CC(OC)=C(OC)C=C2C1CC1CC2C3=CC(OC)=C(OC)C=C3CCN2CC1CC AUVVAXYIELKVAI-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 108010052164 Sodium Channels Proteins 0.000 description 1
- 102000018674 Sodium Channels Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GBOGMAARMMDZGR-UHFFFAOYSA-N UNPD149280 Natural products N1C(=O)C23OC(=O)C=CC(O)CCCC(C)CC=CC3C(O)C(=C)C(C)C2C1CC1=CC=CC=C1 GBOGMAARMMDZGR-UHFFFAOYSA-N 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- JNSBEPKGFVENFS-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC=C1C(F)(F)F JNSBEPKGFVENFS-UHFFFAOYSA-N 0.000 description 1
- WOAORAPRPVIATR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1 WOAORAPRPVIATR-UHFFFAOYSA-N 0.000 description 1
- 238000010317 ablation therapy Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003817 anthracycline antibiotic agent Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 208000009262 apparent mineralocorticoid excess Diseases 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 238000007262 aromatic hydroxylation reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- ARQRPTNYUOLOGH-UHFFFAOYSA-N chcl3 chloroform Chemical compound ClC(Cl)Cl.ClC(Cl)Cl ARQRPTNYUOLOGH-UHFFFAOYSA-N 0.000 description 1
- NDAYQJDHGXTBJL-MWWSRJDJSA-N chembl557217 Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 NDAYQJDHGXTBJL-MWWSRJDJSA-N 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- 230000002060 circadian Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 230000006552 constitutive activation Effects 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004246 corpus luteum Anatomy 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- GBOGMAARMMDZGR-TYHYBEHESA-N cytochalasin B Chemical compound C([C@H]1[C@@H]2[C@@H](C([C@@H](O)[C@@H]3/C=C/C[C@H](C)CCC[C@@H](O)/C=C/C(=O)O[C@@]23C(=O)N1)=C)C)C1=CC=CC=C1 GBOGMAARMMDZGR-TYHYBEHESA-N 0.000 description 1
- GBOGMAARMMDZGR-JREHFAHYSA-N cytochalasin B Natural products C[C@H]1CCC[C@@H](O)C=CC(=O)O[C@@]23[C@H](C=CC1)[C@H](O)C(=C)[C@@H](C)[C@@H]2[C@H](Cc4ccccc4)NC3=O GBOGMAARMMDZGR-JREHFAHYSA-N 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000003748 differential diagnosis Methods 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- NLHWCTNYFFIPJT-UHFFFAOYSA-N disodium bis(trimethylsilyl)azanide Chemical compound [Na+].[Na+].C[Si](C)(C)[N-][Si](C)(C)C.C[Si](C)(C)[N-][Si](C)(C)C NLHWCTNYFFIPJT-UHFFFAOYSA-N 0.000 description 1
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- AUVVAXYIELKVAI-CKBKHPSWSA-N emetine Chemical compound N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC AUVVAXYIELKVAI-CKBKHPSWSA-N 0.000 description 1
- 229960002694 emetine Drugs 0.000 description 1
- AUVVAXYIELKVAI-UWBTVBNJSA-N emetine Natural products N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@H]1CC AUVVAXYIELKVAI-UWBTVBNJSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- OLAMWIPURJGSKE-UHFFFAOYSA-N et2o diethylether Chemical compound CCOCC.CCOCC OLAMWIPURJGSKE-UHFFFAOYSA-N 0.000 description 1
- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 230000023611 glucuronidation Effects 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 208000035392 hereditary 6 prostate cancer Diseases 0.000 description 1
- 208000032154 hereditary 8 prostate cancer Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 229940125697 hormonal agent Drugs 0.000 description 1
- 102000057382 human EPHA3 Human genes 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- WKPWGQKGSOKKOO-RSFHAFMBSA-N maytansine Chemical compound CO[C@@H]([C@@]1(O)C[C@](OC(=O)N1)([C@H]([C@@H]1O[C@@]1(C)[C@@H](OC(=O)[C@H](C)N(C)C(C)=O)CC(=O)N1C)C)[H])\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 WKPWGQKGSOKKOO-RSFHAFMBSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- KFMWDRQCZJWFSH-UHFFFAOYSA-N methyl 4-(1-pyridin-3-ylindol-5-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N(C=C2)C=3C=NC=CC=3)C2=C1 KFMWDRQCZJWFSH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002991 molded plastic Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- SHSPDFATCQXYNT-UHFFFAOYSA-N n-phenyl-1-pyridin-3-ylindol-5-amine Chemical compound C=1C=C2N(C=3C=NC=CC=3)C=CC2=CC=1NC1=CC=CC=C1 SHSPDFATCQXYNT-UHFFFAOYSA-N 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000012740 non-selective inhibitor Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 238000011369 optimal treatment Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000009038 pharmacological inhibition Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 201000005825 prostate adenocarcinoma Diseases 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229950010131 puromycin Drugs 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011472 radical prostatectomy Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000003439 radiotherapeutic effect Effects 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 230000000365 steroidogenetic effect Effects 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32499301P | 2001-09-26 | 2001-09-26 | |
| US60/324,993 | 2001-09-26 | ||
| PCT/US2002/030482 WO2003027094A2 (en) | 2001-09-26 | 2002-09-26 | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461363A1 true CA2461363A1 (en) | 2003-04-03 |
Family
ID=23265979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461363A Abandoned CA2461363A1 (en) | 2001-09-26 | 2002-09-26 | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
| CA002461360A Abandoned CA2461360A1 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461360A Abandoned CA2461360A1 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1432706A2 (https=) |
| JP (2) | JP2005532983A (https=) |
| AU (2) | AU2002340010A1 (https=) |
| CA (2) | CA2461363A1 (https=) |
| WO (8) | WO2003027085A2 (https=) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4160295B2 (ja) * | 2000-12-08 | 2008-10-01 | 武田薬品工業株式会社 | 3−ピリジル基を有する置換チアゾール誘導体、その製造法および用途 |
| 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 |
| US20040147561A1 (en) * | 2002-12-27 | 2004-07-29 | Wenge Zhong | Pyrid-2-one derivatives and methods of use |
| JP4847868B2 (ja) * | 2003-05-14 | 2011-12-28 | ニューロジェネティック ファーマシューティカルズ、 インコーポレイテッド | 化合物、及び、アミロイドベータの調節におけるその使用 |
| ES2222827B1 (es) * | 2003-07-30 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 5-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| CN101675928A (zh) * | 2003-11-14 | 2010-03-24 | 沃泰克斯药物股份有限公司 | 可用作atp-结合弹夹转运蛋白调控剂的噻唑和噁唑 |
| WO2005099711A1 (en) * | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| JP4602686B2 (ja) * | 2004-04-15 | 2010-12-22 | 広栄化学工業株式会社 | 2,6−ジハロゲノ−4−アリールピリジン類の製造法 |
| EP1799659A1 (en) | 2004-10-13 | 2007-06-27 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| MX2007004781A (es) * | 2004-10-20 | 2007-05-11 | Applied Research Systems | Derivados de 3-arilamino piridina. |
| WO2006051723A1 (ja) * | 2004-11-09 | 2006-05-18 | Kaneka Corporation | 1-ハロ-3-アリール-2-プロパノン類の製造法 |
| GB0428514D0 (en) * | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| BRPI0519774A2 (pt) * | 2005-01-19 | 2009-02-10 | Biolipox Ab | composto ou um sal farmaceuticamente aceitÁvel do mesmo, formulaÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel do mesmo, mÉtodo de tratamento de uma doenÇa em que inibiÇço da atividade de um membro da famÍlia mapeg É desejada e/ou necessÁria, produto combinado, e, processo para a preparaÇço de um composto |
| NZ563866A (en) | 2005-05-09 | 2011-03-31 | Achillion Pharmaceuticals Inc | Thiazole compounds and methods of use |
| WO2007016979A2 (en) * | 2005-07-29 | 2007-02-15 | 4Sc Ag | NOVEL HETEROCYCLIC NF-κB INHIBITORS |
| FR2889526B1 (fr) * | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| KR20080066938A (ko) * | 2005-10-07 | 2008-07-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 복소환 화합물 및 그것을 함유하는 의약 조성물 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| CA2635541A1 (en) * | 2005-12-28 | 2007-07-12 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds and their use as mineralocorticoid receptor ligands |
| BRPI0710479A2 (pt) * | 2006-01-18 | 2012-08-14 | Hoffmann La Roche | composto, processo para sua preparaÇço, composiÇço farmacÊutica, uso de um composto e mÉtodo de tratamento de doenÇa ou desosrdem metabàlica. |
| BRPI0706411A2 (pt) * | 2006-01-24 | 2011-03-29 | Lilly Co Eli | composto, composição farmacêutica, método de preparação de um indol ou um sal farmaceuticamente aceitável do mesmo, e, uso de um composto |
| EP2468727A1 (en) | 2006-03-29 | 2012-06-27 | F. Hoffmann-La Roche AG | Pyridine and pyrimidine derivatives as MGLUR2 antagonists |
| WO2008021337A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Oxazinan-2-one derivatives useful as pr modulators |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| WO2008021309A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Imidazolidin-2-one derivatives useful as pr modulators |
| US7618989B2 (en) | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| ATE534642T1 (de) * | 2006-09-21 | 2011-12-15 | Eisai R&D Man Co Ltd | Durch einen heteroarylring substituiertes pyridinderivat und antipilzmittel, das dieses enthält |
| EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| RU2009116632A (ru) | 2006-10-02 | 2010-11-10 | Кортендо Инвест, Аб (Se) | Энантиомер кетоконазола у людей |
| WO2008070350A2 (en) | 2006-10-27 | 2008-06-12 | The Board Of Regents Of The University Of Texas System | Methods and compositions related to wrapping of dehydrons |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| US8183263B2 (en) | 2007-05-22 | 2012-05-22 | Achillion Pharmaceuticals, Inc. | Heteroaryl substituted thiazoles |
| TWI580356B (zh) | 2007-08-13 | 2017-05-01 | 孟山都科技有限責任公司 | 控制植物寄生性線蟲的化合物及方法以及被覆有該化合物之種子 |
| JP5567481B2 (ja) | 2007-10-09 | 2014-08-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | グルコキナーゼアクチベーターとして有用なピリジン誘導体 |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ, インコーポレイテッド | チオフェンおよびホスファチジルイノシトール3−キナーゼ(pi3k)阻害薬としてのその使用 |
| CN101965176B (zh) | 2008-02-08 | 2012-06-20 | 株式会社资生堂 | 美白剂和皮肤外用剂 |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| AU2009330686B2 (en) * | 2008-06-16 | 2014-07-03 | The Ohio State University Research Foundation | Compounds for the treatment of cancer |
| TWI409265B (zh) * | 2008-08-20 | 2013-09-21 | Merck Sharp & Dohme | 經取代之吡啶及嘧啶衍生物及彼等於治療病毒感染之用途 |
| US8536185B2 (en) | 2008-09-22 | 2013-09-17 | Cayman Chemical Company, Incorporated | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| WO2010090716A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| KR20110128942A (ko) * | 2009-03-19 | 2011-11-30 | 사노피 | Hsp90 억제 인다졸 유도체, 그를 함유하는 조성물 및 그의 용도 |
| JP5728487B2 (ja) * | 2009-10-29 | 2015-06-03 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | 三環式ヘテロ環化合物 |
| WO2011051198A2 (de) * | 2009-10-30 | 2011-05-05 | Bayer Cropscience Ag | Pyridin-derivate als pflanzenschutzmittel |
| DE102009058280A1 (de) | 2009-12-14 | 2011-06-16 | Merck Patent Gmbh | Thiazolderivate |
| MX2012010115A (es) | 2010-03-01 | 2013-02-26 | Gtx Inc | Compuestos para el tratamiento de cancer. |
| CN103140490A (zh) | 2010-07-15 | 2013-06-05 | 百时美施贵宝公司 | 氮杂吲唑化合物 |
| KR101823275B1 (ko) | 2010-08-04 | 2018-03-08 | 펠피큐어 파마슈티걸즈 아이엔씨 | 전립선 암종의 치료를 위한 병용 요법 |
| MX2013001660A (es) | 2010-08-11 | 2013-06-03 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| TW201307309A (zh) | 2010-10-13 | 2013-02-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
| WO2012052412A1 (de) * | 2010-10-22 | 2012-04-26 | Bayer Cropscience Ag | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
| US9056855B2 (en) * | 2010-10-28 | 2015-06-16 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US9266880B2 (en) | 2010-11-12 | 2016-02-23 | Bristol-Myers Squibb Company | Substituted azaindazole compounds |
| GB2485404A (en) * | 2010-11-15 | 2012-05-16 | Nat Univ Ireland | Metal-complexed pyridyl-substituted tetrazole compounds and their use in treating cancer |
| CN102675286B (zh) * | 2011-03-07 | 2015-08-19 | 中国科学院上海药物研究所 | 一类吲唑类化合物及其制备方法、用途和药物组合物 |
| AU2012249421B9 (en) | 2011-04-28 | 2015-10-22 | Novartis Ag | 17alpha-hydroxylase/C17,20-lyase inhibitors |
| US20120302573A1 (en) * | 2011-05-25 | 2012-11-29 | Paul Francis Jackson | Methods of inhibiting pro matrix metalloproteinase activation |
| US8969586B2 (en) | 2011-09-27 | 2015-03-03 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| EP2903615B1 (en) * | 2012-10-05 | 2021-04-07 | Merck Sharp & Dohme Corp. | 5-pyridin-3-yl-2,3-dihydro-1h-indole derivatives as aldosterone synthase (cyp11b2) inhibitors for the treatment of hypertension |
| EP2934144B1 (en) | 2012-12-20 | 2017-07-19 | Merck Sharp & Dohme Corp. | Indazole compounds as aldosterone synthase inhibitors |
| JP6835472B2 (ja) | 2013-03-05 | 2021-02-24 | ユニバーシティ オブ テネシー リサーチ ファウンデーション | 癌の処置のための組成物 |
| EP2968219B1 (en) | 2013-03-14 | 2019-04-24 | Pellficure Pharmaceuticals, Inc. | Novel therapy for prostate carcinoma |
| EP3191087A1 (en) | 2014-09-12 | 2017-07-19 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| EP3528799A1 (en) | 2016-10-24 | 2019-08-28 | Pellficure Pharmaceuticals, Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| JP7193071B2 (ja) * | 2017-02-08 | 2022-12-20 | 国立大学法人東海国立大学機構 | 蛍光発光材料および紫外線吸収剤 |
| WO2021126779A1 (en) * | 2019-12-18 | 2021-06-24 | The Regents Of The University Of California | Inhibitors of lin28 and methods of use thereof |
| US20210246109A1 (en) * | 2020-02-11 | 2021-08-12 | University Of Kentucky Research Foundation | Potent and selective inhibitors of cytochrome p450 |
| WO2023049199A1 (en) * | 2021-09-24 | 2023-03-30 | Zeno Management, Inc. | Azole compounds |
| CN117551029A (zh) * | 2023-11-22 | 2024-02-13 | 河南大学 | 一种4-溴-3-氰基吡啶的合成方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK150068C (da) * | 1978-06-02 | 1987-06-29 | Pfizer | Analogifremgangsmaade til fremstilling af aminothiazoler |
| JPS55133366A (en) * | 1979-04-05 | 1980-10-17 | Otsuka Pharmaceut Factory Inc | Thiazole derivative |
| US4536505A (en) * | 1983-05-17 | 1985-08-20 | Ciba-Geigy Corporation | Certain N-(pyridyl) indoles |
| DE3940476A1 (de) * | 1989-12-07 | 1991-06-13 | Bayer Ag | Pyridinylpyrimidin-derivate |
| DE3940477A1 (de) * | 1989-12-07 | 1991-06-13 | Bayer Ag | Hetaryl-substituierte pyridinylpyrimidin-derivate |
| JPH04154773A (ja) * | 1990-10-15 | 1992-05-27 | Green Cross Corp:The | チアゾール誘導体 |
| DE4117560A1 (de) * | 1991-05-29 | 1992-12-03 | Bayer Ag | Verwendung von pyridinylpyrimidin-derivaten zum schutz technischer materialien |
| TW223004B (https=) * | 1991-11-25 | 1994-05-01 | Sumitomo Chemical Co | |
| US5599774A (en) * | 1992-01-22 | 1997-02-04 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5395817A (en) * | 1992-01-22 | 1995-03-07 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5444038A (en) * | 1992-03-09 | 1995-08-22 | Zeneca Limited | Arylindazoles and their use as herbicides |
| HU217661B (hu) * | 1992-03-09 | 2000-03-28 | Zeneca Ltd. | Aril-indazol-származékok, eljárás az előállításukra és herbicidként történő alkalmazásuk |
| AU689972B2 (en) * | 1994-11-29 | 1998-04-09 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
| US6046136A (en) * | 1997-06-24 | 2000-04-04 | Zeneca Limited | Herbicidal heterocyclic N-oxides compounds |
| US5840721A (en) * | 1997-07-09 | 1998-11-24 | Ontogen Corporation | Imidazole derivatives as MDR modulators |
| EP1019399A1 (en) * | 1997-10-03 | 2000-07-19 | Merck Frosst Canada & Co. | Aryl thiophene derivatives as pde iv inhibitors |
| CA2331118A1 (en) * | 1998-05-12 | 1999-11-18 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| AU5227999A (en) * | 1998-07-27 | 2000-02-21 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| AU2001237401B2 (en) * | 2000-03-01 | 2006-11-09 | Janssen Pharmaceutica N.V. | 2,4-disubstituted thiazolyl derivatives |
-
2002
- 2002-09-26 CA CA002461363A patent/CA2461363A1/en not_active Abandoned
- 2002-09-26 JP JP2003530675A patent/JP2005532983A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030483 patent/WO2003027085A2/en not_active Ceased
- 2002-09-26 EP EP02799636A patent/EP1432706A2/en not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030983 patent/WO2003027096A1/en not_active Ceased
- 2002-09-26 JP JP2003530682A patent/JP2005528325A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030981 patent/WO2003027105A1/en not_active Ceased
- 2002-09-26 AU AU2002340010A patent/AU2002340010A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030924 patent/WO2003027100A1/en not_active Ceased
- 2002-09-26 EP EP02778338A patent/EP1432698A2/en not_active Withdrawn
- 2002-09-26 AU AU2002362603A patent/AU2002362603A1/en not_active Abandoned
- 2002-09-26 CA CA002461360A patent/CA2461360A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030979 patent/WO2003027101A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030982 patent/WO2003027095A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030482 patent/WO2003027094A2/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030834 patent/WO2003027107A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002340010A1 (en) | 2003-04-07 |
| WO2003027100A1 (en) | 2003-04-03 |
| WO2003027085A2 (en) | 2003-04-03 |
| WO2003027094A2 (en) | 2003-04-03 |
| WO2003027095A1 (en) | 2003-04-03 |
| WO2003027105A1 (en) | 2003-04-03 |
| CA2461360A1 (en) | 2003-04-03 |
| AU2002362603A1 (en) | 2003-04-07 |
| WO2003027085A3 (en) | 2003-12-04 |
| JP2005528325A (ja) | 2005-09-22 |
| JP2005532983A (ja) | 2005-11-04 |
| WO2003027094A3 (en) | 2003-10-23 |
| WO2003027096A1 (en) | 2003-04-03 |
| EP1432698A2 (en) | 2004-06-30 |
| WO2003027101A1 (en) | 2003-04-03 |
| EP1432706A2 (en) | 2004-06-30 |
| WO2003027107A1 (en) | 2003-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2461363A1 (en) | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors | |
| US20040236110A1 (en) | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors | |
| US20040198773A1 (en) | Substituted 3-pyridyl oxazoles as c17,20 lyase inhibitors | |
| JP6602470B2 (ja) | Mdm2−p53阻害薬としてのスピロ[3h−インドール−3,2‘−ピロリジン]−2(1h)−オン化合物及び誘導体 | |
| JP6488367B2 (ja) | ベンゾイミダゾール誘導体 | |
| EP4598922B1 (en) | Parg inhibitory compound | |
| BR112015023279B1 (pt) | compostos para inibição de fasn | |
| BRPI0619517A2 (pt) | ácidos pirazolo[1,5-a]piridina-3-carboxìlicos como inibidores de ephb e vegfr2 cinase | |
| JP2011510058A (ja) | C−metの阻害剤として活性な縮合ピリジン | |
| EP2598481A1 (en) | Sulfonamide compounds useful as cyp17 inhibitors | |
| US9266880B2 (en) | Substituted azaindazole compounds | |
| US20040267017A1 (en) | 3-pyridyl or 4-isoquinolinyl thiazoles as c17, 20 lyase inhibitors | |
| CN112673009A (zh) | 被取代的三唑并喹喔啉衍生物 | |
| KR20240035515A (ko) | 삼중 고리 테트라하이드로 이소퀴놀린계 유도체의 염의 형태 | |
| Kinoyama et al. | (+)-(2R, 5S)-4-[4-cyano-3-(trifluoromethyl) phenyl]-2, 5-dimethyl-N-[6-(trifluoromethyl) pyridin-3-yl] piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist | |
| JP2013542202A (ja) | Cyp17修飾因子として有用である置換ベンゾイミダゾールおよびイミダゾピリジン化合物 | |
| WO2025093755A1 (en) | Novel parc inhibitors | |
| WO2025133396A1 (en) | Novel bicyclo heteroaryl parg inhibitors | |
| US20040209924A1 (en) | Substituted 3-pyridyl imidazoles as c17,20 lyase inhibitors | |
| CN116848103B (zh) | Hpk1激酶抑制剂 | |
| US20260055106A1 (en) | Parg inhibitory compound | |
| WO2010141247A1 (en) | Hexahydrocyclopentyl[∫]indazole 5-hydroxymethyl ethanols and derivatives thereof as selective glucocorticoid receptor modulators | |
| Srinivas et al. | Design an Efficient Method for the Synthesis of 2-(1, 3-diphenyl-1H-pyrazol-4-yl)-1H-benzo [d] imidazole | |
| BR112021012595B1 (pt) | Inibidores aza-heterobicíclicos de mat2a e métodos de uso para tratamento de câncer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |